I remember the night before we sold RemoteTeam to Gusto. You’d think I’d be celebrating, right? We were on the one-yard line of a life-changing exit. Instead, I was sitting on the floor of my office at 3 AM, staring at a term sheet, and I felt… nothing. Not joy, not relief. Just a deep, hollow emptiness. The hustle had consumed me so completely that I’d forgotten the person underneath it all. I’d burned out so badly the flame was just gone.
Silicon Valley loves a good myth. We worship the 10X engineer, the visionary founder who sleeps four hours a night and codes the rest, the relentless force of nature who bends reality to their will. We see the magazine covers, the TechCrunch articles, the billion-dollar valuations. What we don’t see is the crushing weight of expectation, the anxiety that keeps you awake at night, and the profound loneliness of carrying a company on your shoulders.
It’s a dangerous illusion. And I bought into it for years.
The Rock Bottom Before the Summit
My first company, MovieLaLa, was a rollercoaster. We were scrappy, hungry, and fighting for every user. I wore my exhaustion like a badge of honor. I thought that to win, I had to sacrifice everything else: my health, my relationships, my peace of mind. There was a point where we were running out of money, and I was pitching investors day and night. I remember one V.C. telling me, “You look tired.” I just smiled and said, “That’s the look of a founder who’s about to win.”
He passed on the deal. And you know what? He was right to. I was a mess. My judgment was clouded, my energy was shot, and I was leading from a place of fear, not strength. That experience was a brutal, but necessary, wake-up call. We eventually found a home for MovieLaLa with Gfycat, but I promised myself I would never again build a company at the expense of my own humanity.
Building Your Resilience Toolkit
Founding a company is a marathon, not a sprint. You wouldn’t run 26.2 miles without training, hydration, and the right gear. Why would you try to build a business without a toolkit for your mind? Over the years, and after investing in over 200 companies, I’ve learned that the most successful founders aren’t the ones who just hustle the hardest. They’re the ones who are the most resilient.
Here’s what’s in my toolkit. This isn’t just theory; this is what I practice and what I look for in the founders I back.
Therapy is a Superpower, Not a Weakness
Let’s get this out of the way. Seeing a therapist isn’t a sign that you’re broken. It’s a sign that you’re committed to high performance. The best athletes in the world have coaches for their bodies; the best founders should have coaches for their minds. My therapist has been my secret weapon. It’s a confidential space where I can untangle the immense pressure, process the fear of failure, and get an objective perspective on the challenges I’m facing. It’s not about dwelling on problems. It’s about forging solutions and building the mental fortitude to execute them.
The Power of Saying 'No'
When you’re starting out, you want to say yes to everything. Every meeting, every feature request, every opportunity. But as you grow, the most powerful word in your vocabulary becomes “no.” You have to set boundaries. No, I can’t take that meeting, it’s my one night with my family this week. No, we’re not adding that feature, it distracts from our core mission. No, I’m not checking emails after 8 PM, my brain needs to rest.
This is incredibly hard. It feels like you’re letting people down. But every “no” is a “yes” to something more important: your focus, your strategy, and your well-being. A burned-out founder can’t lead anyone anywhere.
Your Co-founder is Your Co-pilot
Your relationship with your co-founder is one of the most intense you’ll ever have. It’s a business partnership, a creative marriage, and a shared foxhole experience all in one. It can also be a huge source of stress or a huge source of strength. The key is radical, open communication.
You have to be able to talk about the hard stuff: equity splits, role definitions, personal frustrations, and yes, mental health. Schedule regular check-ins that aren’t about the business, but about your relationship. How are we doing? What’s working? What’s not? A strong co-founder relationship is a force multiplier for the business and a critical support system for your own sanity.
Investing in Founders, Not Just Ideas
My journey from founder to angel investor has fundamentally changed how I look at startups. I’ve been fortunate to back some incredible companies like Anthropic, OpenAI, and Scale AI. When I’m considering an investment, I’m looking at the tech, the market, the traction. But more than anything, I’m looking at the founder. Are they resilient? Are they self-aware? Do they have a support system?
I’d rather invest in an A+ founder with a B+ idea than the other way around. Because a great founder will pivot, learn, and find a way to win. A founder on the brink of burnout, no matter how brilliant their idea, is a massive risk. I make it a point to talk to the founders I back about their mental health. I want them to know it’s a priority for me, because I know it’s essential for their success.
The Real Exit
We celebrate the financial exit—the acquisition, the IPO. But the real exit, the one that truly matters, is the one you make every single day. It’s the choice to step away from your laptop and have dinner with your family. The choice to go for a run instead of answering one more email. The choice to be vulnerable and ask for help.
Building a company will test you in ways you can’t even imagine. It will demand more from you than you think you have to give. But it doesn’t have to break you. The hustle is part of the game, but it’s not the whole game. Your greatest asset isn’t your code, your product, or your funding. It’s you. Invest in yourself accordingly.
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.
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.
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 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.