I have 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 sold companies for billions. And across every single conversation, one thing keeps coming up.
The job of the CEO is lonely. It does not matter how big the company is. It does not matter how successful the company is. That job is lonely. I felt it myself building BetterCloud. Your team, your friends, your family, even your investors cannot fully understand how lonely that seat really is.
So instead of one interview this week, I pulled together nine of my favorite conversations on this exact topic. But I did not want this to just be a therapy session. The second half is about what the best CEOs actually do about it.
You are an “n of one” until you realize you are not
Marcus Ryu co-founded Guidewire and ran it for almost two decades, all the way through IPO. From the outside, it looked like a dream run. He told me it was lonely, especially in the later years, that he felt like the only person on earth dealing with his exact set of problems. It was not until after the IPO that he realized how wrong he’d been. What he’d experienced turned out to be nearly universal among founders.
That’s the part that stuck with me. Marcus spent almost 20 years thinking he was alone in something it turns out nearly every founder goes through, and he was so convinced of his own isolation that it took a company-defining event, the IPO itself, to shake it loose. That conviction is exactly what makes the loneliness so dangerous: it’s not just a hard feeling, it’s a false belief that talks you out of asking for help.
Listen to more from my conversation with Marcus Ryu.
The whole job in six words
Chieh Huang, who co-founded Boxed and took it public, explained why the seat is lonely by structure, not by accident. Once you take outside money, he said, you stop working for yourself. You report to a board, the board reports to its LPs, and you’re now a link in a chain of unpopular decisions made with imperfect information.
I keep coming back to that phrase. Unpopular decisions, imperfect information, that’s the whole job in six words, and I think it’s the part I most want people inside companies to actually 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 with you.
Dive deeper into Chieh Huang’s perspective on why the CEO seat is lonely by design.
Nobody sees the switch you have to flip
Adam Dell talked about the tension every CEO lives inside: you want to be honest and transparent with your team, but you also need them to feel like they’re on a ship going somewhere meaningful. You can’t mislead people, but you also can’t let the truth sink morale.
I know that tension personally. There were moments at BetterCloud where I’d walk out of a brutal board conversation, worst meeting of the week, and thirty seconds later be back on the floor with the team, having to turn the energy and optimism on like a switch. Nobody sees that switch. That’s the loneliness. It’s not that people don’t care, it’s that structurally, they can’t see it.
Explore my conversation with Adam Dell on the tension between honesty and optimism.
Even the best culture cannot fully solve it
Nick Mehta might be one of the most people-first, energy-positive CEOs I know. He told me about a recurring dream: he’s a train conductor, and all his employees are riding along, doing amazing things, but eventually each one reaches their destination and leaves the train, because the train was never the point for them. Eventually, he realized, everyone leaves. He’s the one who stays in the conductor’s seat.
That image has stuck with me more than almost anything else in this episode. Even the guy who built one of the most beloved cultures in software history had to make peace with the fact that the seat itself doesn’t change, even when the people around him do. People join, people leave, people get promoted, and you wave them all off at the station, then get back in the conductor’s seat.
Hear the full story behind Nick Mehta’s train conductor analogy.
The default is lonely, but defaults can change
Here’s the turn in the episode. Nadia Boujarwah, co-founder and CEO of Dia&Co, said the founder journey is lonely by default, because nobody else is fully in the position you’re in. But she pointed out that the one thing that can change that default is a co-founder, someone who is genuinely in it with you.
Listen to the word she used: default. Not destiny, not law of nature. A default is just a setting, and settings can be changed. That’s the pivot point of this whole episode. Maybe you don’t have a co-founder. Maybe, like a lot of founders I’ve talked to, even a co-founder can’t fully share the CEO seat. So the real question becomes: what else can you build around you?
Learn more about Nadia Boujarwah’s perspective on changing the default of founder loneliness.
Get a coach, even Tom Brady had one
Chip Hazard, a general partner at Flybridge who’s backed founders for decades, made the case against trying to do it all yourself. Yes, it’s your company, 100%. But that doesn’t mean there aren’t outside perspectives that can make you better. Get a coach. Get an advisor network. No founder can know everything, and the “hero effort” tends to lead to missed opportunities, not fewer of them.
The line that got me was his comparison: even Tom Brady had a coach. The greatest of all time still had someone watching his film, challenging him, making him better. Somehow founders convince themselves they should just figure it out alone.
Go deeper into Chip Hazard’s case for why founders shouldn’t try to do it alone.
