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Playing Catch-Up

When I started this a year ago, I had a vague idea of what I wanted to write about. It was mostly surface-level stuff. News, stories, theory.

I had my own cofounder experience, but I wasn’t sure if any of it would resonate.

So, I started to interview others. How they met, why they became cofounders, their unusual rituals and routines, arguments, and what they wish they’d known.

A few standouts:

• Madeline Park and Benjamin Lee @ Vega.

• Bridger Hart, Carson Hart, and Humberto Morales @ Hoppn

• Alon Shrier, Alon Levy, and Jonathan Faran @ bazarr.ai

• Lillie Sun and Conner Chyung @ Ditto

You can find all the previous editions here.

And then sometimes I come across posts like this:

Can I be envious for a second here?

It’s my full-time job to study and write about cofounderships. To translate complex psychological and sociological principles into something clear and actionable.

I spend an absurd amount of time writing, rewriting, deleting, rephrasing, and then (surprise) rewriting again.

When I come across a sentence I wiiish I’d written, I know it’s worth sharing ↓

Startups are optimized for speed. People aren’t.

A product can go viral overnight. Funding can 10x in a week. Growth curves can spike in days. But people need time.

Time to adapt, process, unlearn, evolve. Emotional capacity doesn’t scale with server capacity. That’s why the job gets harder even as things are going well.

You’re constantly doing things you’re not yet qualified for.

You could argue humans don’t grow perfectly linearly. But that’s not the point.

The point is: as your startup levels up, so do the tradeoffs.

More hours. Nights and weekends. Say goodbye to 9–5 comfort, boundaries, holiday plans, and the role you thought you signed up for.

Cofounder issues are often caused when not everyone is willing to pay the price.

And that’s nobody’s fault, necessarily. People have different runways, responsibilities, and reasons for saying, “this is it for me.”

But to make a startup work, you have to do what Fredrik says at the end.

“Align early, or split early.”

And as I said on Monday:

The mistake isn’t checking out.
The mistake is pretending you haven’t.
Or refusing to name it when someone else has.

That’s all for now,

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