Jerry Colonna on the Founder’s Honest Journey

She's an extraordinary CEO. The company is working, everything is working, and this entire construct is leading to a completely new kind of anxiety, which is, I must be doing something wrong. Why? Because everyone tells her that a CEO's job should be wartime and in the weeds and doing this and doing— and she's like, what am I doing wrong? The company is growing, you're profitable, $100 million in revenue, but that good is in her mind, and she's comparing herself to her peers in the ecosystem, which is also known as the echo chamber.

Welcome to the Startup CEO Show. I'm your host, Mark MacLeod. This is a special episode for me. A, it's the last episode of the Startup CEO Show. Stay tuned for a new, different podcast in the future. But also, this is a really special guest for me, Gerry Colonna, the coach to startup CEOs. The guy who inspired me to be a coach. Amazing conversation. We went into the founder journey, quite a philosophical discussion, as you would expect. Jerry's a Buddhist, I'm a Buddhist. If these kinds of topics and kind of more thinking about the inner journey and self-exploration, self-awareness, radical self-inquiry as Jerry calls it, if that is of interest to you, you're gonna love this episode. And I wanna thank everyone for tuning into the Startup CEO Show over the last 2 years. I really enjoyed it., and as I say, stay tuned for a new podcast soon. Jerry, welcome to the Startup CEO Show. It is a true pleasure to have you here. How are you doing today?

So I'm doing well. Thank you for having me. It's a nice, bright, sunny day today, and that feels good.

Yes.

You know, I try not to be starstruck. I've learned through working with people that we're all the same. We're all born naked and crying. We all die and We all want to love and be loved. But, you know, throughout my career, I've been starstruck. And I remember back when I was a VC, I co-invested with Fred, Fred Wilson, and I did zero diligence on the deal. My diligence was, oh, Fred's leading it. And it was a total zero. But I did it because it was Fred, you know? So I put him on a pedestal.

I have to give him shit.

I don't even remember. I blocked it. It was just like a total— it was just a disaster.

It's a bad memory.

Yeah. And so, but I put him on a pedestal and didn't do my job and didn't do my limited partners a service as a result. And I, you know, newer to coaching than you, and you were a very strong influence, although you had no clue, in me becoming a coach. And so you're kind of a star for me. And so it's a true honor. Wow.

What a sweet and kind thing to say. And hopefully by the end of this conversation, if not sooner, Any starstruckness will have disappeared as the reality of two human beings come together.

That's all. Yes, that's right. And so, you know, I threw out some questions in advance and kind of the first one really could be the entire discussion, which is really about the founder inner journey and maybe just getting your take on that. And maybe I'll give some context for where I thought we could go. There's so much bravado in the startup world, right? You catch up with someone and you ask how they're doing and they're like, yeah, we're crushing it. You catch up with a VC, how's your portfolio? We're crushing it, which is mathematically impossible because most startups fail, right? And so we're busy putting on this brave face, whereas, you know, your work and my work is really about getting people to be vulnerable, right? And like, the only way out is through. Face your fears, like face everything, like Admit that you're scared. And, you know, you are famous for making people cry. That could be a thing we talk about. But I don't know, just, I'm gonna throw it over to you to maybe riff on what I've just said and the inner journey. Maybe, you know, the last thing I'll say is like, for, I think building a startup, especially a high-growth startup, is a personal development journey in the form of a company. Like you cannot help but transform. And there's a huge inner component to that. So maybe let's see where that conversation takes us.

Yeah. So there's a couple of things occur to me. The first is a slight nuance and build on the first thing you said, which was that how the startup world and the venture world is filled with bravado. I would argue much of adulthood is filled with torbado.

It's true.

I think we socialize children to bullshit their way through feelings. And I think that there is a particular noxious version of this kind of delusion in the startup venture world and the ecosystem that stems in part from the over-identification of ego with the entity. And so when, when I started doing boot camps 14 years ago, on the first night I would, I would get up like a, like a good preacher or minister, and I would preach. And I would sit there and I would say, the bullshit spinning stops here. You're all not crushing it. Um, the reason that, that, that took hold was that Um, we train, just as we train children not to actually confront and deal with their true emotions, we train entrepreneurs to spin. We train people to spin. And so, um, this, this propensity to, to be inauthentic, if you will, to pretend, um, is something that's built into the system. Now, why is this so important? Well, first of all, you made a second point about vulnerability, and I tend to be less mindful or less focused on using the word vulnerability. I prefer a different word. The word I prefer is honest. And the challenge with being honest in the context in which we were just talking about is that it can feel vulnerable. But as soon as you change the framing from vulnerability to honesty, people start doing what you just did, which is start typing notes. It's like, oh, right.

