The following is the complete edited transcript of my conversation with Matt Lescault, Founder & CEO of TydeCo, on The Business Philosopher Within You podcast. Minor edits have been made for readability while preserving the meaning and flow of the discussion.

Topics covered in this conversation

• Founder glass ceiling

• Scaling a business

• Leadership evolution

• Founder mindset

• Self-awareness

• Business growth

• Organizational systems

• Building leadership teams

• Entrepreneurial risk

• Business partnerships

• Self-sustaining organizations

What Is a Founder Glass Ceiling?

[00:00:00.01] - Matt

The reason I call it a great glass ceiling is if you want to get past, you got to break that glass ceiling. In a way, you have to break yourself, be honest with yourself and figure out where you need to change and break those pieces of comfort. What makes people avoid change is their fear of messing up what is comfortable to them. That’s the most hard part of change management because you know what can be comfortable to somebody doesn’t have to be positive to them. But it’s what they know. Why, why is my comfort live there? What is my fear that’s holding me back? That was the moment. And, and getting through that and being able to take that from, I think at that point being about $600,000 in revenue, back down to $300,000, reshuffling, and then grow that back up, that I realized I can do this in any moment as long as I’m honest with myself about where I I am the factor that is causing the lack of success. I, I think that’s the fallacy. I think that’s what people see from the outside. I remember signing the paperwork for the bank to get the, the money to buy the South Africa companies, and I was driving home, the same house that I have today, and I think I had a full-on anxiety attack.

[00:01:15.23]

You know, I’m challenged every day as a CEO. What I can tell you is that my imposter syndrome will start to creep back in as we grow and the team grows more. And I’m continued to ask to make decisions that I’m not educated in making. And so I have to spend a lot of time making. And so those will be some of those moments in which we have to ask, you know, there’ll be questions about, am I the right person? And that’ll be its own glass ceiling. At some point, there’s a chance that I don’t end up at the answer that yes, I’m the right person. There is that chance. Now I have a— I’m a pretty confident individual, so I haven’t gotten there yet, but, uh, I always think about that. It’s like, is there going to be this moment in which I decide that I’m not the right person to lead the charge? My confidence has grown tremendously, and I’m not talking about the façade of confidence. I had to have a façade of confidence for a time period, and I think the 22-year-old me had more of a façade of confidence than today me that I’m very comfortable in who I am.

[00:02:24.10]

It is a, a comfort in yourself, a comfort in who you are. I think that’s really important. It’s not just a success of an entrepreneur, but just as we get older, as we are asked to be parents, as we’re asked to be leaders, as we’re asked to evolve and be the next generation.

[00:02:44.04] - Bhavesh

This is the Business Philosopher Within You Podcast. I’m your host, Bhavesh Naik. A question we often explore on this podcast is whether leaders can evolve as fast as the organizations they build. Because at some point, every founder hits a ceiling. The strategies that got you here stop working. The business is ready for its next level and something has to change. Today’s guest calls these moments glass ceilings. Matt Lasco is the founder and CEO of TideCo, a global consulting and cloud technology firm that began in a college attic with $1,500. Today it has grown into a multinational advisory group with more than 120 employees across the US, Canada, and South Africa. He’s a systems-driven leader who has navigated mergers, rapid growth, and his own evolution along the way. I’m so happy to have you on this podcast, Matt.

[00:03:36.22] - Matt

Thank you. It’s great to be here.

[00:03:38.06] - Bhavesh

And a special shout out to you, our listener. Hey, listen, we’re not just a podcast. We are a movement and you are the business philosopher. We learn from each other and grow with each other. Please remember to like, subscribe, follow, share, and comment, but most important, ask and answer questions. Thank you for tuning in.

Building a Business from a $1,500 Startup

[00:03:56.14]

So Matt, take us back to that dorm room, $1,500 startup, right? And you starting a company. And we’re gonna talk about the glass ceilings a little bit, but I wanna get you kind of warmed up here a little bit with your story and how you started this company that became what it is today.

[00:04:15.22] - Matt

So I think the story starts a little bit before that $1,500. It wasn’t a dorm room. I had a house that I had rented. It was in an attic of that house. So I can’t, I can’t take the dorm room credit, but You know, I was very lucky to have gotten into a professional setting while in high school. And so I worked for a government agency in their accounting office and got to do budgets and things of that nature. And I ended up, you know, fast forward a little bit, I ended up becoming a controller of a local construction firm., here in Maryland. And it was an organization that had been around since the 1930s. It was an organization that had, uh, had some different troubles and so forth. And so I kind of came into what would be a mess. And, uh, and there was, you know, multiple years of taxes not filed, different things, the IRS. And I, uh, I had an opportunity to sort of like, in my opinion, there wasn’t— there’s only one direction to go, and that was up. So, right, they had a 40,000-square-foot, uh, warehouse, but they weren’t getting— they weren’t seeing the value, or they weren’t attaining the value that it could be.

[00:05:40.14]

And so as this 21-year-old guy, I was able to, to go into this organization and make a lot of impacts. Um, so I went— we went from half a million to about $3.6 million in revenue in 2 years. I was doing project management, I was doing accounting,. And I was negotiating with IRS and the labor department and so forth. And I remember, and one of my favorite parts of the story is I remember getting a fax, yes, a fax from the local government. And it said, to Matthew Lesko, Esquire. And I’m a 21-year-old guy. And so I go to the owners, I’m like, I get a raise because I just became a lawyer. But, um, all, all jokes aside, what it did was it gave me this confidence and this understanding that if I could, if I could do that, I could propel my career into offering my expertise. And maybe it wasn’t even expertise at the time, but my drive to multiple organizations. And through that, know that as a person, as who I am, that I got bored pretty easily. And if I started my own company, it was always my destiny that I got to drive towards.

[00:07:03.05]

And so that’s when I, uh, I actually put my resume on Craigslist, for those that remember Craigslist and the days that was actually used for, for, for things. And, uh, I got offered a job, uh, and I think I’m at 22 years old now for $120,000 a year. But I had this like want of entrepreneurship. I wanted to start my own thing. And so I went to my parents, I’m still 22, you know, I need to get, I gotta get the parental blessing on what I’m gonna do. So I go to my parents and I say like, I have this, I have this job offer at $120,000 and I don’t want to take it. I want to start the business, but, right. You know what? I don’t have any money, so I might need some money from you. So my mom goes, that’s more money than your dad is making right now. You can’t turn that down. You can’t do that. And my dad looks at me, goes, you go do you. Wow. And, uh, yeah, that’s a blessing. Yeah. Yeah. No, it was, it, it was this moment and Uh, so I, I, I took that $1,500 ‘cause I said to my dad, I said, look, I, I, I need some money.

[00:08:18.18]

I gotta get a lawyer. I gotta put some things into place. Yeah. I gotta incorporate. I gotta do basic things. And so he gave me that $1,500, but I had no clients yet. This was all the dream and the thought. Right. And, uh, and that’s how the, that’s how the business started. And, uh, I went, well, I got a job by posting on Craigslist, so why don’t I just post services on Craigslist? So the way that the company started was me posting free ads for bookkeeping services on Craigslist. And we went from zero to half a million in revenue in 18 months by doing that.

[00:08:54.00] - Bhavesh

That’s crazy. Yeah. Yeah.

[00:08:55.23] - Matt

So that’s, that’s the, that’s the beginning. That’s the origin of where we are today.

[00:09:02.03] - Bhavesh

Absolutely. And, and I’m getting flashbacks here as you’re talking about all these things, not just Craigslist, but fax, right? Someone sent you a fax and, uh, I, I can’t even remember what faxes look like, right?

[00:09:12.09] - Matt

So they weren’t pretty.

[00:09:14.15] - Bhavesh

They weren’t pretty, right?

[00:09:16.17] - Matt

Right.

[00:09:18.07] - Bhavesh

Yeah, we used to— there’s all kinds of movie scenarios where, you know, someone sends you— someone sends someone a fax and, you know, it doesn’t get picked up and, you know, the stuff breaks loose. And so, yeah, so, and again, I think you’re blessed to have some parental figure, a parent, an actual parent who basically says, and go ahead and do it with you at the age of 22. Because a lot of us don’t have that.

[00:09:44.21] - Matt

So I think, I think that, and as a, as a father, so I have an 8-year-old daughter and a 6-year-old son, right? I think that parents impact, uh, the, the direction and, uh, the confidence of their kids in such special ways. And I learned that firsthand through my parents. You know, my father was a union guy, my mother is an artist and really went towards her direction. She’s a very— yeah, in the circles, well-known artist here in the Washington, D.C. area. Um, and so I, I grew up with people that, that chased their dreams and what mattered to them, and that’s, uh, that’s huge.

[00:10:28.23] - Bhavesh

Yeah, absolutely. And here you are chasing— not just chasing your dreams, but, you know, having You realized.

[00:10:35.09] - Matt

Oh, I’m chasing them. I continue every day to chase those dreams.

[00:10:39.02] - Bhavesh

Yes, and then it’s a never-ending chase and that’s the best part about it, right? Absolutely. Yeah, so here you are, you’re 120-employee companies, you are in 3 countries and you have multiple offices and so you’re not a $1,500 startup yet at this point.

[00:10:55.04] - Matt

No, not at this point.

[00:10:56.00] - Bhavesh

Not anymore, all right. So, you know, how you got there is something that we wanna talk about and we talked about this idea of glass ceilings.

[00:11:03.16] - Matt

Absolutely.

[00:11:05.16] - Bhavesh

So you grew to half a million dollars in 18 months. And when do you think you hit your first glass ceiling? Right then. Oh, really?

[00:11:15.09]

Yeah.

[00:11:15.19] - Matt

So, yeah, yeah. Ever say that? At 22 years old, I knew nothing. I mean, right, like maybe less than nothing.

[00:11:23.05] - Bhavesh

Yeah.

[00:11:23.11] - Matt

And so, but I’ve always been really blessed, I guess is the best way to put it. But I’ve been really lucky to have great mentors throughout my life.

[00:11:32.20] - Bhavesh

Sure.

[00:11:33.02] - Matt

People that I could look to and cared about my success and told me how it is, um, but also help guide through that. But, you know, if you’ve met any entrepreneur, we’re all stubborn.

[00:11:47.01] - Bhavesh

Yeah.

[00:11:47.13] - Matt

And we want to do it our way, you know. So you have the mentors that try to tell you, and then you do it your own way and you fail, and you go and you knock back on that door and you say, you know what, you’re right, you’re right, I that, that was the wrong path. But, um, yeah, that first glass ceiling was there right after that 18 months. So I had, I’d grown to half a million, and I went directly into this thought process that I’m going to emulate, um, how accounting firms, CPA firms are built. So I went and got office space, and I went and hired people, and I thought about this third, third, third model. That’s, you know, back in the day and how we did it, like a third of the billable rate is what you pay. And, but I wasn’t confident enough to go and charge enough. So I was like charging like $45 an hour. So the third, third, third, I, I had to pay people $15 an hour, and quality wasn’t there. I couldn’t attract the right people. And so I was— I’ve always been good at generating revenue, but what I saw was this, like, for every client I would get, I’d lose a client because we weren’t really operating within a good quality of service infrastructure.

[00:12:56.16]

And so that first—

[00:12:57.09] - Bhavesh

sure—

[00:12:57.16] - Matt

glass ceiling was, was this idea of like, okay, I’m here, I have revenue, I figured out part of this, but I’m not succeeding. I’m not making much myself. I’m paying other people, and I don’t really feel like I’m succeeding. And it was the first moment in which I realized there was a degree of failure of what I was, uh, what I was experiencing. And, uh, if we think about this, I just want to give time frames, uh, just, just so we’re on the same page. So I incorporated my business in October of 2006. I left that construction firm, uh, in early 2007, call it July 2007. Um, by late 2018 into early— I mean, 2008 into 2000, early 2009, um, I had gotten Class A office space. I had 7 to 10 people working for me, and I hit this glass ceiling, and I was making like $20,000 a year myself. Now luckily I was young, I’m still like 23 going, maybe I’m 24. I didn’t have any bills, I didn’t have kids, I didn’t have anything I had to worry about, um, so I could make ends meet. But, uh, it was this moment in which I realized that I wasn’t truly succeeding.

[00:14:16.00]

And I almost gave up, right? Yeah, I almost gave up on it. I, uh, I was in communications and, and conversations with a firm who was— who had offered to take on the clients, hire me.

[00:14:28.23] - Bhavesh

Yeah.

[00:14:29.13] - Matt

And, right, uh, and take that burden off of me, right? They weren’t going to pay me anything besides a guaranteed salary. I think they had offered me like $60,000 a year. Mhm. And I had this like moment in time and I said, do I, do I think I can do better than $60,000 a year right now? And do I think that I have the ability to figure this out? And what I realized is that I had to change my own mentality. So when I think about glass ceilings, you know, going back to what we’re talking about is glass ceilings are typically self-imposed. So the reason I call them glass ceilings is because you can see through them. Okay.

[00:15:12.07] - Bhavesh

Yeah. Yeah.

[00:15:13.14] - Matt

You, you hit them, right? See the next phase afterwards. But do you have the pain? But do you have the ability to break and to kind of break yourself?

[00:15:25.01] - Bhavesh

Sure. Sure.

[00:15:25.20] - Matt

Break who you are, break how you think about it and change. Because that’s what it’s all about. Like as an entrepreneur, as somebody that guides through it, This is not a perfect world, and there is moments in life in which we have to completely self-reflect and say, am I doing this in a way that’s going to get me to the next level? Um, and so that was that first moment which I said, no, I’m gonna break myself. And so what I did was I got rid of most of my staff and at least half of my clients. I retained a couple key staff members, and I changed my business model. I went to completely virtual. I increased my rates. I kept the clients that made sense, and I— yeah, and I dug in in a special kind of way.

[00:16:15.11] - Bhavesh

Yes.

[00:16:15.21] - Matt

Like, just doing like all the work. I remember, I remember being up until 3 AM doing work and, and, you know, accounting work, like bookkeeping and everything.

[00:16:25.08] - Bhavesh

I was getting to clients, the work, right?

[00:16:28.07] - Matt

And, uh, and so for me, that was the moment, and, and getting through that and being able to take that from, I think at that point being about $600,000 in revenue, back down to $300,000, reshuffling, and then grow that back up, that I realized I can do this in any moment.

[00:16:45.15] - Bhavesh

Yeah, right, right.

[00:16:46.20] - Matt

As long as I’m honest with myself about where I am the factor that is causing the lack of success.

Why the First Glass Ceiling Is Internal

[00:16:54.18] - Bhavesh

Yes. And you know, Matt, I want to get into that a little bit because this is a tremendous example of self-awareness. And you are in your 20s, early 20s, and you hit upon this. It is probably because of your upbringing, background, somehow. But a lot of us don’t have that kind of self-awareness. If we do have it, it is kind of over— it’s covered up by our ego, right? And you talked about this a little bit, right? This, you know, you have a mentor who is saying, don’t do this or do this, and we don’t hear it. We don’t listen. And then you talked about the glass ceiling. Glass ceiling is something that you see through, but it is transparent. It’s clear, but you feel the pain. Because you’re hitting against it. And that’s kind of what you’re describing there.

[00:17:49.23] - Matt

Absolutely.

[00:17:50.10] - Bhavesh

And you said that you had to break yourself down. Is that a term you used, that you had to kind of break yourself?

[00:17:58.02] - Matt

I was talking about more about if the reason I call it a great glass ceiling is if you want to get past, you got to break that glass ceiling. In a way, you have to break yourself. I don’t know, I’m not saying that you have— oh, okay. Some people would hear break yourself as a very, uh, negative way about it, right? Think about it more as like in a change. Be honest with yourself and figure out where you need to change and, and, and, and, and break those comfort those pieces of comfort, because really what, what makes people avoid change is their fear of messing up what is comfortable to them. That’s, that’s the, that’s the most hard part of change management because you know what can be comfortable to somebody doesn’t have to be positive to them, but it’s what they know.

[00:18:50.13] - Bhavesh

That is a profound statement. It, you know, something that is uncomfortable doesn’t have to be positive to you, but it is something that you have to know. That this is where my comfort is.

[00:19:07.02] - Matt

And why is it there? And I have to break through.

[00:19:08.22] - Bhavesh

And why is it there?

[00:19:10.11] - Matt

Why is my comfort live there? What is my fear that’s holding me back?

[00:19:15.12] - Bhavesh

Yes. And what was it for you, Matt?

[00:19:18.11] - Matt

Oh, I mean, in this moment, in that moment, I think my fear was doing it differently than what I was, than what was the norm. And, you know, and it is actually one of the greatest lessons that I learned is like, and I’ve taken it throughout, throughout my entire career since then. It’s like, no, being different is what actually propels us as, as entrepreneurs. If we’re just the same as everybody else, What are we bringing to the table?

[00:19:44.14] - Bhavesh

Exactly.

[00:19:45.06] - Matt

But if we can show how we’re different, how we differentiate the business, the message, the person, yeah, the story, the whatever, then there’s something to hold on to. Now, being different doesn’t mean that everybody’s going to agree with it, but it means that you have something that resonates with you and makes you unique.

[00:20:06.06] - Bhavesh

Yes.

[00:20:06.14] - Matt

And I have a, I have a, a real belief Everybody in this world, every individual in this world does have a unique, something very unique about themselves. And if they can figure out that thing that’s unique, they can propel to the stars. But most people find it very hard to identify their unique thing.

[00:20:32.03] - Bhavesh

Sure, sure. Yeah.

The Leadership Advantage of Embracing Failure and Imposter Syndrome

[00:20:34.07]

And, and identifying the unique thing, there is also the other part of it. So once you identify it, you had to execute from that, meaning that you had to build systems and structure. We’re not even talking organizational structures or hiring people, just ways of doing things where you actually acting from that new level or your difference or what your gift may be. You know, I’m putting words in your mouth, but you know, your strengths, right? And you operating from that. And then that becomes another comfort zone issue where, you know, so, and because something doesn’t work or you, something falls apart and then you kind of go back into your comfort cocoon, if you will, and you begin to doubt yourself and things like that, right?

[00:21:19.01] - Matt

Absolutely.

[00:21:19.13] - Bhavesh

Is that a part of that?

[00:21:20.13] - Matt

Absolutely. Look, imposter syndrome. I’ll say this. I assume everybody knows what imposter syndrome is, but it’s when you feel like you’re not able or capable to be in the position that you’re in. Okay. But I assume most people know this.

[00:21:38.07] - Bhavesh

Sure.

[00:21:38.11] - Matt

I think as an entrepreneur, and maybe not even just as an entrepreneur, but as somebody that’s trying to grow and scale themselves individually, whether a business owner or somebody that’s trying to be an executive within a big corporation or whatever that looks like, if you haven’t experienced or don’t experience imposter syndrome at some point, you’re not trying in a way. Um, yes, yes. Because I can tell you that I’ve experienced that, and that’s part of this glass ceiling conversation. I’ve experienced this. Numerous times throughout my career. I’ve experienced it recently, and I expect to experience it again.

[00:22:14.21] - Bhavesh

Yeah, yeah. And what was your— I think you might have said it, but I want to kind of anchor this. What was your strength that you had identified that is unique to you, your unique talent?

[00:22:26.11] - Matt

You know, you may not like this answer. I don’t know.

[00:22:31.18] - Bhavesh

That’s okay.

[00:22:32.09] - Matt

I don’t. At— I don’t completely know because I think that, yeah, sometimes it’s subconscious to the individual.

[00:22:39.14] - Bhavesh

Yes.

[00:22:40.05] - Matt

Um, my guess is that it’s a willingness to fail.

[00:22:47.11] - Bhavesh

Yes. Yeah, yeah, right.

[00:22:49.22] - Matt

So I don’t think—

[00:22:50.09] - Bhavesh

and that’s huge.

[00:22:51.02] - Matt

Yeah. I don’t think I’m the smartest person out there. I don’t think that I’m the most capable person out there, but I think I’m somebody that has always said Failure’s possible. Let’s get close and see if we can get— if we can navigate through it. Because again, if you’re not getting close to failure at times, you’re not pushing yourself. And I’ve never been— I’ve never been too afraid of that to try to push forward. Now, if you fast forward my story, I went to South Africa. Yeah, on a— maybe not a whim, but I heard a company was looking to sell I went there to negotiate a letter of intent and I had no idea how I was gonna pay for the company, quite frankly.

[00:23:34.06] - Bhavesh

Right.

[00:23:35.01] - Matt

Hmm. I signed a letter of intent, had to come back to the States and start pondering, how am I gonna get the money for this? And it wasn’t so much of like, you know, some people hear that and they think like that ego and everything else. And for me it was, right, there’s not a failure that I, I just have to figure out what, what my levers are to make this happen. But I also knew that by doing this, if that failure was a real option.

[00:24:02.03] - Bhavesh

Yeah.

[00:24:02.23] - Matt

But I was okay with it because I said the reward is so high that the risk is worth it. And I always told my wife, my wife has always been super supportive of what I did. And I said, look, if this fails, we’re not gonna be bankrupt as a family. We’re going to be okay. It’s just going to be very, very painful.

[00:24:23.16] - Bhavesh

Yeah, yeah, yeah.

Taking the Biggest Risk of His Career

[00:24:25.10]

And you’re hitting on something while we’re talking about the South Africa angle. You’re hitting on something important that we need to know what our worst-case scenario is, even as we venture out and do something that is kind of daring, right? So, you know, there’s safety net. There’s this idea of removing the safety net. But if you have a family and if you have family to feed and, you know, you have people who depend on you, There’s always a, you know, a 22-year-old can do things that a 35-year-old cannot do, you know, when they have, when they have a couple of kids.

[00:25:01.22] - Matt

Let’s be clear, when I acquired the companies of South Africa, when I went there and signed that LOI, I had a child. So let’s make sure that it’s clear that I’ve been on the, I don’t have any dependence to worry about. And on the other side being like, okay, I’m risking a lot more than I have in the past.

[00:25:27.09] - Bhavesh

Absolutely, yes. And the thing is that this risk-averseness, if you can call that, to the person who is in that, playing the role of being what the world sees as the risk-averse person, right? Or the risky person, or, you know, to that person, it doesn’t look like that or feel like that. Meaning that if you are a risk taker, you’re just doing the things that make sense to you. And you are, you know, right? The world may see it as a risky move, but— So is that true?

[00:26:04.00] - Matt

I think that’s the fallacy. I think that’s what people see from the outside.

[00:26:08.02] - Bhavesh

Yeah.

[00:26:08.16] - Matt

I remember signing the paperwork for the bank. To get the money to buy the South Africa companies. And I was driving home the same house that I have today.

[00:26:19.18] - Bhavesh

Right.

[00:26:22.02] - Matt

And I think I had a full-on anxiety attack in that car being like, I just signed this. I have just committed this. I never took on debt, you know, before I did the first acquisition before South Africa. And in the acquisition in South Africa, I had spent almost 15 years of my business career, being able to build without ever taking anybody else’s money besides my parents. And I did this and I remember I was like, am I having a heart attack right now? No, I was just, I was, I was in a moment of anxiety. But then again, luckily I’ve always had a degree of ability to think things through. I like the, I like Cookie Monster. You know, stop and think it through. Uh, yeah, I think is Cookie Monster’s, uh, favorite saying, or at least when I was growing up. Um, and calm down pretty quickly. But I do remember that and just being like, holy moly, what did I just sign up for? Um, yeah. And, uh, and, and I tell people to this day, I was like, I had no idea what I signed up for. Like, I went from being this company here in the U.S., local company, 30 people, to buying a company in another country, and I’ve never dealt with anything international, never dealt with anything.

[00:27:42.18]

And it has been such a learning experience. It’s been not even 4 years, and what I learned every day shocks me. It is. And, and it’s, and it’s amazing. Like, at the same time, I have that stress, but I have this like real appreciation for the experiences that I have been able to take on because of this journey. And that’s what I think is so amazing about it. And so I know we’ve gotten a little bit away from glass ceilings in this conversation.

[00:28:15.07] - Bhavesh

I think we kind of, yeah.

The Beliefs That Limit Business Growth

[00:28:17.07]

And I think we’re still talking about that a little bit because you broke through a comfort zone here. You know, you’re just describing the inner experience of someone who has broken through a comfort zone in a way. That anxiety attack is probably, I’m assuming that maybe coming from the comfort zone, having broken through a comfort zone, something you didn’t do before. Never taken a debt before. Now I’m taking a debt to to do an acquisition not in United States but in South Africa, different culture, different everything, right? And different laws, I’m assuming, different logistics. And you made an acquisition, you got to make this work now. And then the anxiety attack, I would believe that that’s kind of outside the comfort zone for you.

[00:28:55.21] - Matt

Absolutely. So I don’t want to harp too much on that. It was a brief moment, you know, but sure, sure. I’m a pretty transparent person. If people ask me, you know, how I feel, you know, the emotional toll that things take on, you know, I, I like to be forthright because I think part of learning, and one of the things that has been really valuable for me and the mentors that I’ve had and so forth, is that honesty around how things have impacted them. And so I’ve always been somebody that’s been transparent about how things have impacted me. But there were so many moments in business before ever getting into Opportunity South Africa that made me have to rethink, change hit those glass ceilings. And it’s, uh, it’s been this amazing journey for me that’s helped me to grow, has also highlighted some moments of, of true failure for myself, whether that’s small moments of how I interacted with people or how I manage people, or larger interactions of, of decision-making that I did and, and how that, uh, impacted our bottom line, top line, and so forth. Yeah, entrepreneurship is not perfect, and we go into this, and I think everybody wants to tell a story about how great they are, and I want to tell a story about the true journey of what it is to try to be great, because I don’t— I’m not great, but I continue to strive to try to get there and to, and, and to set myself separately and set really my company, because another real And I’m going on a tangent here.

[00:30:29.13]

Another real thought process of mine is like, I’m nothing without the people that are around me. My biggest assets are the people that I have. There’s 119— if we use 120 or have— there’s 119 individuals that are with me. What happens if I don’t have them? Nothing.

[00:30:49.03] - Bhavesh

Yeah. So Matt, let’s go back to the idea of glass. And I want to come to that because that’s powerful. I think you’re starting to open up this other whole new dimension about not just me but my people, right? Or the people, right? People who work within an organization. The $600,000 class saving, right? So you broke through and you moved beyond that. Was there a change of belief system that you put in place? So I just kind of want to go into that transition a little bit. You had also talked about that in that South Africa transaction where, you know, you do something for the first time, it’s out of the comfort zone. It has emotional, sensory reactions within the body. And then you move beyond that. And then maybe, maybe that becomes a new belief system. It’s a new way of operating. And then hopefully that becomes your next floor, maybe. The ceiling and floor, right? So what was the new belief system that allowed you to get beyond that $600,000?

[00:31:53.23] - Matt

Before I go there, I want to give a shout out. So I started this company with my best friend, uh, a guy by the name of Ryan Waterman. Um, we went to high school together, uh, we were both in a band, we both played French horns, um, and, uh, we decided to start this company together. And so when, when we had that $1,500 and we went on to Craigslist, it was me and him doing this, uh, together. And when we hit the glass ceiling, it was us together deciding. Like, he was on— he would come on the same path of $60,000 and he would have, um, you know, he had to sign off on anything we did. And so, yeah, he’s a big reason why we continued and broke through these glass ceilings. So I want to be very clear about that, you know, there’s never just one individual that is, is driving this. Um, so we hit that $600,000, we decided to get rid of the offices, we bring it down to almost $300,000 of revenue. All right, and we really shift our business model at that point.

[00:32:56.17] - Bhavesh

Yeah.

[00:32:57.06] - Matt

Okay, we go into a completely virtual— I mentioned this earlier— a completely virtual model. And really what happened is, is that Ryan had his clients and staff that work with him, I had my clients, the staff that work with me, and we kind of operate as two different businesses within the same business.

[00:33:17.05] - Bhavesh

Um, sure.

[00:33:18.12] - Matt

But it worked in that moment well because we could we could sort of drive the overall goal and, you know, our individual goals of where we wanted to take it.

[00:33:30.11] - Bhavesh

Sure.

[00:33:31.16] - Matt

And so we spent the next 3 years building it back up, but we were able to get to $1.2 million, we were able to get to $2 million, we were able to get to $2.4 million. That happened, uh, over about the next 6-ish years. We hit about $2.4 million, I think it was late 2015 or early 2016, and that was really our next glass ceiling.

[00:33:54.11] - Bhavesh

Yeah, yeah.

[00:33:55.16] - Matt

Um, and from my, my perspective, it was— and I see this with a lot of, a lot of businesses— that 1.2 to 2.4, but really that 1.2, you go from being this disorganized business that can kind of be everything, wear every hat that you need to wear, to really having to create process and infrastructure and so forth. Um, and we really struggled with that. I’m a— yeah, I’m an idea guy. I’m a vision guy. I understand what processes need to go in. I understand systems. I can get things to like 40, 50, 60%, but then I get bored. And I knew, I’ve always known that I needed the right infrastructure, the right people around me to, uh, to really help through that process, to be sure, to be the yin to my yang, if you want to put it that way, but to complement us. So Yeah, I don’t know if, if you’ve ever, uh, dealt with or, or went down the path of the idea of behavioral profiling within the business workforce.

[00:34:59.08] - Bhavesh

And a little bit, yeah, yeah, yeah. All the analysis, yeah, yeah, yeah.

[00:35:02.17] - Matt

This can—

[00:35:03.10] - Bhavesh

Myers-Briggs and all the rest of it.

[00:35:05.10] - Matt

We used a product called Predictive Index, which was EEOC compliant, things of that nature, to really— and I got trained in it— to really understand how different people operate and the why they operate and so forth. And it really, at that time, helped me understand what my strengths and weaknesses were, but also what other people’s strengths and differences in how you marry people together to, to have a balanced, uh, team.

[00:35:27.10] - Bhavesh

Right.

[00:35:27.14] - Matt

Side note on that, but, um, we hit this glass ceiling because both myself and Ryan were more your visionary strategy people. We weren’t really a yin to a yang. Um, sure. And, uh, and so I think that, that really stifled us from a growth perspective is because the two of us were kind of similar in a lot of ways. In fact, I think we both took the behavioral assessment and we both were pretty much very similar in our behavioral profile.

[00:35:57.21] - Bhavesh

Wow.

[00:35:58.03] - Matt

Yeah. But if we—

[00:35:59.23] - Bhavesh

if I want to get to that later, but yeah, that’s great because you can do a podcast just on that.

[00:36:05.18] - Matt

Absolutely.

[00:36:06.19] - Bhavesh

1-hour conversation. But sorry, go ahead.

[00:36:08.13] - Matt

Absolutely. Um, in a rewind, uh, in mid to late 2007, my cousin, who is now my current business partner, come into the business. Um, and, uh, he, he really learned and grew up within the, in the company. Um, and through these, uh, this growth and everything else, he became my right-hand man when it came to executing on, on the clients. I had my clients, but he was like my manager, so oversaw the team, everything else. I went and handled the clients, things like that. And we were a really good match in our kind of personality, our profiles, our our focus and so forth. And, uh, and so we grew a team together. And, uh, I think unfortunately Ryan never found that person that really balanced for him, right?

[00:37:02.12] - Bhavesh

Sure.

[00:37:03.15] - Matt

So we get to 2017, and, uh, I would say, you know, Ryan had kids a lot earlier than I did. I’m not so sure that, uh, I would have succeeded if I had the same responsibilities at the same time. Because, yeah, because it was a lot. And it was determined that, you know, he, he decided that he wanted to, uh, to find a different path.

[00:37:31.10] - Bhavesh

Sure.

[00:37:32.17] - Matt

And so he exited the business, um, and I won’t get into the details of like the terms and everything else, but he exited the business. And at the same time, Joseph, my current business partner, my cousin, Yeah, came in as an owner to the business. Yes. And, uh, in that moment, immediately there’s two major decisions. And this is— that— this goes back to glass ceilings. I had a point here. Yeah, just— I’m just navigating. I know you did. Navigating through the story.

[00:38:02.11] - Bhavesh

Yeah.

[00:38:03.00] - Matt

Um, is we, we had really two major decisions that impacted the rest of our, uh, our future to today.

[00:38:14.23] - Bhavesh

Sure. Yeah.

[00:38:16.00] - Matt

One, uh, was we’re not gonna have me have my own clients and Joseph has his own clients as me and Ryan did. I’m gonna handle strategy, vision, kind of operations from an internal perspective.

[00:38:31.00] - Bhavesh

Sure.

[00:38:31.08] - Matt

He’s gonna handle client services. So I’m, I’m growth.

[00:38:34.17] - Bhavesh

Yeah.

[00:38:35.03] - Matt

Yeah. I’m sales.

[00:38:35.21] - Bhavesh

Yes.

[00:38:36.10] - Matt

He’s execution.

[00:38:37.01] - Bhavesh

Yeah.

[00:38:37.16] - Matt

So that was the first thing, because what we did then is we looked at the client base and we said, well, we have different rates for different clients. We, we, we made uniformity around rates, uniformity around delivery, uniformity around— Joseph did that. Um, yeah, the number— the, the second decision is we said QuickBooks is today. We need to find that product of tomorrow, right? And so that’s when we decided to invest in the idea of being Sage Intact partners, right?

[00:39:14.01] - Bhavesh

So QuickBooks and Sage, for our audience, I think there are two accounting software systems basically.

[00:39:19.16] - Matt

So QuickBooks is what I would call a small business solution built for small businesses, has the number one market share in the US. Um, is a great product for those, uh, organizations. But even back then in 2018 when we made this decision, in my opinion, where technology— what the future technology was going to do was going to create what we did or turn what we did into really, um, transactional type services and not value-based services. And that the smallest clients, um, and that we, we serviced a lot, the smallest clients really looked at us as a cost center, as like a, a have-to-have to be compliant, but not a value add where they wanted to really invest money into. And it was our thought that like if we could find a next higher up product, so Sage Intact, um, I looked at Sage Intact, uh, Microsoft Dynamics and NetSuite at that time, right? And made a decision for Sage Intact. Um, as a, what we call an ERP, an enterprise resource planning software. But really what you would say is a, a accounting solution for upper SMB, small, uh, small business, such as small business and midsize, upper SMs and the MBS.

[00:40:42.23] - Bhavesh

Sure, sure. Yes.

[00:40:44.07] - Matt

And, uh, and that decision, we had no idea at the time, uh, is the number one decision that has probably cascaded into everything else that’s happened. Yeah, because the companies that we bought in South Africa, just to, to wrap this all up, were Sage, Intact Partners, and Africa Middle East, right? So if we think about this now, so the glass ceiling there in 2017 was a realization that the business model and the way that we had it and the way that the partners were structured.

