I’ve been through the founder wringer a few times now. Two exits, one to Gusto and another to Gfycat. Over 200 angel investments in companies you’ve probably heard of, like Anthropic and OpenAI. You see the headlines, the success stories. What you don’t see is the cost. The real cost.
It’s not about the money. It’s about what it takes to get there. The mental and emotional toll is the part of the story that rarely gets told. We celebrate the wins, but we bury the struggles. I’m here to tell you that the struggles are not just part of the journey; they are the journey.
The Loneliness of the Long-Distance Founder
People think being a founder is glamorous. It’s not. It’s lonely. You’re on an island, and even when you’re surrounded by people, you’re alone with the weight of the world on your shoulders. Your team, your investors, your family—they all look to you for answers, for strength, for confidence. You can’t show weakness. You can’t have a bad day. Or so you think.
I remember with RemoteTeam, we were growing fast. Everything looked great from the outside. But inside, I was a wreck. I was dealing with a million things at once, from product to fundraising to hiring. I felt like I was constantly putting out fires, and I couldn’t talk to anyone about it. Not really. How could I tell my team I was scared we were going to miss payroll? How could I tell my investors I was worried our biggest competitor was about to eat our lunch? I couldn’t. So I bottled it up. And that’s a dangerous thing to do.
It’s a classic founder mistake. We think we have to be superheroes. We think we have to have all the answers. But the truth is, we don’t. And the sooner we admit that, the better off we’ll be. It’s okay to be vulnerable. It’s okay to ask for help. In fact, it’s essential.
Your Startup is Not Your Baby
I see this all the time. Founders who are so attached to their companies that they can’t see straight. They pour their entire identity into their startup. Their company’s success is their success. Their company’s failure is their failure. This is a recipe for disaster.
Your startup is not your baby. It’s a business. A separate entity. You have to be able to detach yourself from it. You have to be able to look at it objectively. And you have to be willing to let it go. I know that’s hard to hear, especially when you’ve poured your blood, sweat, and tears into it. But it’s the truth.
When we sold MovieLaLa to Gfycat, it was a great outcome. But it was also hard. It was like a part of me was gone. I had to grieve. I had to let go. And it was only then that I was able to move on to the next thing. If you’re too attached to your company, you’ll never be able to make the tough decisions. You’ll never be able to pivot when you need to. And you’ll never be able to sell, even when it’s the right thing to do.
The Burnout is Real
I’ve been there. The sleepless nights. The constant anxiety. The feeling that you’re never doing enough. It’s a dark place. And it’s a place that a lot of founders find themselves in.
Burnout is not a badge of honor. It’s a sign that something is wrong. It’s a sign that you’re not taking care of yourself. And if you don’t take care of yourself, you can’t take care of your company.
I learned this the hard way. There was a point where I was working 18-hour days, 7 days a week. I was running on fumes. I was making bad decisions. I was snapping at my team. I was a mess. And it wasn’t until I hit rock bottom that I realized I needed to make a change.
I started small. I started taking weekends off. I started exercising. I started meditating. I started spending more time with my family and friends. And slowly but surely, I started to feel like myself again. And you know what? The company didn’t fall apart. In fact, it got better. Because I was better.
Therapy is Not a Weakness
There’s a stigma around mental health in the founder community. We’re supposed to be tough. We’re supposed to be resilient. We’re not supposed to need help. But that’s just not true.
Therapy has been a lifesaver for me. It’s given me a safe space to talk about my fears, my insecurities, my struggles. It’s given me tools to cope with the stress and anxiety of being a founder. And it’s helped me to become a better leader, a better husband, and a better person.
If you’re struggling, I urge you to seek help. There’s no shame in it. In fact, it’s one of the strongest things you can do. It’s an investment in yourself, and it’s an investment in your company.
The Bottom Line
Being a founder is a marathon, not a sprint. You have to be in it for the long haul. And the only way to do that is to take care of yourself. Your mental and emotional health is just as important as your company’s bottom line. In fact, it’s more important.
So, take a break. Go for a walk. Spend time with your loved ones. And if you need help, ask for it. Your future self will thank you for it. And your company will too.
The Double-Edged Sword of Angel Investing
After my exits, I dove headfirst into angel investing. It felt like the natural next step. I’ve now backed over 200 companies, including some of the biggest names in AI. You’d think being on the other side of the table would be easier. In some ways, it is. But in other ways, it’s just as hard. I see the same patterns of self-destruction, the same mental traps, playing out over and over again.
I see founders who are so obsessed with growth that they sacrifice everything else in their lives. Their health, their relationships, their sanity. They wear their burnout like a badge of honor, as if it’s a prerequisite for success. I see them making the same mistakes I made, and it’s painful to watch. I try to guide them, to share my own experiences, but at the end of the day, they have to learn the lessons for themselves.
One of the hardest things about being an investor is knowing when to step in and when to let go. You can’t save every company. You can’t save every founder. Sometimes, the best thing you can do is to let them fail. Failure is a powerful teacher. It’s where the real learning happens. It’s where resilience is forged.
Building a Support System That Actually Supports You
Everyone tells you to build a support system. But what does that actually mean? It’s not just about having a few friends you can vent to. It’s about surrounding yourself with people who get it. People who have been in the trenches. People who can give you tough love when you need it.
For me, that’s been a mix of other founders, mentors, and a few close friends who have been with me since the beginning. My co-founders have been my rocks. We’ve been through hell and back together. We’ve seen each other at our best and at our worst. And we’re still standing. That’s a bond that can’t be broken.
My mentors have been invaluable. They’re the ones who have been there, done that. They’ve given me advice, opened doors, and kicked me in the ass when I needed it. I wouldn’t be where I am today without them.
And my friends… they’re the ones who keep me grounded. They remind me that there’s a world outside of startups. They’re the ones who I can be myself with, without any pretense. They’re the ones who will still be there, even if my next company goes up in flames.
Finding your tribe is not easy. It takes time. It takes effort. But it’s worth it. These are the people who will get you through the dark times. These are the people who will celebrate your wins with you. These are the people who will make the journey worthwhile.
Redefining Success
For a long time, my definition of success was tied to external validation. Exits, funding rounds, press mentions. I was chasing the next high, the next accomplishment. But I’ve come to realize that’s a hollow victory.
True success is not about what you achieve. It’s about who you become in the process. It’s about the relationships you build. It’s about the impact you have on the world. It’s about living a life of purpose and meaning.
I’m still a work in progress. I still have my moments of doubt and fear. But I’m no longer chasing the same things I used to. I’m more focused on my own well-being, on my relationships, and on making a positive contribution to the world. And that, to me, is a much better definition of success.
So, I’ll leave you with this. Don’t just build a great company. Build a great life. The two are not mutually exclusive. In fact, they’re inextricably linked. The more you invest in yourself, the more you’ll have to give to your company. And the more you’ll get out of the journey, no matter the outcome.
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.
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.
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.