Yeah.

Wait, because what we're sending is a message that you should be dishonest. You should actually mask how you're really feeling. You should mask how the company is really doing. You should pretend. Your way to leadership. You should pretend your way to adulthood. And as soon as I lay it out that way, all of a sudden the falsity of this construct falls away and you start to see, okay, what are we doing? It's like a kabuki theater that we're all playing. We're all playing games here. And the result is twofold. One, um, companies are misled, employees are misled, and I use that term in both its meanings. They're lied to, and they're poorly led. And the second thing is that that inner sense of unease gets worse. See, when we walk around being inauthentic, being dishonest with how we are really struggling, our capacity to deal with that inner journey is undermined because we do not have the capacity to say, I need help, or this isn't working, or I don't know what to do, or maybe I'm not right for this job. All of those messages not well handled lead to just a miserable experience. And I'll shut up after closing with this. No one launches a startup with the intent of being miserable.

Right.

We do it because we want liberation, we want freedom, we had this inner passion that we want to give voice to. We don't want to report to somebody. We want to be in charge of our own destiny. But nobody says, "I'm going to do this so that I can be miserable." But then we take on this pattern and then they call you or they call me and they get on the phone and the first thing they do is cry. Because they're in so much pain. So this is a long-winded way of saying, be honest. That is the first step on an authentic inner journey that allows you to grow regardless of whether or not the company succeeds.

Yeah, man, so much to unpack there.

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What's coming up for me right away is a word that I'm always on the lookout for, which is "should." I should be doing this. I should be doing what my competitor does. I should be doing what my investors, other CEOs do. And this word "should" implies external expectations. And then often we actually just create them. They haven't actually been explicitly stated to us. Sometimes we just think, you know, we compare the 100% we know about ourselves to the 10% we think we know about our competitor and come up with all these expectations and we're miserable. I think where some of it, that's where some of this hustle culture comes from. I think the root of it at the end of the day is fear. Like I just need to move faster than everyone else. And now in San Francisco, there's this trend that's come from China, 996. I work 9:00 AM to 9:00 PM, 6 days a week. It's total bullshit. And yeah, I'm wondering if that's a pattern you see showing up a lot. Like, I make my clients kind of put a dollar in a theoretical jar every time they use the word "should." I'm like always calling them out.

Well, what occurs to me is I was actually just in a session today with a client. She's an extraordinary CEO, doesn't always know it. But she is an extraordinary CEO. And we got to having this interesting conversation because you may recognize this, the company is working. Everything is working. You know, we've working together now for about 3 or 4 years. She'd been running the business. She found, co-founded the business, I think about 8, 9 years ago. They'll do $100 million in revenue. They're growing 30%, 40% year over year. They will be profitable this year. And a funny disorienting thing is starting to happen, which is that her anxiety is starting to go down because her need to constantly be in the weeds is disappearing because she's created a senior leadership team that for the most part is working. And this entire construct is leading to a completely new kind of anxiety, which is, "I must be doing something wrong." Why? Because everyone tells her that a CEO's job should be wartime and in the weeds and doing this and doing— And she's like, "Jer, what am I doing wrong?" It's like, "Wait, wait, the company is growing. You're profitable, $100 million in revenue, 8 years in." Right? You're a former CFO. I mean, you can appreciate what she has put together. Yeah. OK?

Yeah.