[00:41:21.03] - Bhavesh

Yeah.

[00:41:21.19] - Matt

Was not scalable. Now, right, I’m, I’m going to tell you something I don’t tell a lot of people. At that time, before my, uh, before Ryan, uh, left the business, I was working like 20 hours a week. I was making good money.

[00:41:40.15] - Bhavesh

Yeah.

[00:41:41.02] - Matt

I was streaming shows every day. I’d work my 4 hours. I’d My wife thought I was lazy.

[00:41:50.18] - Bhavesh

A guy who works 20 hours a day, a week.

[00:41:53.14] - Matt

No, a week, 20 hours a week.

[00:41:54.23] - Bhavesh

Oh, it’s 20 hours a week. Okay.

[00:41:56.09] - Matt

Yeah. No, no, I was, I was not working much. I was making good money. I was getting really bored. Yeah. I was getting really bored.

When Founders Must Become Different Leaders

[00:42:05.04] - Bhavesh

And I want to talk about that a little bit because that’s, that’s a tremendous accomplishment for a business leader. And just, I, I, when you first said it, I didn’t register it. I thought it was 20 hours a day. No, 20 hours a week.

[00:42:18.18] - Matt

Well, trust me, I haven’t seen that since. So like, it might have been a, a tremendous, uh, accomplishment at the time, but since then, now I’m like, if I don’t work 20 hours a week, I’m, I’m doing good. Um, I am, I am, I’m working more than, uh, is, uh, and so is Joseph, working way more than we should. But again, We’re in this growth mode. We talk about how I perceive us as really in a startup mode then, right? Even though I say I’ve been in business for 19 years, my 20th anniversary is October this year. But really, right, my current business, not the EIN or anything else like that, but the current structure of business is less than 4 years old. I’m in true startup mode. And we can talk about that because that’s also about reinventing yourself in those moments.

[00:43:05.10] - Bhavesh

Yeah, yeah. And I want to say something else that I kind of picked up on, which is that you’re saying that, so before and after, you know, working 20 hours a week, you got to that. And I call that accomplishment because a lot of leaders can’t get there or won’t get there, you know, for similar reason that you discovered for yourself that 20 hours a week, boring, right? I hate it. Because I talk to founders and this is, they love being in the middle of the business and driving and running it, right? And when they— so there’s this tug of war between stepping back and letting the organization go on its own and then stepping back in and running the show, right? So any insights on that, right? It seems like there is an internal growth here also. And as you broke through this glass ceiling, you kind of broke something deep inside you.

[00:44:01.21] - Matt

So take that concept and now do it in kind of microcosms. What I mean by that is, as an entrepreneur, at least one that starts in the attic of a house and only has himself and a business partner, and then has 2 employees and then 4 employees and then 6 employees, you’ve worn every hat. Uh, and we have to be good at letting things go. Now, I’ve been accused a lot of not letting things go, and my argument is, if I didn’t let them go, maybe you should self-reflect. Because for those people that show me that I can let go, I hand it. And the point that I’m always looking at is I’m looking at gaps within a company, and I’m hiring those gaps so it doesn’t fall on me. And the answer is that if I can find opportunity to eliminate myself out of the situation and put it on somebody that can do it better.

[00:45:00.10] - Bhavesh

Awesome.

[00:45:00.19] - Matt

My problem is that when I see somebody not doing it at a standard that I expect, then I insert myself back into it and that can be a challenge. Now, yes, I’ll also say this. Many business owners take take my path as an example, go and make money, and then elevate how their standard of living, and have to continue to make money and elevate their standard of living and continue to have to make money. And I made a very conscious decision, and so did Joseph, by the way. We were both, um, again, so we’re cousins. My mother, his father are siblings. I think we come from a very grounded upbringing, uh, you know, of not really needing a lot or, or needing flashy things. It’s like, we have never stopped to reinvest into the business and put our own income off to the side because we think that this is how it’s going to propel to get us to where we want to go. And, and that’s another thing of like, that, that’s a different part of glass ceilings, but a lot of entrepreneurs, they’re chasing the money so much that they don’t give themselves the ability to truly scale.

[00:46:12.20] - Bhavesh

Ah, yes. Yeah, yeah, absolutely. And that’s a great point, right? So, and so was this the last glass ceiling or is there one after this?

[00:46:25.10] - Matt

Let’s see. So 2018 happens. It takes a year to get enabled into Sage Intacct. That’s how it does. And so we don’t start selling it until 2019. Um, sure, but we’re at that $2.4, $2.8. We’re having a really hard time getting into $3 million.

[00:46:50.12] - Bhavesh

Yeah, yeah.

[00:46:52.04] - Matt

And what I realized, and it wasn’t our glass ceiling, is, yeah, we were big enough that we needed real systems and real infrastructure, but we didn’t have enough money to truly invest in real systems and real infrastructure. And so that’s when I and Joseph with me shifted into the concept of an acquisition strategy. Okay. And saying, yeah, if we can take lending, if we can acquire, we can grow faster and we can reinvest that. And I have to get— and, you know, through this process I had established business dealings with some other people here locally, and they— right, that person individually Um, which I’m not going to call out in this, in this conversation. I’m not sure if they would want me to, but that individual really sparked my interest in the acquisition component and, and, and drove, I think, a, uh, and a— what’s the right word— uh, drove this, this passion for it that I never had before, never really considered before.. And so, right, even though my business dealings with that individual didn’t transpire for a long term, I think there was a pretty big impact into what my now, my now current place, but my future at that time was.

[00:48:21.15]

And so we sort of said, hey, we don’t have this infrastructure. Let’s try to make this infrastructure. Let’s go and start this acquisition. So we did our first acquisition. In 2021-ish, I think, right? Like 2018, we become Sage Intacct partners. We don’t finish enablement until, uh, until 2019. 2019, we start to go in and we go into this. We get our first client to migrate into Intacct.

[00:48:49.22] - Bhavesh

Sure.

[00:48:50.07] - Matt

2020 happens with COVID Yeah. So now everything changes in what we’re doing. We come out of COVID in 20 21, and we start looking at acquisitions at that point. And we make our first acquisition here in Maryland. And that was a big shift from a— from being willing to take on debt and also learning how you incorporate people into a business and how do you communicate with a new client set that is used to a different business owner, things of that nature. Sure.

[00:49:23.09] - Bhavesh

Absolutely. And Matt, you were at about 120 people, you said, right?

[00:49:29.11] - Matt

Right now. Yeah.

[00:49:31.06] - Bhavesh

And I don’t know if you, if you’re okay disclosing the revenue at this point, the ballpark.

[00:49:36.21] - Matt

Yeah, I’m happy to, but I think that, you know, a disclaimer should come, come with it. So, okay, if you look at what we do in Africa, Middle East, in our South Africa office, we— this isn’t just like a hub to support the U.S. So a lot of organizations will go and hire cheaper labor to, to produce revenue in North America.

[00:50:00.10] - Bhavesh

Sure.

[00:50:00.15] - Matt

It’s not what we did, right? We hired, uh, we acquired businesses in South Africa that were Sage partners, and that had— and we had to maintain the Sage partnership there and the revenue. And if you look at, uh, the cost of living, but the also kind of the rates and everything else, it’s anywhere between 50% to a third of what you see in the U.S. So what we charge for implementations in South Africa is 50% to a third of what we charge here in the US. So the reason I, I, I make this, uh, this clarification is because when I say that we’re doing about $10 million in revenue, you have to understand that if it was all US-based with 120 people, we’d probably be closer to $15 to $18 million, uh, in, in what we’re doing. If you look at the pure statistics of it.

[00:50:53.18] - Bhavesh

Yes. Yeah.

Choosing the Right Business Partners

[00:50:54.14]

So at this point, do you see any glass ceiling on the horizon? And if you could predict, and we’re in a prediction game now, you know how that goes, what do you think it might be?

[00:51:11.10] - Matt

So what I would say is one of the reasons I call it a glass ceiling is because you can’t see it until you run into it.

[00:51:18.17] - Bhavesh

Aha. Yes.

[00:51:19.07] - Matt

Okay. Yeah.

[00:51:20.12] - Bhavesh

Yeah.

[00:51:20.16] - Matt

Um, what could it be? There’s so many possibilities. There’s so many possibilities. I don’t want to, I don’t want to be this AI guy, but what I’m going to say is that AI is going to transform the way we do business.

[00:51:38.14] - Bhavesh

Yeah.

[00:51:39.03] - Matt

And it is going to create or is going to require a degree of investment. And that next glass ceiling could be, do us— and I’m doing more not specifically to Tide Co., to my organization, but to the wider, you know, businesses that are kind of in my size bracket— is like, do we have the ability to invest in a way that’s competitive? And yeah, if we don’t, are we creative enough to understand how we circumvent that, to break through that glass ceiling? So that’s one piece. My simple answer is I’m already thinking and preparing about that right now for our organization. We already invest in a team that does AI deployment components, but we’re doing it much, much differently than other organizations. I think a lot of other organizations are all talking about what they’re deploying to their client base. And what we’re doing is spending a lot of time deploying internally and understanding what, what is possible and also looking at what is being mainstreamed because I think It’s, it’s such a fast-paced thing that you could get— you, you could spend a lot of money investing in something that’s going to be solved by somebody else really quickly.

[00:52:49.08]

And you want to, you want to be careful there. There’s that component of it. Um, you know, I’m challenged every day as a CEO. I think that, um, what I can tell you is that my imposter syndrome will start to creep back in as we grow and the team grows more, and I’m continued to ask to make decisions that I’m not educated in making, and so I have to spend a lot of time making. So those will be some of those moments in which we have to ask, you know, there’ll be questions about, am I the right person? And that’ll be its own glass ceiling. And at some point, there’s a chance that I don’t end up at the answer that yes, I’m the right person. There is that chance. Now I have a, I’m a pretty confident individual. So I haven’t gotten there yet, but I always think about that. It’s like, is there going to be this moment in which I decide that I’m not the right person to lead the charge? And I sure hope I don’t get there, but it’s always in the back of my mind.

[00:53:58.16] - Bhavesh

Yeah. And I’m telling you, I talk to a lot of founders, a lot of leaders, and this level of transparency and being able to talk and this level of self-awareness, I don’t see it. Very often. And most of the people who come on the podcast, they have that. That’s why they’re on the podcast, right? But there’s a lot of folks that I talk to who can’t bring it, right? So I really appreciate that, the level of depth you go into describing your inner landscape and how you navigate through these ideas, right? From comfort zone, these are difficult things to talk about, especially for a leader. You’ve got 120 people who, you know, whose payrolls you’re signing, right? Figuratively, at least, right? Probably not personally. But so having said that, one thing that I want to talk about, we can make a podcast just on this one. Maybe this is our next episode that we might do sometime in future, but about the people, right? As you are hitting your glass ceiling, the entire organization is going through the breaking of that glass ceiling. So there might be, you know, a collection of people who might be facing that glass ceiling, but maybe cannot verbalize it or cannot articulate it, right?

[00:55:18.05]

But the pain is there, right? They cannot see it. Any insights on how a leader like yourself, a founder like yourself, can basically keep their eyes and ears open, and the feelers out as they work with people and talk to people, how to kind of spot the next Glass Ceiling, if that’s— if there’s even such a thing.

[00:55:37.04] - Matt

I, I don’t know you can spot it. Well, I can tell you about the team that you have.

[00:55:41.16] - Bhavesh

Yeah.

[00:55:42.07] - Matt

Um, is there’s certain people that will be on that path with you.

[00:55:50.05] - Bhavesh

Yeah.

[00:55:50.17] - Matt

And there’s certain people that will, will decide to get off of that path with you. And it’s not always evident who those people are going to be.

[00:56:01.14] - Bhavesh

Right. Right.

[00:56:03.19] - Matt

But it’s always important to me to respect their decision of when it’s right and wrong for them.

[00:56:13.19] - Bhavesh

Yeah. Yeah.

[00:56:15.00] - Matt

That it’s not personal unless you make it personal in the sense of like, right. Uh, everybody has their own values, their own culture, and those values in that internal culture evolve over time. And that’s part of human nature. And as an owner, if you can have the grace to allow those people to experience that for themselves and be happy for their decisions, uh, whether or not that’s a decision that you’d like. Um, I think that goes a long way in trust and being able to navigate through, uh, through the hard and good times, uh, of, uh, of business. Because it’s, it’s never all fun and it’s never all bad. Uh, yes. And look, I’ve had, I’ve had people leave and come back, uh, and be successful coming back. I’ve had people leave and come back and be unsuccessful coming back. I’ve had people that I thought would be around forever that are not here anymore. And I’ve had people that I thought weren’t going to last that are still here. Now, one thing that I say to everybody is, if I hire somebody— it’s not high, it’s not I— but if, if the company hires somebody, we will take the time and investment to try to make them work, because we— there’s a reason why we believed in bringing them in in the first place.

[00:57:45.10]

I’m not so sure that that completely answered your question. Um, I don’t know that it’s about identifying the glass ceilings, but sometimes the way that we approach our, our life and our thought process, uh, allows us to navigate those moments that are the glass ceilings where we, we lose that person that we feel like, oh my God, I can’t handle it. But if we take a step back and say, yes, I can, or, um, or those great moments in which we believe that we hired the great, the best person and now we’re going to achieve it. But those are, those are the highs and lows always come back to the middle, you know, as you’re going through it and be true to who you are.

[00:58:23.12] - Bhavesh

Be true to who you are, right? Yeah, you just kind of encapsulated that right there, right? And, you know, I think what you’re saying is, you know, don’t be forcing scenarios where there is no need to, you know, just let things evolve and then work with them as they do. Yep, absolutely.

How Leadership Changes Over Time

[00:58:41.15]

So Matt, the 22-year-old Matt, right?

[00:58:48.00] - Matt

I don’t remember him.

[00:58:48.17] - Bhavesh

And Matt, right? And Matt today. What do you think is the one thing that you can point out that is the biggest shift in how you are today or how you present yourself or how you see yourself inside?

[00:59:12.18] - Matt

My confidence has grown tremendously, and I’m not talking about the façade of confidence.

[00:59:19.20] - Bhavesh

Yeah, you’re right.

[00:59:21.11] - Matt

Um, I was bullied pretty, pretty bad in, in school, in grade school and so forth, and I lost a lot of confidence through that process, and I had to have a façade of confidence for a time period. And I think, yeah, The 22-year-old me had more of a façade of confidence than the today me, that I’m very comfortable in who I am and very confident in who I am. And I think that’s probably the biggest change that I see now. Um, what you should do is, is beg my team to have somebody like my business partner who’s known me since a kid come on and give his perspective, cuz he probably would have a much different perspective on that than I do.

[01:00:06.07] - Bhavesh

Yeah, yeah, yeah. You speak of confidence and the kind of confidence, and you actually qualifying the word confidence, right? Not the confidence that comes from, for example, it may come off sounding like arrogance, right? But the confidence that you’re talking about, it comes across right here in this conversation, is the confidence that comes from humility. It’s a very strange thing, right? That real vulnerable, you may not call it that, but you are basically willing to be vulnerable. And that is the real strength. And that’s the real confidence. That’s what I’m seeing, right? When I hear your story. So—

[01:00:42.10] - Matt

And if I could, if I had a better word, I think I have a decent vocabulary, but not as great as I wish I would. Maybe confidence isn’t the word, but it is a comfort in yourself. A comfort in who you are.

[01:00:59.18] - Bhavesh

Yeah.

[01:01:00.15] - Matt

And, uh, I think that’s really important for— it’s not just a success of an entrepreneur, but just as we get older, as we are asked to be parents, as we’re asked to be leaders, as we’re asked to, uh, to evolve and be the next generation, you know, you know.

[01:01:22.14] - Bhavesh

Sure. So Yeah, absolutely.

Staying Grounded During Rapid Growth

[01:01:26.04]

And Matt, you deal with change all the time. And we’re not just talking about the arc. The entire arc is about change. We talked about breaking through the glass ceilings, but also just day-to-day change. And what’s on the horizon? We got this AI and there’s geopolitical issues that we’re dealing with today. And the whole world seems like it’s a very different place. And there’s a lot of a lot of flux out there, right? A lot of uncertainty. And someone like you in a leadership position like you, what do you do or where do you go to root yourself or ground yourself? It could be literally or metaphorically. Is there a place you go to kind of get in touch with— you’ve talked about being comfortable in yourself, right? The, the definition of confidence. How do you regain that if you ever stray away from that?

[01:02:22.09] - Matt

I don’t have a good answer. I don’t give myself enough time. Um, I’m, I am lucky and fortunate to, I think, have an innate ability to, to keep myself at a balance at times. Um, but at the same time, I probably actually, um, I’m thinking about a specific business coach right now who would say, yeah, you need to spend a little bit more time and, you know, self-reflection, maybe meditation and things of that nature. But that being said, um, I really like to focus on unity. I really— so one of our core values is better together. Um, and what we’re seeing from a geopolitical thing that, that hurts me the most is the amount of divisity.

[01:03:14.22] - Bhavesh

Yeah.

[01:03:15.04] - Matt

That is happening today. And that is one thing that when it comes to our organization, whether internal to ourself or external to those people that we collectively communicate to, is I want to drive a, uh, a culture of collaboration, togetherness, unification. And acceptance of difference of opinions. And, uh, and I think that helps us all stay grounded as individuals.

[01:03:47.15] - Bhavesh

Yeah, yeah, yeah. One of the things that I watch when leaders like yourselves do that just absolutely inspires me is when you try to kind of create a microcosm of the world that you would like to see. As in, you know, you’re in these leadership shoes and you have the opportunity to mold this organization in the way that you would want the world to be. And that’s exactly what you kind of said, right?

[01:04:12.16] - Matt

Maybe I’ll tell you something, you know, it’s the hardest thing as you grow and evolve as an organization is a reality that the culture has less and less to do with me as the individual and more and more to do with the greater organization. And so it almost comes, gets, it almost gets out of your own control, but you have to remember that you do have a major influence on it. And so like, yes, it’s, it’s not my world, it is, it is ours, uh, together. And we hope that we can bring people in that, that hold the same value structure, and we hope that we can exit those people that we don’t, uh, that don’t hold that same value structure, because it does, it it is hard to build and easy to destroy.

[01:05:08.04] - Bhavesh

Yeah. Yes. Yes, it is. Yeah. Yeah.

Breaking Through the Next Founder Glass Ceiling

[01:05:12.02]

And Matt, is there anything that we didn’t talk about today that you would like to give voice to? Anything that you wish I had asked about, but I didn’t get a chance to ask?

[01:05:25.02] - Matt

I think we’ve covered a lot. I mean, I may be a talker. I may have a lot to say and You know, there’s opportunities for other conversations and I’ve really enjoyed being here and having this conversation with you. I thought this was a very easy conversation to have. And so I appreciate that. But I don’t know if there’s anything today that sticks out as like I feel like has been left off.

[01:05:50.14] - Bhavesh

Absolutely great. Yeah. Thank you for the compliment. I think when someone says this was an easy conversation, that’s a tremendous compliment. To a guy like me. I know you have your own podcast. I’m sure that, you know, you will appreciate when someone says, oh, this was a very easy conversation, right? We got into it and just kind of flew. So thank you so much for being here and telling your story and telling it from the heart. You know, you truly are a transparent person, and I love the vulnerability and the humility that you show, even as you are this person who is required and commanded to lead. An organization. Those are very difficult priorities to balance, and you seem to be doing a really good job at it.

[01:06:29.23] - Matt

So we’ll see, you know.

[01:06:31.16] - Bhavesh

Yeah.

[01:06:32.12] - Matt

But I appreciate it. Thank you so much for having me.

[01:06:35.11] - Bhavesh

Sure. How do we get in touch with you? And who are the kinds of people that you would like to kind of reach out to you and connect with you?

[01:06:45.04] - Matt

So, you know, I think this type of podcast is not about drumming up business or finding people that want financial software. I’m the type of person that I’ve been very fortunate. I think I’ve said this a couple different times, but fortunate to have people in my life that help guide me and mentor and so forth. And so what I’d say is I’m always open to conversations and always open to, to being able to give back in the same, same way. Now I’m a busy individual, so I don’t know how many conversations I can take.. But I think when you find people that you’re connected to and there’s a mutual value in that relationship, it can, it can be so valuable that I hope maybe that a little bit, you know, from the business philosopher could come out.

[01:07:39.19] - Bhavesh

Absolutely right. And for our audience, reach out to Matt if you are looking for a mentor. Who you think could be useful to you.

[01:07:49.04] - Matt

Or maybe my next mentor.

[01:07:51.10] - Bhavesh

Or, yeah, yeah. Or someone who can point out the next glass ceiling that Matt hasn’t seen yet, right?

[01:07:57.16] - Matt

Please.

[01:07:58.23] - Bhavesh

There is so many. That’s the problem with it, right? There could be a thousand we can list, right?

[01:08:02.19] - Matt

Absolutely.

[01:08:04.04] - Bhavesh

Thank you so much, Matt. This was an incredible conversation. I really enjoyed it. And you were a great guest. And I’m sure that if and when our audience kind of plugs in and listens to that, and if they come this far, thank you so much for listening and watching. This was a great conversation. Thank you so much.

[01:08:27.05] - Matt

I enjoyed it. Thank you.

Get In Touch with Matt Lescault

For more insights on Founder Glass Ceiling and practical guidance on Matt’s approach to building and leading organizations, reach him via Linkedin or TydeCo website.

This article was created from the live video conversation on The Business Philosopher Within You podcast. The episode was published on YouTube under the title “Every Founder Has a Glass Ceiling. Most Never Break It.” The article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Matt above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Broaden Your Understanding

There is a reason for that.

Systems absolutely matter. But systems alone do not create self-sustaining organizations. You can document every major process in the business, install a proven operating framework, and still remain the bottleneck. You can have more structure, more clarity, and more efficiency, while the organization still depends on you emotionally, operationally, and structurally.

If the real goal is to build self-sustaining organizations, then the conversation has to go beyond process design. It has to move into how the organization thinks, how decisions are made, and whether people are being developed to exercise judgment rather than merely follow instructions.

Systems are valuable, necessary, and a revolutionary invention

It helps to start with clarity. This is not an argument against systems.

Without systems, businesses usually become chaotic. People rely on memory. Work gets done through improvisation. Problems get solved through heroics. Teams spend their days reacting, firefighting, and filling gaps.

Good systems solve real problems. They help businesses:

• Create consistency

• Reduce unnecessary decision making

• Transfer knowledge more effectively

• Improve onboarding

• Support quality control

• Coordinate work across teams

• Increase operational efficiency

• Scale with more predictability

This is why system-driven approaches have been so useful for so many companies. They bring order where there was confusion. They reduce friction. They make execution less dependent on memory and momentum.

But there is a subtle mistake many founders make. They assume that enough systems will eventually make the business independent of them.

That is where things break down.

Why founders still remain the bottleneck after installing systems

A business can be highly systemized and still revolve around the founder.

The founder becomes the person who interprets the systems, enforces the systems, handles the exceptions to the systems, and steps in whenever reality does not fit the documented process. They become the escalation point, the emotional stabilizer, and the final decision maker.

So the business may be more organized, but it is not truly independent.

This is the distinction that matters:

• Operational efficiency is not the same as organizational independence.

• Systems improve efficiency.

• Self-sustaining organizations require something deeper.

If that deeper layer is missing, the systems themselves can become dependent on the founder.

Why building systems often feels draining

There is also a more human reason founders resist system building.

At some level, many people sense that they are trying to pin down something that is constantly moving. A business is not a machine in the strict sense. It is a living human system. People evolve. Relationships shift. Customers change. Markets move. Priorities change. Context changes.

A documented process is a frozen moment. It captures what is true now, or what was true recently. But the business itself keeps moving.

That is why documentation can feel stale almost as soon as it is finished. It is not because systems are useless. It is because systems are static by nature, while organizations are alive by nature.

Once you see that clearly, the frustration makes more sense. You are not failing because you dislike discipline. You are feeling the tension between static structure and living reality.

The real shift: stop treating the business like a machine

When founders try to solve founder dependency with systems alone, they usually stay stuck because they are solving the wrong problem.

The issue is not simply a lack of documentation. The issue is that the organization has often been designed around dependency from the beginning.

The structure may train people to defer upward. The communication patterns may encourage escalation. The culture may reward caution more than judgment. The decision-making environment may leave people unsure what they are truly trusted to own.

So even when a founder wants to step back, the organization does not know how to function without them.

That is why building self-sustaining organizations requires a mental, psychological, and structural shift. The aim is not merely to create compliance. The aim is to develop an organization that can think, adapt, and act without constantly orbiting the founder.

Are your systems helping people think or preventing them from thinking?

This is one of the most important questions a founder can ask.

Most systems are built to create consistency, and consistency matters. But some systems quietly produce a side effect: they train people to stop thinking.

That is a serious problem.

People are hired because they can use judgment, solve problems, adapt to reality, and make decisions in changing conditions. In other words, they are hired for their natural intelligence.

Then many organizations hand those same people a process and signal, directly or indirectly, that deviation is unwelcome. The message becomes: follow the steps, do not interpret, do not think too much, and escalate anything unusual.

When that happens, natural intelligence gets constrained into something mechanical. The business begins treating human beings less like thinking contributors and more like programmed tools.

And once that pattern takes hold, every unusual case travels upward.

Eventually, it lands back on the founder’s desk.

Constraints are not the enemy

It is important not to overcorrect here. The answer is not to eliminate structure.

Every meaningful form of work operates within constraints. A painter works within the boundaries of a canvas. A musician works through an instrument. A sculptor works with the resistance of stone. Constraints are often what make creativity possible.

The issue is not whether there should be constraints.

The issue is whether the constraints in your business are the right ones.

Healthy systems create boundaries that support good thinking. Unhealthy systems replace thinking altogether.

If your systems help people reason better, decide better, and coordinate better, they strengthen the organization. If they eliminate judgment, they increase dependence.

Founder dependency is structural, not just personal

Many conversations about founder dependency focus almost entirely on the founder’s psychology. That matters, but it is not enough.

Yes, founders often identify deeply with the business. The company can become an extension of the self. Letting go can feel uncomfortable, threatening, or disorienting.

But even when a founder sincerely wants to release control, the organization may still be unable to operate independently.

Why?

Because dependency is often built into the architecture of the organization itself.

It shows up in:

• Who is allowed to make decisions

• How exceptions are handled

• What gets escalated and why

• How much context people are given

• Whether people feel trusted to interpret principles

• How confidence and judgment are developed over time

This means the solution is not merely better therapy for the founder, and it is not merely better SOPs for the team.

The solution is structural redesign.

Organizations that become more independent are designed around human capability, not just control. They are built around empowerment, not just compliance. They rely on living principles, not only static procedures.

Why philosophy matters in self-sustaining organizations

This is where business philosophy becomes deeply practical.

A philosophy is not a script. It is not a checklist. It is not a rigid manual for every possible situation.

A useful philosophy is a living set of principles that remains relevant even when circumstances shift. It helps people interpret reality, make tradeoffs, and navigate ambiguity without needing constant supervision.

That is exactly what self-sustaining organizations need.

When people understand the deeper logic behind decisions, they are far more capable of acting wisely in situations that were never captured in a process document. They can adapt without becoming reckless. They can make decisions without becoming disconnected. They can hold consistency and flexibility at the same time.

And this philosophical foundation cannot simply be copied from another company. Just as systems need to fit the actual business, the guiding principles of the organization need to emerge from its own reality, its own people, and its own way of creating value.

Ideally, this foundation is not developed by the founder alone. It is shaped collectively, so the organization begins to own the logic that guides its actions.

How to begin reducing founder dependency this week

There is a simple conversation that can expose a surprising amount of structural dependency.

Sit down with one direct report. Not for a performance review. Not for a status meeting. Not for an operational update.

Have a human conversation.

Ask:

• What is one thing you normally bring to me for approval that you believe you could decide yourself?

Then ask:

• What is stopping you?

Those two questions can reveal far more than a process map ever will.

You may discover that people are escalating decisions because:

• They are unclear about boundaries

• They fear being second-guessed

• They do not know the principles behind the process

• They have never been given permission to exercise judgment

• They lack confidence, not capability

• The structure silently rewards dependency

You can then ask a broader version of the same question:

• What are people bringing to you that they could gradually learn to handle themselves?

This matters because founder dependency usually cascades downward. When one layer depends too heavily on the layer above, the pattern repeats through the whole organization.

The goal is thoughtful empowerment, not reckless autonomy

Reducing dependency does not mean abandoning discipline or encouraging everyone to do whatever they want.

The goal is thoughtful empowerment.

That means helping people:

• Develop judgment

• Build confidence

• Think more clearly

• Interpret principles in changing situations

• Take ownership one decision at a time

That is how self-sustaining organizations are built. Not through one grand reorganization, but through repeated acts of developmental trust. One conversation at a time. One decision at a time. One layer at a time.

What a living organization actually looks like

When this shift begins to take hold, something important changes.

Systems stop feeling like dead bureaucracy. They stop being documents everyone tolerates but few people truly own. Instead, they become expressions of a living culture.

In a healthier organization:

• Systems support people rather than replace their judgment

• Principles guide action when procedures fall short

• Teams adapt without losing coherence

• Decisions happen closer to the work

• The founder is no longer the center of every answer

That is a much stronger model than simple efficiency. It is the beginning of real organizational life.

The hidden second side of founder dependency

There is one more layer underneath all of this.

Founder dependency is not only about the business depending on the founder. Often, the founder is also psychologically dependent on the business. A kind of codependence can form between the identity of the person and the identity of the company.

When that relationship stays untouched, independence becomes very difficult. Even if the business starts to grow in capability, the founder may still be pulled back toward the center because the organization has become part of how they define themselves.

That inner dynamic deserves serious attention because self-sustaining organizations require change on both sides. The company must be redesigned to think and act with greater independence, and the founder must be willing to relate to the business differently.

The deeper truth underneath all of it

Two ideas sit beneath this entire conversation.

First, if you want to build truly self-sustaining organizations, you have to become your own best business philosopher. That means thinking beyond tools and frameworks and asking deeper questions about human nature, responsibility, judgment, trust, structure, and meaning inside the business.

Second, the true life of the business is found in the humanness of its people. Not just in efficiency. Not just in documentation. Not just in compliance. The organization becomes stronger when the intelligence, maturity, and agency of its people are developed rather than suppressed.

That is the shift that changes everything.

Systems still matter. Processes still matter. Structure still matters.

But if the deeper goal is to create self-sustaining organizations, then systems must serve a living organization, not attempt to replace one.

This article was created from the video titled “Why Systems Don’t Build Self-Sustaining Organizations” on the The Business Philosopher Within You podcast. he article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that every time a create a solo episode like the one here, I go through a deep learning experience.

As I create the script, record the video, and then listen to it again and again to write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things I covered. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understanding

That is what makes Founder Syndrome so tricky. It is not always a sign that something is broken. Sometimes it is a sign that the organization is healthy enough to outgrow constant dependence on the founder. The hard part is that success can feel, emotionally, a lot like rejection.

00:00:00 When Success Creates a New Problem

The most dangerous moment can arrive when a founder is no longer the center of every decision. Fewer meetings. Less urgency around your opinion. More leaders stepping in. On paper, that sounds like maturity. Inside, it can feel like your worth is being reduced.

That is the opening wound of Founder Syndrome. A lack of need starts to feel like a lack of value, even when those two things are not the same. If a founder does not recognize that shift early, the reaction can become more damaging than the transition itself.

00:05:00 When Service Became a Mission

The story began with a simple desire to teach kids the joy of serving others. A family in town needed help, and one detail stood out above everything else: their children did not have beds. That small discovery turned a routine church assignment into something deeply personal.

One bunk bed in a garage led to another. What looked like a one-time act of kindness uncovered a much larger problem: children sleeping on floors in communities where most people never even knew it was happening. That is where purpose started replacing the hollow feeling that success alone could not fix.

00:15:00 When Founder and Mission Become One

As the work grew, so did the connection between the founder and the mission. People no longer saw one without the other. That kind of fusion is powerful, and honestly, it helps movements grow. Passion attracts support. Identity gives a mission a face.

But Founder Syndrome often starts here. The founder and the organization become so closely linked that separating healthy leadership from personal identity becomes almost impossible. It feels natural at first, then costly later.

00:17:37 When Passion Meets Scale

Once the mission spread beyond one town, scale demanded structure. Solving child bedlessness was never going to happen from one garage in Idaho. It had to happen locally, chapter by chapter, with clear standards strong enough to protect the mission as it expanded.

The growth was extraordinary. Hundreds of chapters, tens of thousands of volunteers, and hundreds of thousands of beds built for kids who would otherwise sleep on the floor. But rapid growth also accelerates Founder Syndrome, because the founder is evolving in public while the organization is evolving in a completely different way.

00:25:10 Structure Creates Freedom

Scaling a mission means building systems that can survive without the founder touching everything. That includes standards, policies, local leadership, and an org chart that gradually becomes real long before most people are paid. In a nonprofit especially, passion often arrives before qualifications do.

The surprising part is that structure is not the enemy of purpose. It is what protects purpose. If the mission is going to stay true while spreading, freedom comes from clarity, not chaos. And yet every layer of structure can also trigger a fresh wave of Founder Syndrome.

00:29:54 The Power of Passion

People will do incredible work when they care deeply about what they are building. That is true in volunteer organizations and in businesses. A paycheck can create compliance. Passion creates initiative, creativity, ownership, and the willingness to go farther than the job description requires.

The key is buy-in. Give people real responsibility. Let them build something. When they help create the role, the solution, or the process, they become emotionally invested in it. That same force can move an organization fast, which is why passion is both the fuel behind growth and a major ingredient in Founder Syndrome.

00:41:39 When Passion Becomes the Problem

The same passion that launches a mission can later become a liability if the founder cannot adapt. The organization decentralizes. Decisions get distributed. New leaders take on responsibilities that once belonged to the founder alone. That is normal. It is also where the relevance wound begins.

The relevance wound is the most painful stage of Founder Syndrome. Meetings happen without you. Assignments come to you instead of from you. Someone else becomes the public face in a moment you once would have owned. None of that means you are less important, but it can feel exactly that way.

00:50:00 Looking in the Mirror

This is where emotional honesty matters. A founder can tell himself he is being ridiculous, arrogant, or selfish, but that rarely solves anything. The pain is real whether or not it looks logical from the outside. Ignoring it only gives it more room to control your reactions.

Getting through Founder Syndrome requires real self-examination. Not image management. Not just operational skill. The challenge is learning to sit with the discomfort long enough to understand what is actually happening instead of protecting yourself through anger, control, or withdrawal.

