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Hey, I’m Tim! ☕

Every Mon and Fri, I help you become the cofounder your startup deserves.

• Actionable advice: Practical tips you can start applying today.

• Relatable stories: Real-life experiences from people just like you.

• Unique insights: Fresh perspectives that you won’t find anywhere else.

Cherrytree is the blueprint for building your dream cofoundership.

PS — If you really want to answer the unGoogleable questions, book time with me for free. I’ve coached dozens of pre-seed/seed stage cofounders.

The Formula

For the past 7 years straight I’ve obsessed about what makes a good cofoundership. What are the components? The non-negotiables? The dozens of different factors?

I’ve had half a dozen of my own cofounders and interviewed hundreds of others. I have more pages of notes than I can count. There’s 60 editions of this newsletter.

That’s all to say I have a pretty good idea. But whenever somebody asks me, I have a tendency to ramble. There are just so many nuances.

Then, randomly, I was on a plane back from a Valentine’s getaway in Mexico and it hit me. Wit + Grit = Fit.

That’s what it comes down to.

Since then, I’ve been trying to find an exception to the rule because it sounds too good to be true. 3 short words that happen to rhyme? Surely, it can’t be that easy.

But I haven’t been successful so far.

Let me make my case.

Zuck once said the #1 trait he looks for when hiring is raw intelligence. Makes sense — nobody’s out here trying to hire idiots.

I want to take it a step further and say that perhaps more important is they’re witty.

Wittiness requires both intelligence and humor.

In a philosophical sense, whether someone is witty is subjective. It depends on perception of what constitutes humor and cleverness.

The world is full of smart people. But if you don’t find them funny/fun, you’ll be at best bored and at worst miserable as cofounders.

Don’t underestimate the power of a shared sense of humor.

“I finally got being a good startup founder down to two words: relentlessly resourceful.” — Paul Graham, March 2009

People believe that having grit is the ability to eat shit and not break. That’s great, and I think it’s very respectable to not quit when quitting is the easiest option.

You know in the Marvel movies when Captain America’s getting his ass beat and he says “I can do this all day.” I’m sure he can, but I hope he doesn’t.

That covers the relentless piece of it.

But as a founder, you’re dead by default so there has to be an additional layer of nuance to grit: resourcefulness.

Cap's character finally starts developing when he doesn’t have half his team, his high-tech tools, and the backing of the US government. He improvises.

Good fit feels like you belong.

You can be yourself, without the weight of pretense or performance.

Hide Shidara says “if you’re used to chaos, good fit feels uncomfortable for a while. But good fit breeds consistency and that breeds stability and confidence.”

It’s the space where potential and reality align.

Sidenote: people assume fit is a precondition (we’re a good fit, therefore we’ll start) but as you’ve seen IRL and as this formula suggests, fit is a by product.

Wit + Grit = Fit.

That’s all for now,

Tim He

BTW, I’m launching a coffee company for founders so keep an eye out for that.

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