And she gets to go home and take care of her family the way she wants to. And she's turning her attention to bigger strategic issues, like M&A transactions and transactions that will double or triple the size of the business. And I said, it's working. But that should is in her mind and she's comparing herself to her peers in the ecosystem, which is also known as the echo chamber, right? And it's like, no, no, no, no, no, no, no. This is going— and one of the things that was really critically important was we took off the table the goal of going public. And I said to her 2 years ago, "Forget about going public. Just focus on the performance of the business and whatever outcome is going to need to happen will happen. It will take care of itself." And you know what's going to happen? Somewhere in some billion, multi-billion-dollar company is going to come along and say, "That would be a nice company to have." And then everybody gets to go home happy, which is the whole point of it all. Right.

I hear about $100 million, about to be profitable, 30% growth. I think about the $2 trillion of dry powder in the private equity market and like a sponsor's going to be all over that. It's like, right?

Exactly. Exactly. If they want to sell, by the way, there's nothing wrong with just running a really kick-ass business and making a good salary. And building a business that has meaning for other people. There's nothing wrong with that. I know this.

You know, I began my career, I'm a CPA by training, so I began my career work and I never was at Big Four. I was always with owner-managed businesses. And so, I went from this dynamic of like these owner-operators for whom the business served them. It was a vehicle to give them, for sure they worked hard, especially in the beginning, But over time, it became this vehicle that served their lifestyle. It gave me dividends. It was a thing. And like, it worked for me versus me working for it. Right. Whereas I feel like in the tech world, we almost never get there, even though like we're on the top of Maslow's hierarchy, right? Like we should be fully self-actualized. But to your point, we're just like self-flagellating all the time.

Right. Well, that's another one of the shoulds, right? The should. It is like your company is not successful unless, I don't know, Salesforce buys you or you're public. You know, look, I've got a business I've been running for— it'll soon be 12 years. I earn a really good living. Um, I, I— over, over the years, 60, 65 people have worked with or through Reboot all these years.

It's amazing.

We've made some wonderful impact on the world. I do work that is deeply meaningful to me. I'm— I just turned 62. When I'm 70, 72, I'll hang it all up. It'll be done. I mean, I feel so blessed, you know. I get to work with people I adore, doing work that has meaning, that I'm well compensated, and I get to just have an impact. So To me, that's enough.

I love it. Truly. I mean, you've made it, right? And I feel this was something I was actually struggling with myself in the last year. You know, my business is much simpler. You're looking at it. This is the entirety of my company except for my wife helps me with scheduling. But, you know, I was thinking of launching a mastermind community to complement what I'm doing, and I have ultimately decided to do it. But the— I had a struggle for a while because I was like, why am I complicating my life? Like, I've kind of made it. Like, I have these really rich one-on-one CEO relationships. Like, I'm super specialized. I only coach CEO— like, on my one-on-one, I only coach CEOs who've raised venture PE. So they have these expectations and multi-year deep relationships. I literally love these people. And like, to your point, I don't have a big firm like you, but I make a great living. Um, I have lots of time, uh, for practice, for reading. I live in nature. Like, this is good, you know? And, but I struggled with that notion of kind of, um, yeah, I guess reconciling kind of purpose and impact. But not being attached and just be like, I'm doing it because it's, I think it's why I'm here. It's my dharma. It's not for, to your point earlier, hey, for your CEO, like it's not about going public. You just keep serving your clients. You keep putting one foot in front of the other. Good things will happen. This is sort of just the same thing, you know, but I genuinely struggled with it for much of last year.

Yeah. Well, the business that you're describing yourself as running now is the business that I ran in the first 14 years of my career as a coach before I launched Reboot or co-founded Reboot. And to be clear, we launched the business not with the intent of raising venture money and going public, although that was, certainly raising capital was available to me. As an option. And in those years, I watched other firms raise a bunch of money, big valuations, go out and have thousands of coaches. And we're 13 people, 13. It's a happy little band that we get together and we rock music. And what I like about working together as a collaborative group right now is I learn from my colleagues. We challenge each other. We grow in different ways. And that too is something that adds to the experience of running the business. Yes. Do I feel like I've made it? I wiggled a little bit when you said that phrase because I don't know what it meant, but the way I took it in was I feel blessed. I mean, I feel like I said that I was teaching at Barcelona last weekend. I said this to the students. I feel like I am doing the thing for which God breathed life into my body.

I believe that.

And that feels like a blessing to be able to say that. And to be able to, you know, if I were to grow this business, if I had made that decision a decade ago, I'd be further removed from the work that gives me meaning. That's not for me. That's not what I want.