00:56:17 Naming the Monster

Things change when you can finally name what you are going through. Before that, the feeling is just a cloud of hurt, frustration, defensiveness, and confusion. Once you recognize it as Founder Syndrome, the problem becomes workable.

Naming the monster shrinks it. The issue may not disappear, but it stops feeling invisible and unbeatable. Like any hard diagnosis, clarity brings relief. You may not like the problem, but at least now you know what you are fighting.

01:00:16 Creating a Self-Aware Organization

A healthy response to Founder Syndrome cannot rest only on the founder. Boards, executives, and emerging leaders need language for what is happening too. If they misread the founder’s pain as pure ego, they will respond badly and make the transition harder on everyone.

Self-aware organizations recognize that leadership evolution affects more than one person. Employees and volunteers can experience their own version of identity fusion when roles change. The best leaders know how to guide people through those changes without treating emotion like weakness.

01:03:50 Builder → Architect → Ambassador

One of the clearest ways to fight Founder Syndrome is to understand the season you are in. The journey begins as builder, moves into architect, then anchor, ambassador, and eventually mentor. Each stage asks different things of the founder.

Alongside those stages come five disciplines: pause before you protect, name your season, separate worth from need, do the inner work, and choose legacy over proximity. Those disciplines help a founder stop reacting from pain and start leading from clarity.

01:16:15 Building a Legacy That Outlives You

The goal is not to stay central forever. The goal is to build something that can outlive you. That shift is painful because it trades control for legacy. But that trade is often the very thing that allows a mission to keep serving people at scale.

In the end, the real win is not preserving access to every decision. It is knowing you built something strong enough to keep doing good when you are no longer at the center of it. That is not losing your place. That is finishing your work well.

What Founder Syndrome actually looks like in practice

Founder Syndrome is not just a buzzword for difficult leaders. It is a pattern that often develops in organizations built by passionate people who care deeply and sacrifice heavily. The symptoms can be subtle at first, then painfully obvious later.

• Feeling hurt when major decisions happen without your input

• Questioning your value when others take over tasks you once owned

• Struggling to trust leaders you personally helped elevate

• Interpreting organizational maturity as personal rejection

• Reacting defensively when your role changes

• Confusing being less needed with being less worthy

The five disciplines for working through Founder Syndrome

1. Pause before you protect

Before reacting, stop. The first impulse is usually self-protection. A pause creates room to notice whether Founder Syndrome is driving the feeling.

2. Name your season

Say clearly where you are. Builder, architect, anchor, ambassador, or mentor. You cannot lead well from a season you refuse to acknowledge.

3. Separate worth from need

Being needed less does not mean you matter less. That distinction is one of the hardest and most necessary lessons in Founder Syndrome.

4. Do the inner work

This may involve coaching, honest conversations, reflection, or professional support. The point is not to tough it out. The point is to understand yourself well enough to respond instead of react.

5. Choose legacy over proximity

Legacy asks what will endure. Proximity asks whether you are still close to power, decisions, and attention. Healthy founders eventually choose legacy.

Why Founder Syndrome is often a sign of success

This is the uncomfortable truth: Founder Syndrome often appears because the organization is working. New leaders are capable. Systems are maturing. Responsibility is spreading. The founder is no longer required to hold every piece together.

That does not make the emotional experience any easier, but it does reframe it. The pain is not proof that the mission is slipping away. It may be proof that the mission is finally becoming durable enough to survive.

FAQ

What is Founder Syndrome?

Founder Syndrome is the strain that can appear when an organization matures beyond constant dependence on its founder, but the founder’s identity, value, and leadership habits have not fully adjusted to that new reality.

Is Founder Syndrome always a bad sign?

No. It can actually signal that the organization is growing successfully. The danger comes when the founder interprets that growth as personal displacement and reacts in ways that damage trust, culture, or mission.

What is the relevance wound in Founder Syndrome?

The relevance wound is the pain a founder feels when decisions, visibility, and authority begin shifting to others. It is one of the most difficult stages of Founder Syndrome because success starts feeling like exclusion.

How can a founder begin dealing with Founder Syndrome?

Start by pausing before reacting, naming what is happening, recognizing the current leadership season, separating worth from being needed, and doing the inner work necessary to choose legacy over control.

Can employees and volunteers experience something similar?

Yes. Anyone who has helped build a role, team, or system can feel a version of the same pain when responsibilities shift. That is why a self-aware organization should talk openly about leadership evolution, not just performance.

Get In Touch with Luke Mickelson

For more insights on Founder’s Syndrome and and practical guidance on Luke’s approach to building and leading organizations, reach him via Linkedin or Luke Mickelson website.

This article was created from the live video conversation on The Business Philosopher Within You podcast. The episode was published on YouTube under the title “Founder Syndrome: When Your Passion Becomes the Problem.” The article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Luke above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Expand Your Understanding

But sometimes that is exactly when the deeper question begins.

Vish Alluri built two significant companies out of India. One was sold for around $100 million. The second ultimately became a $430 million acquisition by Cisco after growing globally, listing in London, and expanding through multiple international acquisitions. By conventional standards, that is a complete success story.

Yet the more interesting part of his journey is not the exits. It is the inquiry that ran alongside them.

What is leadership, really? What is management beneath the jargon? What is clarity? And what if the inner life of a leader quietly shapes everything in the outer life of an organization?

His answers are practical, philosophical, and unusually unsentimental. He speaks as a builder, not as an armchair thinker. He built products, dealt with customers, scaled teams, handled due diligence, and still arrived at a view of success that has little to do with money for its own sake.

Starting With a Contrarian Idea: Build Intellectual Property Out of India

When Alluri started IMI Software, his intention was clear from the beginning.

He did not want to build a services business based on what he bluntly calls “body shopping.” He had no interest in simply supplying technical manpower. His ambition was to develop intellectual property out of India by harnessing India’s intellectual resources.

That mattered then, and it still matters now. India’s technology sector has often been criticized for producing too little original IP relative to its talent base. Alluri wanted to challenge that pattern early.

So IMI Software was built to create real products for global markets. In its early phase, the company focused on civil engineering software. The products were licensed to companies such as:

• ABB in Italy

• Hyundai in South Korea

• Companies in Spain

• Multiple customers in India

For him, that was a meaningful benchmark. Not just building something technically competent, but building something best-in-class enough to be accepted by major international customers.

Why IMI Mobile Was Born

IMI Mobile emerged later, in 1999, as an offshoot of the earlier business. The context mattered.

Even though Alluri was committed to developing products, many engineers in India were increasingly drawn toward overseas assignments, especially in the United States. Then came Y2K, which accelerated the pull toward export-oriented staffing work.

He refused to follow that route.

Instead, he looked at mobile technology in its earliest days and saw a new revolution beginning. That became the basis for IMI Mobile.

The decision was not framed as a trend-following move. It was an extension of the same philosophy: build something real, useful, and globally relevant, rather than merely supplying labor into someone else’s machine.

What Success Meant Then

Alluri is careful to distinguish between what success meant to him then and what it means now.

In the earlier phase, success meant this:

• Developing a cutting-edge product

• Building to international standards

• Winning acceptance from major global customers

That was the milestone.

Money mattered too, but not in the simplistic personal sense people often assume. He makes a distinction that many founders miss.

A company needs:

• a good top line

• a healthy bottom line

• sustainable profitability

• enough financial strength to attract investors and endure over the long run

Profit, in that sense, is important for the company. It is part of organizational health. But he does not treat personal enrichment as the central measure of achievement.

The Two Exits and What They Validated

The first company, the engineering-focused business, was sold in 2008 for around $100 million to Ramboll, the Danish engineering conglomerate.

Alluri’s admiration for Ramboll was not merely financial. What impressed him was the character of the organization itself.

Ramboll had a trust-based ownership model in which the holding foundation owned the company. The beneficiaries were employees and social causes, not family members. The company published quarterly results not because the market forced it to, but as part of transparency for employees participating in equity-related arrangements.

That kind of structure mattered to him. When Ramboll came to acquire his company, he felt he was dealing with the right kind of people.

At the time, the company had around 1,000 people working across India, especially in telecom-related audit and infrastructure work during India’s telecom expansion.

The second company, IMI Mobile, followed a larger arc. It listed on the Alternative Investment Market of the London Stock Exchange in 2014. Under the leadership of a trusted CEO whom Alluri had carefully chosen, the business expanded globally and acquired around eight to ten companies across:

• the United States

• Canada

• the UK

• South Africa

By the time Cisco acquired it in 2021 for $430 million, the company had roughly 1,100 to 1,200 people and had become part of Webex.

For Alluri, that acquisition validated two things:

1. The quality of the product

2. The robustness of the management process

Cisco, in his view, is such a seasoned and serious acquirer that surviving its due diligence is itself a meaningful test of how well a company is actually run.

A Founder’s One-Line Origin Story: Technical Ignorance and Business Innocence

One of the most revealing parts of Alluri’s philosophy is how he describes his own background.

He was a chartered accountant, not an engineer, yet he built engineering and technology product companies. He jokingly summarizes his journey as one of technical ignorance and business innocence.

That phrase is more useful than it first appears.

By “business innocence,” he does not mean naivety. He means not being trapped in the mentality of putting money in the morning and demanding a return by the evening. He was willing to work, build, and let value emerge over time.

That distance from both technical ego and short-term financial obsession seems to have given him something many founders lose early: perspective.

His Management Philosophy in One Principle

Alluri’s definition of management is strikingly plain:

Management is about preventing goof-ups and lapses in the execution of the job for the customer.

That is his core.

Not presentation decks. Not inflated frameworks. Not management theater.

Just this: Do what was promised, and don’t let execution break down.

He built a guiding principle around it:

Commit what you can deliver. Deliver what you commit.

Everything in management, for him, starts there.

If a customer says the work is bad, arguing is pointless. The customer is the umpire. He uses a cricket analogy here. When the umpire lifts the finger, the batsman is out. You may not like it, but that is the call that matters.

The same logic applies in business. If the customer says the delivery failed, you begin there.

What Management Is Not

Alluri likes approaching things through negation. Before defining what management is, he asks what management is not.

This is not rhetorical. It is operational.

Management is not:

• doing everything yourself

• hiding behind the word “we” when accountability is needed

• allowing mistakes to repeat without tracing their source

• escaping from facts

• suppressing uncomfortable truths

He is especially sharp on language. When someone reported a failure by saying “we didn’t do it,” he would push back. Don’t use “we” as a fog machine. Tell me what you did. Face the fact directly.

In his view, human beings tend to do two things under pressure: suppress or escape. Good management requires neither. It requires seeing what happened clearly enough to prevent recurrence.

Fix the Root Cause, Not Just the Incident

Once a goof-up happens, the job is not simply to patch the immediate problem and move on. You have to trace the origin.

That means asking:

• Was this a one-off transactional error?

• Or is there a recurring systemic weakness?

• What process allowed this to happen?

• How do we prevent this category of failure from happening again?

This is where senior leadership matters most. The top management team must have enough clarity to distinguish a local fix from a systemic fix.

If it is a policy issue, it has to be discussed and resolved at the top. Otherwise the organization simply keeps rediscovering the same problems in different forms.

Clarity Is Not the Opposite of Confusion

This is one of Alluri’s most interesting insights.

He argues that clarity is not the opposite of confusion. Clarity comes from understanding confusion.

The realization that one is confused is the beginning of clarity.

That sounds simple, but it has major consequences for leadership.

Most leaders want to project certainty. They do not want to admit confusion because they think clarity means presenting a firm answer. But if that “clarity” is only a reaction against confusion, it still carries the seed of confusion inside it.

Real clarity begins when the confusion is actually seen.

He gives a practical example. If you reach a crossroads and do not know the destination, the crucial fact is not pretending. The crucial fact is realizing, “I do not know.” Then you stop, ask, and move intelligently.

Leadership clarity begins in exactly that way.

The Inner Turn: Why Awareness Became Central

The deeper shift in Alluri’s life began in the mid-1990s when he encountered the teachings of J. Krishnamurti.

One title struck him in particular: “Where knowledge and silence go together.”

That encounter was, by his description, like lightning. Not because it handed him a doctrine, but because here was someone speaking about the inner life with extraordinary directness and objectivity.

This led him toward a central question:

If the mind is the instrument through which life is lived, should we not understand how it works?

He draws a distinction between the outer and the inner:

• The outer includes work, role, position, money, action, structure

• The inner includes thought, feeling, memory, fear, desire, hurt, confusion

We often behave as if the outer is the real business of life and the inner is secondary. He argues the opposite. Unless the inner dimension is understood, the outer inevitably becomes distorted.

The inner and outer are not separate worlds. They are in relationship all the time.

Awareness Is Beyond Thought

One of the key distinctions in this philosophy is between thought and awareness.

Thought is memory-based. It is conditioned, descriptive, and often tied to the past.

Awareness is different. It is not merely another thought about experience. It is direct perception in the present moment.

Alluri puts it plainly: awareness exists only now. Awareness of yesterday is only a description of awareness.

He also points out that awareness is inseparable from action. When driving, if you see a steep curve, you naturally slow down. If you see danger, you respond. There is no elaborate internal speech required. Awareness acts.

This matters in leadership because many managers think in abstractions while missing what is happening directly in front of them.

The Mirror of Relationship

To make awareness practical, Alluri uses two tools he finds especially useful:

1. The mirror of relationship

2. The tool of negation

The mirror of relationship starts from a broad definition of relationship. Relationship is not limited to romance, family, or close interpersonal bonds. You are in relationship with everything around you:

• your money

• your position

• your possessions

• your beliefs

• your memories

• your colleagues

• your organization

• your own thoughts and reactions

Relationship reveals you to yourself. That is why it is a mirror.

He gives a simple example. If someone drops a $100 bill in the park, what do you do?

• Return it?

• Take it to the police?

• Pocket it?

Your reaction reveals something about what you are.

Or take a luxury car. Is it merely a mode of transportation, or has it become a psychological extension of the self? That distinction matters.

For Alluri, many of life’s distortions begin when a physical relationship turns psychological. A car is physically for transport. A title is physically a role. But when they become prestige, identity, self-image, or emotional armor, trouble begins.

The Tool of Negation

The second tool is negation.

Negation does not mean denial in the usual sense. It means seeing and discarding what is false, inherited, or psychologically distorting.

This includes becoming aware of:

• prejudices

• religious conditioning

• social assumptions

• identity structures absorbed from childhood and culture

Much of life, he says, is lived through influences we never consciously examined. Some of them precede us by centuries. We inherit them, project through them, and call that reality.

Negation is the act of seeing those influences as they operate and loosening their hold.

It is also the same logic he applies to management. Sometimes you understand a thing best by seeing what it is not.

Why Most Leadership Lacks Clarity

Leadership often fails not because people lack intelligence, but because they do not examine their confusion, their motives, or their relationships.

Many leadership systems focus heavily on structure, targets, and review mechanisms. Alluri does not reject those. But he insists that without understanding the human being operating inside the system, structure alone cannot save anything.

This is why awareness matters. If a leader is unaware of their own attachments, fears, vanity, ambition, or confusion, all of that leaks into culture.

The organization begins to reflect the unexamined inner life of its leaders.

You Build Structures Around People, Not People Around Structures

This is another foundational principle in his approach.

You build a structure around people. You do not build people around structures.

Modern management education often reverses that. It creates the org chart first and then tries to fit human beings into it like pieces in a machine.

Alluri sees that as backward.

Yes, you need functions. Finance, sales, marketing, delivery, product management, operations. Those are real requirements.

But after hiring, you must keep observing people. What are their qualities? What is their flair? What kind of work do they respond to? Where are they alive, and where are they deadened?

Structure should serve human capability, not crush it.

He even says that when he was hiring engineers in the early days, he was not fixated on labels like IIT. He was more interested in qualities of the person rather than qualifications of the person.

Culture Is Not Declared Once. It Is Lived Daily.

Alluri repeatedly returns to one practical point: none of this works as a slogan.

You cannot give one inspiring speech about culture and assume the job is done.

Culture is formed through daily interaction.

When a team member says they need more resources, his reply is telling. Often the issue is not resources, but resourceful thinking.

That does not mean people never need help. It means the reflex to outsource responsibility upward must be challenged.

How leaders interact day after day determines whether people become more awake or more mechanical.

As he puts it, this is not a one-off intervention.

It is a living process.

That phrase captures the whole philosophy. Management is not merely a means of livelihood. It is a way of living.

Even Meetings Reveal Whether an Organization Is Awake or Asleep

He extends the same attention to ordinary routines.

Take a Monday review meeting.

The question is not only what gets reported. The deeper question is: How are people attending the meeting?

• Are they present?

• Are they engaged with the spirit of review?

• Or are they just performing ritual?

Once something becomes mere ritual, awareness drains out of it. Then people start functioning like machines. The form remains, but the life has gone.

That is as true in organizational life as it is in religion, which is one reason he is wary of empty repetition in any domain.

Outer Riches and Inner Riches

By the later part of his journey, Alluri’s definition of success had changed deeply.

He now sees success less as accumulation and more as the intelligent preservation of energy.

Every action spends energy. So does thought. So does emotional agitation.

Anger wastes energy. Disturbance wastes energy. Psychological drama wastes energy. Frivolous pursuits waste energy.

A successful life, in this view, is not one that merely acquires outer riches, but one that stops leaking inner energy in needless ways.

That opens the possibility of what he calls inner riches.

Outer riches can be counted, taxed, admired, compared, lost, and stolen. Inner riches cannot.

They do not depend on applause, valuation, title, or prestige. They alter the quality of life itself.

That does not mean rejecting business, wealth creation, or organizational excellence. It means seeing their place correctly. Without the inner dimension, even success becomes restless and hollow.

The Art of Questioning

If there is one practice that ties all of this together, it is questioning.

But not second-hand questioning. Not borrowed inquiry. The real thing.

The question must come from within.

Questions such as:

• What am I doing?

• Why am I doing it?

• What am I not doing?

• Why am I not doing that?

• Am I caught in illusion?

• Am I wasting energy in the pursuit of name and fame?

For him, these are not philosophical decorations. They are foundational tools for living and leading intelligently.

He wrote and shared his work not for money or self-display, but because he feels a responsibility to share the fascination of life with other human beings.

What “Enlightened” Means Here

Alluri is careful with the word “enlightenment.” He does not casually apply it to himself, and he knows the term carries both spiritual and philosophical baggage.

So what does “The Enlightened Manager” point toward?

Not a fixed formula. Not a personal claim. Not a badge.

It points in a direction.

A direction toward greater awareness, inward cleanliness, seriousness of inquiry, and sensitivity to something sacred in life that cannot be approached through a cluttered mind.

His emphasis is on approach, not guaranteed outcome. He is not selling a method for producing billionaire founders or perfectly optimized companies.

He is asking managers to pay attention to the moment, to the reality of their relationships, and to the way their minds operate.

That is why the word “enlightened” in this context is best read as an invitation to seriousness, not self-congratulation.

Why J. Krishnamurti Matters in This Story

Krishnamurti’s influence on Alluri is unmistakable.

He offers a concise account of Krishnamurti’s life. Adopted in 1909 by Annie Besant within the Theosophical movement, Krishnamurti was groomed as a possible world teacher. He later dissolved the organization built around him, rejected spiritual authority structures, returned property, refused personal mythmaking, and said his concern was to set human beings free.

He left no official successor, no religious order centered on himself, and no invitation to become an interpreter or guru in his name.

That anti-authoritarian seriousness matters. It aligns with Alluri’s insistence that understanding must come directly, not through dependence on spiritual middlemen.

What Leaders Can Take From This

Alluri’s philosophy may sound abstract at moments, but much of it is very concrete in practice.

A leader can start here:

• Deliver what you commit.

• Trace goof-ups to their real source.

• Fix systems, not just incidents.

• Do not hide behind vague collective language when accountability is needed.

• Recognize confusion instead of performing certainty.

• Observe your relationship to role, status, possessions, and power.

• Build structures around actual human beings.

• Treat management as a living process, not a ritual.

• Question your motives from within.

• Do not mistake outer riches for a complete life.

These are not separate from business performance. In his experience, they were part of building companies that customers trusted, acquirers respected, and teams could grow inside.

A Different Kind of Success

By ordinary standards, Vish Alluri succeeded a long time ago.

He built internationally accepted products out of India. He scaled organizations. He exited well. He created value. He earned the validation of serious customers and serious acquirers.

But the more durable part of his legacy may be the way he reframed success itself.

Not as fame. Not as psychological enlargement. Not as relentless outer accumulation.

But as clarity. Integrity in action. Intelligent use of energy. Freedom from waste. And contact with inner riches that cannot be priced.

That is a demanding standard. It offers fewer shortcuts and less glamour.

It may also be the more serious one.

Get In Touch with Vish Alluri

For more insights and practical guidance on Vish’s approach to building and leading organizations, reach him via Linkedin.

This article was created from the live video conversation on The Business Philosopher Within You podcast. The episode was published on YouTube under the title “Even As He Built and Sold a $730 Million Company, He Questioned Success.” The article was created with the help of AI after significant input from human intelligence.

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Unlock Your Understanding

We explore steward ownership, perpetual purpose trusts, resilient leadership and the deeper question of what businesses are ultimately designed to serve.

[00:00:00.00] - Brenna Davis

It was so beautiful. And I just remember the moss and I remember the huckleberries and just all the amazing nature that was there in the forest. And it was like a friend to me. It really was. And the forest was gone. And I asked my mom, you know, why, what, what, what happened? Why was this? Because I was just devastated. And my mother said, well, honey, that’s just how business is done. I just remember thinking that it had to be better than that. Like there had to be a better way to build a house. There had to be a better way. It kind of led me on a quest to find out, like, how businesses make the decisions they make. And initially, I really thought that meant just working within existing, you know, business structures. And that’s what I did for many, many, many years. Today, I’m at Organically Grown Company, which is the nation’s largest independent organic produce distributor. I went from a co-op, a cooperative, which is an alternative business model, to a perpetual purpose trust-owned company. Which is an emerging model that is getting more and more popular. In essence, the business exists to serve that purpose and to fund it.

[00:01:05.09] - Brenna Davis

And so the profits that you make flow down into advancing that purpose and is a great option as we hit the silver tsunami that we’re hitting right now in the business world where folks are aging out and wanting to transition but still preserve their mission. And for me as a CEO, That mission and that purpose is really what drives me. So it’s frankly at the heart of the way I lead my— I run my life, the way I live my life, the way I lead. You know, we always have to balance actually making a profit and running a good fundamental business with our purpose. I’m also really fascinated with bees. I’ve always loved bees and just how they share resources and how they share roles. We really worked hard to integrate it into kind of the way we approach our communication. The sharing of resources and information is what makes systems more resilient. As leaders, we’re expected to show up every single day, still be inspirational, still be supportive, still be the best— our best self every single day that we walk through that door or sit down to our desk. And the pressure of it is a lot.

[00:02:13.12] - Brenna Davis

Really, the idea is, as leaders, building the resilience within ourselves so that can flow out to our organization. You know, an organization shouldn’t just rely on their CEO or their executive, that developing the bench strength of the leaders around you and developing the leadership all the way through the ranks. You know, we’ve worked really hard to start to do more work with our leadership at every level, you know, moving down even into the supervisor level to invest in them so that it’s not just relying on one person, so that we are a community of leaders supporting each other. It’s not just the person person that theoretically people say is at the top, but it’s, it’s the whole suite of leaders within an organization that really make things happen. And as a CEO, my job is to articulate the vision, but also clear the way so that the work can happen. Courage isn’t the absence of fear. It’s walking through the fear.

[00:03:07.09] - Bhavesh Naik

This is The Business Philosopher Within You podcast. I’m your host, Bhavesh Naik. A recurring idea on this podcast is that great leaders don’t just manage organizations. They design systems that allow people and institutions to thrive over time. But if organizations are systems, a deeper question emerges. What makes some organizations resilient while others collapse under pressure? And what role does leadership play in building institutions that can endure for generations? To explore these questions, I’ve invited a very special guest to join us. Brenna Davis is the CEO of organically grown company, the nation’s largest independent organic produce distributor. She’s also the author of Leading Through Fire: Resilient Leadership for People, Planet, and the Future. An environmental scientist turned CEO, Brenna brings a systems perspective to business leadership. Her career spans executive roles across 7 industries and companies ranging from $20 million family businesses to $200 billion global enterprises. Today, she leads one of the most prominent examples of trust-based ownership in the United States. I am pleased to have you on this podcast, Brenna.

[00:04:22.06] - Brenna Davis

Oh, thanks for having me, Bhavesh. Really nice to see you and excited to be on this podcast with you.

[00:04:28.12] - Bhavesh Naik

Yeah, thank you for being here. And a special shout out to you, our listener. Hey, listen, we’re not just a podcast. We are a movement and you are the business philosopher. We learn from each other and grow with each other. Please remember to like, subscribe, follow, share, and comment. But most important, ask and answer questions. Thank you for tuning in. So Brenna, take us back. Now, your book, Leading Through Fire, and I sampled it a little bit. I haven’t read the whole thing because I have a reputation of ruining surprises and drop spoilers. So I read just a very small portion of it. But it’s, uh, you talk about growing up in the Pacific Northwest. And as a child, you’re probably about 5 years old, and you are describing this breathtaking moment to me where you’re watching an ecological disaster. And your mom is there. And you ask a question to your mom. Could you take us back to that moment? And you will probably do a much better job, definitely do a much better job describing this moment than I can. So please take us back and tell us what’s happening and what’s the question you ask to your mom.

[00:05:50.07] - Brenna Davis

Yes, I grew up in the Pacific Northwest, spent, you know, kids that grew up in the Pacific Northwest spent a lot of time in the forest and spending time in nature. I was raised, it was in the ‘80s when you could kind of be set free and be feral and run through the woods. And I spent a lot of time on Camino Island, uh, with my grandmother at her place. And, um, you know, I used to play in the woods across the street. My, my, my cousins and I would all be over there, um, running through the woods, looking at the trees, uh, you know, the, the ravens, the tadpoles. Um, there was so much nature there. It was so beautiful. And I just remember the moss and I remember the huckleberries and just all the amazing nature that was there. In the forest. And it was like a friend to me. It really was. When I was a kid, it was like a magical universe and a really incredible ecosystem, although I didn’t have the words for it at that point in time in my life.

[00:06:47.20] - Bhavesh Naik

Sure.

[00:06:48.12] - Brenna Davis

And I arrived after leaving my grandmother’s place and coming back after a few weeks, and the forest was gone. It was completely destroyed. All that were left was a tangle of roots. And I remember the dirt, none of the plants were there. It was just clear cut. And I asked my mom, you know, why, what, what, what happened? Why was this? Because I was just devastated. And my mother said, well, honey, that’s just how business is done. They’re developing that land and they’re going to build houses on it. And I just remember thinking, and I was just thought that it had to be better than that. Like there had to be a better way to build a house. There had to be a better way. Just for things to happen as a kid. And, you know, when you’re that young, you’re idealistic and you just think, yeah, it will be so easy. But it kind of led me on a quest to find out like how businesses make the decisions they make. And it led me on a journey to become an environmental scientist, you know, majoring— there was, there was no sustainability majors back then.

[00:07:52.13] - Brenna Davis

So I had to hack my degree and really to really be able to learn about business and science. So that’s kind of what led me to that point in my life. And it’s really been a thread throughout my career is just this question like, why do businesses make the decisions they do?

[00:08:13.02] - Bhavesh Naik

Yeah, yeah. And you talk about purpose in the book. And I think that this is probably the purpose is the first thing that you talk about. And I think kind of lead with that. That’s my impression. And it seems like there’s some inklings of the purpose right in that moment. You’re 5-year-old, so you probably are not— I don’t know if I— you know, the psychologists say that we don’t form our cognitive mind until a bit later, like 6 years or something like that. So you’re witnessing this and it sparks something. And I think you end up calling it a purpose. Is that correct? Or am I— do I have that wrong?

[00:08:48.08] - Brenna Davis

Yeah, it did sort of become a purpose. My purpose really was how do we protect this beauty, this natural beauty that’s in the world. And as I learned more as an environmental scientist about ecosystems and how they’re all connected and how human beings ourselves are dependent on these natural systems to exist, I realized that really my purpose was both to help people survive, help people have healthy lives, clean air, clean water, healthy food to eat, but also to help all the species also survive. And built into that, as I learned more and more, is this concept of environmental justice and how do we help make all of that access more equitable for everyone. So these are all kind of been one big sort of purpose for me is finding a way to preserve these things, to preserve this beauty, preserve these resources in a way where it benefits all. And that’s really led me through my career. It led me, like you said, through 7 different industries. I did my internship when I was in college in an oil refinery because I really wanted to dive into how what I perceived to be one of the most impactful industries, how they made decisions.

[00:10:11.17] - Brenna Davis

And I learned a lot about that. One of the things I learned is coming from my side of the Washington state, which is more liberal and coming from a family that was more liberal, the words that I used might be environmentalism. The words that someone else might use that worked in a refinery might be conservation or words that I— the thing that motivated me might be to enjoy the beauty of the forest and hike through it. The thing that might motivate another would be hunting a duck or going duck hunting or fishing. So we shared a lot of the same love of nature, we just had different words that we were using. And so that was one of the more profound things I learned. And I’ve found that in my career, I think that most people care about nature. I think that most people care about the environment, but kind of the words we use have gotten in the way. So moving on from the refinery, I did a lot of consulting in the energy sector, including in oil and gas, big multinationals, helping them do key performance indicator roll-ups and environmental management systems work and sustainability work, helping them to have a lower impact on their communities.

[00:11:28.12] - Brenna Davis

And then worked in a, in a utility doing a similar thing, which for, for about 10 years. And ultimately, I found my passion for food working at a, in a health system in Seattle. Helping them to do all sorts of things because running a healthcare system is like running a small town. It’s a 24/7 operation and a million meals served every year. But really my question that I asked was, how can we make these meals more healthy for people and better for the planet? And so work to transition those, that food into Marine Stewardship Council certified seafood and organic food and foods that would help to support people’s health more effectively. And then from there I went to the nation’s largest food co-op working with the team there, leading all of their quality standards, making the—

[00:12:21.01] - Bhavesh Naik

Which is today, right? That’s today.

[00:12:23.06] - Brenna Davis

Not quite.

[00:12:23.19] - Bhavesh Naik

This is before. Okay.

[00:12:24.11] - Brenna Davis

Yeah, yeah. I was on the executive—

[00:12:25.23] - Bhavesh Naik

Go ahead.

[00:12:26.09] - Brenna Davis

Sorry. Yeah. Community Markets, which is the nation’s largest food co-op. It’s 16 stores and about, I think it’s about 1,400 employees now, 1,500. Helping them do a similar thing, reducing the impact, making sure that we had healthy food in our system. And, and today I’m at Organically Grown Company, which is the nation’s largest independent organic produce distributor. Yeah. Which I know we’ll talk about this. I went from a co-op, a cooperative, which is an alternative business model, to a perpetual purpose trust-owned company. —which is an emerging model that is getting more and more popular. And it’s exciting to be a part of that.

[00:13:13.14] - Bhavesh Naik

There are so many threads that we can follow in there. And let’s see if we can do justice to your career and all the things that you’ve done. You talked about going into the belly of the beast, in my terms, going to the oil and gas industry and working there. And what I— the word that popped in my head is perspective. It’s going in and looking at it from their perspective. So you said something very important that we all care about the environment. We all care about the ecology. We want our planet and our world to be a better place and a good place for all of us to live and thrive. And you didn’t choose to become an environmental activist. You didn’t go into government institutions and choose to be a bureaucrat. You know, those are all wonderful professions. You chose to take more of the business angle to things, right? It seems like, you know, you kind of grew into business side of things and leadership. So you grew into a leadership role, right? And I think today you probably call it stewardship more than the leadership. Is there a reason why that side kind of attracted you more than going the other routes?

[00:14:34.03] - Brenna Davis

Yes, I’ve always thought that it made more sense to work, for me, to work within a system to make change for, of the system. And I thought about it a lot when I was in college. I was not popular because I had this internship and all my colleagues were doing really cool work like counting frogs or measuring limbic systems or doing a lot of different things. But for me, I thought they have an important place in the ecosystem of the environmental movement, which is understanding the science. And then there’s the people that are kind of in the activist movement and they have an important role, which is to push society forward. But I always thought for me that if I could understand the system as much as possible, it’s interesting reflecting on this because it’s kind of a little bit of a scientist view, but if I can understand the system as much as possible, then I can more most effectively help it to do a better job. And initially, I really thought that meant just working within existing, you know, business structures. And that’s what I did for many, many, many years. And I do think that you can make a difference within existing business structures.

[00:15:51.12] - Brenna Davis

I’ve seen businesses that have done really great things. You know, we can think of so many businesses that have done great things. And I also think that when, you know, the challenges happen, when, you know, sales dive or there’s some kind of crisis, the trade-off that I’ve seen is always, quite often, I should say, not always, quite often, that they will choose to disinvest in sustainability initiatives or disinvest in the community or disinvest in other things. And so these alternative structures help to preserve that mission and that purpose even in times of challenge.

[00:16:31.23] - Bhavesh Naik

And that brings us to this idea. I think, you know, you talked about PPT, Perpetual Purpose Trust. Did I say that right?

[00:16:39.23] - Brenna Davis

Yeah, you did. Yep.

[00:16:42.17] - Bhavesh Naik

Quite a mouthful, but every single word of those three, I was thinking about those three words and each one of them makes sense because it’s perpetual, meaning that it’s self-sustaining, it goes on beyond generations, right? It’s perpetual. And it has purpose is in there and then trust. So did you— so this is a new thing. And I think before that you were with a co-op. Right? Yes. So can you talk about PPT a little bit? And how— yeah, and how that evolved in your psyche and, you know, how you came upon it? And why did that appeal to you? You know, against a co-op, or now we also talk about B Corporation. I just had a— I just released an episode about someone who’s running a B Corp. So PPT, yeah, take us behind the scenes a little bit.

[00:17:33.14] - Brenna Davis

Yeah, so people, I think, generally understand cooperatives, that people buy in and own the cooperative. And there’s so many applications of them from utilities, all the way to food co-ops, to, you know, farmer co-ops. It’s amazing what they’re doing, cooperative movement. The Perpetual Purpose Trust movement is centered around this idea of putting your business into a trust that exist to serve a purpose in perpetuity. So, OGC, Organically Grown Company, moved into a perpetual purpose trust in 2018. And there were very few companies that had done that at that time. Like it was so unheard of. We had to hunt down, we had to hunt down a lawyer that would help us. And it was hard to get financing to do it and all these other things. But in the past, perpetual purpose trusts were largely applied to Things like a cemetery where it has to exist for a purpose over a long time. So it would be put in a trust to do that. Or like if you had a pet, like a long-living pet, like a parrot. Yeah. Uh, you could create a trust for your parrot so that it would be taken care of over the long term.

