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Welcome to the Cherrytree newsletter, where I share stories and strategies to help you become the cofounder your startup deserves.

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Cofounder Counterweight

The paradox of cofoundership is that the person you build with must be similar enough to see the world with you, but different enough to build the parts you can’t.

This sounds obvious until you realize how unnatural it is for us. In most domains of life, similarity is the glue. We choose friends who share our hobbies, partners who laugh at the same jokes, colleagues who make us feel understood. Familiarity feels safe.

But too much similarity in a cofoundership is corrosive. Two visionaries fight over the wheel. Two operators drift without direction. Two optimists inflate each other’s bubbles until reality intervenes.

The best cofounder relationships are counterweights.

Why We Get This Wrong

You’re not built to select counterweights.

Your instincts pull you toward people who confirm you, not people who challenge you. Robert Zajonc showed decades ago that mere exposure increases liking. You literally grow to like things you see repeatedly, because they become predictable.

Counterweights are, by definition, unpredictable.

They grate. They expose blind spots. They argue. They break the smooth illusion of agreement.

That’s why so many cofounder splits don’t come from incompetence. They come from symmetry. If both cofounders are brilliant at fundraising but allergic to detail, the company will soar through a Seed round and then implode in execution. If both are masterful engineers but allergic to people, the product will sing but no customers will ever hear it.

It feels good to find someone “like you.” But in cofounderships, the person who feels most natural at the start often creates the most pain later.

Evolution’s Lesson

Evolution figured this out long before startups existed. Sexual reproduction is, from an efficiency standpoint, a terrible idea. Asexual reproduction is far quicker and guarantees all of your genes get passed on.

But the reason sexual reproduction dominates is complementarity. By mixing two very different sets of genes, organisms gain resilience against disease, environmental shocks, and mutation.

The discomfort of difference is precisely what keeps species alive.

Even at the ecosystem level. Two similar founders are like an ecosystem with too many predators or too many grazers. It may work for a while, but the lack of balance eventually destabilizes the whole.

The Wrong Kind of Harmony

The Beatles weren’t four Paul McCartneys. In startups, the same applies. Steve and Woz. Hewlett and Packard. Larry and Sergey. Gates and Allen. They were asymmetric, bordering on unstable.

The mistake founders often make is confusing peace with progress. A cofounder relationship that feels too easy may simply be untested. The absence of friction early on is like the absence of market competition. It feels good, but it should make you suspicious.

Markets and Cofounders

Cofounder selection has the same trap as market selection. The “obvious” markets are crowded with competitors. The “obvious” cofounders, aka people who look like you, think like you, move like you, create crowded blind spots.

What feels slightly “off” is often the thing with hidden leverage.

Markets that don’t make sense at first glance often end up defining new categories. Cofounders who don’t “feel like you” often end up building the parts you couldn’t have imagined.

The irony is that the very friction we try to avoid is the signal of fit. You don’t need someone who agrees with you. You need someone whose disagreements make the company stronger.

The deepest test of cofounder judgment is not whether you can find someone brilliant. The real test is whether you can stomach the daily discomfort of someone brilliant in a way you aren’t.

That’s all for now,

Tim He

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