And that's why I say you've made it, right? Because you're not striving for something that is not here today, right? When people think for years, I think when people have thought of coaching for startup CEOs, they think of you and therefore, You know, you've just been like living in your zone of genius, having these deep, rich relationships for a long time, and then you've built a little family around you. Like you get to have this mix. Most of it you can do it from home. You go to these retreats, like it's great.

Yeah.

I get to write books. I get to have deep, meaningful conversations with people. Uh, for some reason. God gave me a gift of being able to put words together in such a way that people listen.

Mm-hmm.

That creates a sense of moral obligation to say things that had meaning, um, to comment upon the inequities and to, to speak about the ways in which we have moral and ethical responsibilities, those of us who have power. Um, you know what it comes down to, Mark? And you know the story, I'm sure. When I walked away from being a VC myself with my former partner Fred, I walked away because I was not living the life that I was supposed to live, no matter how skilled I was at it. It was disconnected from who I really am. And now, 30 years later, I get to live every day connected to how I'm supposed to be in the world. Now, to be clear, there, there are plenty of times where I wake up with anxiety or I worry about, you know, will I have enough money in retirement? I mean, crazy thoughts, but almost always those are proxy anxieties for the state of the world or, you know, some other deep concern that I carry. And I feel skilled in my ability to cut through my own bullshit, my own delusions, and get right to, okay, what are you really worried about, Jerry? What are you really concerned about? And almost always I can get to it and find a way to respond to them in a way that feels healthy for me.

I was walking in the minus whatever it is degree temperature here in Canada today and just thinking about our call and I was going to go there later, but maybe you've opened the door if you don't mind. I've certainly listened to many conversations with you and read your first book. The second book is in the on deck circle. I freak my wife out because I'm constantly buying books and not reading them at the same pace. In any event, and you have this longstanding Buddhist practice. And just something that part of it is, it's actually, this is a feature, not a bug, because you have this eloquence and this way of speaking that is heavy. And you have, you know, you have this history that you've shared that hasn't all been sunshine and roses, but it's shaped you. It's who you are.

Right.

And you're open about it. And I just wonder, like, with this deep practice, like, Do you find, like, do you ever escape dukkha? Do you escape suffering and just, you live in joy? Do you ever, does it become lighter ever? Yeah. Okay, good.

Oh yeah, sure. And I also don't always take myself so seriously. This is my podcast voice. I'm kidding. But does one ever, does one, let's change your question. Does one ever escape dukkha? That's a great question. My teacher Sharon Salzberg and I are having a series of conversations for my podcast on the end of suffering. And, you know, I have been accused of being heady. I do gravitate, I find myself moving towards suffering almost like a first responder would. And I think that may be part of what you're picking up. Um, I don't find it heavy. I find meaningful, thoughtful, real, honest conversations enlivening.

Mm-hmm. Mm-hmm.

You know, yesterday, um, there's a group of men that we first convened shortly after George Floyd's murder. Uh, unlike me, they're all men of color, and we had been gathering together. We call ourselves Warriors. We have been gathering together for 6 years now. And in the last 9 months, our calls have been infrequent. People have gotten engaged. I became a grandpa. You know, things have sort of pulled us. Yeah. Yeah. Ask me, you know how I have this famous question, how have I been complicit creating this? Okay. My new favorite question is ask me about my granddaughter.

I love it.

Um, but yesterday, um, and we're speaking just after a couple of days after the murder of Alex Pretty, um, in Minneapolis. And yesterday one of the group texted the full group and said, I'm really, I'm really having a hard time. And so the bat signal went up and we all gathered and we were in pain together.

Mhm.

Nobody fixed, nobody had the answers, nobody was sitting there saying, okay, you should do this and I'm going to do this. It was like men of meaning and consequence came in an honest expression of their suffering. And at the end of the call, we all felt a little lighter. So yeah, maybe I, I'm heavy because I feel heavy, because there's a gravitas to the world right now. Uh, there's a gravity about what we have to contend with.