[00:18:44.17] - Brenna Davis

It was more novel to be used, um, to put a business into it, but in essence, the business exists to serve that purpose and to fund it. Yeah. And so the profits that you make flow down into advancing that purpose. Mm-hmm. Mm-hmm. So we transitioned into it in 2018, and since then we’re close to 100 businesses that have also transitioned, including Patagonia, which is really exciting. Um, yeah. And so the movement is growing. I’m on the board of a new organization called the Purpose Trust Ownership Network. Right. Which, um, just had our first conference, uh, uh-huh. Uh-huh. Awesome. In Austin, and it sold out. Yeah. Uh, which was really exciting. And so there’s just a growing movement around the country to embrace this model. Yeah. Um, the model itself, there are safeguards. So rather than just having a board, like a typical business that would run everything, you have a board, but also some, some roles that have oversight to make sure that you’re heading towards that purpose. And there’s a grievance process for that. So it really keeps you on course. And you’re consistently asking the question, you know, are we advancing our mission?

[00:19:53.18] - Brenna Davis

And in the case of Organically Grown Company, It is advancing organic food systems, organic agriculture. In the case of Patagonia, they’re focused on climate change and really dealing with climate change. But there are many— there’s also employee-owned trusts. So really what that is is that the purpose is to advance, to help employees and to advance employees. So it’s really a great growing movement that I think more and more business leaders are learning about. And is a great option as we hit the silver tsunami that we’re hitting right now in the business world where folks are aging out and wanting to transition, but, or to exit, but still preserve their mission. This is a great model for that.

[00:20:41.10] - Bhavesh Naik

Yeah. Yeah. And I wanna just kind of make some connections for our audience. I think OGC is the company of which you are a CEO right now. Yes. Yes.

[00:20:51.01] - Brenna Davis

Yes. I’m the CEO of Organically Grown Company.

[00:20:53.08] - Brenna Davis

That’s correct. Right. And that’s OGC and that is under PPPO. You organized it as an entity under this PPP framework, right? Yes. Okay. And what is the purpose of OGC?

[00:21:05.23] - Brenna Davis

Our purpose is to advance sustainable and organic agriculture and really to support independent and values-aligned businesses that are a part of our ecosystem, for lack of a better word.

[00:21:20.00] - Bhavesh Naik

Absolutely. Yeah, and you were actually distributing the organically growing food. Is that produce?

[00:21:25.13] - Brenna Davis

Is that correct? Yes, yes. So from the back, from the high-level purpose to the day-to-day, day-to-day work. Yes, we’re, we, we buy organic produce from growers and sell it to retailers. We have, we serve 8 states. We have about 300 employees, about 400 trucks that go up and down the West Coast. We also do logistics for kind of refrigerated cold storage logistics for companies that need to transport their goods. We’ve been around since the ‘70s. We were formed in Eugene, Oregon. And so it’s a quite, it’s a very mature business that decided to kind of move to this model. We’ve had real, we’ve had solid profitability. We’re growing. Yeah. Which is really nice. And we’re also, you know, have been really thinking a lot about how do we integrate our supply chain. And so we recently purchased a citrus ranch in Northern California. Very nice. So we’ve got a lot going on. And I think the really exciting part is just the really smart employees that we have, the coworkers that I work with. We call them coworkers. Um, our, my coworkers are just so, um, intelligent, smart, thoughtful, um, really some of the smartest people I’ve ever worked with.

[00:22:47.19] - Brenna Davis

And, um, we just, uh, we’re at it every single day, just putting that food on the table. Yeah. One, one of, one of the things that really drives us too is helping these independent, um, retailers thrive and survive. Yeah. Uh, we work with a lot of cooperatives or mom and pop owned companies. Mm-hmm. Um, yeah. Independent grocers. The folks that might not get the same level of service from other companies that, or other produce houses. And so we make sure that they have a really great offering so that they can compete with the big guys that, you know, that’s, it’s hard to do on a day-to-day basis. So that’s really what drives us is helping keeping the food system sort of not just homogenous, but really diverse and interesting for everybody. Absolutely right.

[00:23:36.04] - Bhavesh Naik

That seems like an exciting day-to-day and the purpose, which is kind of purpose touching the ground, right? It’s being actionalized, if that’s a word. I don’t know if that’s a word or not, but— No, I think it is actionalized.

[00:23:49.01] - Brenna Davis

Yeah, I like it. Actionalized, right?

[00:23:50.12] - Bhavesh Naik

Activated, right? And that must be exciting for you because you’re actually bringing that mission, that personal mission into an organization that’s, I’m assuming, is aligned with your personal mission. Yes. Right? Yes.

[00:24:04.01] - Brenna Davis

I mean, every day I’m excited to wake up and I’m excited to do the work. And just the product we sell is a product that helps to build a better world. And that is that it sequesters more carbon. That is organic food sequesters more carbon. It uses less energy. Organic agriculture has more drought tolerance. It’s also better for farmers. It creates a better income for them. And it, it creates a healthier farmer too, cuz they’re not exposed to all these pesticides, um, that conventional farmers have. And then also it’s better for farm workers. They’re not exposed to it. Their, their children aren’t exposed to these chemicals. So it’s, um, it’s really a great, um, uh, flywheel of, uh, a, a virtuous flywheel. Um, and every day the product we sell is, is just better, better for the planet and, and helping to improve things. Absolutely.

[00:24:57.19] - Bhavesh Naik

And the words that your mom said, that’s how businesses work, or to that effect. I don’t know if I’m saying it exactly the way she said it. Yeah, that’s true. But, and you’re running a business today. And so what’s that feel like? Do you feel like it’s the business that would be devastating the ecological system that you witnessed, or, you know, you’re more of the And I think the answer is clear, but I just kind of want to get the feeling that you feel when you run an organization like that, which is actually on purpose and mission. So what’s it like, you know, your internal experience to be running an organization that is so well aligned with your personal mission and purpose?

[00:25:41.12] - Brenna Davis

It feels very fulfilling. It feels like it’s very aligned with my values. Feels, um, feels good to show up to work every day. Feels good to talk about the work we do. I’m very proud of the work that my coworkers and I do every single day. Um, and you know, when I think on the days where I get tired or the days when I get, uh, you know, I’ve had an overloaded week or I’ve traveled too much, I, um, I, I, I, I reconnect with that. Purpose, so the reason why we’re doing it, and it gives me more fuel and I’m able to keep going. I also, I do prioritize rest too, and, and so I try to balance my life. But, um, but you know, those are, there are those times as a leader when you just feel overwhelmed, and in those times, the, the purpose and knowing that it’s making a better world, um, is, is, uh, energizing for me.

[00:26:37.12] - Bhavesh Naik

Absolutely. And PPT, who is the owner of PPT? Now we know in for-profit world, it’s the shareholders, whether it’s a public company or private company, there are people who have stake in financial stake in the company and they are the shareholders. And then you have the customers and there are the stakeholders, but there’s always this idea of who owns the company. Is PPT different in that regard a little bit?

[00:27:02.15] - Brenna Davis

Yes, it is because it’s owned by a trust. Yeah. So it sits in a trust and it’s managed by a board and it has oversight from an oversight body. In some cases it’s called a trust enforcer, but really their role is to make sure that the mission is being carried out or the purpose is being carried out. There’s never an, and in our structure we have some preferred shares that we also took on when we took on debt. They’re non-voting. Yeah. And those are, uh, yeah, we have that, but, um, but ultimately there’s never going to be an owner, um, telling us that we need to not pursue our mission in order to, to just do profit. Like, yes, it’s never going to be someone telling us, okay, you have to stop doing organic and only do conventional. Um, yeah, we, our mission is preserved within that ownership structure. —rather than sort of being at the mercy or the whim of that particular owner. And I think our founder— definitely our founders designed it that way because of their passion for the mission.

[00:28:16.05] - Bhavesh Naik

Yes. I think I’ve heard you say at one point, I don’t know if it— probably not in this conversation, but before, that the purpose is an owner or purpose is the owner.

[00:28:26.08] - Bhavesh Naik

Is that correct or? Yes. Yes. So, that’s another way of saying it. That exists in a trust and that ultimately the purpose is the owner. That’s right. Right.

[00:28:39.09] - Bhavesh Naik

Here’s a question. What if the purpose changes? You know, if a leader is running an organization and purpose is ultimate basically, right? No, we’re not gonna change the purpose no matter what, right? What if, or is there room for changing the purpose? Is there a mechanism for it? Like, you know, we have in the United States, we have the Constitution, right? You know, you can amend it or you can change it and vote on it, things like that. What happens if the purpose changes a little bit or if it evolves?

[00:29:09.00] - Bhavesh Naik

Yes, yes. How does the leader handle that? Yeah. Yeah, yeah. So the trust is under a trust agreement that outlines the purpose. So everyone knows what that is. And we’re owned by, our trust is Sustainable Food and Farming Agricultural Trust. Is the name of it. Quite long. Yeah. So if someone in the business, like if the board or the CEO or people that were running the business decide to move away from that purpose or shift it away, then there’s a grievance process that exists so that someone could bring a grievance and there’s a mechanism to sort of bring it back to the purpose. I think if all the You know, we’ve only been doing this, I think it’s, we’re in year 8 of this really movement growing. And so, you know, we’re not at the point where we would want to change our purpose, but I would imagine that if a company decided or trust decided they wanted to change their purpose, that they would need to amend their trust agreement and then go through that whole process as a group. But it would be quite arduous and it would be quite difficult, I would imagine.

[00:30:19.12] - Brenna Davis

Yeah.

[00:30:21.14] - Bhavesh Naik

Have you been in a situation with OGC? So far, I know it’s— I realize it’s a young model and probably still experimental a little bit.

[00:30:30.06] - Bhavesh Naik

But as a leader of OGC, have you ever been in a situation when you had to say, “Mm, we’re drifting off the purpose here a little bit, so let’s bring it back in alignment.”

[00:30:40.18] - Brenna Davis

Yeah, you know, every day we talk about our purpose, and I really make an effort in our leadership meetings where we’re always reconnecting with how this, how what we’re doing could impact coworkers or how what we’re doing, you know, feedback from coworkers and reconnecting with our mission and how that would, how, how what we’re doing impacts our mission. So it’s kind of a constant conversation that we have in our business. So far, there hasn’t been a moment for me where we felt like there was a major drift from that because we’re constantly hitting that touchpoint. And for me as a CEO, that mission and that purpose is really what drives me. So it’s frankly at the heart of the way I lead my— I run my life, the way I live my life, the way I lead. So I haven’t seen it yet, although I’m sure it could be a possibility at some point. I know, you know, we always have to balance actually making a profit and being a— running a good fundamental business.

[00:31:43.05] - Brenna Davis

With our purpose. And that’s one thing that I tell folks is, um, one of the best things we can do for the Perpetual Purpose Trust movement is to run a business with solid financials, with a great balance sheet, with, um, you know, money in the bank and the ability to grow, and with growth happening in a way that’s sustainable for everyone. And we’re doing that, which is really exciting. So, um, so for us, I haven’t yet— I haven’t yet felt that. For me personally. Yes, yes, yeah.

[00:32:13.16] - Bhavesh Naik

In your book, something that kind of jumped out at me was this idea. And I don’t know where it was written. It might have been one of the testimonials that I was reading of the people who wrote testimonials right before the book. And it’s around this idea that nature is a teacher, especially when it comes to this. Nature is a great teacher. Especially in how to run organizations, resilient organizations. So nature itself is an organization. It’s an organism. It’s an organization. And there is the quality is there is fragility and it’s fragile, right? And yet that fragility is also probably its strength. I don’t know, right? Because A good ecological system will be self-sustaining, it’ll be self-perpetuating, you know, that word in your—

[00:33:07.10] - Brenna Davis

Yeah, that’s great.

[00:33:09.01] - Bhavesh Naik

Right? So, and then we have organizations that are made of people. Right? Do you draw any parallels between the ecological systems and the, you know, you said, you know, people, you know, these are our coworkers, we call them coworkers, we don’t, you know, it’s not like corporate leadership structure. Are there any parallels between the two, the ecological system and the organizational system that— Oh, yes.

[00:33:36.23] - Brenna Davis

I mean, you know, I’ve always been fascinated with kind of the parallels with nature and kind of business, you know, from the kind of mycelial network. I think a lot about the organic movement and how there’s a mycelial network in the forest or a fungal network where trees can share nutrients between each other. And I think a lot about that, um, through that lens about different movements that we’re building or different, um, ideas that we’re sharing across different organizations or in communities, or even in, in our organization of how we share information and resources between each other. Um, I’m also really fascinated with bees. I’ve always loved bees and just, um, you know, how they, um, share resources and how they share roles and, and how they work together as a community to communicate and to, um, to support each other in, you know, finding honey and— or sorry, finding flowers to make honey. How they support their young. There’s so many different pieces of nature you can look at. And sometimes I think through designing my own or designing solutions to my own problems, you know, how would the bees do this? Or how would you do this if you were in the forest?

[00:34:55.00] - Brenna Davis

Or how would, you know, how would Ants do this, you know, ants are fascinating too and kind of the way they work. So I’m often thinking through that biophilic lens. Yes. And I don’t always articulate it, so it’s interesting you’ve asked me that, but it is, I am often thinking about it.

[00:35:13.18] - Bhavesh Naik

Yes, biophilic lens, what’s that term? Could you explain that? Oh, biophilic. You also used another technical term just a while ago.

[00:35:20.19] - Brenna Davis

Yeah, oh yeah, it’s looking, it’s exactly what you’ve described, it’s using nature as a model as a model for solving problems. And there’s a whole movement around biophilic solutions and understanding and using nature to solve societal problems because so many of— so many solutions already exist in the world. And so why not dive into nature to find a solution?

[00:35:46.19] - Bhavesh Naik

Exactly. Yeah, exactly. Yeah. And, and, uh, you know, so Could you give us an example of, you know, so going back to the purpose, right? And then you have the hive that’s around you of the people that you work with, right? Using your terminology. How do you communicate that? It’s— I know that you probably kind of express it. Is there a process where they get to buy into it? You know, there is a quote by— might be Aristotle Socrates, I forget, but I think he said, “What you express, you impress.” Whatever we talk about, we actually buy into it ourselves more and more. Is there a process where they get to have a buy-in to this purpose from their own perspective? Do you have some kind of process that you have?

[00:36:38.06] - Brenna Davis

Yeah, we’ve done a lot of thinking around how we integrate our purpose into the way we train folks, the way we communicate, the things we communicate communicate. We include it in our orientation to make sure that people understand the purpose and why we’re doing it. We made sure that we included signage and kind of little touch— visual touch points to kind of remind people of why we’re doing what we do. We have all coworker meetings where we talk about our purpose. We also do sampling and get to— people get to try different fruits and veggies. Yeah. We also share our fruits, you know, fruits and vegetables with our coworkers so that they can try things and can have, have, have like healthy, more additional healthy food to bring to their families. And then we also have something called a Hive Chat. Interesting you said that. I love it. Which is, you know, a monthly meeting when we don’t have all coworker meetings where people can come and ask any questions they have. And we talk about what’s going on in the organization. And, um, so there’s that piece. Um, and then we, you know, we have weekly, um, it’s called Buzz of the Biz, another, uh, weekly, um, business announcements that kind of highlight different purpose elements in addition to what’s happening in the business.

[00:38:02.23] - Brenna Davis

So we really worked hard to integrate it into kind of the way we approach our communication. Yeah. And always, um, always trying to touch back on the why, the, you know, why we’re there, why we’re doing what we’re doing. You know, in a warehouse, it can be the turnover on certain jobs is higher than in other professions. And so it’s something that we’re still learning about how to reach everyone because it’s challenging when you have, you know, you folks that are salespeople that might be there for a very long time. You have folks that might be, you know, stay less long in certain roles. And so, you know, working hard on retention and also how do we get the news out to newer people. And so, it’s still a work in progress. I won’t say that we’ve totally nailed it, but I will say that in our coworker surveys, more than 80% of people say they’re proud to work at OGC and they’re proud of our mission. So, it’s pretty, it’s been pretty successful, although we’re always working at it. We’re never done.

[00:39:09.11] - Bhavesh Naik

Yeah, it’s always a moving target. And it’s as it should be, right? On that point, we live in a world that’s always changing, always shifting, right? And you talk about, in your book, you talk about resilience. I think that’s one of the themes that I think, you know, you’ve addressed quite a bit, resilience. And resilient systems like ecological systems are resilient. And an organization can also be resilient. And at the same time, both of those systems are also fragile. Right? And I always wonder, and I’m just kind of thinking out loud with you. Yeah, yeah. What is it? You know, the same system, this is kind of like a paradox here, right? It’s the same system that is so fragile, also has this strength that it’s also resilient. Right? What do you think is the common thing? What is it that— what is something in there that makes the same thing that’s resilient but also fragile? Any thoughts on that?

[00:40:13.13] - Brenna Davis

Yeah, I think, you know, so much to say about that. You know, I think where I’ll start is that connection is so important, like, and, and, uh, the sharing of resources and information is what makes, um, systems more resilient. Yeah. Um, and so, so I think for me, thinking about, um, you know, my own resilience as an individual, which, um, I wrote the book Leading Through Fire, uh, resilient leadership for people who plan the future, because I wanted to support leaders in this time where we’re in the middle of this multiple crises all at once, which people are calling the polycrisis. I mean, today as we’re recording this, we have a conflict in Iran. We have, you know, immigration crackdowns that have been very hard on people, extremely hard. We have, you know, all the other crises that are layered under it, the ecological crises, societal crisis. I mean, there’s so many things that we’re holding and then as leaders, we’re expected to show up every single day, still be inspirational, still be supportive, still be the best, our best self every single day that we walk through that door or sit down to our desk.

[00:41:32.15] - Brenna Davis

And the pressure of it is a lot. I mean, everyone I know that, um, all the elder CEOs that I know have said that this is the hardest time to lead in. It’s the hardest time. We came out of COVID And we came into all these multiple crises that still weren’t resolved. Yes. And so the question for us leaders is how do we maintain our own resilience in the face of this? How do we maintain our own sort of, I would say, inner— I don’t know if the word is like a strength. Yeah, inner strength in the face of all this. And really what that is about is, making sure we’re taking care of our bodies, making sure that we’re compassionate towards ourselves and others, making sure that we’re cooperating with others and not doing what Western society often says, which is— and American society often says, which is you need to be— you’re an individual, that individualism above all else. And this is a point in time where we need each other. We need each other’s support. We need to be there for each other. So thinking about that, how do I cultivate that in my life?

[00:42:46.01] - Brenna Davis

Yeah. And in my friendships and in my professional life. And then, you know, the other pieces are around purpose. Like the purpose can help you get up every morning. The purpose can help you, whatever that might be. If your purpose is to help kids or your purpose is to help people be healthier or your purpose is to get information to people so that the world can be a more educated or whatever it is, you know, that can help you wake up every day. So really, the idea is, as leaders, building the resilience within ourselves so that can flow out to our organization. Yeah, I love it.

[00:43:25.10] - Bhavesh Naik

You brought this idea, which I think is so powerful. What you’re saying, I think, is that the system can be fragile or it can be sustaining or perpetual. It can last in perpetuity. But what makes that connection, what makes that perpetuity happen is the leadership, the right kind of leadership and all the things that you talked about in what that means, what it means to be that kind of leader, right? Would you say anything about that? Agree, disagree, feel free to disagree if I’m putting words in your mouth. But it’s leadership or stewardship or some role that you play where you take care of your own resiliency. And you bring it to the world. I don’t know what the term is for that.

[00:44:07.23] - Brenna Davis

Yeah, yeah. Well, I mean, you know, I’ve been hearing lately that there’s record CEO turnover right now, that the average time of CEO turnover is down to less than 4 years. And, you know, that’s some new data. That’s huge. Did you hear that? That’s huge. Yeah. Yeah. Well, that’s huge data. It’s like a record level of turnover. And, you know, boards, when they’re thinking about from a governance perspective about retaining CEOs, like, it’s pretty critical to think about how is that individual as a human being, as a human being that is being a leader, you know, supporting, you know, supporting themselves and how resilient is that person and how can we support that person in their resilience. Yeah, um, I, I, I think that, you know, an organization shouldn’t just rely on their CEO or their executive, that developing the bench strength of the leaders around you and developing the leadership all the way through the ranks— because, um, I’ve always thought that, um, I agreed with something one of my mentors said, which was, you know, everyone’s a leader. If someone is looking up to you, then you are a leader, whether that’s your, your little sister.

[00:45:23.23] - Brenna Davis

Well, that’s your— yes, you know, you’re, you’re, uh, the guy in grocery store that sees you, whatever, then you’re a leader. So I’ve always, um, you know, we’ve worked really hard to start to do more work with our leadership at every level, um, you know, moving down even into the supervisor level to invest in them, um, so that it’s not just relying on one person, so that we are a community of leaders supporting each other, that if there’s a challenge, then you can pick up the phone and you can call someone and there’s someone on the other line, or you can text someone, hey, this challenge is happening. What are you doing right now with that? And so just building those connections between the leaders too has been really critical for us. So I think it’s not just the person that theoretically people say is at the top, but it’s the whole suite of leaders within an organization that really make things happen. And as a CEO, my job is to— articulate the vision, but also clear the way so that the work can happen.

[00:46:26.01] - Bhavesh Naik

Right. Clear the way. Yes, absolutely. Yes. So the whole hive of leaders, right? Yeah, the hive of leaders. And that’s what makes it resilient. Yes, that’s right.

[00:46:39.14] - Brenna Davis

Yeah, that’s interesting. Yes, because, you know, that’s exactly the model that bees follow.

[00:46:44.06] - Bhavesh Naik

Yep. If you can hold up your book. Oh, sure. Do you have it in front of you? Yeah. Here’s the book. There you go, yeah. It’s probably flipped, we’ll see, but for our audience, we’ll flip it so that they can read it. Does that come from experience, leading through fire?

[00:47:00.01] - Brenna Davis

Yes, it sure does, it does, absolutely. You led through fire. I think you and I talked earlier, one of the things about working on environmental issues is that your work is never done. It’s not like you are a bricklayer or you built a house where you can see at the end of the day, you know, the house is built and you, you know, I guess mission accomplished, I did it. It’s something that’s really a long haul and some might say, and it can feel like a lost cause at times, like working on climate, climate issues. There’s been so many times where I would just grieve because we didn’t make it as far as I wanted to. Or right now, you know, we’re above 1.5 degrees Celsius in terms of global warming on the planet. We haven’t, we haven’t kept it below levels that are going to, um, really impact future generations. Um, but, uh, working on those causes gave me a lot of insight in how to keep going, you know, which is, uh, to really focus on healing yourself and to focus on healing, um, and building that resilience within yourself so that you can continue on in the movement And so many folks that work on social issues or environmental issues or issues that are long-haul issues, sometimes we will just burn out.

[00:48:24.05] - Brenna Davis

And I found a parallel between that and being a CEO. And when, you know, when I saw the world kind of shifting earlier last year or late last year, I kind of locked myself in a room and tried to write down everything I could as fast as I could to try to get what I know about how to stay resilient out to others leader. So really, it’s, it’s a love letter to them. It’s, it’s a, um, and I wrote it so that you can, um, I like to read in the morning, so I wrote it, uh, so that it’s— each chapter is very easy to read, um, over a cup of coffee. So it’s not a, uh, you know, it’s not a scientific tome, it’s not a, uh, you know, something that’s really hard to, to, to get through. It’s an easy read, and at the end of each chapter, there’s some clear takeaways that you can apply that day, uh, for to improve your leadership. So it’s meant to be, it’s written for other executives.

[00:49:24.04] - Bhavesh Naik

Yeah, it’s a love letter to them, as you said. Yes. And I love the framing. Walking Through Fire. We talk about one thing that we talk about on this podcast a lot is just kind of internal change that we all go through. And leaders who lead, ultimately, we had a writer, another author, Tobe Folarin, and he said something so beautiful. He said that As a writer, and I think this applies to any creation, if you’re a business owner or painter or what have you, your creation at one point as you’re creating it is going to call out to you and challenge you and say, “You need to grow to be able to do justice to me.” Yeah. Right? It forces you to grow and expand and self-develop. You know, Growing resilience and growing in many different ways. So, has there been a moment— and when we talk about what I call the dark night of the soul moment, it doesn’t have to be so dark all the time, but has there been a moment that was like a defining moment where you thought that it was like the bottom? That, you know, okay, this is a lost cause.

[00:50:31.13] - Bhavesh Naik

I’m not going to come out of this. It could be career, it could be business, It could be personal setback, anything like that that you can talk about from your experience, from your career life.

[00:50:44.15] - Brenna Davis

Yeah, you know, I did have a moment kind of mid-career when I considered shifting what I was doing. I just remember feeling like I kept hitting my head up against the wall in this organization I was working at. Like, they were kind of, I felt like, giving lip service to it. I felt like, you know, the work I was trying to do, which was to kind of improve the sustainability of the company, wasn’t well valued. And they sort of let me do it, but they weren’t really bought into it. And I was running a green team, which is kind of like the sustainability team. And I just remember the executives— there’s one executive that seemed interested. And I had a situation where, you know, the CEO wasn’t very responsive and in fact a little dismissive. I would— not a little, a lot dismissive. Um, and I considered quitting. Um, uh, I considered going into another field and maybe just doing environment, you know, environmental work somewhere, or not working in the business world because it just seems so, um, not valued. Um, but I kept going. I, I realized that this is really what I wanted to do after a long contemplative process.

[00:51:56.15] - Brenna Davis

I think it took me 6 months to kind of really, um, really recover from it. And, um, I promised myself, because I read in the Harvard Business Review that, um, women don’t apply for jobs unless they have 80% of the qualifications, but men will apply if they have something like 30. And so I promised myself I would apply after reading that to my dream job, right? Um, no matter what, if I thought the qualifications— so I applied to a dream job and I got it. And that was a defining moment. Like, I had so much freedom in the other job. I was respected for my, um, what I shared, and I had the courage really to apply for it, which for women sometimes takes more. But ladies, remember this, this, this, this, this thing, which is that men will apply for 80% when they— when men will apply with 30% of the qualifications, women wait until we have 80. So always put your hat in the ring, ladies. I’ll just say that. Um, there you go. But I got this great job, so inspiring, and ended up working, um, multinationally. I ended up like at the Paris Climate Talks.

[00:52:58.01] - Brenna Davis

I did such incredible work at the White House twice. I ended up on a panel, um, after doing really great work on climate with Vice President Gore. I just had these incredible experiences. And so, you know, that dark night of the soul sort of turned into something like it just blossomed, I guess. Wow. And I will say too that later I got some, I heard someone talking about the work that I did years ago and that they were, they had started using it and were still using it in the organization. So what I didn’t see back then was that the work I was doing was really important, even if people didn’t value it, and that today it lives on in that organization 20 years later. So, so I think sometimes we don’t see all of our impact in the moment, or we’re— maybe we’re ahead of the curve, ahead of the times. Yeah. Um, but having, having courage to try something different and also having the courage to kind of keep going and to do what you’re doing, uh, also was is a good thing. And remember, like, courage isn’t the absence of fear, it’s walking through the fear.

[00:54:08.19] - Bhavesh Naik

I love it. Yeah.

[00:54:10.06] - Brenna Davis

Courage isn’t the absence of fear, but it’s walking through it, walking through fear. Yes. Courage. Yeah. I love it.

[00:54:18.09] - Brenna Davis

Yes. So it doesn’t mean I wasn’t afraid when I clicked that button. In fact, I had a little glass of wine and then I clicked the button to submit that application. But, you know, Yeah. But I was able to walk through it. And it was the same thing when I was asked to go on morning television one time, and I’m an introvert, like, just walking through it.

[00:54:39.19] - Bhavesh Naik

Yeah. Yes. And, you know, if that’s not a definition of resilience, I don’t know what that is. Because, you know, you hit your, you know, the dark night of the soul moment, and you come out of it with a success story. So that’s resilience. That’s resilience defined in my view. What do you think the future holds for us 20, 30 years down the road? You know, we are in a very strange place right now. And are you optimistic? I suppose we all have to be, but— and, you know, what’s your take on it? Where do you think we’re going overall as a humanity, as a nation, you know, as a civilization.

[00:55:24.12] - Brenna Davis

You know, I, I have a— we’ve been through a really rough period where I’ve seen things happen in this country that are not aligned with my values, and where, um, I— things have gotten a lot more challenging than I would ever have guessed in my lifetime. Um, and I, I do— one of flickers of hope is that I’m seeing that people aren’t agreeing with it. I’m seeing that the majority of people are not happy with how the direction that things are heading right now. And so I, I do have hope that things are going to shift, and I do have hope that ultimately we’re going to come out of this with kind of a new sense or renewed sense of commitment commitment to other people, commitment to human rights. And I think in the future, it’s gonna be challenging for us. I mean, if you look at the science in terms of climate change, we’re gonna get more severe storms, we’re gonna, you know, weather patterns are gonna shift and all of it. But one of the things is that I have a lot of hope because I have hope in human resilience. I have hope in the creativity of human beings that, We’re going to need to develop these skills to be adaptive, to be flexible, to be nimble.

[00:56:49.23] - Brenna Davis

And, you know, we’re seeing movement in the produce world of people growing, moving their production. Really? I mean, we’re— yep, we’re already seeing that. There’s already been climate migration that’s happening globally, and there are people migrating, climate migration happening in the US too. So all of this is happening right now in real time. Um, but I think I just, I have hope in the, like I said, the creativity of human beings and the adaptation, um, that, that we’re going to have to do, um, and that we already do. And I, I do think that the majority of people are, are decent and are, um, loving and care about each other. And so, um, yeah, I have confidence, you know, maybe it comes from working on kind of both sides of the spectrum in the refinery, or maybe it comes from being exposed to all sorts of people with different perspectives and having respect for them. But I do think that we’re going to come out of this better. It’s going to be tough.

[00:57:48.12] - Brenna Davis

It’s going to be tough. And we’re going to come out of this better.

[00:57:51.19] - Brenna Davis

Yes. And it’s like that dark night of the soul moment, right? Maybe this is our collective dark night of the soul moment. And we’ll find, we’ll dive deep within our own souls and collective soul, singular, and find solutions that move us forward as a humanity and as a civilization.

[00:58:14.18] - Brenna Davis

Yeah, and we’re making exponential improvements in the energy world right now. And some people are saying, well, you know, obviously AI is having huge implications on society and shifting how we do work, shifting the type of work we do, shifting all sorts of elements of of society. And, um, it’s also shifting the energy that we have and the amount of energy that we’ll be able to produce. And I think shifting— it’s driving, um, the requirement that we will produce more energy, and that is leading to more clean energy innovation. So I’m really confident that, you know, right now we’re, we’re facing— as we record this, we’re facing kind of a fuel challenge as the Strait of Hormuz is closed down to a trickle, and that’s 20% of the world’s petroleum coming through plays. Um, and so I think, you know, having that experience again as a society may, may drive us towards more of that clean energy. So we had kind of a double, double, double, double influence here, which is, you know, needing more energy for AI, which largely has been the clean energy sphere, and then also this piece around electrification, um, of transportation.

[00:59:25.11] - Brenna Davis

So I’m hoping, um, You know, that we get through this tough period and then that’s how we’ll emerge. Yes. Yeah.

[00:59:34.00] - Bhavesh Naik

I heard somewhere, you know, it’s darkest before dawn. So maybe that’s what it is. I hope so.

[00:59:39.02] - Brenna Davis

Yes. I really hope so. I pray that that is true. Yes. Yeah.

[00:59:44.22] - Bhavesh Naik

Is there anything that I didn’t ask that we didn’t, you didn’t get to talk about, but that is very close to your heart and you would like to kind of share with the audience?

[00:59:52.21] - Brenna Davis

I think we’ve covered a lot and, um, yeah, I feel like I’ve I’ve shared, I’ve really enjoyed the conversation and yeah, now I feel great. Excellent.

[01:00:05.17] - Bhavesh Naik

Your book, how do we find it?

[01:00:08.22] - Brenna Davis

Yeah, the book is on Amazon, it’s on Barnes Noble, Apple Books. So it’s easy to find and it’s all over the place so you can pick one up. And I also made an audiobook because I really believe that. Oh, that’s awesome. Yeah, I really believe that, I got in this debate once at a dinner party where someone said that reading an audiobook isn’t the same as re reading a book. And I, um, I really am passionate about, um, people that have neurodiversity. And I know sometimes for those folks it’s easier to listen to a book. So I wanted to make sure that I provided access for them, but also busy, busy people. We like to listen to audiobooks in the car. So anyway, I made sure we had an audiobook. Um, and then if you’re interested in learning more about Organically Grown Company, You know, we have a website, organicgrown.com, and, you know, Perpetual Trust Ownership Network has a great website if you’re interested in the Pitons’ work. And then I have my own personal website, which is brennadavis.com. Okay. We’ll put all of those links in our show notes.

[01:01:16.19] - Bhavesh Naik

Okay, great. We put them, we have show notes section underneath, and we’ll put all those links so that folks can get hold of you. So, Brenna, I so appreciate this time we spent together. This was an exciting conversation and also very thoughtful, very deep conversation. And those are the kinds of things that we do on this podcast. So I really appreciate you thinking out loud with me. Thank you. On a lot of these issues that affect all of us. Thank you.

[01:01:42.23] - Brenna Davis

Yeah, I appreciate it too. And evidently my dog has joined us here.

[01:01:46.18] - Bhavesh Naik

So bring him or her over and let’s see. Say hello to the audience.

[01:01:51.23] - Brenna Davis

He is, he is my husband, but if I remember, he just left. Anyway, yes, I’ve really enjoyed it too. And I really want to say thank you for the work that you’re doing to try to illuminate these other business models and to support the leaders that are making this happen right now in the world. It’s so critical that they get the support and the new ideas and are exposed to different ways of working. So that future generations can thrive and so that they can thrive as human beings.

[01:02:22.02] - Bhavesh Naik

Absolutely. I think we come from the perspective that the best renewable resource we have is here and here. Yes. So it’s the head and the heart and center. So, you know, as long as we are tapping into that, you know, there’s always hope. So with that, thanks again. Thank you. We’ll continue this conversation in other ways.

[01:02:44.06] - Brenna Davis

Yes, yes, I would love to.

Contact Brenna Davis

Brenna can be reached through her website at https://www.brennadavis.com/ or through her Linkedin profile.

