Second Acts

Howdy Founders,

Hope you’re still in the game—or at least still enjoying the snacks at the game.

It’s John again. I’m back from traveling and raising my kid (I’m still raising the kid).

Today I want to talk about something that doesn’t get enough airtime: founder longevity and what happens after your “big thing” (or your big flop, or your big “meh”). In other words: Second Acts.

The Myth of the Forever Founder

Let’s get real. Most startup stories end with a whimper, not a bang. Even if you “make it,” there’s this weird expectation that you’ll just keep doing it forever, like some kind of VC-funded Sisyphus. But here’s what nobody tells you: longevity as a founder is less about grinding yourself into dust and more about learning how to reinvent, recharge, and—sometimes—let go.

The First “Exit” Hangover (I learned recently that people are now saying “I exited my last company…” when the company dies, lol)

Here’s a fun fact: nobody prepares you for what happens after you sell, shut down, or step aside. I’ve seen friends (and felt it myself) wander around for months after an exit, thinking, “Wait, who am I if I’m not the CEO of Theranos?” It’s like the world’s lamest identity crisis. The LinkedIn dopamine wears off fast.

What I’ve learned:

• Take some time off. Really. Don’t just say you will, then start angel investing three days later.

• Give yourself permission to be bored. That’s where the next good idea usually sneaks up on you.

• Don’t feel guilty if you don’t want to build another venture-backed startup. There’s no shame in going small, weird, or even non-tech.

Second Acts: The Good, The Bad, and The “Why Am I Doing This Again?”

Some folks go straight back into the arena. Some become VCs, advisors, or professional Twitter threaders. Others open a surf shop in Bali and never look back. I’ve tried a few of these (minus the surf shop, but give me time).

What’s worked (and what hasn’t):

• Advising and Angel Investing: Fun for a while, but I missed building things. Turns out, I’m happiest when I have skin in the game (and a little chaos).

• Joining Someone Else’s Rocket Ship: Humbling, but honestly, it’s a relief to not be the one making payroll for once. (More on my experimentation here next week)

• Starting Something Completely Different: Terrifying and awesome. Highly recommend. The second time around, you actually know what not to do (which is at least half the battle).

Longevity: How Not To Burn Out (Again)

Let’s be honest: most of us are adrenaline junkies with questionable boundaries. But if you want to stick around long enough to enjoy your wins (or survive your losses), here’s what I’ve learned:

• Build a life outside your company. Friends, family, hobbies. Yes, even if you suck at pickleball.

• Learn to say no. The world is full of shiny objects and “quick” projects that will eat your soul.

• Take care of your health. Not in a “I bought a Peloton” way, but in a “I actually sleep and go outside sometimes” way.

It’s Okay to Change Your Mind

I used to think I’d be a founder forever. Now? Who knows. Maybe I’ll start a dog-walking empire or become really into pottery. The point is, you get to choose your second act—and your third, and your fourth. There’s no rulebook.

What do you think? Ever reinvented yourself after a big win (or loss)? Still figuring it out? Hit reply and let me know. I genuinely love hearing these stories.

Go easy on yourself. The best founders I know are the ones who keep showing up—just not always in the same costume.

💡 Non-Business Idea of the Week

You’ve heard of the “Fractional CMO” and the “Fractional CFO”. Well it is my pleasure to introduce to you:

The Fractional Therapist

This is just a friend (Preferably another founder) who texts you “Hey, you good?” once a week.

¯\_(ツ)_/¯

Thought that’d be nice.

😱 The best hackathon you’ve ever facilitated.

Would you like to really piss off your employees while making them better at their jobs? No? Well check this out anyway:

“Chaos Lab”

I’m back in love with this hackathon concept I learned a decade ago (Before AI tools!) that I’ve facilitated a few times and can’t wait to do it again. Let me know if you want me to come run this for your team, for free.

Here’s how it works:

• Break the team up into pods containing a PM, a Designer, and Engineers

• Draw ideas from a hat that are at least Loosely related to their daily work (Like, if you’re in Health Tech, make these health tech concepts)

• Set a clear timeframe like 8 hours for them to build a “Functioning” business that will be judged on Creativity, Realistic Viability, and MASSIVE bonus points for any Revenue generated (This part is optional, I can see why you might not want these teams going rogue and hitting up your customers for money for their new thing).

• SET A GOOD PRIZE (Like cash)

• Here’s the part you’ve been keeping a SECRET: At the end of the 3rd quarter (so like 6 hours into an 8 hour hackathon) SHUFFLE THE TEAMS randomly where only the PM stays. This is where the Chaos comes in. You will see bewilderment, anger, and maybe tears.

• Let them know the deadline is the same and you expect to see their presentations in 2 hours (or whatever it is).

👿 Chaos

Nobody is going to quit over this. They will see the parallels to real life at a startup and will appreciate the opportunity to practice handing off tasks and jumping into new features and products with which they’re unfamiliar. It’s a rush. Try it!

THE END

This purpose of this newsletter is to spend a few minutes thinking about the psychology of being a founder. If that sounds good and you think it hits the mark, please stick around.

Next week we’ll talk to a founder of one of the fastest growing unicorns ever. Interesting story!

Until then,

I love you,
— John