Do you think the world is heavier now, or is it just that we have CNN and X and we have the ability to see everything that's wrong in the world before 8 a.m.? But I would argue, like, I don't know, in like the Crusades, there's been times where like people are being murdered probably with similar relative frequency. We just didn't know because we didn't have media.

I think that the capacity for human beings to hurt each other has always been and will always be part of the human experience. And, um, I think it's a both situation, Mark, to your, to your question. I think that, um, the immediacy, you know, look, I, I, I'm so fucking old, I remember when social media got That's how old I am. Okay.

I'm not far behind you.

Look, I mean, and there are times when I say, what the hell have we wrought? Okay. And the rise of social media in whatever form you want to pick on exacerbates the constancy of suffering, just the way the rise of cable news exacerbates the constancy of that suffering. But oddly, one of the things that I have found comforting of late is to recognize, um, the, the history of this. So for example, I just recently watched via Netflix a documentary called Undercover, and it's a documentary about the life of Seymour Hersh, the journalist who was the first to reveal the My Lai Massacre in Vietnam in the 1960s. He was also the first to break the news about Abu Ghraib and the torture that US soldiers were doing in Iraq. And it was a reminder that we have always battled these darker forces. You're skilled and sophisticated enough to understand that Carl Jung comment, the closer to the light we get, The deeper the shadow. We are constantly battling between light and shadow. And the shadow that we're talking about is not just a malignant evil that walks the earth. It's the shadow. It's the evil that lies within all of us. It's our capacity for violence. You know, my teacher, the man to whom I can often feel starstruck, is Parker Palmer, you know, the Quaker rare. And he has wisely taught that violence is what we do when we don't know what to do with suffering.

Mm.

Wow.

Violence is what we do when we don't know what to do with suffering. And so the more suffering that we have in the world, the more violence we have in the world. And the more violence we have in the world, the more we have suffering. And the truth that the Buddha woke up to all those years ago was that it's the truth of suffering. Life is filled with suffering. But he also taught the truth of the end of suffering, right? That's the third noble truth, the dukkha. And that the pathway, put simply, is love and compassion. What are we supposed to do with suffering so that we don't do violence? We're supposed to meet it with compassion. We're supposed to go into suffering armed with compassion and love. And thereby alleviate that suffering and my suffering as well.

Right.

Yeah.

I mean, when you receive violence in whatever form, to realize, well, that person is suffering, right? That is compassion. As opposed to then react and then strike them, be it verbally or physically, right? Whatever the, the nature of it is like that, that takes practice. But that, yeah, that's what the world needs. It's like the Dalai Lama said, right? If everyone meditated, there would be no war in a generation.

I once had a friend, she's a committed practitioner now, but back then, 15, 16 years ago, she said to me, "You Buddhists, all you do is sit around and meditate. What do you think is going to happen? Everybody's going to be happy?" And I said, "Yeah, I think everybody will be happy." Yep.

How about that?

And that's what happened.

Was she a New Yorker? I was just picturing like a thick New Yorker.

She was actually— you're right, she was born in New York.

