They tell you to be relentless. To be a machine. To eat glass and stare into the abyss. And for a while, you believe them. I know I did.
I’ve been through the Silicon Valley wringer twice with successful exits—RemoteTeam to Gusto and MovieLaLa to Gfycat. I’ve placed bets on over 200 companies, including some you probably use every day like Anthropic and OpenAI. From the outside, it looks like a highlight reel. But the reality? It’s a highlight reel with a lot of dark, silent footage left on the cutting room floor.
Let’s be brutally honest: the founder journey is a mental meat grinder. We celebrate the IPOs and the billion-dollar valuations, but we whisper about the breakdowns, the divorces, and the depression. I’m tired of whispering. It’s time to talk about the most critical, yet most overlooked, aspect of building a successful company: your own mind.
The Crushing Weight of Being Alone
I remember one night, around 2015, sitting in our tiny office in Palo Alto. We had just closed a seed round for MovieLaLa. We had a team of five, a product people seemed to love, and money in the bank. I should have been ecstatic. Instead, I was sitting on the floor, back against a cold wall, feeling a sense of isolation so profound it felt like I was suffocating.
My team was looking to me for all the answers. My investors expected a 100x return. My family wondered why I was never home. I was surrounded by people, yet I had never felt more alone. I couldn't tell my team I was scared we were about to run out of money. I couldn't tell my investors I was worried a competitor was about to eat our lunch. I couldn't tell my wife that I felt like a complete fraud.
That’s the founder’s paradox. You’re the leader, the visionary, the one who is supposed to have it all figured out. But inside, you’re often just a person, wrestling with doubt and fear, with no one to turn to. This isn't just a feeling; it's a well-documented phenomenon. Studies have shown that founders are 50% more likely to report having a mental health condition.
I had to make a decision to pivot the entire company. We had built a product that was getting some traction, but I could see the writing on the wall. The market was shifting, and if we didn't change course, we were going to die. I spent weeks agonizing over the decision, running the numbers, talking to customers, and staring at the ceiling at 3 AM. I couldn't share the full extent of my doubts with the team, for fear of causing a panic. I had to project an aura of confidence while my insides were churning with anxiety. When I finally announced the pivot, it was one of the hardest days of my life. Some team members left. I had to face angry investors. But it was the right decision. And I had to make it alone.
The Glorification of Burnout
Our industry has a sick obsession with “the hustle.” We wear our 80-hour workweeks like a badge of honor. We brag about sleeping under our desks. I’ve done it. I’ve pulled the all-nighters. I’ve sacrificed weekends and holidays for years on end. And you know what it got me? A severe case of burnout that almost cost me my company and my health.
It was during the early days of RemoteTeam. We were growing fast, but the product was buggy. I was trying to be the CEO, the head of product, and the lead engineer all at once. I was working 18-hour days, fueled by caffeine and anxiety. I stopped working out. I was eating junk food. My relationships were suffering. I thought I was being a hero. In reality, I was being an idiot.
One day, I woke up and I just couldn't get out of bed. The exhaustion was bone-deep. My mind was a fog. I had hit a wall. And it was a wall of my own making. I had to take a week off, completely unplugged, just to feel human again. That week was a turning point for me. I realized that burnout isn't a necessary evil. It's a sign of a broken system. A system that I was perpetuating.
I see this pattern repeating itself with so many of the founders I invest in. I remember one founder, let's call him Alex, who was building an incredible AI company. He was brilliant, driven, and completely committed. He was also running himself into the ground. I could see the dark circles under his eyes. I could hear the exhaustion in his voice. I pulled him aside one day and said, 'Alex, you’re going to burn out. And when you do, you’re going to take the company with you.' He protested, of course. He said he was fine. But a few months later, he called me. He was in the hospital. He had collapsed from exhaustion. The company almost died. We managed to save it, but it was a brutal wake-up call for him, and for me.
The Elephant in the Room: Depression
This is the one nobody wants to talk about. But we have to. Founders are twice as likely to suffer from depression. The constant stress, the pressure, the isolation—it’s a perfect storm for mental health issues. And the tragic reality is that many founders suffer in silence, afraid that admitting they are struggling is a sign of weakness.