Your blind spots become their blind spots
Kathryn Minshew, founder and former CEO of The Muse, had a coach for nearly the entire life of her company, plus founder peer groups. She made a distinction I hadn’t heard put so clearly: a coach who only ever talks to you can only ever see your version of reality. If your blind spots are all they have to work with, your blind spots become their blind spots too.
Her own coach actually sat in on her real meetings, that’s the upgrade she was describing. Someone with independent context on your business, your team, and you, not just your side of the story. I’ve felt this myself with the companies I advise. At this point, I’ll really only take on companies where I can spend time with the team a level down, because I can help so much more when I do.
Explore Kathryn Minshew’s take on what makes coaching actually useful.
I own my house because of one man’s advice
Mike Grossman has been CEO of six companies and now coaches first-time CEOs. He told me the number one challenge he sees across all of them isn’t strategy or go-to-market, it’s mental health. Founders tie their identity to the company and have nobody to talk to.
Mike understands that so well because for about a decade, he had someone to talk to himself: Bill Campbell, the legendary “coach of Silicon Valley,” Steve Jobs’ most trusted advisor, who also coached the founders of Google. Mike met with him once or twice a week for ten years. Bill had no agenda beyond being helpful, he wasn’t doing it for money. And Mike told me, plainly, that he owns the house he lives in today because of advice Bill gave him at a critical moment.
That’s what makes this whole section more than a nice idea. The support system isn’t soft, and it isn’t optional, it shows up in the actual outcomes. And notice the flywheel: Bill coached Mike for a decade, and now Mike spends his time coaching first-time CEOs, paying it forward. That’s what the best support systems do. They don’t just carry you, they turn into something that carries others.
Go deeper into Mike Grossman’s decade with Bill Campbell and the advice that changed his life.
It does not have to be the destiny
I’m closing with Kyle Porter, who founded Salesloft, because he’s proof that all of this actually works. When I asked him about the famous loneliness of the founder journey, his answer was different from everyone else’s: he never really felt it, because of his wife, his dad, and the friend network he had. He talked about being able to call a fellow founder, share problems, and realize he wasn’t a “shitty CEO,” just a founder going through what every founder goes through.
Kyle and I were building our companies at exactly the same time, and honestly, those calls were probably more valuable to me than they were to him. Kyle didn’t feel less pressure than anyone else in this episode. He built the same company under the same stress. The difference is he never sat in it alone.
Hear more about why Kyle Porter never experienced the founder loneliness so many CEOs describe.
Nine founders is a lot of proof points, and none of them add up to a way to make this job not lonely. That is not what any of them found. The seat is lonely by design: you make unpopular decisions with imperfect information, your team only ever sees half of what you carry, and you are the one final decision maker, full stop.
What changes, across every one of these conversations, is not the loneliness itself. It is whether someone decided to sit in it alone or not. A co-founder. A coach who sits in on your real meetings. A peer group. A wife, a dad, a friend network. None of them make the decisions for you.
That part is still yours, and it always will be. But it is the difference between carrying the full weight and carrying something you can actually hold.
Guests Featured in This Episode:
Marcus Ryu, Co-Founder & Former CEO, Guidewire — LinkedIn
Adam Dell, Founder & CEO, Domain Money — LinkedIn
Chieh Huang, Co-Founder & Former CEO, Boxed — LinkedIn
Nick Mehta, Co-Founder & Former CEO, Gainsight — LinkedIn
Nadia Boujarwah, Co-Founder & Former CEO, Dia&Co — LinkedIn
Chip Hazard, General Partner & Co-Founder, Flybridge — LinkedIn
Kathryn Minshew, Co-Founder & Former CEO, The Muse — LinkedIn
Mike Grossman, CEO (6x) & Author, Failure Is an Option — LinkedIn
Kyle Porter, Founder & Board Chair, Salesloft — LinkedIn
Ways to Tune In:
Substack:
Spotify:
Apple Podcasts:
Chapters
00:00 – Trailer
00:48 – Intro: Why This Episode
02:20 – Marcus Ryu: The N of One
03:34 – Adam Dell: What Your Team Can’t See
04:57 – Chieh Huang: The Job in Six Words
05:59 – Nick Mehta: The Train Conductor
07:26 – Nadia Boujarwah: The Default Can Change
08:43 – Chip Hazard: Even Tom Brady Had a Coach
10:10 – Kathryn Minshew: Blind Spots
12:34 – Mike Grossman: The Trillion Dollar Coach
15:38 – Kyle Porter: It Doesn’t Have to Be the Destiny
16:38 – Closing Thoughts
18:05 – End
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.