So yeah, okay, there we go. Yeah, I, um, I mentioned earlier this, uh, mastermind that I'm launching, uh, it's called Limitless. Got the swag, nothing else but just the swag. But I would love your, your reaction to the premise behind it, uh, because it what you've talked about here, where you were going with meditation, made me think of it. So the whole idea, basically, like most of us, most founders are— we're doing this wrong, right? The hustle, sleep when I die, sacrifice sleep, sacrifice exercise, never present, sacrifice your relationship. Absolutely. And then, you know, I've personally sold over a billion dollars worth of startups, and the number one reason why founders came to me— it's different if someone comes in like, hey, 'Hey, I want to buy you.' But when a founder chooses to sell, the pattern I've seen is they just burnt out. They can't go on any longer and they can't separate themselves from their company. And then of course, all of their net worth is tied up in these illiquid shares. And anyway, it kind of struck me last year that there's a better way, which is the opposite of the default state, which is like if you actually prioritize physical health, mental health, and spiritual health, it gives you more energy, clarity, and inspiration that you then direct towards unlocking your business. All right. And so that's the whole thing that I'm trying to achieve and getting folks to, you know, sleep is the first thing that we sacrifice. And then we say, well, I can't go to the gym because I don't have energy, even though going to the gym gives you energy. If I ask people, you know, they might, a lot of the founders eat something in like their fourth Zoom meeting of the day. And if I were to ask them an hour later, hey, what did you have for lunch? They're like, I don't know. And then, you know, if you think about a CEO's job, ultimately it's to make decisions. Every day you're making decisions, some big, some small. And how do you make decisions when it's like a jumble and a constant, you know, the monkey mind, right? And then of course, what are we trying to do? We're trying to create. You're literally creating, you're building a company, you're building a product, a team, a culture. And it's really hard to create when you're stressed. Whereas when you actually give space for intuition to show up, the insights, they're effortless. The problem that you might have been struggling with is just instantly solved. Anyway, so I'm just trying to create a movement of founders who are are thinking about this differently, you know, completely differently. And I brought 19 of them down to Tulum in November. Wonderful. For a retreat. And what was amazing was how receptive they were to spiritual concepts, actually, but that they needed permission to do this, to, you know, to realize like meditation It's actually strategic. Like, I can actually tie it back to— there's lots of reasons to meditate in and of themselves, but I could actually be selfish and like, if I meditate, I'll be a better CEO because I'll actually be able to, well, pay attention and marshal all of my resources and make really informed decisions and be really present with you when I'm with you, like, versus you know, fight or flight all over the place. Like, anyway, I'll stop rambling. But like, when you talked about meditation, you made me think about this. So this is, this is what I'm doing with the Mastermind.

I think you're doing good work in creating the containers for people to be able to see the benefits and to experience the benefits. It doesn't surprise me that they feel like they need permission to do that. Um, you know, this, this links back to how we raise children, right? You know, and I focus on that partially because as a grandfather, I'm very connected to my children and grandchildren. But what I'm very interested in, what are the messages we learn as children? And part of the reason that I think folks— this goes back to what we're saying before about the Schutz— folks think that, uh, Somehow, you know, my language is to be, I want you bored at 4 o'clock on Friday afternoon, quitting early, you know. Um, and I want you not dreading Monday morning on Sunday night, right? I want you looking forward to coming into the office and be creative. And all the things that you've talked about are essential elements in provoking that creativity, you know. So I think it's good work that you're doing.

Yeah, I, um, yeah, I've been really, really pleased with the reception. Do you think, uh, venture capitalists resist this message that— of balance, of sustainable balance that you, you just mentioned and that I'm talking about?

I think that there's, uh, there are multi-stages to it. I think, um, there are plenty of extremely successful, financially successful people who live in remarkable balance. This is all pure projection because I don't know anything about him, but I often think of Warren Buffett. Warren Buffett doesn't strike me as someone who spends a shit ton of time worrying about the shoulds. Nope. He doesn't even eat well, right? He's got his morning drive-through at McDonald's, but somehow he still manages to live life. And if you want an example of someone who has grown wealthy, because he didn't start off that way, as an example, there's something to it. And I guarantee you he doesn't work 996.

Absolutely not.

I guarantee you that he's thoughtful 996, maybe even 997. But I have this image of him as just chuckling at the knuckleheads who think that the only path to that kind of success is self-immolation and burnout. I mean, just— Right. It's like people who are truly powerful don't need to assert their power. People who truly live in their gravitas don't need to tell you that they live in their gravitas. They just are. And that to me is the epitome of, of, uh, of a role, you know, for a capitalist structure. I, I think now that said, there is a certain part of the capitalist system that needs you to stay on your toes and to be really insecure and worried about things. Yeah, for sure. But I don't think it's like some nefarious hand of people who control everything and say, okay, let's make sure the park stays nervous, right? Yeah, right. I just— it's just part of the system. And part of growing up, to use language that I like to use, part of growing up is learning how to be and stand back from the systems that would pull you in and make you be somebody than, than who you really are.

I love that you brought Warren Buffett up because I think it was either Warren or Charlie Munger who said that the most powerful force in the universe is compounding. And, you know, when we compound year after year, that's how magical companies get built. But if you burn out along the way, the compounding stops. And that's been some of my message to VCs, who'd be like, I know that you're chasing the crazy growth. I know that your fund relies on power law outcomes. But like burnout, it stops magic from happening, stops market-leading generational companies from being built, and like you're contributing to it. So basically don't.

