In this compilation episode of the Not Another CEO podcast, host David Politis explores the pervasive loneliness that CEOs experience, regardless of company size or success. Drawing on interviews with over 100 founders—including Marcus Ryu, Adam Dell, Chae Hwang, Nick Mehta, Nadia Bojarwa, Chip Hazard, Catherine Minshew, Mike Grossman, and Kyle Porter—the episode diagnoses why the CEO seat is inherently isolating: CEOs make unpopular decisions with imperfect information, bear the final responsibility, and their teams cannot fully perceive the weight they carry. The conversation reveals a common misconception that this loneliness is a personal flaw; instead, it is a structural design of the role. The episode then shifts to solutions, highlighting the "default" of loneliness and how it can be altered through intentional support systems. Strategies discussed include co‑founders, peer groups, advisors, coaches (with deep contextual involvement), investors who act as mentors, therapists, and personal relationships. Notable analogies such as the "hero effect" (the myth of the lone founder) and the "coach as Tom Brady's trainer" illustrate the need for external perspectives. Real‑world examples—Bill Campbell’s decade‑long coaching of Mike Grossman, Catherine Minshew’s founder groups, Chip Hazard’s investor‑coach analogy, and Kyle Porter’s reliance on family and peers—demonstrate how robust support networks transform the CEO experience from solitary to sustainable. The episode concludes with a call to action for leaders to deliberately build these support structures to mitigate the inherent loneliness of the role.
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At this point, I've now interviewed over 100 CEOs on this podcast. Founders who bootstrapped, founders who raised hundreds of millions of dollars, CEOs who took companies public and who sold their companies for billions of dollars. The job of the CEO is lonely.
I was lonely, especially later on. It ended up being quite lonely, and I had a sense I'm an N of 1.
Your team has no conception of how lonely it is to be the CEO.
It's actually quite a lonely job.
The CEO seat is lonely. That's not a flaw in you. It's the design of the job. Here's the thing you can control. You can decide whether you sit in it alone. Hello everyone. David Politis here. At this point, I've now interviewed over 100 CEOs on this podcast. Founders who bootstrapped, founders who raised hundreds of millions of dollars, CEOs who took companies public and who sold their companies for billions of dollars. And across all of those conversations, there's one thing that comes up over and over. The job of the CEO is lonely. Doesn't matter how big the company is, doesn't matter how successful the company is, that job is lonely. I felt it at moments, many moments while building BetterCloud. Every single founder that I meet one-on-one brings it up in some way, shape, or form. And the reality is your team, your friends, your family, even your investors, they can't understand how lonely the CEO seat is. So today's episode is a compilation on exactly this topic. You're gonna hear some of my favorite guests describe it in ways that honestly give me chills.. And then, because I don't want this just to be a therapy session, we're gonna get into the answers, what the best CEOs do about it. So first up is Marcus Rue. Marcus co-founded Guidewire and ran it for almost 2 decades, took it all the way through IPO. One of the great vertical software companies ever built. From the outside, a dream run. Here's how it actually felt from the inside.
It was lonely, especially later on. It ended up being quite lonely, and I had a sense I'm an n of 1, walking a completely lonely, isolated path. And one of the things that happened after the IPO was I realized, no, there's a deep universality to this founding journey. And what I experienced and continue to experience here is relevant to other people. And that's kind of ultimately what led to, you know, to becoming a VC now.
A quote unquote, an N of 1. It's a perfect way to describe it. That's exactly what it feels like. Like you're the only person on earth dealing with this specific set of problems. And here's the kicker. He was wrong. And he only found out about that after the IPO. He spent nearly 20 years thinking he was alone in an experience that it turns out is nearly Universal. You'll hear that over and over in this episode. Next up is Adam Dell. Adam has seen this game from every seat— founder multiple times over, investor, operator inside a big company.
We were talking about navigating a pivot, and he said the thing about your own team that I think every CEO feels but nobody says out loud: your team has no conception of how lonely it is to be the CEO and how, how hard it is to navigate the, the optimism and the, you know, focus that you need to have in a startup while at the same time, as I said earlier, being transparent and honest with them. It's a very hard thing to do. You don't wanna mislead people. You don't wanna bullshit them. You want to give them the honest truth. At the same time, they need to feel as though they're on a ship that's gonna go somewhere meaningful.
The tension he's describing is so hard to deal with on a daily basis. You want to be honest and transparent, but at the same time, make sure that you're keeping people motivated and believing. I remember at BetterCloud, there were moments where I'd walk out of a brutal board conversation, like worst board meeting ever. And then 30 seconds later, I'm there on the floor with the team and I have to turn on that energy and optimism. No one sees that switch that you have to flip. That's the loneliness. It's not that people don't care, it's that structurally they can't see it. So why is the seat lonely? Chae Hwang, who co-founded Boxed and took it public, talked about it from a board angle.