The episode was also published on YouTube under the title “What If a Company Didn’t Belong to Its Owners? | CEO, Organically Grown Company.” If you watch your videos and podcast on YouTube, subscribe on YouTube as well do you will get notified when the new episodes drop.

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As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

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Deepen Your Discernment

Kevin Gaskell’s career is a powerful case study for that idea. He is a former CEO of Porsche, BMW, and Lamborghini, where he led major turnarounds and growth strategies. He is also an active entrepreneur who has built fifteen companies, creating teams that have generated over eight billion dollars in shareholder value, and is currently building five companies.

What stays constant through that kind of change? His answer is simple and surprisingly demanding: when you commit to achieving a goal, you either do it or you do not. “Try” is not a management approach. It is a form of uncertainty.

The constant: realism plus a belief that goals can be achieved

Many people label him an optimist. He does not reject the word, but he prefers “realist.” His realism is not pessimism. It is confidence rooted in repetition: if you set a goal and bring a team with you, it becomes possible.

That is true whether the goal is reaching the North Pole or taking a business from performance level one to level ten. The common denominator is not the environment. It is how leadership defines success, tells the truth, and mobilizes the team.

“There’s nothing as ‘try.’ You’re either going to do it or you’re not.”

A leadership philosophy that starts with people, not numbers

Across business and expeditions, Gaskell’s philosophy keeps returning to one theme: ordinary people can achieve extraordinary goals when they work together with clarity and commitment.

That clarity has a specific structure. He does not start with revenue targets or profit numbers as the primary story. He starts with a vision of success people can visualize emotionally and operationally.

Vision of success: what success looks like, sounds like, and feels like

In leadership terms, “vision” is not a motivational poster. It is a shared sensory picture that becomes the target of the team’s attention.

When leading a CEO team or building an expedition plan, he brings the group together and asks:

• What does success look like?

• What does success sound like?

• What does success feel like?

For “sound,” he means how people communicate when the organization is operating like a world-class unit. For “feel,” he means how it feels to be part of it. People are not energized by abstract spreadsheets. They are energized by belonging to something extraordinary.

Yes, monetary success matters. But the point is sequencing. You do not inspire a team by saying the job is to “make 100 million” or “hit pounds profit.” You inspire them by making the goal world-class, then letting the financial results follow because the organization plays great football, not just great numbers games.

The truth: only one version of reality

Once the vision is defined, leadership must do a second, equally non-negotiable step: tell the truth about where the organization is today.

Gaskell calls it “honesty” and he is direct about it: there is only one version of the truth. There is no hidden story for leadership to protect itself. No embarrassment. No blame game. Just reality so the team can plan the journey from here to there.

This step matters because a vision without truth becomes fantasy. A truth without vision becomes despair. Leadership needs both.

The journey framework: Commit, Connect, Create

Between vision and truth sits the actual work. Gaskell breaks that work down into a framework that works in business turnarounds and expedition operations.

1) Commit: what we are committing to achieve

Commitment means the vision is not “someone’s idea.” It becomes the team’s agreement about where you are going and what it will feel like to reach it.

When commitment is real, you can feel it in the organization’s energy. If the business feels slow and stuck, people start to drift away from the mission. If it feels urgent and alive, they lean in.

2) Connect: make sure everyone has a role

Commitment is the goal. Connection is how the goal spreads into the organization.

Gaskell’s principle is blunt: there is no such person as “only” a sales director or “only” a cleaner. No role is too small to matter, and if someone does not have a meaningful role in the journey, the leadership must question why they are there.

Connection is also leadership presence. Gaskell repeatedly talks about walking the business, making the priorities visible, and inviting people to take control of the part of the plan that sits in their responsibility.

When leaders connect successfully, two things happen:

• People see they are critical, not interchangeable.

• Ideas flow because ownership creates momentum.

3) Create: creating “magic” through shared execution

Create is where teams stop merely agreeing and start acting. It is “magic” in the sense that performance rises when people work together with a shared goal, shared responsibilities, and the authority to change things.

A key leadership behavior here is trust with accountability. He gives people authority to execute. If it does not work, the team discusses it and finds a better path, rather than punishing the attempt.

In practice, Create looks like:

• inviting people to contribute ideas

• making the priorities visible so debate is focused

• encouraging small experiments to move closer to the vision

And crucially: positive energy is contagious. Negative energy is too. Leadership must actively cultivate optimism through action, not by wishing.

Automotive turnaround example: taking Porsche from last to first

One of Gaskell’s clearest examples is his Porsche experience. The company had lost its way. The marketplace shifted. Product strategy was ineffective. Dealers lost confidence. Staff morale collapsed. Cash hemorrhaged. The situation was severe.

When he was appointed to manage the business, he asked a straightforward question to start: What does success look like?

The team had data that made the challenge unmistakable: among 32 brands, Porsche was number 32 for customer satisfaction. Sales were down 20%, and there were three years of unsold new car inventory. “Doesn’t get much worse than that,” he notes.

Then they debated what customer satisfaction success meant. They discussed top half, top five, and finally a bold ambition: number one.

The goal was not chosen because it sounded inspiring. It was chosen because the team believed customer satisfaction would define long-term success.

Turning vision into priorities (and cutting the noise)

In the Porsche turnaround, the leadership shift was not only what they wanted. It was what they decided to stop doing.

When leaders face too many possible initiatives, nothing happens. So he describes a prioritization method:

1. List the actions needed to reach the vision.

2. Rank them from priority A through C (or further).

3. Draw a line halfway on a whiteboard and throw away the bottom half. “We’ll never do them.”

4. Then prioritize the top half and draw a second line.

5. Focus on roughly the top 25% of critical actions.

That focus became the shared operating system. It also enabled fast decisions, including dramatic cost-base reductions and actions to reduce new car inventory.

He emphasizes a cultural point: he does not believe in incremental change as the main solution. The alternative is to inspire people to go somewhere completely different.

Transformational growth thinking: from 25 to 1, not 24 to 20

When people ask for 4% growth because the market grows at 2%, that is incremental thinking. He pushes the team to think in jumps that force real creativity.

To help teams shift mental models, he asks a “make it easy” question: not “What would it take to grow 40%?” but “What would you do to go 400%?”

That exercise breaks the habit of safe budgeting and encourages the team to identify the real levers that could change the game. Those levers are often the ones that inspire the team, because they are clearly connected to the mission.

In Porsche’s case, the outcome was dramatic: in four years, the company moved from number 32 to number one.

How this becomes culture: trust, clarity, honesty, and visible execution

Culture is often talked about abstractly. Gaskell treats culture as something you build with concrete behaviors.

He summarizes his culture foundation with three pillars:

• Trust

• Clarity

• Honesty

In the boat manufacturing example, he spent half of his working week in factories walking around, talking to teams, and asking for their expertise: “You tell me how we can do this better.”

Then he operationalized priorities into a plan that people could see. His tool is intentionally simple and hard to ignore: a one-sheet plan, printed and posted in the office.

One-page plan and the timeline: 100-day and 1000-day planning

The plan is visible, not buried in software tools that no one opens. He uses two planning horizons:

• 100-day plan: stop the bleeding, build stability, get control.

• 1000-day plan: build something world-class.

The point is alignment. People need to know what matters now and what builds capability over time.

Creating authority and innovation: give people the right to change things

One of the most interesting practical details is how ideas enter the system.

Gaskell rejects the idea that people should be paid a small amount for submitting ideas. Instead, he treats ideas as part of the job: “Bring your brain and put it to work because that’s why we employed you.”

But he still rewards innovation in a more meaningful way: when the organization succeeds, bonuses and equity follow. The motivation is not “get paid for a suggestion.” The motivation is “build a world-class organization with outcomes people can share.”

He also makes it safe to try things. The leader’s job is to create a culture where experimentation is expected, and where failure is handled without fear.

Prioritizing in real time: when you do not have luxury for disagreements

The expedition world reveals why preparation matters. On a transocean rowing journey, time to discuss is limited because the work is relentless. There may be only short breaks, such as a 20-minute pause during New Year’s Eve, with everything else continuing on schedule.

So priorities must be aligned before the expedition begins.

In the Atlantic crossing example, they aimed to:

1. Win a race

2. Set the world record

3. Do it as friends

That order matters. If everything goes wrong, the team needs a shared way to return to priorities rather than argue in the moment.

Failures happened: seat bearings broke, the water maker packed up, people got sick, and the team lost significant body weight during the 35-day crossing. In those conditions, the team needed roles, trust, and a focused process for decision-making.

The lesson for business is clear: you cannot invent alignment while things are falling apart. Planning is what allows the team to respond calmly.

Why “slow down” in business: build belays and anchors before you climb higher

Gaskell’s advice to growing businesses sometimes surprises people: slow down.

He explains it with rock climbing. Climbers move in pitches, then lock in solid anchors before continuing. If you fall beyond an anchor, you can fall far enough to fail completely.

Business growth is similar. When scaling dramatically, leaders must still build foundations:

• consolidate what works

• ensure safety and systems

• train teams properly

• improve products in the right direction

“Sometimes those anchors are six months apart,” he notes. That means consolidation and safety are not always immediate. But they must still be real.

In growth, haste can create waste. If you fall, you do not want it to be past the anchor.

Handling failure: invite experimentation, but catch people in

Failure is part of success. Gaskell’s perspective is not “avoid risk.” It is “manage risk intelligently.”

He differentiates two types of leadership behavior:

• Leaders who create safety nets so people can experiment and learn.

• Leaders who create fear so people avoid mistakes and stop trying.

His guiding line is: “Catch people in, not catch people out.”

If something goes well, celebrate openly and discuss what led to success. If something goes wrong, keep the conversation calm and focus on learning and adjustment.

That approach builds a culture where people feel safe to drive change. If leaders punish mistakes, then the organization will never move far enough to reach its best potential.

Why he keeps doing hard things: memories over wishes

People often ask why a successful business leader would keep choosing extreme challenges. Climbing mountains. Rowing oceans. Walking to polar extremes.

For him, it is not performance. It is not ego. It is excitement. It is curiosity. It is the desire to end life with memories, not dreams and wishes. He rejects the “I’d love to do that, but…” pattern. Decide what you want, then do it.

He also stresses humility. You do not “tame” oceans. You stay a guest in them. If arrogance creeps in, nature teaches quickly how small a person can be.

His definition of success today

After decades of leadership, his idea of success is not only the accumulation of titles or achievements.

He measures success in three practical ways:

• Stewarding businesses safely: handing off organizations so they remain secure and continue growing, without asset-stripping or short-term exploitation.

• Helping people grow: recruiting leaders early and then watching them become more capable over time. He still values conversations with people he helped launch.

• Creating contribution beyond one person: building platforms to share proven processes and leadership tools with entrepreneurs and corporate professionals.

He also values balance and leisure now because he is not as young as he used to be. Still, he works because he enjoys it. When you love what you do, work feels less like work.

How to apply Commit, Connect, Create in your own organization

If you want a practical starting point, use his framework like a leadership checklist.

Step 1: Define success in sensory terms

• What does it look like?

• What does it sound like?

• What does it feel like?

Step 2: Tell the truth about where you are

No hiding. No blame theater. Just one version of reality.

Step 3: Commit, Connect, Create

• Commit to the goal as a team.

• Connect everyone to a meaningful role.

• Create execution: authority plus accountability, supported by visible priorities.

Step 4: Prioritize and cut the noise

List actions, rank them, draw the lines, and focus on the small set you can actually execute. Ignore the rest.

Step 5: Build anchors before you climb higher

Consolidate systems, train people, and ensure stability. Growth needs belays.

Parting thought: leadership is a safety net for ambitious change

What transfers in leadership when the industry changes is not a list of tactics. It is the ability to hold a team to principles: belief in achievable goals, clear vision, honest reality, priorities that cut through noise, and a culture that allows experimentation while leaders take responsibility for the safety net.

If you want to be successful, that may mean climbing higher than you planned. But do it with anchors in place.

Get In Touch with Kevin Gaskell

For more insights and practical guidance on Kevin’s approach to leading organizations, building businesses and charting expeditions, visit his website at kevingaskell.com or reach him via Linkedin.

This article was created from the live video conversation on The Business Philosopher Within You podcast. The episode was published on YouTube under the title “Catch People In, Not Out: The Philosophy of World-Class Teams | Keving Gaskell.” The article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Kevin above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understanding

Bill Kasko, CEO of Frontline Source Group, argues that real philosophy has to survive those moments. Not survive in theory. Survive in the daily grind where hiring collapses, processes break, and people wonder whether the company will make it through.

What follows is the kind of business thinking that turns into execution: a practical loop where people, process, and service keep reinforcing each other, even when the environment punishes slow movers.

The myth: “People problems” are often process problems

One of the clearest insights from Kasko’s experience is how often leaders misdiagnose what’s actually happening.

In the real world, teams tend to label breakdowns as “people problems.” Someone wasn’t motivated. Someone didn’t care. Someone made a mistake. Then the leader tries to solve it by changing personnel.

Kasko’s counterpoint is simple: the root cause is frequently a process problem that creates a service failure, which then gets interpreted as a people failure.

That’s why his framework begins to look less like corporate wallpaper and more like a diagnostic tool:

• People: are we hiring well, staffing correctly, and building a team that fits and grows?

• Process: are we doing the work consistently, documenting how decisions get made, and following through?

• Service: are clients experiencing reliability, responsiveness, and results?

When something goes wrong, you do not just ask “Who caused this?” You ask which pillar broke, and how the other two pillars amplified it.

How trust becomes a system, not a feeling

Trust is often treated like a mindset: be honest, be respectful, show integrity. Those things matter. But Kasko’s experience pushes trust into something more operational.

For Frontline Source Group, trust is enforced through behaviors and mechanics, not just intentions:

• Honesty is non-negotiable. No creative storytelling. No “let me sell you on an outcome.”

• Ethics show up in agreements, clarity, and full disclosure.

• Respect is treated as a requirement. If you don’t respect people, you shouldn’t be there.

• Communication is treated as a core value, meaning people can give input and ask questions without being shut down.

And this is where philosophy becomes enforceable. In his words, calls are recorded and agreements are signed. The point is not bureaucracy. The point is: you can’t build trust on vague promises.

Frontline’s origin story: an idea that refused to stay an idea

Many founders start with a vision. Kasko started with one, too. But his story is not about staying loyal to the original plan. It’s about learning what traction actually forces you to become.

He began in human capital staffing with an early focus on a very niche direction, even imagining he could run things largely from home. The industry, however, did not care about the plan.

Within months, the placements shifted. What began as one specialty evolved into others because the client needs kept coming first:

• Administrative, HR, legal, and accounting needs showed up before the IT focus fully materialized

• Then the company expanded into additional specialized roles, including oil and gas

A memorable example was the first time a client asked for 20 geologists. The conversation went from “Not a problem” to “What does it pay?” and suddenly the company realized it would need to learn an entirely different world to serve that client well.

That moment helped shape a truth that repeats in his leadership approach: you do not build a company by clinging to your first idea. You build it by building the capability to fulfill what the client actually needs.

Why clients chose Frontline Source Group: coming from the void, not the script

Kasko describes a structural advantage he was early to adopt: instead of trying to “beg for business” through constant calling, he designed a way for clients to approach him.

He created an internet-first path long before it was common in his industry. The website wasn’t just branding. It was functional and positioned around what irritated large clients:

• They were tired of phone calls.

• They were tired of gimmicks.

• They wanted an easy way to find solutions without being interrupted constantly.

One example he mentions: early online chat availability on the website, so prospects could ask questions any time and then transition into a phone conversation only when it made sense.

This is not just “marketing.” It is philosophy expressed through service design.

The diagnosing lens: when the boat is big, you still have to turn it

Large companies often have plenty of salespeople and not enough recruiting depth, and Kasko noticed a mismatch in how resources were allocated.

But his deeper point is about timing. Growth triggers change. Businesses that do not recognize the indicators become late to reinvention. And when they try to turn a massive ship later, they spend more time struggling than moving.

So Frontline’s early advantage was not merely being smaller. It was being more adaptive in the moment when clients were ready to adapt too.

The three pillars emerged through execution, not through inspiration

One of the most important parts of the story is how Kasko describes the emergence of his framework.

During harsh conditions, like the late-2000s recession period, the company kept running into failures that were never isolated. The problems showed up as:

• a people breakdown

• a process breakdown

• that produced a service breakdown

In other words, he discovered in real time that the company’s problems were interconnected. Once he recognized that, solving individual symptoms stopped being enough.

That’s when the framework “clicked”: the pillars were not separate categories. They were the system.

He also connects the pillars to everyday human life: we live by people, process, and service personally and professionally. Relationships shape us. We follow routines. We give back to others through service. The business version just makes those principles explicit and repeatable.

From insight to action: the 5-year placement warranty bet

Frontline’s most famous differentiator is something rare in staffing: a five-year placement warranty that acts as a negotiation tool and a proof of confidence.

The idea started with a personal moment. While working through financing for his daughter’s first car, he discovered a five-year warranty and joked that their staffing company typically “only did 90 days.”

But the question followed: why not five? He and a group of managers locked themselves into a conference room and drew the model out on a whiteboard for eight hours. The critical part was stress-testing the economics:

• How could the company avoid losing money?

• How could it prevent gaming the system?

• How could it stay fair while still being compelling to clients?

They beta tested it for three months, then launched it. The company was bashed publicly. Yet the pushback became confirmation, not discouragement.

Why it mattered: during and after COVID-related rehire cycles, companies remembered Frontline’s model. They asked for the warranty again, and Frontline honored the spirit of the commitment through a good-faith approach.

That’s how trust becomes a system: the company doesn’t only promise something. It builds a structure that remains coherent under disruption.

What the warranty actually means

Kasko is careful with language. They do not use “guarantee.”

They describe it as a longer-term warranty concept around placement and the likelihood of tenure. Since average tenure at many role levels is commonly measured in about a couple of years, the model is positioned around the idea that if someone leaves after the early window, it is less about “failure” and more about outcomes that the warranty can address economically.

Instead of refunding the fee, the company reduces the placement fee when the client comes back for another hire of that same role under the warranty terms.

In Kasko’s view, that matters because recruiting is hard and time-consuming. In staffing, the industry too often sells on short windows and failure framing. Frontline wanted to sell on a positive outcome: promotion and retention, not panic and penalties.

Process matters because recruiting is inherently difficult

Kasko emphasizes something every HR and talent leader recognizes: recruiting is not easy. It isn’t revenue-generating, so companies often treat it as an overhead function. But that perception causes underinvestment.

Recruiting requires:

• time and persistence

• high-quality interviewing

• emotional intelligence when candidates are stressed or guarded

• consistent decision-making so the service experience stays dependable

So Frontline built process early. Kasko describes being process-driven from his IT background. At first, he didn’t document everything. But as the company evolved, the process became a “playbook” that could be repeated, trained, and improved.

That documentation is what prevented the philosophy from collapsing when leadership couldn’t manually hold everything together.

Pressure tests: recession, oil bust, hurricane “bug-out boxes,” and COVID

Business philosophy is easy when everything is stable. It becomes real when the company is forced to adapt instantly.

Kasko describes multiple shocks that changed how the organization operated:

• The Great Recession: survival mode, uncertainty, and the need to identify what pillar was actually failing

• Oil and gas bust around 2016: large client positions pulled away, offices closed, and the company shifted toward remote operations

• COVID: hiring and business collapsed overnight, large clients disappeared, jobs were lost, and everyone shifted to working from home

But the key difference was preparedness. The company had already invested in digital interviewing and technology, and it treated process as a foundation rather than a temporary workaround.

He even mentions hurricane readiness in Texas. They prepared “bug-out boxes” so teams could mobilize, go home, and keep operating without a total shutdown. Then COVID arrived, and a similar logic applied: if disruption forces a new service need, the company can adapt quickly because the operational muscles already exist.

When a public need emerged like large-scale parking-lot swabbing, they said no at first, then adjusted. They learned how to help in that context and kept hundreds of people working across the state.

That is philosophy translated into execution. It is not “we care.” It is “we built systems that make care operational.”

AI and the “stay ahead” challenge: the tech changes faster than the hype

Kasko credits their early digital readiness for helping with AI readiness too. In his view, it is not that AI is scary. It is that the marketing around AI can be full of disinformation and confusion.

He points out that while other technology cycles used to give companies time (18 to 36 months in many cases), AI moves far faster now, changing every 18 to 36 days.

So the real challenge is not “Are we on AI?” It is:

• Are we testing and learning?

• Are we using automation where it improves the service level?

• Are we separating hype from practical capability?

• Are we staying skeptical of claims?

His comparison to past technologies like the microwave is on purpose: technology can enhance work, but you still need cooks and chefs. People determine how to use it well.

Building a business you can step back from: what “run without me” really means

A sustainable organization is one where operations do not collapse when a founder steps away. Kasko doesn’t claim he has an easy “go on sabbatical for six months” button.

He says he has considered it. Yet after 22 years, his role evolved into something he can still do effectively: running a desk, recruiting, running a niche division, and personally placing talent in a specialized area. He even describes a peer who is still running an agency in his 90s, suggesting longevity can be part of the structure.

But there is a more important operational truth behind his answer: Frontline has already resized by leveraging technology and process.

He notes that many large competitors carry thousands of internal employees for recruiting and staffing functions, yet many will not survive because they do not scale their operating model in time. Frontline, he believes, was already moving in that direction, doing the work of a much larger force with fewer people.

For him, that is how a business becomes less founder-dependent. Not by removing the founder, but by institutionalizing the system.

Values that actually get enforced: everything starts here

Values only matter if they show up in behavior and decision-making under stress.

After the late-2000s recession period, Frontline began using a motto tied to an internal philosophy: “Everything starts here.”

It is an acronym rooted in four values:

• H for honesty

• E for ethics

• R for respect

• E for entrepreneurial (allowing people to act, test, learn, and even make mistakes in controlled ways)

Later, a vice president added the part Kasko says they had forgotten: C for communications. The internal motto became cheer everything here, emphasizing that people must communicate openly and collaboratively.

He also talks about enforceability as culture. If someone cannot follow the honesty, respect, and ethical standards, they should not be in the organization.

Execution loops: weekly one-on-ones and Wednesday video calls

Having values is one thing. Having a feedback loop that keeps values alive is another.

Frontline uses recurring communication rituals:

• Wednesday video calls with everyone, longer than a standard meeting, focused on recap and full alignment

• Weekly one-on-ones with managers and with Kasko, typically around 30 minutes and centered on support and barriers

The theme is “over-communication” without micromanaging. Kasko describes it as reducing distance and making it collaborative, not “open door” theater.

Importantly, he also describes a leadership stance on mistakes and healing:

• Face it

• Fix it

• Heal it

• Move forward

He acknowledges how painful it can be to look back at decisions like terminations or firings. But he also says they learned from outcomes and, in many cases, later heard that the person leaving was ultimately the right move.

The most underused leadership skill: listening (especially across generations)

Kasko argues that leaders get more effective by becoming better listeners. Not occasional listening. Continuous listening, including:

• learning from boards and policy groups

• surrounding himself with people smarter than him

• adopting tools used by the next generation

He gives a telling example at a family dinner where younger relatives explained they do not “Google” the way older generations do. Instead, they use TikTok to look up what they need.

That wasn’t a marketing trick. It was a signal: if you aren’t listening, you’re designing for a world that no longer exists.

He also relates this to Frontline’s content growth. When advised to improve their approach to video subscriptions, they changed execution and increased engagement through consistent daily posting.

What to do when you feel like quitting

Even leaders with strong systems face moments where it feels like too much. Kasko describes multiple “I’m not sure I can do this” periods.

The Great Recession was the first major time. A mortgage financing collapse and the resulting uncertainty forced tough financial and operational recalculations.

Another came with the oil bust, where expanded offices and clients suddenly disappeared. The company closed locations and shifted toward virtual operations.

In the later 18-month period before the conversation, he described a different kind of strain driven by shifts in hiring and how candidates behave, including ghosting during job searches after a hiring power shift during the Great Resignation period.

His response was not to pretend it didn’t hurt. He dug deeper into what still made him happy, what still excited him, and how to sell differently by showing value rather than pushing a script.

He also made a hard decision: Frontline fired about 40% of clients that were “tire kickers” who consumed resources without writing checks. In his definition, they were not fully clients until payment actually happened.

Philosophy you can live by: “Be a better listener” and “sell on positive”

Kasko’s leadership message has two repeated themes that make philosophy usable:

• Be a better listener: you cannot execute what you do not understand about reality, people, and change.

• Sell on a positive: avoid selling on failure and short-term windows. Build differentiation and value that clients remember.

That last part shows up in his “deal” philosophy for sales teams. He contrasts the way his wife and daughter shop: they always come back saying they got a deal, not that they paid full price.

In his coaching, HR and leadership teams want savings and measurable value they can report back. Frontline’s aim is to give the client a story that makes them look like a rock star internally.

Where to start if you want philosophy to hold up under pressure

If your company’s culture and values feel fragile when conditions worsen, Kasko’s approach suggests a starting point that is less about slogans and more about systems.

1. Adopt a diagnostic framework: when something breaks, identify whether it is a people, process, or service failure and how the pillars interact.

2. Document your process: philosophy without repeatable steps turns into chaos when scale or stress increases.

3. Build trust as mechanics: agreements, transparency, communication rhythms, and recorded accountability can turn values into lived reality.

4. Differentiate through execution: warranty models, digital client engagement, and service design are philosophy made concrete.

5. Run an execution loop: weekly one-on-ones and periodic company alignment keep values enforced, not ignored.

6. Listen across generations and channels: technology and social behavior shifts faster than leadership assumptions.

The “business philosophy” that actually works is the kind that survives recessions, pandemics, AI acceleration, and leadership transitions. It’s philosophy that can be run, tested, and refined under real consequences.

If you want your organization to hold when pressure hits, don’t just define what you believe. Build the pillars, document the playbook, enforce the values, and create the feedback loop that keeps everyone aligned while the world changes.

Get in touch

For more insights and practical guidance on Frontline Source Group’s approach to people, process, and service, reach out through their official website or connect via LinkedIn.

This article was created from the live video conversation on The Business Philosopher Within You podcast. The episode was published on YouTube under the title “When Business Philosophy Actually Works in the Real World | 200+ Employee CEO.” The article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Bill above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understanding

Rob Gaedtke, President & CEO at KPS3, describes the uncomfortable shift that comes when your organization stops being “about you” and starts needing to operate without you in the room. That transition is not just a leadership change. It is a culture change. And it requires leaders to reframe beliefs they have carried for years.

The $2M to $10M shift is really a “dependency” shift

Many founder-led businesses begin with a natural advantage: the founder is charismatic, present, and problem-solving on demand. Clients get confidence because the founder is the face of the company. Teams get clarity because the founder decides.

The hidden risk is dependency. When everything flows through one person, the business cannot scale on its own. Even if growth is strong today, the operating system is fragile. The question becomes: what happens when the founder is unavailable?

Rob’s team asked that question directly. He stepped away, including a real test: a month sabbatical after being the CEO for years. The point was not for him to “be away.” The point was to prove the company could still run, still serve clients, and still execute without him as the daily center of gravity.

When leaders stop being the center, the company gets stronger

Founder-led organizations often run on one person’s identity. In Rob’s earlier explanation of KPS3’s first phase, the founder and the brand were essentially the same. That is a powerful early-stage model, because the founder creates energy, reputation, and momentum.

But scaling requires a different model. Rob describes the limitation simply: it becomes unrealistic for one individual to maintain real relationships across growth, regions, clients, and time zones.

So KPS3 shifted from being “owned by the founder” to being owned and managed by the people doing the work. Today, they have multiple owners and a goal of expanding employee ownership further.

Stop managing people, start leading people

Rob’s leadership mantra is “stop managing, start leading.” In practice, this means managers behave less like decision bottlenecks and more like coaches who clarify direction, ask questions, and create space for others to own outcomes.

It also means trust is not a slogan. Trust shows up in systems that work even when the top leader is not there.

The philosophy behind letting go: autonomy, mission, and replaceability

KPS3’s culture is commonly summarized as “Human on Purpose.” Rob treats it as more than a tagline. In his view, it is part of a real leadership philosophy built on three practical pillars:

• Autonomy to storm the hill
  The company has plans and targets, but people are empowered to take action that moves the mission forward.

• A mission everyone can repeat
  Rob emphasizes that every expectation document includes a clear mission statement. The rule is simple: if you do your mission, you win.

• The leader is replaceable
  Rob says this without ego. The organization should be able to handle real work while he is away. There is no “CEO dependency” hiding inside the culture.

This is why the sabbatical mattered. It was a stress test for the operating system. If the company collapses without you, the culture is not ready for scale.

Confidence without control: the manager’s job is curiosity

Scaling autonomy only works if managers know how to lead without dominating. Rob describes common manager behavior that signals confidence without control:

• Ask questions and talk less

• Encourage people to reach the idea themselves

• Trust that your solution is not the only right solution

That kind of leadership takes a particular form of confidence. Not the loud kind that insists on being right. The stronger kind that can sit back and admit: I may not have the answer, and I can still guide us there.

Guard rails instead of rigidity: creativity needs constraints

One tension in every creative business is obvious: you want freedom, but you also need outcomes, budgets, timelines, and quality. Rob’s approach is to treat requirements as guard rails rather than rigid rules.

He explains it as focusing on the goal, budget, and timeline, while leaving room for teams to figure out the “how.” Even timelines are negotiable as long as the client outcome is achieved.

This is not theoretical. KPS3 uses examples from both leadership and real projects.

Example: adapting constraints like a climb

Rob uses rock climbing as an analogy. If the plan is five days but you realize you did not bring enough water, the constraint is not the clock. The constraint is your resources. The team adapts by changing the approach, like climbing through the night and compressing the schedule to summit.

In business terms, when a client expects ABCXYZ by a certain date, constraints will appear. The discipline is not forcing the plan. The discipline is accomplishing the mission in a way that still works under reality.

Example: launching with a micro-site instead of a full rebuild

KPS3 has a client in education software, PeopleGrove. For a brand launch, the full existing site was too large to rebuild and go live in time. So KPS3 launched a micro-site to hit the launch window, prepared internal materials, and rolled the broader solution out over the next two weeks.

This is how you balance creativity with delivery. You do not ignore constraints. You redesign the path.

Growth breaks old beliefs, and culture pays the price

A scalable business cannot keep every belief from the early days. Rob calls it the difference between old beliefs and new beliefs.

One of KPS3’s shifts was about overdelivering. Early-stage survival and differentiation often come from saying “yes” beyond the scope. At smaller sizes, that mindset can work. People can absorb overtime. Write-offs stay manageable. And teams feel proud of going above and beyond.

But at scale, “free work” becomes expensive. Rob shared that their write-offs due to over-delivery reached more than a million dollars in a year. Even worse, the clients who benefited did not necessarily value the extra. The company valued it. The client often treated it as “nice, but no big deal.”

So KPS3 got intentional. If they over deliver, it has to be because the client will value it. Otherwise, they stick to the promise and deliver with excellence inside scope.

That kind of shift always creates resistance. Rob says the pushback was significant, especially from the “old guard.”

Designing the next version of the company (without losing yourself)

Scaling is not just a process upgrade. It is identity work. Rob admitted it was hard to reframe a belief that “the CEO must be the face of the company.”

He described a real moment: there is a big client board meeting where he does not attend. For a long time, his value proposition in his own mind was “show up and represent.” But with seven owners, the meeting does not need him as the universal face.

The question he still struggles with today is simple and personal: what is my true value when the company does not need me in every room?

Advice for leaders who are reframing beliefs

Rob’s guidance is direct:

• Do not write the old and new beliefs down until you are ready
  Most leaders can identify their flaws. Few can truly change behavior. Waiting to capture the beliefs until you are ready to act prevents superficial self-awareness.

• Embrace the psychological reality of belief change
  It is not a mechanical exercise. It is a real readiness shift.

That advice matters because many leaders try to “think” their way into culture change. But culture change happens in decisions, systems, and what you stop doing.

Human on Purpose: why people-powered beats process-driven

Rob’s most consistent theme is human connection. Technology can automate. Technology can polish. But marketing is ultimately a human interaction designed to create behavior change through one connection with one person.

He argues that every AI-driven component still exists to support the human conversation. Without intention, it is easy to default to convenient “machine-like” outputs. His point is that human-to-human interaction produces insights, trust, and meaning that machines can imitate but not truly recreate.

That is the “Human on Purpose” idea. It is not against technology. It is about remembering what technology is for.

How to stay grounded while everything changes

Belief reframing and culture scaling happen while the external world keeps shifting. Rob shared a grounding practice from his family. He and his family built a personal value system over two months by answering questions like what they love and what they value.

His core grounding principles are:

• Everything I do has to be truthful

• Everything I do has to come with love

• Everything I do is driven

The reason this matters for leaders is simple. When things go sideways, you need a reference point that is not dependent on quarterly performance, not dependent on praise, and not dependent on your role as the “face.”

Final question: does your company still need you?

The founder dependency epidemic is not solved by working less. It is solved by building an organization that can operate without your daily presence.

That requires:

• autonomy tied to mission

• managers who lead with curiosity

• guard rails that protect creativity while keeping outcomes on track

• new beliefs that replace early survival mindsets

• a culture that treats human connection as a competitive edge

If your company still needs you in every room, you are not scaling a business. You are scaling your personal capacity.

The leaders who reach $10M and beyond usually do something harder than hiring. They do the identity shift. They become less replaceable emotionally, and more replaceable structurally. And that is what lets the company finally grow on purpose.

Contact

Rob is reachable via LinkedIn, on his company website or through the Gaedtke Family website (inspiring!) where they lay out their life philosophy.

This article was created from the live video conversation on The Business Philosopher Within You podcast. This episode was published on YouTube under the title “The $2M to $10M Shift: When Your Company Stops Needing You.” The article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Rob above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understanding

What a B Corporation and the Triple Bottom Line Really Mean

A B Corporation, or benefit corporation, is a rigorous certification that frames business decisions through more than just finance. For PAE that means measuring impact on people, planet, and profit. Profit matters — “no margin, no mission” — but it is one of three pillars, not the only one.

Christian summarized PAE’s strategic filter in three clear pillars:

• Accelerate impact — take on the work that advances their mission (clean air, water, and energy for all).

• Technical tools — invest in the engineering and systems that make regenerative outcomes possible.

• People — create a workplace where staff belong, grow, and are empowered to lead the next generation.

Stoic Leadership and a Practical Reflection Practice

Christian combines ancient Stoic ideas with very modern leadership habits. Stoicism’s four cardinal virtues — wisdom, courage, justice, and temperance — are translated into five practical operating principles he uses every day:

• Focus on what you can control; accept what you cannot.