Well, it's, again, if you look at where motivation is, you know, you have these financial incentives for, built into IRR, internal rate of return. And IRR has two components, the absolute dollar return measured against time. And so to maximize IRR means maximum return in the shortest amount of time. That thinking undermines what we were just saying about compound. Yeah, it's that kind of thinking. I mean, Warren Buffett started buying GEICO in the 1940s, I think. You know, we anticipated soldiers coming back from warm veterans needing insurance, right? Or, uh, no, that's USAA. I think Geico was the government, right? He anticipated the more government employees growing, you know, that's compounding. And that was very wise investing on his part. But that doesn't produce the returns that, say, a limited partner in a venture fund is used to getting.

So I'm curious, so your practices, do you— and obviously meditation is an important part of your life. Do you bring that to your CEOs? Do you encourage them to take an inner practice as well?

I used to, but don't so much anymore. I think that what happened— well, first of all, when I first started as a coach, nobody was meditating. Now it's common enough that they actually tend to bring it to me and they will bring questions to me about it. But it's not something that I built into sessions or something like that. It is, of course, it has always been part of the retreats that we run. Or if I do a T-Maw site, there's little exercises. They don't realize that I'm getting them to meditate. I call call it something else, but that's fine. Um, by any means necessary, you know, you bring it to the state. But, um, I think what's more interesting right now is that there's a tremendous curiosity about deepening a level of consciousness, whether it's through psychedelics or through meditative states, or just simply bringing a, a sharper awareness of what is going on inside in that inner journey. And I find there's much more welcoming exploration of that than it was, say, 25 years ago when I first started.

I agree with that. Yep. I've had several CEOs talk to me about psychedelic experiences, insights that have come from them, be more open to Yeah, thinking about consciousness. Like when I was at this Tulum retreat, on the first day, I was kind of like, hey, I don't want to be woo-woo, but— and then I'd say what I had to say. And on the first night, one of the CEOs who I've known for a while called me out and he's like, Mark, stop holding back, we can handle it. And so on the second day, I unleashed and everyone— I thought I'd scare everyone off, but they were totally embracing it. And, you know, the thing I told them Like, again, we're chasing these— first of all, like, everyone has these role models. Like, I used to be Shopify CFO, and so I was with Tobi back when they fit above— like, they were all in one office above a Starbucks, and now they're 10,000 people. And so Tobi illustrates what we all have, which is limitless potential. Anyone can become anything, and everyone who we admire was once no one, right? And we tap into this infinite spirit, this infinite capability, right? And this is the nature of spirituality. Obviously, it's infinite, right? And I talk about to my CEOs about like that word inspiration, right? What is it like, you know, you see, I don't know, virtuoso cellist delivering a performance or like, I don't know, LeBron James just like crushing it. And what do you say? You say they're inspired. What is that word? It's in spirit. I am connected to spirit. And like, that's where I'm trying to get my CEOs versus right now they're completely— they're closing the door to spirit. They're in fight or flight. Their sympathetic nervous system's jacked. They can't think straight. They're using coffee, taking sleeping pills, you know, on their laptop until they crash, rinse and repeat. So it's like the total opposite. I don't know what got me onto that rant and where I was going.

Well, you were asking, you had asked me about my experience working with folks and whether or not they'd been coming to me with meditation, and then you were connecting it back to your own experience in that way. And you were sharing the experience of whether or not you bring out the fullness of you. I love the fact that the retreat participant called you out on the way in which you might have been living in your own land of shoulds. I shouldn't be bringing this forward. So good for you. Thank you for that.

Well said. I'm wondering, you've been coaching CEOs for a long time now. Are there— and CEOs come in all shapes and forms, but are there certain kind of traits or patterns you see in the CEOs that are able to to kind of keep scaling year after year and keep growing faster than their companies?

