PERSONAL UPDATE!!

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

Want more? Book time with me or join the community.

TLDR: The Cherrytree community is officially live! First cohort is in, and maaassive thanks to Sydney Parno, our lovely community manager. None of this would exist without her. And thanks to our early members, for taking a bet on us.

Read on for the journey — the ride, the rollercoaster, the “how we got here” story.

That’s what July 2024 felt like.

I had just decided to start another company. This time, doing something I was already good at: helping cofounders. I previously wrote a book about my experience with my cofounders. Lessons, fun stories, mistakes, all of it. I’ve lectured 800+ entrepreneurship students, mostly on the same topic.

And I've always liked writing. Even as a kid. So I thought, why not a newsletter?

It sounded perfect. Low lift. I could start by copy-pasting excerpts from my book. The unit economics were incredible. Writing for 1 person costs the same as writing for 1 million.

But I quickly realized that while I was only a few clicks away from starting a newsletter (shoutout beehiiv), I was far from turning it into a business.

I had a plan, though:
Blitzscale subscribers. Then monetize. Simple, right?

Wrong.

The first 100 subscribers were brutal. I DM’d people on LinkedIn. Ghosted. I posted and commented on Reddit. Banned. I ran ads. Nothing. I offered referral incentives. Broke. Hence, hitting a nail with a banana.

Eventually, I found my way and grew to a couple thousand subscribers. That meant that twice a week, thousands of cofounders read my newsletter. I effectively impacted thousands of companies every week.

(I'll write another post about the messy middle).

In November, I started monetizing. Notion was one of my first sponsors. Then Gamma. Then others. I thought I’d found the way.

One day, a subscriber replied to an email asking for personalized advice.

Lightbulb.

I could charge for private coaching. Why didn't I think of that before? Why. Didn't. I. Think. Of. That. Before.

I charged the guy $50 an hour. This was roughly what I made at my last job. It was an amazing, addicting high. I started promoting my coaching service.

After a few more happy clients, I increased my price to $75/hr. Then $100, $125. Big jump to $250. Finally $500. (Free for students and nonprofits).

Buuut I was stuck in a loop:

More subscribers → more coaching clients → more content → more subscribers → more coaching clients → more content.

That was the trap. I kept chasing. More subs. More clients. More subs. More clients. Round and round. At first, it was thrilling. Then exhausting. Then impossible.

After 94 posts about cofounderships, I was running out of fresh angles. Interviews with dozens of cofounders a week were insightful, but things were starting to feel repetitive. At some point I realized I had no leverage.

This newsletter isn’t in a niche where I could scale to a million subs. The lifespan of a post is less than a week. And coaching is limited by my time. It’s 1:1 or at most 1:2. In other words, this was never going to be a $1B company.

But I also realized something else. The leverage comes from you.

The audience. The relationships. The attention that compounds over time. That’s what opens doors to higher-leverage opportunities without abandoning what I’ve built.

And that’s exactly what led to Cherrytree’s next step.

So many clients were asking me the same questions. Different ages, different stages, different industries, different numbers. But fundamentally the same questions.

Why don’t I help you help one another?

Because that was always the magic in a classroom. Students helping each other, alumni giving back, speakers sharing wisdom. So that’s why we started the community.

It’s a place where you (cofounders, early hires, and founders-to-be) can swap stories, share lessons, and ask the questions that never make it into a newsletter. Your experiences, perspectives, and curiosity are what will make this community thrive.

Join Here →

That’s all for now,

Tim He

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