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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 put into use 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 to 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.

Married to the Mission

Abigayle Peterson, founder of The Netwrk (the #1 community to help you land a top 1% career), has a spiky view on cofoundership.

After working with several cofounders, she’s concluded: the only person you should be cofounding with… is your spouse.

She says, “they are the only one who loves you enough to be willing to sacrifice enough to make the idea work.”

Plus, it’s a known fact that cofounders tend to spend more time with each other than their respective spouses, and that can’t be healthy for their marriages.

I came to a slightly different conclusion, but I can’t deny the logic behind hers.

At each step of your cofounder journey, there are either different types or levels of sacrifices that are necessary.

Along the way, you make a series of what I call milestone sacrifices.

• You give up the chance to work with other potential cofounders.

• You let go of all the other projects you could’ve pursued.

Each choice narrows your path, but it also deepens your commitment.

Then there are the perpetual sacrifices that come with the journey.

• Time: Long hours, late nights, and missing out on personal events.

• Financial stability: Taking a pay cut or working without a salary indefinitely.

• Mental peace: Constant stress, uncertainty, and emotional highs and lows.

• Career opportunities: Passing up a stable job or lucrative offers elsewhere.

• Relationships: Losing touch with loved ones due to startup demands.

The problem is that somewhere along the staircase, cofounders decide the sacrifice just isn’t worth it anymore.

Maybe their personal runway has dried up. Maybe it’s taking too much time away from their kids. Maybe they got a million-dollar job offer.

Whatever the reason, their heart’s not in it anymore — but they don’t leave.

If they were brutally honest and left, there’ll be damage to the company but at least they could preserve the friendship.

If one cofounder moves forward while the other is unwilling to sacrifice, the cofoundership is doomed.

Abigayle has a point.

Maybe it’s easier to be cofounders with your spouse because some of those sacrifices aren’t applicable:

• You’re not spending less time with your partner if you work together.

• You have somebody to share the emotional burden with.

• You both understand the demands of the company.

Driven Apart

Here’s the true story of Zipcar’s cofounders:

• Antje backed her cofounder Robin's bid for unilateral firing power, only to be blindsided and fired by Robin just 2 hours later.

• This exposes their tension, as Robin’s frustration with Antje’s lack of commitment and contribution finally erupts.

• Meanwhile, Antje, balancing her Harvard job and Zipcar, felt increasingly sidelined by Robin’s all-in dedication to the company.

• As the company came together, its cofounders grew apart. Once a promising partnership, they now haven’t spoken in over a decade.

I want you to know that when a cofounder refuses to sacrifice, it’s not always out of malice or greed — it can stem from external pressure, ignorance, or other factors.

The important thing for you to focus on is actually explicitly mapping out where on the steps the company is and where each of the cofounders are.

Then, make a tangible list of sacrifices that are necessary to unlock the next level.

Decide if you’re in it together. If not, discuss how to delegate, transition, and compensate accordingly.

That’s all for now,

Tim He

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