I think, you know, uh, well, I'll answer it this way. Um, there's, uh, many years ago I hit upon what I referred to as the reboot equation. So mentally picture this equation: practical skills plus what I refer to as radical self-inquiry plus peer sharing equals enhanced leadership and greater resilience. So the, the top 3 working together equals the bottom 2. And what I often say is that what typically prompts someone to openly reach out for help is the wish to be more effective at what they're doing. But in that first conversation, I'm sure you experienced this as well, What happens is the suffering and the struggles start to come forward. And what gets revealed is the wish for a greater resilience, or as I said in my second book, Reunion, actually I said in the first book, Reboot, what they're really looking for is equanimity. They're looking to feel at peace. And so I think that if we were to diagnose or reverse engineer those who are most successful. It's those who'd managed to understand that the process of being honest about the things that they're struggling with, the process of being honest, even if it feels vulnerable, and sharing that with colleagues, peers in the business, coaches, enables one to do the radical self-inquiry work that's so essential in their inner journey, which then makes doing the pragmatic and practical work of building the company just a little bit easier, so that I then emerge a better leader and most importantly, less likely to be suffering in this process. And what I have found is those who do those first 3 things, practical skills, radical self-inquiry, and sharing honestly are the ones who have the greatest staying power, who grow and really enjoy themselves and have a blast regardless of what the struggle with the company is.

I love that. On equanimity, something I've shared with my CEOs is like, All living things seek balance except for humans. And it's not limited to ambitious humans. Like, I think even— I'm going to completely stereotype here, but like, just the regular human who has a job that they hate comes home and just binge watches Netflix and is unconscious and doesn't sleep and rinse and repeat. And obviously the ambitious founder is just like, how do I cram more into the day? How do I completely ignore ignore what my body's telling me and just keep grinding, right? And whereas, like, like I say, every other living thing just seeks homeostasis and balance. And anyway, I think what humans need to remember is we're not separate from nature. We're not above it. We are part of it. We came from the soil. We will go back to the soil. We are nature.

It's well put. It's well put. And I like the linkage between homeostasis and Yeah, yeah.

I also have an equation emerging for me. I'm like beta testing here with you. So you have a reboot equation. I have a limit. I'm now calling it a limitless equation. I didn't even come up with that nomenclature before. But anyway, it's sort of like this, which is like, I'm trying to get my CEOs to design their role and company and lives around energy. Like, again, takes energy to create. So rather than thinking of energy as this thing that I can just abuse, we're actually trying to solve for it. What that means in practical terms inside the company is we need to design the role in your company around your superpower. So you're spending more and more time in flow. And then we're, again, it's effortless and therefore it's energy gaining, not energy draining. So that's kind of the first part. Second is, you talk about radical self-inquiry. I talk about self-awareness, like getting you to go through just an explicit learning loop, literally every day. What went well? What didn't? What can I learn? What changes do I need to make for tomorrow? Like, can you get 1% better every day? And then can you direct all of this energy that you've created and all of this knowledge into the single biggest driver of valuation. Because again, I only work with the venture-backed companies, which is unlocking revenue growth, right? Kind of all else being equal, the single biggest driver of valuation is the rate of revenue growth. And then that rate of revenue growth is the magnet that attracts investors, ambitious talent, customers looking for the safe market leader, and then ultimately the buyer Scared shitless of you. What do you think about that as a simplification of things?

I, I think, I think it, it summarizes well, uh, the work that every CEO has to do. And I think, uh, the, the work that you're offering in that regard.

Tell us about poetry, why you're drawn to poetry, and do you think we should be reading more poetry?

Oh, absolutely. I think all art has a way to speak to our hearts and has a way to cut through the clutter and the monkey mind and the noise. Poetry in particular works well for me because the poet forces himself to use sparse language, to speak succinctly and sparingly. And the result is an intensity around the words. And I find it particularly useful It's like a, you know, a good quote that just cuts through the bullshit that we have and enables us to remember the things that really matter.

I love it. Well, Jerry, thank you so much for making time to come on the show. It's just, it's been a true pleasure for me.

Thank you. You're welcome, Mark. Thank you for reaching out and good luck with Limitless.

Thank you. All right. You be well.

All righty. Take care.

Hey, thanks for listening to the Startup CEO Show. If you'd like to connect with me, be sure to visit my website at markmacleod.me or follow me on LinkedIn @TheMarkMacLeod or Twitter @MarkMacLeod_. And if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We'll see you next time.