The minute you take outside money, you don't work for yourself. Like you have a board that you report to, and the board actually reports to then probably their LPs as well. So you're, you've then put yourself in this chain. And so it's actually quite a lonely job, uh, at the end of the day because you're making oftentimes very unpopular decisions based upon imperfect information. Um, and that just creates this kind of vacuum that you have to sit in yourself oftentimes.
Unpopular decisions based on imperfect information. That's the whole job in 6 words. And that is the part I want people inside companies to hear. When your CEO makes a call that looks wrong or confusing from your seat, there's usually a whole layer of context they couldn't share. Nick Mehta might be one of the most people-first, energy-positive CEOs in the history of SaaS companies. Gainsight was famous for its culture and Nick carried it. He told me about a dream he had And it's the best image of this entire topic I've ever heard.
I had a dream and it was basically like, I'm this like railroad conductor on a train and I'm driving this train and then all the employees are coming on the train and doing amazing things for us. But eventually they get to their destination and they leave the train because they're, they're on the train to get somewhere and the somewhere isn't. Just being on the train. And so eventually I realized, you know what, every, eventually everyone will leave GameStop. Every single person, there'll be new people, but there's nobody that'll be here. Uh, and it's possible that nobody be here as long as I have, although I could easily get fired. So that could happen too. But, um, the, that's a bit of a psychic emotional thing. You have to sort of like, I think I've had to process in my head. It's kind of lonely. Um, you know, you're like, oh wow, like I'm, this is, I'm the one that's on this train, you know, everyone else is on the train to get somewhere.
For you, the train is the somewhere. People join, people leave, people get promoted, and you wave them all off at the station, and then you get back in the conductor's seat. Even the guy who built one of the most beloved cultures in software had to make peace with that. So that's the diagnosis. And if we stop there, this would be a pretty tough episode, pretty depressing episode. But here's the turn. Nadia Bojarwa, co-founder and CEO of Dia Co, said something early in our conversation I think is the key to this whole thing. Listen to the word she uses: default.
But I think the founder journey can be so difficult and is like a default for a founder journey is lonely.
It's like there's—
because there's nobody else who's like fully like in the place that you are in terms of your responsibilities. And the only thing that can change that, I think, is a co-founder.
The default is lonely. And what do we know about defaults? They can be changed. For Nadia, the answer was a co-founder, the one other person who's fully in it with you. But maybe you don't have a co-founder, or maybe, like I heard from a lot of founders, even the co-founder can't fully share the CEO seat. So the question becomes, what else can you build around you? So that's what I want to go into in the second half of this episode, the support system. And the CEOs I've interviewed have built in some fascinating ways. Now, I want to actually start the support system conversation with an investor's perspective. Chip Hazard is a general partner at Flybridge. He's been backing founders for decades. He's seen hundreds of these journeys up close. And when we talked about founders trying to do it all themselves, he used an analogy that I think settles the debate.
It is 100% your company as the founder. True statement. But the idea that there's not perspectives in the marketplace that can make you better. You know, the, you know, even Tom Brady has a coach analogy, like, like get a coach, get an advisor network, you know, get someone because, because you can't as a founder know everything and you should be always looking for outside perspectives and advice and guidance.. And if you can get that in a good venture capitalist, that's great. If you don't have that in your venture capitalist, get it somewhere else. But you shouldn't just say, oh, I'm going to do the hero effort because I think the hero effort is going to lead you to missed opportunities.
Even Tom Brady had a coach. The greatest of all time still had someone watching his film, challenging him, making him better. And somehow Founders convince themselves they should just figure it out alone. I also love that he named this trap the quote unquote hero effect. It feels when a found— what it, what a founder's supposed to do feels noble, and it quietly costs you opportunities that you never even get a chance to see. Okay, so, so get a coach. But Catherine Minshew, founder and former CEO of The Muse, would tell you not all coaching is created equal. She had a coach for essentially the entire life of her company, plus founder peer groups, and she has one of the sharpest one-liners I've heard about why a coach who only talks to you isn't enough.
I had a coach almost the entire time that I was at The Muse. I also had, I had a lot of really great, um, kind of founder groups or other CEO groups. There's, um, there's a group here in New York, actually it's not just in New York, but called The List that I was part of really early on, which was all women across tech and media. People were extremely open and honest with each other, and that I think is, is critical to learning because most of learning is figuring out where you're fucking up. I think if you can have somebody you trust who is, whether they're an advisor, an investor, or a coach, who's just one level deeper than just talking to you, Because when someone's just talking to you, your blind spots become their blind spots.