• Improve what you touch. Ask: did I help or hurt?

• Lead with calm; act with courage.

• Serve with purpose. Are my actions in service of others and the mission?

• Practice gratitude and reflection. Use these to align actions with values.

His daily routine begins with gratitude and a short reflection on the previous day: what went well, where he could improve, and how to show up better tomorrow. He also does a longer-form exercise every decade of life: imagine advising your 45-, 35-, and 25-year-old selves to surface lessons, priorities, and purpose.

Decision-Making: A Lens, Not a Checklist

When major choices arrive — acquisitions, project bids, staffing — Christian and his team evaluate through the triple bottom line lens. If an opportunity does not serve one of the three pillars, they don’t pursue it. That discipline forces clarity about what to say no to, which is often harder than deciding what to do.

A few practical metrics and policies PAE uses to make those trade-offs visible:

• Utilization target: PAE aims for about 55–56% utilization, not the industry top tier of ~65%. That creates time for non-billable work (learning, thought leadership, pro bono, volunteering).

• People-first investment: 20 hours of paid volunteer time per employee per year and a goal to give away roughly 1% of revenue annually.

• Retention: PAE retains around 90% of staff — a signal that culture and purpose translate into long-term value.

Regenerative Design in Practice: The Living Building and Healing Spaces

Theory becomes concrete in projects. Two stands out:

• Wounded warrior recovery center (Bethesda) — a trauma-informed project where design choices (rounded corners, biophilic elements) reduce anxiety and promote healing.

• PAE’s Living Building (Portland) — PAE designed and occupies a living building built to the Living Building Challenge: net positive energy through renewables, self-sufficient water systems that harvest and treat rainwater, low embodied carbon via mass timber, and very low energy use through passive strategies. The firm serves as anchor tenant and equity partner, accepting higher upfront cost in service of demonstrating what’s possible.

The payoff is not just green credentials. The living building has attracted talent, improved employee engagement, and drawn thousands of tours, which amplifies impact and leadership in the market.

Balancing Profit and Purpose: “No Margin, No Mission”

Christian is clear: profitability is required to sustain purpose. The trick is to keep profit and purpose in balance. Running an efficient business provides the resources to invest in impact. That means making difficult trade-offs openly and transparently, constantly testing whether decisions align with the three pillars.

Culture, Trust, and the Mechanics of Psychological Safety

Culture at PAE is practical and layered. Christian points to two consistent themes from employee feedback:

• People love their colleagues. Connections and teamwork are the main reasons people stay.

• Transparency and trust matter. Leadership approval ratings dipped during transition, but Christian treats that as data: trust must be earned over time through visible action and accountability.

Concrete practices that build psychological safety and coaching capacity:

• Pods: Small groups of 4–5 people meet weekly to check in, combat isolation, and flag concerns early.

• Crucial Conversations training: Equip leaders to handle high-stakes conversations without defensiveness.

• SDI (Strength Deployment Inventory): Teach people how they are wired to communicate and how to adapt for others.

• Human feedback loops: Beyond surveys, PAE interviewed 85 randomly selected staff for deeper qualitative feedback, then turned findings into action plans.

Vulnerability, Growth, and the Dark Nights

Leadership requires vulnerability. Christian shared two pivotal struggles:

1. Early days building the California office: isolation, imposter feelings, and the anxiety of starting over. The remedy was doing the work, building relationships, and showing up consistently.

2. Receiving blunt 360 feedback that his intent (care and concern) was sometimes received as condescending. The solution: executive coaching, honest self-work, and demonstrating change over time.

The lesson is simple and human: admit flaws, invest in learning, and keep showing effort. People notice and give leaders the benefit of the doubt when progress is visible.

Practical Habits You Can Try Next Week

• Start each day with two minutes of gratitude and one reflection question about the prior day: what went well, what to improve?

• Do a 10-year self-advice exercise: imagine what you’d tell your 45-, 35-, and 25-year-old self and let those answers reveal priorities.

• Use a triple-filter for decisions: does this accelerate impact, improve our technical tools, or serve our people?

• Try the “have to” → “get to” reframe: shift mindset from obligation to opportunity to boost motivation and perspective.

• Create small regular check-ins: pods, 1:1s, or lunch conversations to surface problems early and build trust.

Parting Thought: Know Your Personal Why

If there is one anchor Christian returned to, it is this: know your personal why. Clarify the impact you want to have, then organize your choices and daily habits to serve that purpose. Business frameworks, certifications, and retrofit projects matter, but without a personal why those efforts feel hollow.

“What we do now echoes in eternity.” — a reminder that legacy is built in the day-to-day choices we make as leaders.

Contact

Christian welcomes connections from leaders working on highly sustainable projects and individuals interested in board or nonprofit service. He is reachable via LinkedIn.

This article was created from the live video conversation for The Business Philosopher Within You podcast. This episode was published on YouTube under the title “Triple Bottom Line: Why This CEO Says Profit Isn’t Everything.” The article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Christian above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Dive Into Deeper Learning

Todd Greenbaum, president and CEO of Input 1, built a company that evolved from a five-person operation managing $10 million in premiums into a platform that handles more than $16 billion in annual premiums and serves over two million users. His path offers practical lessons for founders and leaders who want to build something that endures.

Start with a real customer problem

The company began with a simple, specific problem: banks wanted to enter premium financing but lacked the technology and operational know-how. Solving a narrow, well-defined customer pain gave Todd and his team traction. The lesson: find a distinct, urgent problem and solve it well before you chase scope.

Grow by concentric circles, not by boiling the ocean

Ambition matters, but so does restraint. Todd describes a conscious pattern of expansion: take core capabilities and apply them to adjacent needs. Start as a tech-enabled service for banks, then sell the software, then extend into billing and digital payments for insurance carriers and brokers.

The advantage of concentric growth is simple: you reuse expertise, reduce unknowns, and protect your reputation while increasing total addressable market.

Practical framing

• Master a bucket before you try to boil the ocean.

• Reuse intellectual property across adjacent problems.

• Test product tweaks on your core customers before broad rollouts.

Let your vision evolve

Vision is not always a static manifesto. For many founders the initial “why” changes as the business and market reveal new opportunities. Todd’s founding why—help banks offer premium financing—morphed into a broader mission: let insurance companies focus on product creation while Input 1 handles billing, collections, and payments with scalable technology and operational excellence.

Design culture to support scale

Culture isn’t an optional add-on. It’s the operating system that decides whether processes and products deliver consistently as you scale. Todd emphasises kindness, curiosity, respect, and active support: treat every person with dignity, encourage questions, and back people when they stretch into new roles.

Practical cultural elements to adopt:

• Create expert groups focused on specific functions so feedback is actionable.

• Encourage curiosity and remove the stigma of asking “stupid” questions.

• Reward humility and introspection in leadership.

“Make sure that you’re always double checking yourself and that you’re not getting too big for your britches. Make sure that you are not kind of buying your own BS.”

Build a unique, sustainable advantage

In regulated industries, differentiation can come from product breadth tied to operational excellence. Input 1’s platform supports all three ways to pay an insurance premium—one-time, carrier billing, and financing—on a single system. That single-platform approach reduces friction, improves user experience, and increases customer stickiness.

Innovation matters—especially in a lagging sector

Insurance historically lagged in digitization, creating a runway for insurtech. Practical AI use cases already delivering value include:

• Automated claims assessment (drones and image analytics).

• Faster underwriting through rapid data evaluation.

• AI agents that handle routine customer questions and escalate only when necessary.

Stay at the edge of invention—don’t assume “good enough” will stay good enough.

Listen to customers and build surgical feedback loops

Customer conversations are the best product research. Todd’s team slices customers by product, geography, and relationship type, then runs expert groups that translate nuances into product and workflow changes. The result: incremental improvements that remove friction and increase adoption.

Make meetings purposeful and measure behavioral change

Communication cadence matters—quarterly leadership reviews, monthly division check-ins, weekly team meetings—but so does discipline. Reduce useless meetings. When you meet, have clear agendas and outcomes. Most importantly, check whether meetings create behavioral change, not just information transfer.

The onboarding crisis and the discipline of restraint

Growth without operational readiness can create catastrophic customer experiences. Todd recalls a painful episode when several large clients were onboarded too quickly, exposing weak mid-level management and forcing senior leaders to step in constantly. The recovery taught a crucial lesson: be methodical about ramp-up times, resource allocation, and internal training before you accept new, large customers.

People scale differently from software

Properly architected software can often scale without breaking. People and culture do not scale the same way. Preserve cohesion by:

• Hiring durable leaders and investing in middle management.

• Keeping long-tenured employees engaged and passing cultural norms to new hires.

• Planning growth so culture remains intact as headcount increases.

Remote work: preserve culture deliberately

Remote teams need intentional culture maintenance. Watercooler spontaneity disappears over virtual lines, so compensate by creating rich virtual rituals, occasional in-person gatherings, and deliberate onboarding experiences. Bringing remote people to headquarters for concentrated interactions can reignite enthusiasm and deepen connection.

Grounding practices matter for leaders

Leadership is high-energy work. Todd finds balance in two personal rituals:

• Playing in a band—music as a weekly reset where problems fade for a few hours.

• Consistent exercise—discipline that powers long-term health and cognitive stamina.

Practical checklist for leaders who want to build a lasting company

1. Start narrow: Solve a clear problem for a specific customer segment.

2. Grow concentrically: Extend into adjacent markets using the same core strengths.

3. Prioritize operational readiness: Only onboard large customers when people and processes are prepared.

4. Design culture deliberately: Promote humility, curiosity, and mutual support.

5. Listen surgically: Use expert groups to turn customer feedback into product and process changes.

6. Keep innovating: Treat technology and AI as ongoing investments, not one-time projects.

7. Measure meeting impact: Stop meetings that don’t change behavior.

8. Protect culture in remote setups: Invest in rituals, periodic in-person touchpoints, and intentional onboarding.

9. Stay introspective: Leaders must continually check themselves and remain humble.

Final thought

Building a company that lasts is less about a single brilliant leap and more about disciplined, iterative decisions: choosing the right customers, expanding thoughtfully, building operational muscle, and protecting culture. Ambition fuels growth, but restraint and humility make that growth sustainable.

If you want to explore how a single platform can simplify premium billing and payments across payment methods, start by talking to the people who run those platforms and listen closely. The next big product insight will often come from an honest customer conversation.

Get In Touch With Todd Greenbaum

Todd can be reached through his Linkedin account. To find out more about Astound Digital, visit their website.

This article was created from the live video conversation for The Business Philosopher Within You podcast. This episode was published on YouTube under the title “How to Build a Company That Lasts 40+ Years | Todd Greenbaum, Input 1’s CEO.” The article was created with the help of AI after significant input from human intelligence.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Ilya above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understanding

From a living-room bookstore to Astound Digital

Ilya told the origin story: three friends built an online bookstore while in school. The early product worked from a DSL connection in an apartment, but without marketing the site saw no traction. By 2000 they committed full time and registered the company under a name that reflected their technical ambitions. The company name changed with each phase of growth — from EcoFabric to SysIQ, then Astound Commerce, and finally Astound Digital — each name signaling a shift in what they wanted to be known for.

Two moments accelerated the company’s trajectory:

• The dot-com crash, which left customers and platforms available to acquire, helped them pivot from a single product to service-based e-commerce implementation and hosting.

• The post-2008 retail acceleration, when e-commerce became a core channel, invited rapid growth and larger enterprise clients.

The three pillars of scale: people, processes, partners

Ilya distilled the company’s success into three interlocking elements. This is as much a framework for running a services business as it is a checklist for durability.

1. Partners

Strategic technology partners — platforms like Magento, Shopify, and Salesforce — served as crucial growth levers. Being a trusted implementer of major platforms opened access to enterprise work and global accounts.

2. People

As a services company, talent is the product. Astound invested heavily in hiring, training, and retaining engineers and specialist teams. Ilya emphasized a people-first priority when making hard choices: people first, then clients, then the business. That waterfall created a culture where teams felt protected and empowered to deliver for clients.

3. Processes

As work expanded, the company invested in rigorous documentation and a repeatable Solution Development Lifecycle. Mistakes were treated as learning opportunities: run a post-mortem, extract lessons, then update processes and templates so the same issue does not recur.

Culture: defined values and daily execution

Nine years into the company’s life the founders codified core values: integrity, respect, passion, commitment, continuous improvement, shared success, and teamwork. Those were not academic declarations. They were distilled from how the company had actually operated and then used as a filter for day-to-day decisions.

Ilya explained a simple principle they applied when values collided: prioritize people first, then clients, then business. This created disciplined decision-making under pressure and helped maintain morale in downturns and transitions.

“Taking care of our people first, then our clients, then the business.”

Leadership and organizational design that scale

What happens when one founder is responsible for 200 direct reports? It does not scale. Ilya described how Astound built a middle layer of management and moved to a hybrid structure combining direct functional management with matrixed project teams.

Key elements:

• Matrixed project teams led by project or account managers who coordinate cross-functional work

• Functional managers who recruit, train, and develop deep skill in each discipline (front-end, back-end, QA, business analysis)

• Processes and training that let functional teams plug into matrix projects quickly and consistently

Acquisitions: accelerating capability while respecting culture

Acquisitions were tactical: bring in specialized design skills or expertise in a platform the company wanted to support. But acquisitions also bring friction. Ilya was candid: integration is challenging and requires deliberate change management.

Best practices Astound adopted:

• Create transition teams that include leadership from both organizations

• Make a plan for experience and cultural alignment, not just technology or revenue targets

• Invest time to explain the “why” and how the combined organization will work together

Applying philosophy to execution

One of the recurring themes was that values only matter if they are applied practically. Ilya pushed back on abstract philosophizing — leaders must translate ideals into processes, templates, and day-to-day behaviors.

“Leaders who are good at big things have to be good at little things.”

That means showing up, helping on small tasks when needed, coaching junior people, and demonstrating the behaviors you want to see in every interaction.

AI adoption: top-down encouragement and bottom-up experimentation

Astound has been proactive about AI adoption. Their approach combined leadership-driven expectation setting with grassroots experimentation: identify curious people in each discipline, incubate use cases, document best practices, and then scale them across teams.

The win is increased efficiency and happier teams who do not want to go back to old workflows. The risk is structural: AI can automate junior tasks and if organizations are not deliberate, the pipeline for developing future senior talent can dry up. Ilya called for purposeful approaches to mentoring and training juniors in the age of AI.

Hard lessons and personal grounding

Every long journey has friction. For Ilya one of the hardest persistent realities was corporate politics. Even in an organization that tries to ignore politics, human behavior creates it. His approach was to refuse to engage while still trying to be pragmatic and lead by example.

How did he stay grounded? Two things: family and health. Ilya started the company while newly engaged and raised a family alongside the business. He also made a deliberate pivot in his 30s to take care of his body through diet and exercise. His advice mirrors airplane safety guidance: secure yourself first so you can care for others.

What to protect if you step away

When I asked which single principle he would insist remain unchanged if he ever left the company, his answer was immediate:

“Taking care of our people.”

He emphasized honesty and humanity, even when delivering bad news — the method matters. The way you treat people in hard times is how culture earns its credibility.

Practical takeaways for leaders

1. Prioritize people first. Design decisions around human outcomes and the business results will follow.

2. Document processes and learn from mistakes. Convert post-mortems into updated playbooks and templates.

3. Build two structures in parallel. Develop strong functional capabilities while enabling matrixed project teams.

4. Treat acquisitions as change programs. Plan integration teams, cultural onboarding, and experience mapping for people joining the organization.

5. Adopt AI deliberately. Combine top-down expectations with bottom-up pilots, and create career paths that still develop junior talent.

6. Lead culture daily. Culture is not delegated to HR; it is shaped by leader behavior minute by minute.

Final thought

Scaling a services company is not a formula; it is an ongoing practice of trade-offs, attention, and continual improvement. Ilya’s story is a reminder that growth depends on clear choices: who you partner with, how you develop people, and which processes you commit to repeat. Those choices create a virtuous cycle when paired with honesty, humility, and daily leadership.

Get In Touch With Ilya Vinogradsky

Ilya can be reached through his Linkedin account. To find out more about Astound Digital, visit their website.

This article was created from the video “Why Kind Leaders Build the Most Scalable Companies (0–1000 Employees)” with the help of AI.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Ilya above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Sharpen Your Insights

This article opens with a vivid historical story that might seem intense at first. It’s meant as a metaphor, a way to explore the timeless challenge leaders face when confronting uncomfortable truths. My goal is not to dwell on the past or shock you, but to highlight the vital role of courageous questioning and awareness in building organizations that endure.

If you stick with me, you’ll see how this “fool” figure offers a powerful lesson for today’s business leaders, especially in an age where real insight and self-awareness are more valuable than ever.

What Sustainable Leadership Has Always Required

I know Halloween is long behind us and we are now in the festive season of good tidings.

So when I begin with a slightly gruesome story about a monarch who was up to some terrible things, believe me, it’s not meant to dampen the holiday spirit. It’s meant to celebrate it.

Henry VIII was a 16th-century king of England who executed between 20,000 and 57,000 people during his 37-year reign. Among them were two of his wives and some of his top advisers, including Thomas More, his Lord Chancellor and a renowned humanist, and John Fisher, Bishop of Rochester.

These advisers were tasked with counseling the king on governance and administration. It was a perilous role, carrying a constant risk of falling out of favor and ending up on the chopping block. Quite literally.

It was a perilous role, carrying a constant risk of falling out of favor and ending up on the chopping block. Quite literally.

If you advised the king, you would be extremely cautious about what you said and did. One misguided word or a wrong glance could land you in the Tower of London, tortured and hoping for a swift death by sword.

In the midst of this mayhem, there was one adviser who spoke to the king fearlessly.

He called out Henry’s grand dreams as hallucinations. He laughed at his visions of fortifying the kingdom and conquering France. He mocked the king’s romantic infatuations and even called him names.

And yet, he outlived the king by several years.

Not only did this adviser make it through Henry’s reign with his head attached to his body, he also outlived the next monarch, Queen Mary, later known as Bloody Mary for her own brand of terror.

Do you know who this adviser was?

It was William Somers, the court jester, more commonly known as the Fool.

In a court where speaking truth to power could mean death, the Fool held a unique position. Shielded by humor and irreverence, William Somers could call out the king’s grandiose dreams without fear. He could challenge illusions, laugh at absurdities and remind the monarch of reality.

William Somers went on to serve in the court of Queen Elizabeth I for many years, playing his part in bringing about England’s golden age of enlightenment.

There’s a profound lesson here: the fool we tend to underestimate is often the catalyst for breakthrough insights and lasting wisdom.

The Death of a Consultant

William Somers’ primary tool for truth-telling was humor.

In the corporate boardroom, humor has its place, but it is not always appropriate. Irreverence also has clear limitations and ultimately offers diminishing value in modern advisory roles.

For this reason, the modern fool in the business world needs to develop a new set of tools and a more refined skill set for truth-telling.

The modern fool in the business world needs to develop a new set of tools and a more refined skill set for truth-telling.

You see, the traditional role of advisers - sometimes also known as coaches, consultants and guides - has not worked very well in the last few decades.

As we became a knowledge-based society and information became widely available to us all, the adviser’s role gradually shifted.

The function of a modern adviser is less about being a source of subject knowledge and expertise and more about being an agent of insights. In the business world, a modern adviser is someone who also helps apply those insights to our world and to our work.

The advent of AI has only accelerated this shift. Today, every business person, from a corner office executive to a fresh graduate in her first job, has access to the entirety of human knowledge right in the palm of their hand.

The function of a modern adviser is less about being a source of subject knowledge and expertise and more about being an agent of insights.

Information and subject knowledge have been flooding us since the 1980s. In recent years, thanks to AI, that flood has turned into a tsunami, much of it diluted into irrelevant slop salad delivered straight to our devices.

We don’t need more experts, consultants or advisers who operate in the traditional way. What we need are those who help others access their own wisdom, even as they bring their expertise and subject matter knowledge to the advisory table.

The role of a modern adviser to leadership then is not necessarily to speak truth but to help leaders discover their own wisdom.

You Can Be a Fool Too

Don’t think for a minute that the skills of being a fool are only reserved for professional advisers. In the age of AI, we all need to be fools. Each and every one of us needs to be a source of wisdom, inspiration, clarity and lucidity to those we care about.

And we need to bring them this wisdom and inspiration not by giving motivational speeches or delivering eloquent monologues. Instead, we need to help them discover the wellspring of wisdom that is already inside them, waiting to be unleashed.

There are two basic skills we need to develop to be an effective fool in the modern business world: one, asking meaningful questions and two, listening openly and without judgment.

Whether we are advising a client, closing a sale, managing a team member, working with a boss, collaborating with a coworker or supporting a friend, we need to help them access their own insights and ideas.

This is a skill, and like all skills, it needs to be developed.

The good news is that with a bit of mindful attention, we can start developing this skill no matter where we are in our careers.

There are two basic skills we need to develop to be an effective fool in the modern business world: one, asking meaningful questions and two, listening openly and without judgment.

And you can start practicing these skills right this very minute. I’ve shared a resource in this article to help you begin developing your advising abilities. And to to make it actionable, I’ve also included a quick, clickable quest.

But before these two skills can become effective, there is a mind shift you need to consider.

Mind the Gap

Our most prized, most premium mental real estate today is not information. It’s not the collected facts, knowledge or expertise. It’s not even learning in the traditional sense.

It’s the gaps in between.

This gap is where we bring awareness to all that we deal with.

This gap is the place where insights happen. This opening in time is the moment when inspiration and ideas bubble up. Over time, a continuous process of self-awareness emerges, through which our inherent, innate wisdom finds its outlet and takes outward expression.

For leaders and founders who value self-sustaining endurance over a short-sighted chase of proverbial riches - the fool’s gold - this expression of wisdom can result in an enduring organization that outlives them.

That, in the truest sense, is the legacy they leave behind.

Our most prized, most premium mental real estate today is not information. It’s not the collected facts, knowledge or expertise. It’s not even learning in the traditional sense.

If you are into self-development like I am, or if you ever end up advising founders, leaders and organization builders like I do, your greatest weapon that truly moves the needle is not what you say or how you say it.

It’s your ability to craft insightful, powerful questions.

Questions designed to bring the leaders you work with face to face with their own truths.

The truths they’ve been avoiding.

The truths they’ve been hiding from.

Good questions are powerful because they allow you to see beyond your existing mindset: those deeply held beliefs that have quietly become your limitations and barriers. They cut through the noise of assumptions and habitual thinking, creating space for fresh perspectives.

Good questions are powerful because they allow you to see beyond your existing mindset: those deeply held beliefs that have quietly become your limitations and barriers.

They invite you to challenge what you thought was true. And in doing so, they unlock possibilities you hadn’t seen before.

Right questions, asked at the right time and in the right context, open a space in your mind - a space of awareness.

It’s in that space where real reflection happens, hidden assumptions surface and new insights begin to take shape.

This is the moment when leadership moves from reacting to responding, from repeating old patterns to creating new possibilities.

This is where shifts happen, shifts that can bring profound, inside-out transformation. Not just in the leaders you work with but also in those they lead.

It creates a ripple effect that flows through the entire organization, paving the way to break barriers and ignite meaningful transformation.

Awareness sparked by the right questions becomes the catalyst for lasting change, fueling cultures that adapt, innovate and thrive.

The Lasting Gift of the Fool

So, who is the fool?

The fool is the one who holds up a mirror, not to mock, but to create awareness. This awareness is the bedrock beneath every enduring organization. It is the space where leaders confront their own truths, break free from limiting beliefs and open themselves to transformation.

The fool is the one who holds up a mirror, not to mock, but to create awareness.

Through this awareness, leaders do not just react; they respond. They do not simply manage; they inspire. And from this place, a culture takes root that adapts, innovates and thrives long after its founders are gone.

In that sense, the fool’s greatest gift is not in the words spoken but in the questions asked: the questions that spark awareness, the catalyst for lasting change. That awareness, that inner light, becomes the foundation of organizations that endure.

And that, in the truest sense, is the legacy of the fool.

Give a Gift of Aware Understanding

For me, most of these conversations happen behind closed doors.

However, over the past two years, I’ve had the privilege of sharing many such deep conversations publicly on my podcast, The Business Philosopher Within You. In these two years, I have had 34 such conversations, 22 of them in 2025.

At the heart of every episode lies the same undercurrent: the awareness that opens when a question is asked. Often, the answers that emerge from that space are some of the most profound.

So this holiday season, my gift to you is a challenge. Become a better fool at my expense.

Critique my questioning and listening skills.

Here’s the challenge:

• Scroll through the list of 22 conversation titles below.

• Pick one that resonates with you. (Don’t overthink this!)

• Click the link to watch that conversation on YouTube for about 5 minutes.

• As you do, come up with a question you would like to ask the guest.

• Share that question in the comments section of the YouTube video.

That’s it!

Bonus points: If you share a question I did not ask in the conversation, you’ll get a mention in the following episode where I use your question.

Don’t stop there. Once you get the hang of asking contextual, meaningful questions, take your newfound skills into your next conversation.

Give the gift of deep understanding, meaningful questioning and open listening to at least one person this holiday season.

Happy Holidays!

Bhavesh.

With Deep Gratitude to Our Guests

Before you dive into the conversations below, I want to pause and acknowledge the guests who made them possible.

Each of these leaders chose to step into conversations that were unscripted, unhurried and, at times, uncomfortable. That willingness to think out loud, with the depth that we strive for, is rare.

I’m deeply grateful to every guest who offered their time, attention and trust.

List of The Business Philosopher Within You Episodes from 2025

The Challenge:

• Click on a conversation link to watch on YouTube.

• Come up with a question you would like to ask the guest.

• Share that question in the comments section of the YouTube video.

• Bonus: If you share a question I did not ask in the conversation, you get a mention in the episode where I use your question.

• For a deep dive and the full catalog of episodes, check the Comments section.

1. Culture as the Operating Rhythm

How healthy organizations are built from the inside out.

Episodes featuring:

• Geoffrey Toffetti >> (YouTube Link ➡) Scaling Culture with SaaS

• Mike Chaput (Part 1) >> Can You Scale Revenue Without Sacrificing Values?

• Mike Chaput (Part 2) >> Activating Your Company Culture

• Carol Cone >> Purpose-Driven Culture

• Carrie Klewin Lawrence, MFA >> Culture Through Story

• Melanie Cook >> Neurodiversity & Culture

• Matt Remuzzi >> Culture That Scales

• Ben Greiner >> Culture as the Foundation of a Successful Exit

2. AI, Tech and the Future of Human-Centered Organizations

Where technology, AI and humanity meet.

• Mike Ettling >> (YouTube Link ➡) Ubuntu Leadership in a Tech World

• Jonathan Schneider >> AI, Code Modernization, Leadership & Culture

• Johan Colvig >> AI-Driven Financial Philosophy

• Sri Ramaswamy >> Transforming Insurance with AI

3. Leadership, Self-Management & Awareness as Practice

The inner disciplines that shape outer results.

• Bruce Kasanoff >> (YouTube Link ➡) Leadership from the Heart

• Fabiana Lacerca-Allen, JD, LLM >> Situational Awareness & Crisis Leadership

• Steven Puri >> Flow State & Effortless Productivity

• Jeff Patterson >> Meditation & Leadership Presence

4. Learning Organizations & Human Systems

Because an organization is a learning organism, or it stagnates.

• Joanne Lockwood >> (YouTube Link ➡) Inclusion vs Belonging

• Dr. Christie Vanorsdale, Ed.D, Ms.Ed. >> Collaborative Learning

• Chris Vaughan, PhD >> Why Associations Outperform Corporations

5. Financial Clarity & the Philosophy of Sustainable Growth

Where numbers, behavior and business philosophy intersect.

• Ellen Wood >> (YouTube Link ➡) The Virtual CFO Model

• Brett Bernstein >> Financial Advisory in the Age of AI

• Anupam Nandwana >> Scaling a 300-Employee SaaS Busines

What makes a value system executable?

Mike shared a simple framework that explains why most core values fail: they are either forgettable, vague, or misaligned with the company mission. To be useful a value system must be memorable, clear, deep, aligned, and complete.

• Memorable: Use branding and imagery—an acronym or icon helps people recall and repeat the values. Mike uses RSVP as an easy mnemonic.

• Clear: Each value should be explained in plain language. Two-word labels plus clarifying belief statements work well.

• Deep: Provide layered source material—belief statements, detailed descriptions, and recommended reading—for leaders who must live the values.

• Aligned: Values must manifest the mission. If living your values does not move you toward the vision, change one or the other.

• Complete: The set should be balanced; missing levers create blind spots and behavioral drift.

Example: RSVP stands for Respect & Connect, Servant’s Heart, Value (customer value), Progress over Comfort. Each letter has two-word labels, an icon, four belief statements, and deeper material for leaders. That combination makes values memorable, usable, and teachable.

Core values are constraining behaviors

Constraint gets a bad rap. But constraints create meaning and enable teamwork. A value system tells people what to do and what not to do so they can cooperate without constant negotiation.

“If you want to act disrespectfully, you might be free to do that—but then everyone else is free to act disrespectfully too. The constraint has to apply to the whole culture.” — Mike Chaput

Constraining behaviors are not oppression; they are the rules of the game that make the game worth playing. People often want freedom, but they thrive when constraints align with their own ideals.

Hire for culture first, skills second

Hiring is the most important lever when building a culture. Mike explained the practical approach Endsight uses to prioritize cultural fit without neglecting skill.

• Interview for story and beliefs: Candidates map a life timeline—highs and lows—and tell that story. The goal is not therapy but evidence of values, resilience, and fit.

• If you do not share your story, you fail the interview: Cultural fit comes before technical assessment. Candidates who are unwilling to share personal context rarely fit.

• Skills come next: After cultural alignment, move candidates through a lab or skills-based interview. Pass both and you extend an offer.

The result: an exceptionally high offer-acceptance ratio and new hires who feel like they already belong.

Onboarding and rituals that keep values alive

Values are not alive because they are printed. They live because they are practiced, rewarded, and taught.

• Two‑hour cultural cohort with the CEO: Every new hire sits down to read and discuss each belief statement, ask questions, and learn the sources behind the values.

• Regular rhythms: Quarterly company meetings, town halls, weekly manager meetings—all start with value recognition and end with value stories.

• Public recognition: A “wheel of awesome” or similar ritual celebrates people who exemplify values and makes behaviors visible.

• Manager routines: Start manager meetings with good news and value-based shout-outs so leaders model what matters.

Operationalizing excellence: processes, tools, and culture

Great people need great tools—and great processes. But Mike emphasized an important truth:

“It’s better to have a mediocre process that’s followed relentlessly than a great process that’s never followed.”

Operationalizing excellence is detail work and cultural work combined. Practical steps to make it real:

1. One-on-ones as the primary place for coaching and problem solving.

2. Gemba—managers must observe work where it happens so they understand real problems.

3. Problem registers to capture persistent issues, prioritize them, and harvest strategic objectives from them.

4. Lean tools such as A3 problem reports to force clarity, root cause thinking, and owner-driven solutions.

5. Continuous improvement or Kaizen: small iterative changes driven by teams who care about outcomes.

Operational success requires people who want to follow process, the discipline to make processes stick, and the mechanisms to improve them over time.

Why margins matter

Endsight runs at approximately 20% EBITDA, which is well above the typical MSP market average. That margin is not an ego metric—it is the fuel for strategic investment.

Margins allow a company to:

• Invest in better tools and technology for high-performing teams.

• Build new practices like cybersecurity, business intelligence, and AI consulting.

• Protect the business during downturns and retain employee confidence.

Without healthy margins, growth becomes fragile. Private capital can extract short-term gains while eroding culture; sustainable margins let you keep investing in value for customers and employees.

One non-negotiable: culture (but iterate thoughtfully)

When I asked Mike what he would never allow a successor to change, his answer was surprisingly straightforward: culture. But he also emphasized a key nuance—iterate early, hold steady when it works.

When you are discovering product-market fit and organizational identity, keep culture malleable. When culture begins to consistently manifest the results you want, protect it. If a new inflection—such as AI—requires cultural shifts, make careful, evidence-based adjustments rather than sweeping rewrites.

AI: disruption and opportunity

Mike believes AI will be more disruptive than broadband internet. That does not mean instant replacement of jobs, but it does mean a redefinition of the problems organizations can solve.

How Endsight is positioning for that future:

• Rolling out enterprise AI tools internally and training employees to invent with them.

• Creating an AI practice to help customers implement AI responsibly and effectively.

• Using AI to move up the value chain—shifting from break/fix support to strategic outcomes for clients.

The future belongs to companies that combine human judgment with machine scale. Those that resist will be disrupted; those that lead will create outsized customer value.

Resilience: surviving the dark moments

Entrepreneurship is full of gut punches. Mike shared moments that tested his resolve: bankruptcy caused by partner theft, employee sabotage aimed at stealing customers, and a long-term controller who embezzled funds. Each event could have become a reason to harden, withdraw trust, or go defensive.

Instead the response was radical honesty and recommitment. A letter to the company announced one simple decision: double down on trust. That choice accepts the risk of being taken advantage of again in exchange for preserving an identity that made the company successful in the first place.

Staying grounded: practices that restore balance

Mike’s day-to-day resilience practices are practical and instructive:

• Music: playing instruments creates flow and a break from executive thinking.

• Somatic work: body-focused routines, foam rolling, and deliberate attention to physical sensation clear the mind.

• Family and close friendships provide perspective and consistent emotional support.

These practices are reminders that leadership is embodied and sustained by regular restorative rituals, not simply mental toughness.

Practical takeaways you can apply today

• Create a memorable, branded value system. Use icons, an acronym, belief statements, and source material.

• Interview for culture first. Use life stories to surface values and alignment before testing technical skills.

• Onboard new hires into the value system with cohort sessions and CEO-led explanations.

• Make processes simple and enforceable. Prioritize follow-through over perfection and use Kaizen to improve.

• Track problems in a register, assign owners, and convert the biggest issues into quarterly objectives.

• Protect margins so you can invest in tools, talent, and new practices such as AI.

• When crisis arrives, consider the long-term identity of the company before choosing fear-driven reactions.

Final words

Culture is the sustaining architecture of any company that wants to last. It shapes hiring, operations, product quality, and financial health. Build values that are memorable and actionable. Hire slowly for fit and then validate skills. Operationalize through discipline, observation, and continuous improvement. Protect margins so you can invest in the future. And when the inevitable hard moments come, lead with honesty and a commitment to the identity you want to preserve.

