I’m Still Tired. And If You Are Too, I Get It. | Saa Str

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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. Fourteen years, to be exact.

Since then, we’ve built Saa Str AI into an eight-figure media and events business. Done 14+ Saa Str global events and 11 Saa Str AI Annuals. Invested

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.

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 24x 7x 365 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.

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

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.

I’m not writing this for sympathy. I’m writing it because I talk to founders every week who feel this way but think they’re alone.

If you’re in Year 3 or Year 7 or Year 10 and you’re exhausted in a way that weekends don’t fix… I get it.

If you exited years ago and still feel like you’re recovering… I get it.

If you’ve built something successful but still wake up anxious for no reason… I get it.

The founder journey leaves marks. Some of them fade. Some of them don’t. That’s okay.

I’m not going to pretend I’ve solved this. But a few things have helped:

Movement. Running every day isn’t about fitness for me at this point. It’s about processing. About giving that nervous system energy somewhere to go.

Building things with lower stakes. The apps I build now? They’re not “must succeed or the company dies.” They’re creative outlets. It’s reminded me that building can actually be fun when existence isn’t on the line.

Talking about it. For years I didn’t. Founders are supposed to be resilient, optimistic, unbreakable. Admitting you’re tired felt like weakness. But the more I’ve talked to other founders, the more I’ve realized this is nearly universal. We just don’t say it out loud.

Accepting it. Maybe the tiredness doesn’t fully go away. Maybe it’s just part of who I am now. And maybe that’s okay.

Not quitting.  If you let yourself quit, it might briefly feel better.  But in the end, it doesn’t help.

If this resonates with you—if you’re tired too, in that bone-deep way that only founders understand—well, I see you.

You’re not broken. You’re not weak. You just did something incredibly hard for a very long time.

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• Free e Books

    e Book: Hiring a Great VP of Sales
    e Book: Raising Capital
    e Book:  The First $1m ARR
  

• University All Posts University Podcasts The Top CROs VC Fundraising Top Videos Q&A Best of Saa Str #1 Bestselling Book Search Everything Join the Community

• Free e Books

    e Book: Hiring a Great VP of Sales
    e Book: Raising Capital
    e Book:  The First $1m ARR
  

• London 2025 Annual 2026 Events Overview Sponsors

    Event Sponsorship
    Media Sponsorship
  

• Digital AI Day 2025 (Free) Speaker Submissions Speaker Requirements Overview