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Hey, I’m Tim! ☕

Your cofounder walks out. Now what?

It’s happened to me before, and if it hasn’t happened to you yet, chances are it will.

I’ve helped a handful of cofounders split and stay friends. I’ve also helped some step back from the brink of breakup, even when they thought they’d hit the point of no return.

Here’s exactly what to do if you see the storm brewing.

When ‘Co’ Turns ‘No’

Will your cofounder leave?

I hope not. That’s kind of the entire point of Cherrytree.

But here’s what the data says:

• Cofounders are now twice as likely to bail in the first year compared to 2015.

• A quarter of cofounders split before hitting the standard 4-year vesting mark.

• But once you survive that 4-year hurdle, things tend to level out.

Before the Storm

If your cofounder tells you they want to leave, don’t beg them to stay.

Cofounder breakups kill 65% of companies. It’s this big, bad, terrible thing and yet here I am, telling you to not fight tooth and nail to prevent it.

Hear me out.

If your cofounder wants to leave you, it’s the result of deeper issues. Things you can’t fix with a few more late-night talks or promises of a better future.

If they’re truly ready to go, forcing them to stay might feel like securing the stability of the company in the short term, but it almost certainly spells trouble for the long term.

Frustration or burnout is one thing, but a desire to leave you is something else entirely.

No matter how skilled or committed they once were, their disengagement can poison the decision-making, slow down progress, and introduce tension into the relationship.

The moment you beg them to stay, you’re not only risking resentment from both sides, you’re also putting your company’s future in jeopardy.

It’s easy to think that a split is an all-or-nothing scenario. You either:

• force them to stay and everything “goes back to normal”

• or you let them leave and the company crumbles

The real danger lies in trying to sustain an unhealthy dynamic.

Your energy and focus will be drained from keeping the peace instead of building the company, and in that time, the opportunity you once had will slip away.

A healthier approach is to let them go. With time, they’ll either realize the decision was wrong — or they won’t.

Here’s the key (pun intended): don’t block the door but don’t lock it either.

If they genuinely want to leave, let them. But do so in good faith.

Let them go on their terms, and if they want to come back later, that’s okay too.

The idea of leaving isn't tied to unresolved tensions or the guilt of making a "bad" decision.

Keeping the door unlocked shows that you trust them to make their own decisions.

As long as it’s not a rage quit, I think this is the best way forward.

Also, it’s the only way to keep the friendship intact.

I’ve had cofounders leave, and we just flew to see each other over the holidays.

As a cofounder, you can justify more transactional behaviors for the good of the company.

As a friend, you can’t. You have to want the best for each other, or else the friendship doesn’t work.

Great companies, like great friendships, are built — not forced.

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Thanks y’all,

Tim He