Your blind spots become their blind spots. Think about that. If your coach or mentor only knows what you tell them, they can only ever see your version of reality. Her coach actually sat in, in her exec meetings. That's the upgrade. Someone with independent context on your business, on your team, and on you. I've personally felt this with the companies that I advise. Actually, at this point, I'll only advise companies where I can spend time with their team, the next level down. And, and I feel like I can help 10 times more when I do that. This next one might be, as it relates to coaching, my favorite in this whole episode. Mike Grossman has been the CEO of 6 companies. 6. Today, he coaches first-time CEOs. And when I asked him the number one challenge he sees across all of them, his answer wasn't strategy or go-to-market. He said they struggle with their mental health. They tie their identity to the company and they have nobody to talk to. But here's why Mike understands this so deeply. For about 10 years, Mike had someone to talk to once or twice a week, every week. His name? Was Bill Campbell. If you don't know that name, Bill was a college football coach who became known as the coach of Silicon Valley. He was Steve Jobs' most trusted advisor. He coached the founders of Google. There's a bestselling book about him called The Trillion Dollar Coach. And for a decade, he coached Mike. I asked Mike to tell me about him.
Yeah, Bill, uh, was a remarkable guy. He, he started out his career as a college football coach. And then when he was about 40 years old, he decided that he was gonna go into business instead. And he had a meteoric rise, or within about 5 years, he was the head of sales and marketing for Apple. And then in subsequent years, he ended up becoming the CEO of Intuit and then eventually came to be known in Silicon Valley as the coach of Silicon Valley. He was on the board of Apple. He was, he was Steve Jobs' most trusted right-hand guy. He, he played a very critical role in helping Google and the senior people at Google, a lot of the most prominent Silicon Valley folks. But he also more quietly helped a lot of people who were less well-known and folks like myself who were trying to build an early-stage company. And he would provide an enormous amount of time. I mean, I met with him once or twice a week for about 10 years. He was always accessible. At any moment in time. He would just, you needed to get him, he would take the call. He had no agenda beyond trying to be helpful. I think that's the most profound thing. I mean, on one level, he was incredibly talented. He was, you would, you give him a small number of facts and he would immediately see the entire picture. And he was very savvy, very smart, and enormously empathetic. But he also, as I said, had no agenda. He wasn't doing it for money. He was doing it because he wanted to just be helpful to people who needed the help. He was a coach still, you know, the college football coach. He was still that coach. And he had a very big impact on how I learned to do the job of CEO. My first company, I mean, the house I'm sitting in right now, I own this house because of the advice that Bill gave me at a very critical moment in time. So that's a very tangible benefit that came from that. And frankly, the book that I wrote to a very significant extent and the help I provide to CEOs is a reflection of what I learned from Bill. I basically decided I want to pay it forward.
I own this house because of the advice Bill gave me. Think about that for a second. The support system isn't soft. It isn't a nice to have. It shows up in the outcomes. In Mike's case, literally in the house he lives in. And notice the flywheel. Bill coached Mike for 10 years, and now Mike is spending most of his time coaching first-time CEOs, paying it forward. That's what the best support systems do. Doesn't just carry you, it turns into something that ends up carrying others. Honestly, that's a big part of why this podcast exists. And I'm gonna close with a clip here from Kyle Porter, who founded Salesloft, because Kyle is the proof that everything we just talked about actually works. When I asked him about the famous loneliness of the founder journey, listen to his answer.
Read blog posts, you hear a lot of like, entrepreneurship's a lonely journey, you know? And that's one that I never really felt. And I think that's because of my wife and my dad and the friend network we had. I mean, even our relationship was so important to me because I could call you and share the problems and then you would like share your problems. And then I didn't feel like a shitty, you know, like a shitty CEO, like I was a loser because we both had the same problems, you know, or we had different problems. Like, I don't know, like sometimes you feel like if things are going wrong, you suck and it's like all on you. And, but entrepreneurship is all about going through all that stuff. And, and so I had a lot of people that I could really count on and April was the biggest.
Kyle and I were building our companies at exactly the same time, and truthfully, the calls he's talking about were just as valuable to me as they were to him. Actually, probably even more valuable to me. And that's the point. Kyle didn't feel less pressure than anyone else. He built the same company under the same stress. The difference is he never sat in it alone. In his case, it was his wife, his dad, peers, the loneliness that we talk about as the default, it doesn't have to be the destiny. So after 100+ of these conversations, here's where I land. This seat is lonely. The CEO seat is lonely. That's not a flaw in you. It's the design of the job. You'll make unpopular decisions with imperfect information. Your team won't see half of what you carry. And at the end of the day, You are the one and the only final decision maker. That doesn't change. And honestly, we signed up for this. Nobody forced us into this seat. But here's the thing you can control. You can decide whether you sit in it alone. Go spend time building your support system. Do it today. Find yourself a peer group, an advisor, a therapist, a coach, someone or a group of people who can be there with you through the journey. None of those people will make the decisions for you. That part is still yours and it always will be, but it eases the burden. It shrinks the weight to something you can actually carry. I really hope for any CEOs listening to this that this was helpful and look forward to seeing you for the next episode of Not Another CEO Podcast.
