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The Star Deal That Almost Broke Me

I remember the term sheet hitting my inbox. It was from one of the biggest VCs on Sand Hill Road. The valuation was insane, the kind of number you dream about when you're eating ramen and coding in a garage. This was for my first company, MovieLaLa. We were on fire, and this deal was the rocket fuel. I thought, "This is it. We've made it."

I was wrong. The next six weeks were the closest I've ever come to a complete mental breakdown.

Most people see the exits, the headlines, the "overnight success." They don't see the 3 AM cold sweats, the strained relationships, the crushing loneliness of knowing that a single wrong move could vaporize everything you and your team have worked for. They don't talk about the dark side of being a founder. I'm going to.

The Myth of the Invincible Founder

Silicon Valley has a poster child. It’s a young, brilliant, probably-a-dropout who works 100 hours a week, sleeps under their desk, and thrives on pressure. They are a machine, a visionary, a force of nature. They are also a myth.

I’ve invested in over 200 companies, including giants like Anthropic and OpenAI. I’ve seen two of my own companies get acquired. I can tell you with absolute certainty: founders are not machines. We are human beings, and we are running a marathon at a sprinter's pace. The mental toll is immense, and we are terrible at admitting it.

Why? Because we’re taught that vulnerability is weakness. Admitting you’re struggling feels like telling your investors, your team, and yourself that you’re not cut out for the job. So we bottle it up. We pretend. We post the smiling pictures from the TechCrunch party while internally, we’re in a freefall.

My Battle with the "Big Four"

When I look back at my own journey and talk to the founders I mentor, the same four horsemen of the founder apocalypse show up again and again: depression, stress, loneliness, and relationship strain.

1. The Silent Killer: Founder Depression

During that "star deal" negotiation for MovieLaLa, I stopped sleeping. I’d lie awake, my mind racing through every possible doomsday scenario. What if the due diligence turned up something I missed? What if our top engineer quit? What if our growth numbers for next month dipped by 2% and the whole thing fell apart?

I lost interest in everything. Food tasted like cardboard. I’d snap at my co-founder for no reason. I felt a constant, low-grade hum of dread. This wasn’t just stress; it was the beginning of a depressive episode. I felt like an imposter, convinced that at any moment, everyone would realize I had no idea what I was doing.

It’s more common than you think. A study from UC Berkeley found that 72% of entrepreneurs are directly or indirectly affected by mental health issues. Think about that. The majority of us are struggling. You are not alone in this.

My Advice: Schedule therapy like you schedule board meetings. It’s non-negotiable. I’ve had a therapist for years. It’s not a sign of weakness; it’s a sign of a professional who wants to operate at their peak. It’s a dedicated hour to untangle the spaghetti monster of anxieties in your head. Find a therapist who understands the founder journey. They exist, and they are worth their weight in gold.

2. Stress: The High-Interest Loan

Stress in a startup is a given. It’s a tool, even. It can push you to do incredible things. But chronic, unmanaged stress is like taking out a high-interest loan on your health. Eventually, the payments come due.

I remember one specific week at RemoteTeam. We were pushing a major product update. A bug in a third-party API brought our entire system down. Customers were churning. My phone was blowing up with angry emails. I felt a physical weight on my chest. I worked for 48 hours straight, fueled by caffeine and pure adrenaline. We fixed it, but I was a wreck for a week. My body literally felt like it had been in a car crash.

That’s the interest payment. You can’t keep borrowing from your physical and mental reserves without consequence.

My Advice: You need a system for managing stress. Not a vague idea, but a concrete, scheduled system. For me, it’s three things:

Daily Exercise: Non-negotiable. Even if it’s just a 30-minute walk. It’s not about getting ripped; it’s about clearing your head and burning off the cortisol.
Time Blocking: I live by my calendar. I block out time for deep work, for meetings, and—crucially—for breaks. If it’s not on the calendar, it doesn’t exist.
A "Hard Stop": I have a time every evening when I shut down my computer. The work is never, ever done. You have to force it to be done for the day. Go home. Be with your family. Read a book. Your brain needs to reboot.

3. The Loneliness of Command

Being a founder is the loneliest job in the world. You can’t be fully transparent with your employees; you’ll scare them. You can’t be fully transparent with your investors; they’ll lose confidence. You can’t even be fully transparent with your co-founder sometimes, because you need to be the strong one.

I felt this acutely after we sold RemoteTeam to Gusto. It was a huge success, a life-changing exit. But the day after the deal closed, I felt… empty. Lost. My entire identity had been wrapped up in being "Sahin, CEO of RemoteTeam." Who was I now? My friends, who all had normal jobs, couldn’t understand why I wasn’t just celebrating on a beach somewhere. The loneliness was crushing.

My Advice: Build a personal board of directors. This is a small group of 3-5 other founders who you can be brutally honest with. They’ve been in the trenches. They get it. You can call them at 10 PM when a deal is falling apart and they won’t flinch. They’ll just say, "Okay, I’ve been there. Here’s what I did." This has been my single greatest tool for combating loneliness.

4. The Relationship Wreckage

Startups are relationship incinerators. Your focus is so absolute, so all-consuming, that the people you love the most often get the worst of you. They get the tired, stressed, distracted version of you. Your partner, your kids, your friends—they get the leftovers.

During the most intense periods of building my companies, my wife got used to me being physically present but mentally a million miles away. We’d be at dinner, and she could see I was just running through a bug list in my head. It’s a terrible feeling, for both people.

My Advice: You have to be as intentional with your relationships as you are with your product roadmap. Schedule date nights and put your phone in a drawer. When you’re with your family, be with them. Be present. It’s harder than it sounds. One trick that worked for me was creating a "transition ritual." When I came home, I’d take 10 minutes in my car to just sit in silence, consciously shifting from "CEO mode" to "husband and dad mode." It sounds silly, but it made a world of difference.

It’s Not About "Balance," It’s About Integration

People love to talk about "work-life balance." I think that’s a flawed concept for founders. It implies two separate things that you need to keep in perfect equilibrium. That’s impossible.

Your startup is a part of your life. A huge part. The goal isn’t to balance it against the rest of your life, but to integrate it in a way that doesn’t destroy you. It’s about building a life, not just a company.

That star deal for MovieLaLa? It eventually went through. It was a huge win for us. But I learned a more valuable lesson. The company is not you. Its success or failure does not define your worth as a human being. You are a founder, yes. But you are also a partner, a parent, a friend, a person. Tending to your own mental health isn’t a distraction from building your company; it is the very foundation upon which a great, enduring company can be built. '''

Frequently Asked Questions

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.

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.

Star deal will make especially try.