I’ve had my own battles with the darkness. Moments when it felt like the weight of the world was on my shoulders and I couldn't see a way out. It’s a scary place to be. But I’ve learned that there is no shame in asking for help. In fact, it’s one of the strongest things you can do as a leader.
Whether it’s talking to a therapist, joining a founder support group, or just being open with your co-founders, seeking help is not a liability. It’s a strategic imperative. Your company is a reflection of you. If you’re not healthy, your company won’t be either.
I once had a co-founder who was struggling with depression. He was brilliant, but he was also erratic and unreliable. He would disappear for days at a time. The team was losing faith in him. I had to make the difficult decision to have a frank conversation with him. I told him that I was worried about him, and that his behavior was impacting the company. It was a painful conversation, but it was also a necessary one. He ended up taking a leave of absence to get the help he needed. It was a setback for the company, but it was the right thing to do. And when he came back, he was a different person. He was focused, engaged, and a much better leader.
Building Your Mental Armor
So how do you survive the mental gauntlet of being a founder? It’s not about being invincible. It’s about being resilient. It’s about building a set of practices and a support system that can help you weather the storms. Here are a few things that have worked for me:
Find Your Tribe: You need a group of people you can be completely honest with. For me, it’s a small group of other founders. We have a monthly dinner where we can vent, share our struggles, and just be real with each other. No bullshit. No posturing. Just honest conversation. We talk about the things you can't talk about with your team or your investors. We talk about the fear, the doubt, the loneliness. And just knowing that you're not the only one going through it is incredibly powerful.
Set Boundaries: The work will always be there. You have to be disciplined about taking time for yourself. For me, that means no meetings on Fridays. That’s my day to think, to read, to recharge. It also means taking real vacations. Not the kind where you’re still checking email every five minutes. I once went on a two-week trip to Japan and left my laptop at home. It was one of the best decisions I ever made. I came back with a clear head and a renewed sense of purpose.
Move Your Body: I can’t overstate how important this is. When I’m feeling stressed or overwhelmed, a hard workout is the best medicine. It’s not about getting ripped. It’s about clearing your head and releasing endorphins. I make it a non-negotiable part of my day. I've found that a morning run is the best way to start my day. It gives me time to think, to plan, and to just be with myself before the chaos of the day begins.
Celebrate the Small Wins: The founder journey is a marathon, not a sprint. You have to find ways to celebrate the small victories along the way. Shipped a new feature? Pop a bottle of champagne. Hit a new revenue milestone? Take the team out for a nice dinner. These small moments of joy are what will sustain you through the tough times. I remember when we hit our first $10,000 in monthly recurring revenue at RemoteTeam. It was a tiny number in the grand scheme of things, but we celebrated like we had just won the Super Bowl. It was a moment of pure joy that I'll never forget.
Practice Gratitude: This might sound a little woo-woo, but it works. Every morning, before I check my email, I write down three things I'm grateful for. It could be something as small as a good cup of coffee or as big as a new customer. It's a simple practice, but it helps me start the day with a positive mindset. It reminds me that even on the tough days, there's still a lot to be thankful for.
Your Mind is Your Greatest Asset
I’ve been lucky enough to have a couple of successful exits. I’ve invested in some of the most transformative companies of our time. But I can tell you, without a doubt, that the most important investment I’ve ever made is in my own mental health.
Your company is not your life. It’s a part of your life. A big part, for sure. But it’s not everything. Don’t sacrifice your well-being on the altar of success. Because the truth is, you can’t have one without the other. Not in the long run.
So, let’s stop glorifying the struggle and start glorifying the resilience. Let’s stop celebrating the hustle and start celebrating the wholeness. Let’s build companies that are not only successful, but also sustainable. And that starts with you. Take care of your mind. It’s the most valuable asset you have. And it's the one that will ultimately determine your success, both in business and in life.
Frequently Asked Questions
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.