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Sprinting on Stilts

There comes a moment in every cofoundership, often suddenly yet subtly, when you realize your problem:

• Isn’t lack of ambition (you’re starting a company).

• Isn’t lack of information (you have me 🫡).

• Isn’t lack of talent (you’re cracked).

It’s something messier. Slipperier.

You aren’t failing because you don’t give enough of a shit or aren’t grinding hard enough. It’s that you’re trying to do those things on a weak foundation.

Trying to sprint on stilts.

No matter how many Goggins videos you binge,
No matter how many pep talks you give each other,
No matter how much you whiteboard your next move,
The outcome still won’t hit like it should.

Unless…

You stop duct-taping over dysfunction and start rebuilding the actual foundation.
Not the roadmap. Not the branding.

The relationship.

But if it were so easy and straightforward, you would’ve done it already.

The thing about strong cofounderships is that they can’t be sustained through raw willpower alone. They must be grown from the inside out.

And that’s the hardest thing I’ve ever had to do.

I was born with a broken heart.

Literally. A ventricular septal defect, aka a hole in my heart. That wasn’t all. Add a deformed lung to the mix and things weren’t exactly looking great.

I weighed just 2 pounds, 11 ounces. The average newborn boy is 7 pounds, 6 ounces. 

I couldn’t see, eat, breathe, shit, or move on my own. My first 40 days were spent motionless in the ICU. I was tethered to tubes and monitors, a tiny bundle of vulnerability and uncertainty. I was so completely dependent that it was impossible to imagine me growing into anything beyond this fragile state.

Doctors told my parents not to get too attached, not to name me too soon, just in case. They prepared them for the worst, warning that even if I survive, I’ll likely face serious challenges down the line, both physical and mental.

Because of all this, expectations for me were understandably low. 

Everyone tiptoed around me, wrapped me in bubble wrap, coddled me like a porcelain doll. A beautiful, breakable, miracle of a doll. The world seemed to expect me to be weak, frail, to barely make it through.

It was as if “handle with care” was tattooed on my forehead.

And that fucking pissed me off.

Not right away, of course. I didn’t come out of the ICU flipping off the world. But somewhere along the way, maybe in the subtle looks, the lowered voices, the constant hovering, I got the message: you’re lucky to even be here, so don’t push it.

And I’ve been pushing it ever since.

• Don’t expect me to run in races? Cool, I’ll win them.

• Don’t expect me to speak up? Cool, I’ll be unignorable.

• Don’t expect me to make the team? Cool, I’ll be captain.

• Don’t expect me to take charge? Cool, I’ll be CEO.

As a cofounder, that fire shows up in ways I’m still learning to untangle. I charge headfirst into chaos. I don’t wait for approval. I carry the weight like it’s a badge of honor because I’ve been carrying something since the day I was born.

But there’s a dark side, too.

I hate asking for help.
I equate rest with weakness.
I bulldoze when I should collaborate.
I flinch when I sense fragility in others because I remember what it felt like when people assumed I’d break.

So I overcorrect.

And in a startup where you're supposed to move fast and build trust this kind of wiring can get tricky. Resilience becomes rigidity. Drive becomes dominance.

That’s why cofoundership isn’t only about knowing your strengths.
It’s about knowing your stuff.

Your traumas. Your triumphs.
Your patterns. Your blindspots.
Your assumptions. Your coping mechanisms.

And not just knowing them but knowing how they show up at work.
In meetings. In tension. In silence. In the way you communicate, or don’t.

Because only when you can name them, can you control them.
And only when you can control them, can you build the cofoundership you deserve.

That’s all for now,

BTW — The Cherrytree cofounder community is now open. Join here →

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