I still remember the day we sold RemoteTeam to Gusto. The deal was done, the wire transfer hit the bank, and my co-founder and I were officially 'successful'. Everyone was celebrating. My phone was blowing up. But my first real feeling? A hollow pit in my stomach. It was over.
For five years, RemoteTeam was my entire identity. We went from three guys in a cramped apartment to a team of 50. I knew every line of code, every customer, every employee's dog's name. Then, in an instant, it wasn't mine anymore. This is the dirty secret of the startup world. We fetishize the exit, but we never talk about the morning after.
The Myth of the Invincible Founder
Silicon Valley loves its superheroes. The founder who lives on Soylent and 3 hours of sleep, who codes all night and then nails a board meeting at 8 AM. I've been that guy. I wore the 100-hour work weeks as a badge of honor. It's a toxic culture, and it's a lie. That 'invincibility' is just a mask for deep-seated anxiety.
The truth is, being a founder is one of the most mentally taxing jobs on the planet. You’re responsible for everything. Your team’s livelihood, your investors’ money, your customers’ satisfaction – it all rests on your shoulders. The pressure is immense, and it never lets up. It’s a recipe for burnout, anxiety, and depression.
I can name a dozen friends, brilliant founders, who have completely burned out. People who built nine-figure businesses but couldn't get out of bed in the morning. They're terrified to talk about it. They think admitting they're struggling will make their investors pull out or their best engineers quit. It's a prison of their own making.
My Battle with Founder Loneliness
One of the hardest things for me to deal with was the loneliness. As a founder, you’re in a unique position. You can’t vent to your employees about how stressed you are. You can’t complain to your investors about how scared you are. You’re at the top of the pyramid, and it’s a lonely place to be.
After the MovieLaLa exit, I was set. I had 'f*ck you' money, as they say. But all I felt was 'what now?'. I'd walk around Hayes Valley, see all these people hustling, building, and I felt like a ghost. My purpose was gone. It was the most successful and the most miserable I'd ever been.
That's when I stumbled into angel investing. I started writing small checks into companies I found interesting. Now it's over 200, including some absolute monsters like Anthropic, OpenAI, and Scale AI. The returns are nice, sure. But the real reason I do it? It gives me a front-row seat to the struggle again. I get to be the guy in the founder's corner that I never had. I can tell them, 'Hey, I've been there. It's supposed to be hard. You're not crazy.'
Building a Mental Health Playbook
Over the years, I’ve developed a set of strategies for managing the mental and emotional challenges of being a founder. It’s not a magic bullet, and it’s not a one-size-fits-all solution. But it’s what has worked for me, and I hope it can help you too.
- Find your tribe. You need a group of people you can be completely honest with. For me, it’s a small group of fellow founders who I meet with regularly. We share our wins, our losses, and our fears. We hold each other accountable, and we remind each other that we’re not alone.
- Prioritize your physical health. You can’t have a healthy mind without a healthy body. For me, that means starting every day with a workout. It’s non-negotiable. It clears my head, reduces my stress, and gives me the energy I need to tackle the day.
- Disconnect. In a world that’s always on, it’s more important than ever to disconnect. I make it a point to have at least one day a week where I don’t check my email or look at my phone. I spend that time with my family, in nature, or just reading a book. It’s amazing how much of a difference it can make.
- Celebrate the small wins. As founders, we’re always focused on the next big milestone. The next funding round, the next product launch, the next exit. But it’s important to celebrate the small wins along the way. It’s what keeps you going when things get tough.
It’s Okay to Not Be Okay
So if you're a founder out there feeling like you're losing your mind, listen to me: It's okay. The crushing weight on your chest is normal. The loneliness is part of the deal. It doesn't mean you're failing. It means you're in the arena.
The most important thing is to ask for help. Whether it’s from a therapist, a coach, a mentor, or a friend. Don’t suffer in silence. The world needs you and your ideas. And you can’t change the world if you’re not taking care of yourself.
The ‘Success’ Hangover is Real
Let's talk more about that post-exit hangover. It’s a weird, disorienting experience. You’ve been sprinting a marathon for years, and suddenly you cross the finish line. Everyone is cheering, but your body doesn’t know how to stop running. My mind was still racing, conditioned to solve problems, fight fires, and build. But there were no more fires to fight. No more problems to solve. It felt like I was a soldier without a war.
I tried the typical Silicon Valley ‘successful founder’ things. I took a long vacation. I bought a ridiculously expensive car I didn’t need. I went to fancy dinners where people wanted to hear my ‘story’. It all felt hollow. The thrill of building, of creating something from nothing, was gone. And I realized that the process, not the outcome, was what I was truly passionate about. The money is a byproduct, not the goal. The real drug is the journey.
More Than Just a Job: The Identity Crisis
For a founder, a startup isn't just a job. It's an extension of yourself. Your identity becomes intertwined with the company's. When someone asked me what I did, I didn't say 'I'm a CEO'. I said 'I'm the founder of RemoteTeam'. When the company was doing well, I was doing well. When we hit a rough patch, I felt it personally. This is a dangerous game to play.
When you sell the company, you're not just selling a business. You're selling a piece of your identity. And that's a hard thing to let go of. I had to rediscover who I was outside of being 'Sahin, the founder'. It was a painful process, but a necessary one. I had to learn to separate my self-worth from my net worth. I had to remember the things I was passionate about before I ever wrote a line of code or pitched a VC.
The Angel Investing Chapter: A New Purpose
My journey into angel investing was almost accidental, born out of a need to reconnect with the world of building. I started by advising a few friends' startups, and I found that I loved it. I loved being in the trenches again, even if it was just as an advisor. I loved the energy, the optimism, the sheer audacity of the founders.
So I started writing checks. Small at first, then bigger as I got more comfortable. And I found that my experience as a founder was my biggest asset. I could see the patterns, the pitfalls, the opportunities. I could empathize with the founders in a way that most investors can't. I knew what it was like to be in their shoes, and that made all the difference.
Now, with over 200 investments, I see my role as more than just a source of capital. I'm a mentor, a therapist, a cheerleader, and a friend. I'm the person who will take a founder's call at 2 AM when they're freaking out about a server crash. I'm the person who will celebrate their smallest wins and help them navigate their biggest challenges. It's given me a new sense of purpose, and it's been one of the most rewarding experiences of my life.
Redefining Success
For a long time, my definition of success was tied to external validation. Funding rounds, valuations, exits. But I've come to realize that true success is about something much deeper. It's about building something you're proud of, something that makes a difference in the world. It's about the relationships you build along the way. It's about finding a sense of purpose and fulfillment in your work.
And most importantly, it's about being able to look yourself in the mirror at the end of the day and know that you're living a life that's true to yourself. That you're not just chasing someone else's definition of success. That you're building a life, not just a company.
So, to all the founders out there, I want to say this: take care of yourselves. Your mental health is your most valuable asset. Don't be afraid to ask for help. And remember that you are not alone. We're all in this together.
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.
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.