They don’t tell you about the silence. After the acquisition party, after the champagne flutes are cleared and the last congratulatory email is archived, there’s just… silence. When we sold RemoteTeam to Gusto, I thought I’d reached the summit. Two successful exits. A portfolio of over 200 angel investments in companies like Anthropic and OpenAI. On paper, I was the quintessential Silicon Valley success story. But in the quiet of my home office, I felt like a complete fraud.
My calendar, once a chaotic tapestry of back-to-back meetings, was suddenly empty. The constant firehose of problems to solve had been turned off. And in that void, a different kind of problem emerged, one I couldn’t solve with a pitch deck or a term sheet. I was adrift. The very identity I had built for a decade—the founder, the builder, the leader—was gone. And I was terrifyingly, profoundly lonely.
The Metrics of Misery
As founders, we live and die by metrics. Monthly recurring revenue, churn rate, customer acquisition cost. We track everything. We A/B test everything. But we have a massive blind spot for the most critical metric of all: our own mental and emotional health.
I remember a specific board meeting during the early days of MovieLaLa. Our user growth was explosive. Our engagement numbers were through the roof. My investors were thrilled, slapping me on the back. I smiled, nodded, and presented the upward-trending graphs. Inside, I was running on fumes. I hadn’t had a full night’s sleep in months. My diet consisted of lukewarm coffee and whatever I could grab from the office snack wall. I was irritable with my team and disconnected from my family. The company’s hockey-stick growth curve was directly proportional to my own nosedive into burnout.
We celebrate the hustle, the grind. We wear our sleep deprivation like a badge of honor. But there’s a fine line between dedication and self-destruction. I crossed it. I ignored every warning sign my body and mind were screaming at me. Because admitting you’re not okay feels like admitting your startup is not okay. It feels like failure.
The “Founder Strong” Facade
There’s this unspoken rule in the startup world that you have to be “founder strong.” You have to be the unshakable pillar of strength for your team, your investors, and your customers. You’re the captain of the ship, and the captain can’t be seen trembling.
This pressure is immense. It forces you into a state of emotional isolation. You can’t talk to your employees about your fears—that would spook them. You can’t always be honest with your investors—they might pull their funding. You can’t even talk to your friends and family, because they often don’t understand the unique pressures of the founder journey. They see the TechCrunch articles and the funding announcements, and they can’t comprehend why you’re not on top of the world.
So you build a fortress around yourself. You put on the mask of the visionary leader. This was my life for years. I became an expert at compartmentalizing. But the thing about fortresses is that they’re also prisons. The loneliness I felt wasn’t just a lack of company; it was a lack of genuine human connection where I could be my whole, unedited self.
My First Therapy Session
My breaking point came on a Tuesday. I was sitting in my car in the parking lot of our office, and I couldn’t get out. The thought of facing another day of faking it was physically paralyzing. I just sat there for an hour, watching people walk in, full of energy and purpose, while I felt completely empty. That was the day I booked my first therapy session.
Walking into that office was one of the hardest things I’ve ever done. It felt like a bigger risk than starting a company with no money. I was terrified of being labeled, of being seen as weak. But what I found wasn’t judgment. It was a space where I could finally take off the mask.
Therapy wasn’t a magic bullet. It was hard work. It was unpacking years of ingrained habits and unhealthy coping mechanisms. My therapist helped me see that my identity wasn’t my company. My worth wasn’t tied to my latest valuation. It was a process of rebuilding myself from the inside out. It taught me the language to understand my own emotional state and the tools to manage the immense psychological weight of being a founder.
Building Resilience, Not Just Companies
We talk a lot about building resilient companies, but we need to talk more about building resilient founders. The journey is a marathon, not a sprint, and it’s filled with more valleys than peaks. Here are a few things that have helped me stay sane:
- Schedule Your Downtime: I mean it. Put it on your calendar like a board meeting. An hour to go for a run. A weekend with no laptops. Protect that time ruthlessly. Your brain needs to decompress to be effective.
- Find Your Tribe: You need a small group of fellow founders you can be brutally honest with. Not for networking, but for genuine support. A place where you can say, “I’m terrified we’re going to miss payroll,” and have people who get it.
- Decouple Your Identity from Your Company: This is the hardest one. Your startup is something you do, not something you are. Pursue hobbies. Nurture relationships. Have a life outside of your company. When I started angel investing, it helped me see the bigger picture and not have my entire ego tied to one venture.
- Go to Therapy: I can’t say this enough. It’s not a sign of weakness; it’s a sign of strength. It’s preventative maintenance for your most important asset: your mind.
The entrepreneurial path is a wild ride. It will demand everything from you. But it shouldn’t take your soul. The real win isn’t the exit or the IPO. It’s building something meaningful without losing yourself in the process. It’s finishing the marathon, not just with a successful company, but with your own well-being intact.
Frequently Asked Questions
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.
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.
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.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.