I want to share something about the founder journey that may surprise many of you.
I sold my last startup over a decade (!) ago. And … I’m still tired.
What do I mean? I sold my second startup to Adobe waaaay back in 2011. That’s quite a long time ago.
Since then, we’ve built SaaStr AI into an eight-figure media and events business. Done 14+ SaaStr global events and 11 SaaStr AI Annuals. Invested $200M+ at SaaStr Fund across two funds into 7 unicorns. Written every single day since 2012—over 4,000 posts. Done 1-2 videos and podcasts a week, every week, for over a decade. Tried to answer questions from thousands of founders. Managed a business that has done well over $100,000,000 in revenue.
By most measures, things have gone well. Really well.
But honestly? I still haven’t gotten “un-tired” since I was a founder.
I still have some PTSD. I know I probably shouldn’t use that term for “just” being a founder. But I don’t know what else to call it. The symptoms are real. The rewiring is real.
I still struggle. I still hit walls. After 10 years of pushing boulders up hills and trying to do the impossible, day after day, it just… rewires your brain. And that rewiring doesn’t fully go away.
The Thing Nobody Tells You
A lot of folks think I’m high energy. And perhaps in some ways I am. I still run 5-7 miles a day, 360+ days a year. I still build apps in my spare time — over 20 on Replit! I still write constantly.
But underneath all that? I’m still tired from a decade of endless 24x7x365 stress as a founder.
The stress of almost running out of money—multiple times. Of doing customer support myself, seven days a week, for years. Of being one bad release away from losing our top customers. Of having payroll due and not knowing if we could make it. Of having co-founders leave. Of having key employees quit at the worst possible moment. Of competitors with 10x our funding copying everything we built.
Those experiences don’t just disappear when you sell the company. In fact, they rewire your brain. Not if you sell your company in 12 months. But for sure if you do it for 5, 10, 20+ years.
What I’ve Learned About Founder Fatigue
What I’ve seen:
- The tiredness is cumulative. Every near-death experience for your company, every Sunday you worked instead of seeing your kids, every 2am customer escalation—they add up. You don’t pay them off when you exit. You carry them.
- Your nervous system remembers. Even when things are going well, part of your brain is still scanning for threats. Still waiting for the email that says your biggest customer is churning. Still bracing for impact. That hypervigilance served you well as a founder. It’s harder to turn off than you’d think.
- Success doesn’t cure it. I’ve talked to founders who sold for $10)M, $500M, $3B, more. Many of them still have it. The exit doesn’t flip a switch. You don’t suddenly relax because your bank account changed.
- The comparison game is brutal. When you see founders posting about their wins, their energy, their next big thing—it can make you feel broken. Like you should be “over it” by now. But everyone processes this differently.
- The exit doesn’t create happiness. An exit is an important goal, as is liquidity. But in the end, it rarely creates happiness. Not on its own, at least. Not for most of us.
Many Are Quitting Now. You Shouldn’t. But I Get It.
So many founders I talk to are thinking, at least conceptually, of quitting in the Age of AI. Their growth has slowed which Cursor goes from $1B to $2B ARR in … 90 days. It can seem impossible to get back to growth.
And if you don’t will it back to growth, it will be impossible.