“Freedom through discipline. That’s where the creativity and the joy show up.” — Mike Chaput

If you want to continue the conversation, Mike is active on LinkedIn and publishes thought leadership regularly. Engage with these ideas, test them in your organization, and share what works and what doesn’t. Great cultures are built by iterations, not declarations.

Get In Touch With Mike Chaput

Mike can be reached through his Linkedin account. To find out more about Endsight, visit their website.

This article was created from the video “Can You Scale Revenue Without Sacrificing Values? (Lessons from a CEO)” with the help of AI.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Mike above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understanding

The origin story: why the name Endsight matters

Mike’s company name came from a moment of constraint and creativity. They were hunting for a domain and backed into Insight, then made it into Endsight to capture two ideas: ending poorly managed IT and seeing customers and people thrive on the other side. That backstory matters because it shows how a company narrative can be discovered and shaped to reflect a deeper purpose.

What vision really is—and who it is for

Too many leaders treat vision as a private mental map or a static slogan. Mike reframed vision as a living, externalized description of a future state that must be useful to every constituency: customers, employees, shareholders, partners, and the broader ecosystem. A useful vision does three things:

• Includes as many winners as possible so the future benefits multiple stakeholders.

• Functions as a constraint and a guiding north star for daily decisions.

• Becomes the rum line—a long-term target that guides shorter-term tacks and actions.

“One of the primary jobs of a CEO I think is to create a vision that can include as many winners as possible.”

Leadership as the first follower of an externalized vision

Mike made a sharp point: leaders should think of themselves as the first follower of an externalized vision. When the vision is visible and tangible, it leads the organization. The leader follows it, reinforces it, and checks that tactics align with that picture of the future. This avoids whipsawing the organization every time external news or an instinct pulls the founder in a new direction.

Choose a BHAG and use it as a rum line

Small, uninspiring goals rarely generate drive. Mike recommends a big hairy audacious goal (BHAG) as the rum line that orients every tactical decision. That long-range target gets fractionated into five-year, one-year, quarterly, and daily actions—so everyone can track progress and experience the psychological lift of moving toward a target.

There is a biological reason for this. Our emotions are tied to progress toward goals. No goals equals no natural positive emotion. A clear target gives people the structure needed to feel accomplishment and purpose.

Employee engagement: move people from toil to meaning

Work can feel like digging a hole and filling it back up—or like playing an engaging game. The difference is whether people experience progress toward a meaningful target. Leaders create opportunities for people to feel progress by setting targets, recognizing wins, and making daily work clearly connected to that rum line. The line between toil and meaning is very thin; a great vision shifts work from the former to the latter.

Endsight’s founding: survival, iteration, and learning

Mike’s early entrepreneurship began at 24 with a business that barely survived the dotcom collapse. Those years taught him that a survival-focused vision is uninspiring and hard to rally people around. When he founded Endsight he leaned into a recurring managed services model after learning from peers. But even then the early strategy needed evolution—vision is iterative, not one-and-done.

Quality as a differentiator: lean thinking and the highest-quality MSP rum line

Endsight’s grand vision is to be the highest-quality managed services provider in the world. That BHAG works as a rum line because it creates clear downstream expectations: customer retention, efficient delivery, high billable-time utilization, and sustainable profitability. Quality at Endsight is informed by lean thinking—minimizing waste, reducing error, and relentlessly improving processes.

Quality becomes the lens for strategic decisions. If an initiative or revenue stream contradicts the noble promise of helping others thrive, it is excluded, even if profitable in the short term. The moral and strategic alignment here is essential to long-term durability.

How to cascade vision into daily operations

Turning vision into daily behavior comes down to rhythms, structure, and communication. Mike described a clockwork cascade:

1. Annual strategic leadership retreat to set the long-range rum line, five-year and one-year targets, and quarterly rocks.

2. Weekly strategic leadership meetings to review strategic objectives and an active problem register.

3. Daily or team huddles to track metrics, escalate blockers, and solve problems in real time.

Start the weekly meetings with recognition and good news to reinforce the human connection. Keep a live problem list and make the meetings the forum to escalate, decide, and remove obstacles.

One-on-ones, the racecar metaphor, and accountability as a gift

One-on-ones are non-negotiable. Mike used a racecar metaphor: if you slow down to make the curve, your tires grip and you exit faster than someone who blows through and loses traction. In organizations that means taking the time for consistent one-on-one coaching, development, and problem solving even when it feels costly or time-consuming.

“Accountability is a gift.”

Great managers do more than monitor metrics. They get curious, go to the gemba (the place where the work is done), and empirically observe what is happening. Metrics flag the issue; observation explains it. The manager then coaches, clarifies expectations, trains, or holds an accountable conversation. Done well, this is a partnership: managers help people win, develop, and grow.

Radical candor and the human backbone of feedback

Mike referenced Kim Scott’s Radical Candor to describe how feedback should land. The ideal quadrant combines direct challenge with sincere personal connection. If you challenge without connection you become abrasive. If you protect feelings without candor you become ruinously empathetic. Radical candor is about being both human and direct.

Start a one-on-one by asking how the person is. Build trust. Then use data and observation to surface issues and collaborate on solutions. Frequently a manager’s job is to diagnose whether the problem is capability, clarity, or motivation and then tailor the next steps accordingly.

Values that actually work: memorable, branded, deep, and aligned

Mike shared a practical approach to values that I want to call out because so many companies fail here. Values fail when they are:

• Unknown to most people

• Poorly articulated or forgettable

• Unaligned with strategy

Endsight uses a compact, branded values framework: RSVP. It is memorable, clear, and layered:

• R Respect and Connect

• S Servant’s Heart

• V Value Value Value

• P Progress over Comfort

Each letter comes with two words for quick recall, four or five belief statements that describe behaviors, and a deeper library of source material and books that provide philosophical grounding. This creates a values system that is memorable, deep, aligned to the vision, and complete enough to guide behavior.

Why brand your values

Branding values makes them accessible. People remember images, acronyms, and icons. When values are both memorable and tied to clear behavioral examples, they become actionable operating rules rather than inspirational wallpaper.

Putting it all together: a practical checklist

If you want to start applying these lessons this week, here is a short checklist inspired by Mike’s playbook:

• Write or revise a BHAG that functions as a rum line for 5 to 10 years.

• Make your vision external and visible. The leader should be the first follower.

• Create a short, branded values mnemonic and pair each value with clear behaviors and source material.

• Set annual, quarterly, and weekly rhythms: offsite strategy, weekly leadership syncs, daily huddles.

• Institute regular one-on-ones. Use them for connection, coaching, and accountability.

• Use data to flag problems, then go to the gemba to observe and diagnose.

• Prioritize quality as a systemic discipline informed by lean thinking and measure it.

Final thoughts

Scaling revenue without sacrificing values is not only possible—it is an advantage. When vision, quality, and a values-driven operating system align, you get durability, higher engagement, better financial returns, and a company people want to be part of. As Mike put it, the leader’s job is to create a future where multiple stakeholders can win. That is both a moral stance and a sustainable business strategy.

If you are ready to build that future, start with one thing: make your vision visible and your values memorable. The rest is a disciplined practice of rhythm, coaching, and ruthless prioritization.

Get In Touch With Mike Chaput

Mike can be reached through his Linkedin account. To find out more about Endsight, visit their website.

This article was created from the video “Can You Scale Revenue Without Sacrificing Values? (Lessons from a CEO)” with the help of AI.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Mike above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understading

The spark: why the virtual CFO was needed

Ellen’s story begins not with a business plan but with a personal need. As a young CFO working on complex M&A transactions for a telecommunications company, she confronted how little practical training executives often receive for irregular but mission‑critical events—acquisitions, integrations and financing rounds. Those high‑value activities are episodic in most small and mid‑sized businesses. To stay engaged in them without becoming a full‑time employee of a single company, Ellen realized she needed to serve multiple clients at once. That realization was the genesis of VCFO: a firm structure that made fractional, high‑level financial leadership both accessible and sustainable.

Market timing and the Austin tech ecosystem

VCFO’s founding in Austin in 1996 was fortunate timing. The city was beginning to attract venture activity and early tech investment—Dell, Austin Ventures and other players were shaping a market that needed scalable financial expertise. Ellen’s early work with newly funded tech companies proved the model: early-stage teams wanted CFO‑level reporting and strategic guidance without the cost of a full‑time CFO. From there VCFO expanded into a broader base of industries, emphasizing an important principle Ellen recommends to every firm building out its client mix:

• Diversify your client base: Finance skills travel across sectors; avoiding over‑reliance on one industry reduces risk.

What VCFO actually does

VCFO provides everything that lives in the “office of the CFO,” delivered on a fractional or virtual basis. Ellen’s team includes CFOs, controllers, staff accountants and a full HR practice. Their engagements typically follow a consistent logic:

• Start by understanding what the owner or CEO wants to accomplish—exit, scale, optimize, or survive.

• Assess the current financial and operational foundation, including cash flow and forecasting.

• Deliver tactical fixes where urgent (audits, clean books) while building a phased strategic roadmap to improve operational excellence and value.

One concrete early deliverable Ellen highlighted is the 13‑week rolling cash flow. For many small and mid‑sized businesses, cash is the most immediate risk—and getting a clear short‑term picture is often the first thing that unlocks better decision making.

Phased engagement and transition

VCFO advises clients in phases, targeting the highest‑impact fixes first and working within budget constraints. When appropriate, the firm helps clients hire their own full‑time finance staff—Ellen describes this as being “the CFO you’d want, but at the right price point.” As a client grows, the engagement often transitions from fractional to full‑time internal hires, with VCFO continuing in advisory or interim roles as needed.

Who is the ideal client?

Ellen summarized her typical client as a company with $10M–$100M in revenue and roughly 20–200 employees, often led by a CEO or founder who needs strategic financial leadership but not necessarily a full‑time CFO. There are exceptions—VCFO has supported larger organizations in special circumstances—but this range represents their core sweet spot.

Culture, people and the finance connection

One of the most powerful themes Ellen emphasized is the interdependence of finance and human capital. VCFO embeds HR capability into its offering because culture and people have real, measurable impacts on the bottom line—turnover, regulatory missteps, visa compliance and unpaid payroll taxes can all produce material cost and risk.

“Put people first.”

That phrase is central to VCFO’s values, with integrity following closely behind. Ellen explained that assessing culture, retention and process often reveals hidden drains on value—missed revenue opportunities, higher cost of sales, and inefficiencies that don’t show up as explicit line items on a P&L.

Building VCFO from the inside: systems, EOS and accountability

Internally, Ellen attributes a major part of VCFO’s scalability to disciplined operating systems and clarity of roles. Key initiatives included:

• Adopting the Entrepreneurial Operating System (EOS) in 2018 to create an accountability chart rather than a mere organizational chart—clarifying roles, responsibilities and meeting rhythms.

• Using RACI (Responsible, Accountable, Consulted, Informed) for key processes so everyone knows who does what and who needs to be looped in.

• Applying hiring tools such as predictive index assessments and gathering employee NPS to constantly tune culture.

Ellen credits that operational clarity with allowing VCFO to pivot quickly—most notably during the COVID lockdown in 2020 when the team shifted seamlessly to remote operations.

Riding crises and the lesson of 2008

Ellen has weathered multiple downturns, and she shared both tactical and philosophical lessons from the 2008–2009 crisis, when expansion and infrastructure investments collided with a dramatic market collapse:

• Take stock early—don’t bury your head in the sand.

• Create contingency plans with clear tripwires for action.

• Be willing to “pull the lever” and execute cost reductions decisively rather than delay and lose optionality.

• Act as a resource for your community—VCFO convened clients and introduced alternative financing sources when banks tightened credit.

Her core counsel for leaders facing shocks is simple and actionable: prepare, decide, execute—and keep looking for opportunities that crises can create.

Leadership, learning and personal grounding

Over decades of leading a professional services firm, Ellen says she’s become more tolerant and empathetic. A guiding maxim she shared:

“There are 13 sides to every story—hear them before you decide.”

Being grounded, true to your values, and open to learning from others are not contradictory. Ellen believes the more secure you are in who you are, the better you can listen, learn and change course when warranted.

Advice for founders: focus on shareholder value

Perhaps the clearest strategic takeaway Ellen left with my audience is this: at every stage of your company’s life, measure and manage for shareholder value—not just topline growth or headcount. She recommends entrepreneurs pause periodically and honestly ask:

• What is my company worth today in the marketplace?

• What things (customer concentration, cultural gaps, regulatory risks, weak margins) are depressing that value?

• What measurable changes can I weave into my strategic plan to improve value over 12–36 months?

This shift in perspective reframes decisions—investment, hiring, process and even M&A—around long‑term value creation rather than short‑term revenue metrics.

A real client story

To illustrate VCFO’s approach, Ellen told me about a family‑owned business in Colorado with a 15‑year relationship. VCFO began by installing a fractional CFO and controller, helped build HR infrastructure, and then supported the company through growth, turnover and recruitment cycles. Today that client still engages VCFO for CFO leadership while relying on internal hires for other roles—exactly the phased evolution Ellen described.

Where to start and how to connect

If you’re a founder, CEO or board member curious about embedding operational finance and people strategy into your growth plan, Ellen suggests a practical first step: take stock of your value today and build a contingency/strategic plan that includes clear tripwires.

She’s open to conversations and can be reached via LinkedIn for questions about finance, HR, or board roles.

Closing thoughts

From my conversation with Ellen Wood, three themes stood out for anyone building a business that lasts:

1. Design for value: Measure and manage your company as an asset, not merely a revenue machine.

2. Integrate finance and people: Culture, compliance and HR are core drivers of operational performance.

3. Build disciplined systems: Clear accountability, contingency planning and operational rhythm let you pivot and scale.

Ellen’s journey from a single CFO confronting M&A complexities to leading a firm that has guided thousands of companies is a powerful reminder: the right combination of domain expertise, empathy and disciplined execution creates services that truly scale—and businesses that stand the test of time.

Get In Touch With Ellen Wood or VCFO

Ellen can be reached through her Linkedin account. To find out more about vcfo, visit their website.

This article was created from the video The Rise of the Virtual CFO: Building a Business that Lasts.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Ellen above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Unleash Your Understanding

The origin story: why XML was born

Brett and his partners left Merrill Lynch in 2004 with two big convictions: (1) they wanted to be entrepreneurial, and (2) they wanted to deliver advice and service that wasn’t hamstrung by conflicts of interest or the overhead structures of large wirehouses. The name XML? A cheeky nod to “ex‑Merrill Lynch” rendered as bold Roman numerals — and, as Brett laughed, the numerals even pointed to an IRS tax code about asset acquisition. The point was symbolic: bold, independent, and a little ironic.

They started small — a tight team serving mass‑affluent to high‑net‑worth clients who needed real financial planning, emotional guidance and independent investment advice (not corporate investment banking or pay‑to‑play product placements). The model: build a firm that only charged clients for what they actually needed and always put the client’s interest first.

People first: independence, trust and client focus

Brett describes his ideal client as someone who needs thoughtful planning, emotional support during life transitions, and independent investment strategy — but not the bells and whistles of large bank corporate services. Being independent meant XML could choose planning software, investment managers and processes without influence from a research or investment banking arm. That freedom, he says, directly improved client outcomes.

“If you can be replaced, then either you’re not adding the value or you have the wrong client.”

Growth by design: from organic build to M&A acceleration

XML grew the old fashioned way: listening to clients and replicating what worked. But when Brett and the partners reached a crossroads in 2016 — keep the firm as a lifestyle practice or turbocharge growth — they chose to scale. They partnered with Focus Financial Partners to accelerate mergers and acquisitions while retaining operational independence. The result: XML moved from roughly $500M in client assets to nearly $4B, while expanding from a handful of people to more than 50 full‑time staff across multiple locations.

How Brett approached M&A

• Prioritize talent, not just assets. Brett looks for teams that add depth.

• Listen first. Understand what made the acquired firm successful before prescribing change.

• Respect culture. Integrate via committees and cross‑firm collaboration rather than forceful mandates.

• Make non‑negotiables clear. Compliance, CRM and security often require standardization; other processes can adapt through education and collaboration.

Building a legacy, not a lifestyle practice

From day one Brett and his partners wanted XML to outlive any single leader. That meant designing a company that could be passed on — not tied to one charismatic founder. Concrete practices reinforced this vision:

• Equity is available broadly. Today there are multiple equity partners representing different roles and genders — a deliberate move to put “money where our mouth is.”

• Open door and mentorship. People are encouraged to say what they want in their careers; if the firm can help them grow personally, professionally and financially, it will.

• Focus on retention and wellness. Happiness and productivity are connected — happier employees serve clients better and stay longer.

“I want every person who comes to XML to be able to retire at XML.”

Culture in practice: small gestures, big impact

Culture isn’t a slide deck you install — it’s a lived experience. Brett shared simple stories that illustrate this: taking down a well‑meaning “swearing jar” after acquisitions that felt juvenile, and recognizing when flexibility (hybrid work) is more valuable than forcing everyone back to an office. Small signals — respect, trust, and setting clear expectations — compound into dramatically better wellness and performance. One new hire even reported better sleep and lower stress in his first week because the culture fit him so well.

Measure the right things: a bottom‑up approach to KPIs

Brett believes measurement works best when it starts with people. Rather than dictating corporate targets from the top, he asks every team member to map personal and professional goals (CFP, MBA, client acquisition, life milestones). From those individual goals he builds the firm budget and KPIs — so company objectives align with what people are trying to achieve.

• Make goals specific and trackable: did you get your CFP? Did you bring in 10 clients?

• Connect firm success to individual success: company outcomes should support personal development.

• Use accountability and shared incentives: benefits and rewards are often tied to firmwide performance.

Leading while producing: the CEO who still advises

Brett continues to be a practicing adviser. He insists this keeps him grounded: “I can’t properly lead if I’m not doing the actual job we’re all about.” That dual role is demanding and requires a team that supports the leader, but it brings credibility and keeps the CEO “in the weeds” of client work, making strategy and product decisions much more informed.

Weathering the low moments

Growth and success don’t eliminate hard days. Markets fall, clients leave, and personal health problems can take a toll. Brett shared how those moments used to hit him harder when he was younger. Over time he learned to take setbacks as lessons, reflect and adapt. For him, the controllables are how the firm communicates with clients and how the team responds during volatility.

AI and the human advantage

Brett is pragmatic about automation and AI: it will make many things more efficient and will change jobs, but it can’t replace human empathy in moments that matter. You won’t get the same comfort and judgment from an algorithm after a loved one dies, or in nuanced life‑planning conversations.

“AI is the wave of the future and is going to make some jobs obsolete. But if your advisory services can be replaced by AI, you probably chose the wrong business.”

He recommends embracing AI where it adds efficiency, while doubling down on human‑centered services that require judgment, empathy and relationship building.

Practical checklist for founders who want to build a people‑centered, AI‑resistant business

1. Start with who you want to serve. Design products and pricing around real client needs, not firm conveniences.

2. Make independence meaningful. Remove conflicts of interest and choose tools that serve client outcomes.

3. Hire for talent and culture fit — prioritize people who add depth, not just assets.

4. Listen first during integrations. Create collaborative committees so acquired teams have voice and ownership.

5. Share equity and create clear career paths so people can grow into leadership without leaving.

6. Use a bottom‑up KPI process that ties personal goals to firm objectives.

7. Embrace AI for efficiency but protect the human moments that define your value.

8. Communicate. Pick up the phone. Solve problems with real conversation, not only chat or email.

What’s next for XML — and how to connect

XML aims to continue growing thoughtfully: hitting $5B and moving toward $10B in client assets through a blend of strategic M&A and organic growth — but always with the “right people” and the same cultural thread. Brett also plans to enjoy more travel and family time as his daughters leave the nest, while keeping fitness and health a priority after long struggles with surgeries.

If you’re an adviser considering a partnership or a client who wants to learn more, Brett suggests visiting xmlfg.com or emailing him directly at brett@xmlfg.com.

Final thought

Building a business that lasts is not about the latest tech gimmick or a culture deck you paste over existing behavior. It’s about committed leadership that listens, a company structure that rewards people for staying and growing, and a relentless focus on human experiences that technology can enhance — but not replace. If you’re building a firm in any industry, start there.

Get In Touch With Brett Bernstein

Geoffrey can be reached through his Linkedin account. To find out more about XML Financial Group, visit their website.

This article was created from the video How to Build a Sustainable Business that AI Can’t Beat.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Brett above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Understanding

Geoffrey is the leader behind a company that partners with more than 2,500 hotels across 100+ countries, helping frontline teams—front desk agents, servers, bartenders, valet staff—generate millions in incremental revenue. In this long-form write-up I synthesize that conversation, highlight the frameworks and stories Geoffrey shared, and extract practical guidance for leaders who want to scale culture without sacrificing performance.

Why frontline culture matters (and why most leaders underestimate it)

We start with a premise that should be obvious but so often gets lost: guests don’t experience a brand in a spreadsheet. They experience it the moment they enter the property. A piece of trash in the parking lot affects perception; the valet, the front desk, the bell person, the server—all of these touchpoints shape revenue and loyalty.

Geoffrey put it plainly: “Sales done right is actually service.” This flips the standard sales-first mentality on its head. Instead of forcing a transactional mindset on service teams, treat the interaction as an act of service that educates and aligns guests with relevant products and experiences. The result is better outcomes for guests and incremental revenue that is often two to three times more profitable than pre-booked room revenue.

The origin story: from hospitality roots to an outcomes-driven company

Geoffrey’s own career began in hospitality—as a car valet in Florida—and he rose through operations and service roles before joining and scaling startups. FPG’s founder, Ziad Khoury, started Khoury Consulting in 1993 and later rebranded the business to Frontline Performance Group as it moved beyond a founder-led consultancy. Geoffrey joined the company when it was still small and helped transform the business from a pure services model into a technology-enabled, subscription-driven company.

One early anecdote captures the grit and validation that shaped FPG’s journey: their first hotel client was the Waldorf Astoria New York—a high-pressure, unionized, prestige environment. Geoffrey remembers being told they were sent there to fail. Instead, they tripled revenue at that property. “We were sent there to fail,” he said. “We actually thrived. We tripled the revenue and it went great.” That win validated the approach and set FPG on a path of international expansion and productization.

Service-based sales: sell by serving, not selling to

Three phrases encapsulate how FPG trains frontline people:

• “Sales done right is actually service.”

• “Sales is not something you do to your customer. It’s something you do for them.”

• “The best service you can offer your customer is to offer your best services.”

These aren’t just slogans. They shape training content, incentives, and daily dialogues at the front desk and in restaurants. Hourly workers often see themselves as order-takers. FPG reshapes that identity: the hourly associate is a revenue driver whose job is to enhance the guest experience with tailored offers—what Geoffrey prefers to call “guest enhancements” rather than upsells.

What makes incremental revenue so powerful?

Two defining characteristics:

• Highly profitable — incremental revenue generated by frontline teams often has no variable cost (beyond the incentive payout), so profit margins are significant.

• Perishable — if you miss a one-night suite upgrade, that revenue opportunity is gone when the guest checks in the next day. These are time-bound experiences.

For hotels, a modest increase in revenue per available room (RevPAR) is transformative. Geoffrey explained that a front-desk-driven improvement of 5-6% is realistic, and their clients typically see returns quickly: the subscription year is often paid for within the first two to three months. On average, FPG reports about a 20:1 ROI for their clients—an extraordinary metric for any service-driven transformation.

From consulting to SaaS: the strategic pivot

FPG’s evolution provides a playbook for other service businesses that want to scale without losing the craft of what made them successful. The steps they followed:

1. Document and digitize intellectual property. What do your consultants do that produces repeatable results? Capture it in learning modules and processes.

2. Build tools that support consultants and clients—analytics, learning management, and employee engagement features—so client teams can self-serve and sustain change.

3. Move from intensive on-site delivery (not scalable) to a hybrid and then primarily virtual model that amplifies the same human expertise.

Geoffrey recounted how the company began introducing basic technology in 2015 to make consultants more efficient. That technology ultimately became a client-facing platform with three main pillars:

• Analytics: visualize performance at outlet, property, and individual levels.

• Learning: a learning management system (LMS) that houses proprietary training—hundreds of hours and thousands of short video segments—covering everything from mindset shifts to sales dialogues.

• Motivation & culture tools: incentive plans, contests, recognition, team feeds, leaderboards—mechanics that provoke the “pyon effect” (peer upward pressure) and make frontline performance visible.

Rather than being technologists who looked for a problem to solve, FPG was field-first: “We were on the ground practitioners who saw how we could digitize the toolkit,” Geoffrey said. That orientation produces better product-market fit because the tools solve problems consultants already knew how to solve in person.

Acquisitions in a crisis: strategic moves during COVID-19

Between 2015 and 2021, FPG acquired two established competitors: Drake Beal & Associates in the U.S. and TSA Solutions out of Singapore. Both deals helped FPG scale quickly into markets and client relationships they would have otherwise taken years to build.

The TSA acquisition was especially noteworthy because it closed during the pandemic when most hotels were closed and revenue had evaporated. Geoffrey described a creative enterprise-value construct that tied value to recovery—allowing both sides to weather the downturn and benefit as travel rebounded. He emphasized relationships: “We were pretty confident that if we got to meet their clients they would like us. We're very relationship-driven. Our greatest strength is our relationships.”

Who is the customer? Four personas to align with

FPG doesn’t target a single buyer. Instead, they design solutions for four interlocking personas inside client organizations:

1. Corporate executives — operational and revenue leaders with portfolio-level P&L responsibility who see the big picture.

2. Hotel general managers — accountable for property-level P&L and culture.

3. Department heads — front office managers, outlet managers—the ones who supervise teams daily and whose behavior changes determine success.

4. Frontline employees — the agents, servers, bartenders, and valets who interact with guests and execute the offers.

FPG aligns its own team to serve each persona: account executives and executives to corporate buyers, directors and managers to GMs, and customer success consultants to department heads and frontline staff. This layered alignment helps bridge strategy and execution.

Changing behavior: the Khoury Performance Equation

At the heart of FPG’s approach is a framework developed by Ziad Khoury, the founder: the Khoury Performance Equation. It answers the central question: how do you change behavior sustainably?

The equation has three components:

• The right environment — culture, psychological safety, managerial tone, and explicit support.

• The right actions — specific behaviors, dialogues, scripts, and accountabilities taught and practiced.

• The right measurement — transparent metrics and feedback loops so people can see how they’re doing and compare to peers.

When you combine these three elements, Geoffrey explained, you begin to change mindsets and embed new habits. At the individual level FPG emphasizes three motivators: recognition (leaders noticing and praising progress), reward (top performers must earn more than bottom performers), and accountability (clear expectations and visible leaderboards).

Geoffrey summarized it this way: “If you put those three things together, which is what our technology does… you can then begin to change their mindset.”

Practical tactics to scale culture using SaaS

From Geoffrey’s experience I distilled practical steps any leader can apply when aiming to scale culture through technology:

1. Document core rituals and scripts. Capture the dialogues, prompts, and small procedural behaviors that produce results. Make them short, repeatable, and trainable.

2. Start with a minimum viable tech stack. You don’t need to build a perfect product on day one—create an LMS + basic analytics + recognition mechanics and iterate from real user feedback.

3. Make metrics visible to the players doing the work. Push performance data down to the frontline so they can see their own KPIs and how they compare.

4. Incentivize fairly and transparently. Ensure top performers materially earn more than lower performers; otherwise, you’ll have a motivational problem.

5. Use managers as proxies for consultants. If you can certify managers to coach daily, you get stronger results than intermittent external visits.

6. Preserve human touch. Digital tools amplify human judgment; they don’t replace it. Keep empathy and role-playing in training loops.

Leadership lessons from the crucible

Becoming a capable executive often involves going through what Geoffrey calls “the crucible”: multi-year stretches of hard work, long hours, underappreciation, and political friction. These periods steel leaders. Geoffrey’s advice for anyone aspiring to leadership:

• Don’t resent the grind—use it to build resilience and judgment.

• Find mentors who can shorten your learning curve and help you avoid dumb mistakes.

• Learn to promote your work without being self-promotional—make sure the right people know the impact you’re delivering.

He summarized the career paradox succinctly: you are judged both on the quality of your work and on how people perceive it. Fix both if you want to progress.

Culture inside FPG: trust first, care with accountability

FPG had to send employees into client environments around the world—sometimes to tense, even hostile workplaces. To do that, Geoffrey argued, the company had to be a “safe haven” for its own people. The internal culture he built emphasizes:

• Trust first — leaders give trust freely and expect people not to break it.

• Care and fairness — give people as many chances as reasonable to perform; only separate people who violate the culture.

• Transparency and accountability — be honest about expectations and quick to call out behavior that undermines others.

Geoffrey told a story that always lands in leadership rooms: he once told an exec team that “you can expect your guests to be treated exactly the way you treat the people you lead.” If executives are abrasive, your front line will reflect that tone.

Personal grounding: faith, legacy, and mentors

We touched on what grounds Geoffrey as a leader. Faith is a part of his life and gives him perspective; he also carries a personal drive rooted in family legacy—being the first in his family to reach certain professional milestones. Mentors also played a pivotal role in his development. These sources of grounding help him pick his battles and steer the company through difficult seasons.

Common objections and how to answer them

Many leaders resist digitizing culture because they believe high-touch service can’t be systematized. Geoffrey’s response is instructive: being practitioner-led changes the dynamic. If you are an expert at a domain and you thoughtfully distill your knowledge into a system that enforces process and accountability, you can scale 10x without collapsing quality. In fact, in many cases outcomes improve because local managers become daily proxies for consultants rather than episodic recipients of advice.

When to keep a human hand in— and when to automate

FPG still offers on-site consulting for clients that need intensive handholding. But Geoffrey emphasized the disproportionate value of certifying managers and delivering live instructor-led training via video. The coronavirus pandemic accelerated comfort with remote learning, even among hourly employees. The rule of thumb:

• Keep humans in for culture-setting and difficult change management.

• Automate predictable training, measurement, and recognition mechanics.

• Use technology primarily to govern quality, not to displace human care.

Measures of success: what to track

To determine if a frontline transformation is working, track a blend of financial and behavioral KPIs:

• Incremental revenue per month (upsell/guest enhancement revenue).

• Payback period on the program/subscription (FPG usually sees payback in 2–3 months).

• Return on investment (FPG reports ~20:1 ROI as an average).

• Frontline engagement metrics: participation in training, leaderboard activity, peer recognition posts.

• Manager adoption: frequency of one-on-ones, coaching notes, and verified certifications.

Practical checklist to begin your own frontline transformation

1. Map every guest touchpoint and list the revenue opportunities that are perishable (upgrades, experiences, add-ons).

2. Document the one-minute pitch for each enhancement—how an employee explains the benefit to a guest.

3. Create a simple leaderboard and recognition flow that highlights top performers publicly.

4. Build an incentive plan that ensures top performers earn materially more than bottom performers.

5. Capture scripts and training modules and deliver them via short video segments; supplement with weekly live coaching for managers.

6. Introduce analytics so everyone can see results—outlet-level down to individual-level performance.

7. Iterate weekly for the first 90 days and celebrate small wins loudly.

FAQ

Q: How quickly can a hotel expect to see results from a frontline program?

A: According to Geoffrey’s experience, clients typically see payback on an annual subscription in the first two to three months. The trajectory depends on baseline performance, but the combination of training, incentives, and measurement produces early wins that compound.

Q: Is it possible to digitize culture without losing the human element?

A: Yes—if you design digital tools to amplify human behaviors rather than replace them. Use technology to make expectations clear, to make recognition instant, to present leaderboards, and to deliver bite-sized learning. Keep coaching and empathy human.

Q: What metrics should leaders use to justify investment?

A: Track incremental revenue (upsell/guest enhancement), ROI (ratio of revenue gained to cost), payback period, and behavioral adoption metrics like training completion, contest participation, and leaderboards. A 20:1 ROI is possible when the program is executed well.

Q: Does this approach only work for hotels?

A: While hospitality is a natural fit, the principles apply wherever frontline teams influence revenue—retail, spas, theme parks, car rental, and food-and-beverage outlets. Any business with perishable experiential capacity benefits from the approach.

Q: How do you handle underperformers without damaging culture?

A: FPG’s culture prioritizes trust and second chances. Give people the tools, show them transparent metrics, and provide recognition for improvement. Only separate people who violate cultural values (dishonesty, disrespect). Don’t fire for initial performance; manage toward development.

Parting thoughts: start with service, scale with systems

Scaling culture isn’t about deploying software and hoping people will change. It’s about starting with service—teaching your teams how to genuinely help guests—and then using technology to sustain, measure, and multiply that help across a geographically dispersed organization.

Geoffrey’s journey from valet to CEO of a 300-person company shows how practitioner-led product design, anchored in trust and powered by transparent measurement, can turn front-line teams into consistent revenue generators. The ingredients are deceptively simple: clear scripts, credible incentives, visible metrics, and a culture that trusts employees first.

If you’re a leader wrestling with how to grow without losing the soul of your brand, begin by asking three questions:

• Which guest interactions are perishable and under-monetized?

• Can we capture and teach the small behaviors that convert those opportunities?

• How will we make this performance visible and rewarding to the people who execute it?

Answer those, and you’ve started the work of scaling not chaos—but culture.

This piece summarizes my conversation with Geoffrey Toffetti on The Business Philosopher Within You. If you want to explore how these ideas can apply to your frontline teams—hotels, restaurants, retail, or other experiential businesses—look for partners who combine practitioner expertise, a learning-first approach, and lightweight analytics that make results visible and repeatable.

“The best service you can offer your customer is to offer your best services.” — Geoffrey Toffetti

Get In Touch With Geoffrey Toffetti

Geoffrey can be reached through his Linkedin account. To find out more about Frontline Performance Group, visit their website.

This article was created from the video Scaling Culture with SaaS: Lessons from a CEO with the help of AI.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Geoffrey above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Elevate Your Understanding

Below I’ve captured the core lessons, stories, and practical steps Carol shared, presented as a guide you can use personally and organizationally. If you lead a team, an entire company, or are simply trying to align your own career with what matters, this is the roadmap to making purpose real: not as a poster on the wall, but as a strategic force embedded in strategy, products, people, and performance.

What Is Purpose? The “Why Beyond Profit”

Purpose is deceptively simple in definition and profound in effect. At its core, purpose answers one question: why do we exist? Carol phrases it as “an organization or a brand’s why,” the reason beyond making a profit. It’s grounded in humanity: in how work, products and relationships touch minds hands, and hearts.

"Employees don't wake up in the morning to make money for somebody else. They want to do something that engages their head, their hands and their heart."

