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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.

PPS — Scale smarter with a Fractional CTO. Get expert tech guidance without the full-time costs from my friend Bulama Yusuf.

Cherrytree’s Catch-22

For this edition, I wanted to get a little meta and talk about Cherrytree as a business.

We’re all founders here, so I figured this would be interesting, especially since I’ve never really shared much from this side.

If you’re building in public, connect with me on Linkedin so I can support you!

Cherrytree is obviously educational content, and educational content is the ultimate vitamin. You don’t need to read it, but you do because you know it’s good for you.

This presents an interesting situation from a business model perspective.

For us to work, two things must be true:

1. Your cofoundership is worth the effort it takes to get it right.

2. I’m the one you trust with advice to make sure it’s on track.

But before you found Cherrytree, you probably had some assumptions.

“Cofounder issues are a sign the business is doomed.”
“Cofounders need to have complementary skills.”
“Never do business with your friends.”
“Trust takes a long time to build.”
“Equity splits are hard.”

You might’ve just accepted these things as the status quo.

Once again, we find ourselves in a dichotomy.

1. There’s latent demand because you’ve assumed cofoundership is broken.

2. I have to give you a new approach or perspective to solve the problem.

On the bright side, this isn’t a very crowded space. I’ve had the opportunity to chat with a few others in it and they’ve all been delightful.

Tanis Jorge and Nicki Coe have amazing newsletters about cofoundership. Dr. Matthew Jones and Dr. Lisa Choi are brilliant cofounder counselors.

The tricky part is that because you’ve accepted (or even internalized) the problem, there are a lot of duct-tape solutions out there.

• Top threads in r/startups, r/entrepreneur are rants about shitty cofounders.

• People complain about matching sites like YC’s and Coffeespace.

• How many “X Questions to Ask Your Cofounder” lists have you seen?

I’m not saying those tools aren’t great — they absolutely are.

But they’re designed to tackle just one piece of the cofounder puzzle. So, don’t get mad when they fail to deliver the perfect cofoundership. It’s just not their job.

I’ve now taken on the job of eliminating these bad habits and misconceptions. This is hard because routines and rituals are so ingrained and founders are dogmatic.

It’s kind of like fitness. The people who care, care. Those who don’t usually neglect it until a bad blood test. But everyone can benefit from having good habits.

Correct me if I’m wrong, but I believe the only way to do this is to give you an original solution to something you assumed would always stay broken.

Of the 300+ cofounders I’ve interviewed, not a single one has denied the importance of a solid cofoundership.

I have to first educate the market, then capture the opportunity.

And that’s where things get interesting.

Changing Behavior at Scale

Most businesses either solve an urgent, obvious problem or create something so new that people didn’t even realize they wanted it.

Cherrytree sits in the middle.

You know cofoundership is important, but you haven’t thought of it as a skill. Not as something you can actually work on and improve.

That’s the new perspective.

I’m not just competing with other cofounder advice. I’m competing with the default state of not thinking about this at all.

In other words, I’m fighting inertia.

Most problems hit you hard: fundraising, churn, shipping product. Cofoundership issues don’t scream as loudly. They creep up over months, which makes them easy to ignore.

So how do we win?

By making cofoundership impossible to ignore.

• By showing you the blind spots in your own thinking.

• By giving you frameworks that help you take action.

• By making this feel as urgent as everything else in your startup.

Building new habits requires brute force to push through initial resistance and sheer volume to reinforce the behavior until it becomes second nature.

That’s why I’m flooding every channel with cofounder insights. This newsletter, coaching, legal services, accelerator workshops, university talks, podcasts, TV, guest blogs, LinkedIn, online resources, my book, and community forums.

Wherever cofounders are, I’m there.

Because at the end of the day, your startup isn’t just product and code. It’s people. And if you get the people part wrong, everything else eventually falls apart.

This is the bet I’m placing with Cherrytree.

And if I’m right, it means we’re only just getting started.

That’s all for now,

Tim He

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