That triad — intellect (head), behaviors and results (hands), and emotional connection (heart) — is a useful way to check whether a purpose is complete. A strong purpose appeals to people’s reasoning, gives them something tangible to do, and moves them emotionally toward the company’s mission.

Personal Purpose vs. Organizational Purpose

Purpose shows up in two complementary ways: as personal purpose and as organizational (or brand) purpose. The most powerful situations are where the two align.

• Personal purpose is what gives someone direction and meaning in life and work. Carol’s own personal purpose, for example, is to help organizations and individuals discover and live their purpose.

• Organizational purpose is the collective “why” of a company, brand or nonprofit. It needs to be authentic to the company’s history, products and impact.

When personal and organizational purpose meet, you don’t just get motivated employees, you get people who stay, produce better work, and recruit others who resonate with the mission.

Examples That Make Purpose Real

Concrete examples help translate abstract ideas into practical models. Carol shared several that illustrate different kinds of purpose in action:

• Unilever: Paul Polman led a transformation grounded in the company’s origins (e.g., Lifebuoy soap’s handwashing history). Unilever’s purpose, “making sustainable living commonplace,” wasn’t a marketing line; it became a lens for product choices, brand investments and employee engagement. The brands that embraced authentic purpose grew faster and contributed disproportionately to profit.

• Patagonia: A founder-led purpose with a planetary focus: “We exist to save our home planet.” Patagonia aligns every business decision, including donations and corporate structure, to that mission.

• Mars: “The world we want tomorrow is how we do business today” is a simple, ambitious phrase that translates into long-term corporate behavior across products, supply chains, and investments.

• Lineage Logistics: A B2B example where cold-storage warehouses framed their work as feeding the world and eliminating food waste. That elevated a functional business into a purpose-led supply-chain partner and inspired new initiatives like large-scale meal donations.

• Aflac: Turning the iconic Aflac duck into a social robot for kids fighting pediatric cancer demonstrates creative product-level purpose: a tangible invention born from both brand assets and societal need.

Why Purpose Isn’t a Slogan; It Must Be Lived

A danger many organizations encounter is treating purpose as a marketing headline. Purpose must be embedded across the business to be strategic and durable. Carol’s research over thirty studies makes that clear: purpose drives results when it is authentic and operationalized.

Key pitfalls:

• Letting the loudest voice in the room define purpose, rather than listening broadly.

• Creating a beautiful statement, then failing to weave it into values, behaviors, product decisions, and KPIs.

• Starting the work in the middle of the organization and hoping it spreads upward — Carol is clear that real transformation needs CEO commitment.

The Discovery Process: How to Find Purpose (Personal & Organizational)

“Discover” is the operative word. Purpose is typically found rather than invented in thin air. Carol’s firm uses a framework called P3: Precision Purpose Programming. It’s a deliberate, evidence-driven process that combines archival work, interviews, surveys, workshops, and quantitative research.

Here are the practical steps distilled from that approach:

1. Start with history. Look back to the company’s origins. What was the original problem the founders solved? Lifebuoy soap’s hygiene mission was a seed for Unilever’s later work.

2. Map products, services, and customer relationships. How do existing offerings already impact people and communities? Where is there natural resonance?

3. Interview broadly. CEO-led initiatives are essential, but you must interview people at every level: the CEO, senior leaders, factory workers, salespeople, and frontline staff. If you don’t interview enough people, the loudest voice wins — and that risks producing a shallow or inauthentic purpose.

4. Survey employees. Ask what causes matter to them, where they find pride in the company, and what changes would make work meaningful. Survey data complements qualitative interviews and can be especially useful for global organizations where you can’t conduct workshops everywhere.

5. Define ambition and scope. Is the purpose global in scope, or focused on a local community? How much budget and energy do you want to commit? Clarity on ambition influences the nature of the purpose.

6. Prototype and refine. Bring draft language to workshops, adjust based on feedback, and test reactions across regions and business units.

7. Make it measurable. Embed purpose in KPIs, performance evaluations, product roadmaps, and supply-chain decisions.

Discovery is collaborative. Carol emphasizes co-creation because when people participate in the creation of purpose, they more readily buy into its execution.

Launching and Activating Purpose: From Statement to Strategy

Even the best-crafted purpose needs a launch and a living plan to make it stick. Carol shared how effective rollouts include storytelling, leadership visibility, and practical integration:

• CEO sponsorship is non-negotiable. The CEO must champion the work publicly and personally. When the CEO introduces purpose at a global meeting, it sends a signal that this is strategic, not cosmetic.

• Create a compelling launch. Off-site launches with creative assets — especially video — help convey the emotional and practical dimensions of the purpose. Employees need to feel it and understand their role in delivering it.

• Embed it everywhere. Review values and behaviors: if purpose changes the company’s why, values must be revisited. Translate values into observable behaviors and link them to performance metrics.

• Use purpose as a decision lens. Product investments, M&A decisions, supply-chain policies (e.g., sourcing free of child labor), and divestitures should be tested against the purpose. Kerry Group used purpose to decide which businesses to divest.

• Keep measurement and follow-through. Regularly measure how well purpose is being lived. Too often organizations have purpose on the wall but not in practice.

Embedding Purpose into Business Decisions

Purpose should guide the hard choices. Carol gave the example of Kerry Group: after defining its purpose (“Inspiring Food. Nourishing Life.”), leadership used that lens to refocus the company and divest businesses that were not aligned. Purpose, properly applied, becomes a strategic filter that simplifies choices and reduces mission drift.

CEO Responsibility: Why Purpose Needs Top-Level Commitment

Who leads purpose work? Carol is unequivocal: it starts at the top. CEOs set direction and allocate resources. Without CEO commitment, purpose initiatives risk becoming a middle-management project that never achieves scale.

Why the CEO matters:

• CEOs set the operational tone: values, behavior expectations, and allocation of capital.

• CEO visibility during launch demonstrates seriousness and prevents cynicism from spreading.

• CEOs can align boards, investors, and external stakeholders around long-term commitments required for lasting change.

Carol noted that purpose rarely works when initiated from the middle out. The CEO and C-suite must be present in interviews, in priority-setting conversations, and in the public rollout.

Proof That Purpose Moves the Needle (The Data)

Purpose is moral and it’s measurable. Carol’s decades of research, and third-party studies, demonstrate the business case:

• Unilever: Not every brand needed a purpose, but the 30-ish brands that found authentic purpose grew faster and contributed disproportionate profit. Carol cites that these purpose-led brands grew about 69% faster and produced around 75% of the profit among Unilever’s brands that embraced purpose.

• Deloitte/Other research: Companies that authentically live their purpose can achieve materially better financial results. Deloitte’s research, for instance, found that purpose-driven companies can deliver up to three times greater returns (exact figures vary by study and methodology, but the pattern is consistent).

• Internal P3/B2B work: In a sample of about 2,000 B2B respondents, 86% claimed to have a purpose, but only 24% truly lived it. That gap illustrates that intention alone doesn’t equal impact; embedding purpose into the business does.

• Public opinion: After a recent election, Carol’s team asked Americans whether companies should invest more in social impact. Forty-six percent said companies should do more. Support varied by party (66% Democrats, 49% Independents, 36% Republicans), but the overall takeaway is clear: citizens expect corporate contribution to societal well-being.

And when asked what issues companies should address, health and well-being rose to the top, with mental health emerging as a cross-partisan priority.

From "Me" to "We": Societal Trends and the Purpose Pendulum

Society swings between "me" and "we" over time. Whether this is cyclical or generational, purpose and social responsibility are part of a larger cultural conversation. Carol — someone who grew up in the activist eras of the 1960s and 70s — believes that when people and businesses prioritize the collective wellbeing (the “we”), companies that embed purpose create more resilient, future-ready organizations.

Two points to keep in mind:

• The planet is a stakeholder. Beyond employees and communities, businesses must incorporate planetary health into decisions. Paul Polman summarized it bluntly: “We need more trees and more people.”

• Younger generations are hungry for meaning. Gen Z and Millennials care about purpose and are increasingly choosing employers and brands that align with their values. They also lead cultural practices: putting down phones, seeking nature, prioritizing mental health.

How Individuals Find and Activate Personal Purpose

Personal purpose is discoverable. It often emerges through self-reflection, experimentation, and connection. Carol suggests practical steps for individuals:

1. Explore what energizes you. What are the activities you lose time doing? What makes you feel alive?

2. Talk with trusted peers. Honest conversations with friends or mentors help surface consistent themes.

3. Be curious. Read, listen to podcasts, try brief stints in different industries before locking into a long-term path.

4. Try roles that align with your strengths. If you like words and ideas, find roles that let you write, design, or shape narratives.

5. Find companies that mirror your values. If societal impact matters to you, consider working for B Corps, mission-driven firms, or foundations.

6. Don't rush. Personal purpose often crystallizes through time and repeated experience.

And a practical career tip Carol emphasizes for younger professionals: be a great student of your craft. Study, prepare for interviews, and show up with curiosity and competence.

Superpowers, Creativity, and Invention: Stories That Inspire

Carol’s work frequently combines a superpower (her own is “connection-making”) with brand assets to create novel purpose-led initiatives. Two standout projects illustrate this inventive approach:

• My Special Aflac Duck: Carol paired Aflac’s iconic duck with a social robot designed for children battling pediatric cancer. The product is an emotional, practical tool: a toy that helps children communicate, manage treatment days, and feel less isolated. Aflac donated thousands of the robots to hospitals and families.

• Whirlpool washing innovations: Recognizing that billions lack electric washing machines, team members designed hand-cranked or low-resource washers that deliver dignity and hygiene to communities where women spend many hours washing by hand.

These projects matter because they turn brand identity into measurable societal outcomes. They also demonstrate that purpose is fertile ground for product innovation and partnership design.

Practical Checklist: Bring Purpose to Life in Your Organization

If you’re leading purpose work, here’s a condensed checklist that combines Carol’s guidance with practical execution steps:

1. Secure CEO sponsorship and board alignment.

2. Conduct broad discovery: archival research, interviews at all levels, global workshops (if relevant), and employee surveys.

3. Define ambition, scope, and budget so the purpose is actionable, not aspirational without teeth.

4. Draft the purpose statement and test it with employees and customers; iterate until it feels right and real.

5. Launch with storytelling assets (video, employee testimonies, leadership Q&A) and clear examples of how the purpose will influence decisions.

6. Revisit values and behaviors. Translate values into observable actions and build them into performance metrics.

7. Use purpose as a decision lens for product development, M&A, divestitures, supply chain sourcing, and community partnerships.

8. Measure and publicize outcomes. Track employee engagement, brand growth, product performance, and societal impact.

9. Train managers and leaders to embody the purpose daily; avoid making it a one-off communications campaign.

Common Missteps to Avoid

• Putting purpose in marketing only. If an organization markets purpose but doesn’t operationalize it, employees and customers will sense the mismatch and call it out.

• Starting from the middle out. Without C-suite commitment, purpose rarely achieves the scale required to impact product choices and financial performance.

• Failing to measure. Purpose initiatives without measurable goals and KPIs become feel-good projects without sustaining effects.

• Rushing the rollout. Purpose work is long-term by nature; it requires patience and continuous reinforcement.

Final Thoughts: The Power of Head, Hand and Heart

Purpose is strategic and soulful at the same time. It equips organizations to make better choices, design better products, and build deeper relationships with employees and customers. But for purpose to create lasting business value it must:

• Be authentic — rooted in history and honest about capabilities.

• Be collaborative — created and owned by people across the organization.

• Be operational — embedded in values, behaviors, KPIs, and product decisions.

"You can do work that truly involves your head, your hand and your heart."

That is the practical promise of purpose. When done right, purpose is not a soft-end initiative. It’s a strategic resource that helps companies accelerate growth, protect long-term value, and make stronger, more aligned choices for people and planet.

For Individuals and Young Professionals

If you’re early in your career, Carol’s advice is particularly helpful:

• Experiment with industries and roles, but avoid changing jobs every six months. Build depth that employers notice.

• Identify your superpower and find roles that make use of it.

• Be curious: read, listen, get off your phone, and spend time in nature. Those practices sharpen the inner signals that point to purpose.

• Look for organizations with genuine commitment, not just marketing copy. B Corps, social enterprises, and companies with transparent measurement are a good starting point.

What’s Next

Carol continues to pursue big ideas — invention, product-led social impact, and creative partnerships — and her teams are looking for collaborations that turn corporate assets into measurable social outcomes. For business leaders, the invitation is clear: start with the why, involve people broadly, and then commit to living the purpose every day.

If you’re a leader wondering where to begin: start by asking the people who know your business best, your employees, what matters to them. Then bring that feedback to the C-suite and make the commitment to act. Purpose is not a trend. It’s a durable way to build organizations that matter.

Parting Note

Purpose moves organizations from transactional to transformative. It bridges business and society, aligns personal and corporate meaning, and — when properly discovered, launched, and embedded — delivers measurable growth and stronger communities. It’s worth the hard work because the payoff is nothing less than companies that last.

For leaders, the question is no longer whether to have a purpose; it’s how to make yours real, measurable, and central to the business so that it guides decisions and mobilizes people. As Carol reminded me: when purpose is authentic and activated, it becomes the living, breathing execution of why we’re here.

Get In Touch with Carol Cone

Carol Cone ON PURPOSE

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This article was created from the video How Purpose-Driven Leaders Transform Organizational Culture with the help of AI.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Carol above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen Your Learning

Why this matters now

We spend a huge portion of our lives at work. If work is merely transactional the rest of life gets squeezed. If work is meaningful and readable as progress toward personal goals the quality of life improves. That is why the phrase flow state, effortless workplace productivity matters. It is not a slogan. It is a practical description of a state of concentrated production where time feels different and output multiplies. In our hour together Steven described how the film industry has been practicing different modes of work for a century long before the current debates about remote, hybrid, and office-first work. The film model contains lessons that are ready to be applied across industries.

What is a flow state

Steven quoted Mihaly Csikszentmihalyi’s classic research on flow. The description is simple and exact: flow is a concentrated state where you feel carried forward by a river of consciousness. You become so absorbed in an activity that you lose track of time. You forget mundane needs like eating or checking a phone. You feel a direct line between attention and accomplishment. That is the state most of us mean when we say we are genuinely productive.

"You become part of a river of consciousness that carries you forward." — Mihaly Csikszentmihalyi, quoted by Steven Puri

This is not mere entertainment or brief distraction. You can be deeply engaged with something that makes you sad, or scared, or joyful. Engagement is not the same as amusement. When you are engrossed in creative work, whether writing, coding, designing, or composing, you are in a place where flow state, effortless workplace productivity shows up.

Five core conditions for entering a flow state

Steven mapped out a short checklist of conditions that research and experience repeatedly confirm. These are the levers you can experiment with immediately.

• Skill meets challenge: The work must be something you can do, not something trivial but not wildly beyond your skill level. A gap between your skills and the challenge creates focus without anxiety.

• Sense of meaning: You need a reason to care. Great leaders help teams connect daily tasks to a larger purpose. When the task matters it allocates emotional energy to that work.

• Clear, bounded time blocks: Interruptions are costly. Studies show it can take 17 to 22 minutes to reenter focused work after an interruption. Timeboxing reduces that drag.

• Space that cues work: Our brains associate places with actions. Writers, directors, and designers often use the same room or coffee shop to trigger creativity. The right environmental cues can prime flow.

• Sound and sensory design: Nonvocal music, soundscapes, or nature recordings help many people reach deep concentration. For others silence is needed. Know which works for you, then make it available.

When these elements align you increase the odds of achieving a flow state, effortless workplace productivity. Steven emphasized that these conditions are accessible, not exclusive. They can be engineered into daily routines and team practices.

Lessons from film that translate to any workplace

One of the most striking parts of our conversation was the way Steven used the film production lifecycle as a model for modern work. Film projects naturally cycle through phases that mirror remote, hybrid, and in person work.

Here is the typical arc:

• Remote starting phase: Writers work alone in coffee shops or home offices to develop the idea.

• Small in person team phase: Producers, scouts, and designers meet in a production office to organize logistics and budgets.

• High intensity in person phase: Principal photography is location based and everyone is on set together for long stretches.

• Post production hybrid phase: Editors, sound designers, and visual effects artists work from remote studios then come together as needed.

Film teams have practiced moving between these modes for more than a century. Leaders in film have developed rituals and infrastructure to preserve creative energy through those transitions. Translating this to tech or corporate environments means recognizing which tasks need in person collaboration and which require long uninterrupted stretches of deep work. When leaders make this distinction and protect time for focus they create conditions for flow state, effortless workplace productivity.

Meaning as the silent multiplier

Steven used a story from Sukha Company to show how meaning shows up in small but decisive ways. During Sukha’s early days a member told him the service bought him back three clocks in his life. He could be with his kids at 3pm. Steven and his wife connected that description to a Sanskrit word known as sukha, interpreted as self fulfillment and ease. That conversation reframed sukha’s tools as a path, not the end point. The tools are helpful only when they serve the purpose you truly want: more meaningful time with family, finishing projects, or launching a side business.

If a leader can communicate how a task connects to a meaningful outcome, individuals are more likely to invest in concentrated attention. That is the soft multiplier for flow state, effortless workplace productivity.

Remote work, in person work, and where flow thrives

We are in the middle of heated debates about return to office versus remote work. Steven made a nuanced point: film practice suggests a mixed model is natural. Work shifts between modes depending on the phase. Some work benefits from in person chemistry. Other work requires solitude and deep focus. The ideal manager identifies which roles and tasks need which mode and then designs policies to respect those needs.

Some examples:

• Creative planning, brainstorming, and whiteboarding usually benefit from in person contact to catch nonverbal cues and rapid iteration.

• Deep design, coding, and drafting work benefit from long uninterrupted blocks outside of frequent meetings.

• Administrative and transactional work can be scheduled into shorter micro blocks where responsiveness matters more than concentration.

Once you align the mode of work to the task, you get closer to flow state, effortless workplace productivity across the team.

Community and ambient accountability

One of the strongest themes Steven discussed was the power of community. He described a coffee shop in West Hollywood that felt like a clubhouse where many writers showed up to work. People were rarely talking, yet everyone felt accountable to each other’s presence. That ambient energy increases focus. Steven built that same vibe into Sukha by allowing members to show periodic photos of themselves working. Those faint social cues replicate the coffee shop magic online.

Community does several things:

• It reduces the friction of isolation.

• It creates gentle accountability without policing.

• It supplies emotional uplift on hard days and reciprocation when others need support.

When organizations build communities aligned to work rhythms they increase the chances that people will experience flow state, effortless workplace productivity more often.

Timeboxing and goal setting as practical tools

Steven and I spent time talking about simple tools that change behavior. Two are essential: clear goals and timeboxing.

Clear goals operate at two levels. Short term daily goals answer the question: what will I accomplish this sitting? Longer horizon goals answer: where am I headed this quarter or this year. Both are necessary. The short term goal creates a mission for the current block of attention. The horizon goal gives context and meaning.

Timeboxing is a simple habit that transforms vague intentions into concrete action. If you say you will finish a design before lunch and you have a two hour time box your brain invests differently. Remind your team to treat meetings as boundaries and protect blocks for deep work. Steve pointed to a practical rule his teams use: designate core hours with no recurring group meetings. For example, no meetings from 9am to noon. That simple policy reduces interruptions and creates long blocks where flow state, effortless workplace productivity can emerge.

Deep work versus flow

We clarified a useful distinction. Cal Newport’s deep work concept describes the type of work that requires high concentration and produces high value. Flow is the internal state you enter when deep work is working. Deep work is a task category. Flow is the subjective experience. You can schedule deep work. Flow will be the result when conditions align. That is why leaders should protect time and provide the environment that makes deep work more likely to generate flow state, effortless workplace productivity.

Designing workspaces and schedules that cue productivity

Steven offered practical design ideas you can try this week.

• Assign specific spaces to specific activities. Writers rent the same villa when they want to recapture a prior creative state. You can create the same effect by having a focus room, a collaboration room, and casual zones. The brain learns the cue and associates the space with performance.

• Use soundscapes. Not everyone likes music. Some people want absolute quiet. Offer a menu: binaural tracks, 60 to 90 BPM instrumental playlists, rain and nature recordings. Steven recorded rain in the Himalayas and found people loved it. When people can choose their sound environment they enter their optimal concentration faster.

• Block meetings. Protect large blocks for work. Even as few as three hours of uninterrupted work in a day can produce breakthrough progress for designers and engineers.

• Curate ambient community cues. A feature in Sukha takes snapshot photos of members working. That tiny visibility reduces isolation and creates the coffee shop accountability effect.

These steps are simple to implement. They are not free. They require leadership choices. But the return is material. Teams report higher output, less burnout, and faster project completion when these practices are in place.

How leaders can enable the flow state across a team

Leaders should see their job as configuring conditions that let individuals do their best work. Steven gave a short list of actions that any manager can start today.

• Hire for alignment. Hire people with the right skills and shared values. A value aligned team will more easily find meaning in the work and stay committed when deep effort is required.

• Communicate the why. Make sure every assignment carries a clear why. Link tasks to outcomes people care about. Meaning motivates attention.

• Protect deep work windows. Declare core focus hours and limit meetings. Reduce the expectation of instant response during those hours.

• Provide tools not rules. Give people access to noise options, timers, and community channels that support concentration. Let them pick the mix that suits their chronoype and preferences.

• Measure outcomes not hours. Define work as what got done. Move away from valuing late nights or presenteeism. Reward high impact results.

These are the most direct levers leaders can pull to increase the frequency of flow state, effortless workplace productivity across their teams.

What to do when people are different

Not everyone benefits from the same cues. Steven and I discussed sensors versus intuitives, music lovers versus silence aficionados, night owls versus morning people. The practical answer is personalization. Give team members autonomy to choose when and where they do their deep work. Set team agreements rather than one size fits all mandates. Respect different chronoypes and provide shared infrastructure that accommodates the range of preferences.

For example, create optional quiet hours, provide headphones and sound options, and set asynchronous collaboration norms. These moves create a baseline that lets different people find their own path to flow state, effortless workplace productivity.

Real world examples and stories

Steven shared moments from his life that illustrate the human side of this work. He started companies, won Oscars for visual effects early in his career, then moved into film production and later back into tech. He raised roughly 21 million dollars in venture capital over many years. He also failed and learned from those failures.

One memorable Sukha member told Steve he paid for three clocks. The platform got him back time with his family. That comment reframed Sukha as a pathway to a life people wanted. Another story involved writers who rented the same villa to capture a habit cue that had supported their earlier success. The villa became a creative anchor. These stories are small research moments that point to larger truths about environment, ritual, and meaning.

On a very personal level Steve described times he felt shame and isolation after companies failed. He also described a recent health scare that made him reexamine priorities. Those experiences made him more compassionate and a better listener. These human notes matter because flow state, effortless workplace productivity is not just a productivity hack. It must be rooted in humane leadership and compassion.

Practical checklist to increase flow in your week

Below is a compact checklist you can use to convert the ideas from our conversation into practice.

• Identify one deep work project this week and reserve a 90 to 180 minute block to work on it without interruptions.

• Remove notification expectations during the block. Tell your team this is your focus window.

• Choose a space that cues concentration. If you are remote pick a cafe or a particular room. If you are in the office use a focus room.

• Test two soundscapes. One instrumental playlist and one nature sound. Track which one increases uninterrupted time.

• Write a one sentence why for the task. Keep it visible while you work.

• At the end of the block note what you learned and how much you produced. Reinforce output over hours.

• If you are a manager, block shared no meeting hours and measure how it affects throughput after two weeks.

Following these steps will lift you closer to the experience Steven calls flow state, effortless workplace productivity.

Tools and resources

Steve mentioned several resources and authors that are helpful if you want to study this deeper. Here are a few he recommended during our chat.

• Mihaly Csikszentmihalyi’s book on flow for the foundational theory.

• Cal Newport’s writing on deep work for task design and scheduling.

• Product tools such as timers and curated playlists that enable focus blocks.

• Community mechanisms like shared working channels or virtual coffee shop features to create ambient accountability.

Use these readings to create a shared language on your team so you can experiment quickly and iterate.

Why this is not about happiness at work in the party sense

Steven and I were clear: the point is not to turn work into a continuous party. The goal is to design work so people feel fulfilled and effective. Many people confuse a happy workplace with constant entertainment. That is not what we mean. A team that experiences flow state, effortless workplace productivity will be engaged even during hard moments. Engagement can coexist with seriousness and depth. That kind of workplace sustains people over long careers rather than burning them out quickly.

Measuring the impact

How do you know if these changes are working? Steven suggested a few practical metrics:

• Output per time block rather than hours logged.

• Percentage of work time spent in protected deep work windows.

• Qualitative surveys about perceived meaning and wellbeing.

• Retention and progress on major projects across sprints.

When leaders measure outcomes not hours and when teams track time in protected blocks, you will see tangible improvements in both quality and speed.

Final thoughts from our conversation

We all have something great inside us that often never gets expressed. A combination of the right skills and a caring environment increases the chances that talent becomes output. Leaders, teams and individuals can choose to create the conditions that invite flow. The tools are not the goal. They are the path toward the goal, which is a life where work is meaningful and enjoyable in a way that does not rely on stress and overwork.

Steven summed it up beautifully: Sometimes leaders or colleagues help unlock potential. Sometimes we unlock it ourselves. The work of designing systems, spaces, and schedules is a human act. It is about creating a context where people can do the great things they are meant to do.

Where to learn more and reach Steven

If you want to learn more about what Steven is building at Sukha or want to ask a question he invited people to reach out. He is open to emails and to sending reading recommendations from authors like Cal Newport or James Clear. The company he founded is The Sukha Company, and the purpose of the tool is to help people work faster, feel healthier, and finish projects that matter. Use the buttons below to get in touch with Steven and the Sukha Company.

The Sukha Company

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Get started this week

To put this into action choose one item on the checklist and commit to it. If you are a manager, try a single week of protected focus hours. If you are an individual contributor, pick a 90 minute block and try both a music playlist and a nature soundscape. Watch how your attention changes. As you and your team learn, iterate on the environment over the next two sprints.

The greatest gift you can give yourself and your team is the permission to make work a human experience that produces more with less stress. That is the promise behind flow state, effortless workplace productivity. It is modest, practical, and within reach.

Closing

If you enjoyed this summary of my conversation with Steve Puri on The Business Philosopher Within You please try at least one of the experiments this week. Small changes compound. If you are leading a team you may find that protecting three hours a day is the single most effective move you can make to increase collective output and wellbeing. Flow is not mystical. It is the outcome when meaning, time, space, and skill align. That is where real work becomes a beautiful human experience.

This article was created from the video Tap Into Your Flow State: Secrets to Effortless Workplace Productivity with the help of AI.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Steven above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Enrich your understanding

In this article, podcast host Bhavesh Naik interviews Dr. Christie Vanorsdale, a Learning Systems Architect who transforms complex organizational challenges into sustainable learning ecosystems.

Drawing from Christie’s deep expertise in learning sciences and organizational design, this article explores how leaders can revolutionize their approach to learning by fostering collaborative, inclusive, and scalable learning ecosystems.

"We learn better when we co-create knowledge as a community." – Dr. Christie Vanorsdale

About Christie Vanorsdale

Dr. Christie Vanorsdale is a distinguished learning systems architect. With over 15 years of experience across continents like Asia, Europe, and the Americas, Christie transforms complex challenges into sustainable learning ecosystems. Her unique blend of expertise in learning sciences and practical engineering has empowered countless organizations.

Christie specializes in building frameworks that not only scale but also adapt to support every trainer and learner. Her passion lies in designing inclusive environments that drive business impact while ensuring everyone feels supported.

What Is Learning? Perspectives That Shape Effective Organizations

Understanding what learning truly means is foundational to designing impactful learning environments. Learning can be viewed through multiple lenses:

• Behavioral Change: Learning as a change in behavior aligns with traditional behaviorist theories. Organizations focused on results often see learning as the driver of different and improved behaviors that lead to better outcomes.

• Cognitive Learning: From a cognitive perspective, learning involves retaining and applying knowledge, not just memorizing facts. The ability to transfer learning to new contexts is a hallmark of deeper understanding.

• Insight-Based Learning: Sometimes learning happens through “aha moments” — sudden realizations that shift our mindset permanently. These moments often occur in environments where anxiety is low and motivation is high, allowing the brain’s working memory to process new information effectively.

These perspectives highlight that learning is not one-dimensional. For organizations, this means designing learning systems that consider both measurable behavior change and the internal, psychological experiences of learners.

Designing Learning Environments: The Two-Pronged Approach

Creating effective learning experiences requires a balance between methodical goal-setting and fostering the right environment for learners to thrive.

1. Starting with the End in Mind: Backwards Design

Leaders and learning architects must begin by clearly defining the desired outcomes. This approach, known as backwards design, involves:

• Identifying specific goals learners should achieve by the end of a training or program.

• Designing materials and assessments that directly support those goals.

This ensures that every aspect of the learning experience is purposeful and aligned with organizational objectives.

2. Creating the Right Learning Environment

Beyond content, the environment where learning takes place is critical. This includes:

• Psychological Safety: Learners need to feel safe to be vulnerable, ask questions, and take intellectual risks without fear of judgment.

• Low Anxiety and High Motivation: Reducing stress and increasing motivation opens working memory capacity, enabling better information processing.

• Accessibility and Intuitiveness: The learning system should be easy to navigate, with clear instructions and minimal frustration. If learners struggle just to access training, motivation plummets.

Design thinking principles are invaluable here. By deeply understanding learners’ needs, motivations, and contexts—often through interviews and prototyping—organizations can craft environments that truly support learning. This user-centered approach avoids the pitfall of creating training solutions that look impressive but fail to meet learners where they are.

Breaking Down Silos: Collaborative Learning as a Catalyst

One of the most powerful outcomes of well-designed learning ecosystems is the breakdown of organizational silos. When departments like sales, marketing, operations, and finance collaborate on learning initiatives, several benefits emerge:

• Improved Communication: Shared learning projects foster transparency and understanding across functions.

• Unified Brand of Learning: Developing a consistent approach and voice to training that reflects the organization's culture and values.

• Enhanced Employee Engagement: When learners from different parts of the organization co-create knowledge, motivation and retention increase.

For example, involving multiple stakeholders in reviewing training materials before launch encourages dialogue and reveals insights that might otherwise be missed. This collaborative process not only improves the quality of training but also builds a culture where learning is a shared responsibility.

Who Benefits Most from Learning Ecosystems?

While every organization can benefit from fostering learning, the impact is often greatest when leadership—especially roles like Vice Presidents of Operations or CXOs—champion these initiatives. Their broad oversight allows them to:

• Ensure alignment across departments and break down silos.

• Implement governance around content creation, user management, and quality control.

• Gain visibility into training effectiveness at a granular level.

By embedding learning into the operational fabric, these leaders help create ecosystems that not only support compliance but also drive employee growth, customer satisfaction, and organizational agility.

From Compliance to Culture: Making Learning Meaningful

Many organizations initially approach learning out of necessity—compliance with regulations or mandatory training. However, viewing learning as merely a checkbox creates low motivation and engagement.

Transforming compliance training into an opportunity for growth involves building a culture where learning is valued and linked to personal and organizational goals. When employees see that their company invests emotionally and financially in their development, compliance courses become just one part of a broader, inspiring journey.

Adult Learning Principles: Meeting Learners Where They Are

Adult learners bring complexity to the training environment. Unlike children, adults balance multiple life responsibilities and often have preconceived notions or ego barriers that impact motivation. To design effective adult learning experiences, consider:

• Clear Rationale: Adults need to understand why they are learning something and how it applies to their work or life.

• Managing Expectations: Communicate upfront about time commitments and activities involved.

• Plain Language: Use accessible language to reduce cognitive load and anxiety, especially for learners with diverse backgrounds.

Creating a low-anxiety, high-motivation environment tailored to adult learners maximizes their engagement and retention.

Overcoming Challenges: A Personal Journey of Growth and Resilience

The path to becoming a learning systems architect is often filled with hurdles. Navigating the complexities of designing scalable learning ecosystems requires perseverance, adaptability, and continuous self-reflection.

One vital lesson is transitioning from a reactive, survival mindset to a proactive, purpose-driven approach. This shift involves:

• Developing a clear business strategy beyond just delivering projects.

• Seeking support such as business coaching to refine focus and goals.

• Embracing anxiety as a natural part of growth while fostering trust and love for the work.

This personal transformation mirrors the organizational change leaders seek to inspire in their teams.

Practical Steps to Start Building a Learning Culture Today

Not every organization can implement large-scale learning ecosystems immediately. However, small, deliberate actions can spark meaningful change:

• Create channels like a Slack group or discussion board where employees can ask questions and receive support.

• Start with one targeted change or improvement in your learning processes.

• Encourage leadership to take responsibility for employee growth and model learning behaviors.

Remember, when employees thrive, the business thrives.

Connecting and Moving Forward

If you are a leader or learning professional interested in transforming your organization’s learning culture, consider partnering with experts who specialize in creating bespoke learning ecosystems tailored to your unique needs. By focusing on your organization's specific goals, culture, and learner personas, you can build a sustainable framework that supports continuous growth and collaboration.

Whether you are aiming to overhaul your entire learning infrastructure or simply want to initiate one small improvement, there are strategies and tools available to guide you on this journey.

Contacting Christie Vanorsdale

Christie can be reached through her website or through Linkedin.

If you want to explore nurturing a learning culture into your organization, from high-level conceptual design to the nuts-and-bolts of learning management systems, you can schedule a conversation with Christie.

Book a Free Call with Chrities

Vanorsdale Learning Lab

Linkedin

Conclusion

Revolutionizing leadership through collaborative learning is not just about deploying training programs—it’s about creating an environment where learning is embedded in the organizational DNA. By understanding diverse learning perspectives, designing learner-centered environments, breaking down silos, and fostering a culture of trust and motivation, organizations can unlock the full potential of their people.

This approach leads to sustainable business growth, higher employee engagement, and a competitive advantage in today’s dynamic marketplace. As leaders, embracing this philosophy and investing in learning ecosystems is an investment in the future success of your organization.

This article was created from the video Revolutionize Leadership with Collaborative Learning with the help of AI.

Get the Unfair Advantage I Have

One of the perks of hosting this podcast is that I go through the episodes such as the one with Steven above multiple times.

As I watch the video, listen to the audio and write about it, I can’t help but have new insights about the content we covered and deepen my understating of the things we discussed. I have the benefit of coming to this material from different modalities of learning.

But I want to level that playing field for you. I also want you to have the benefit of engaging with this material from different angles without getting bored or jaded. For this reason, I have created yet another experience for you to work with.

Click the button below to engage with this episode in yet another way.

Deepen your understanding