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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.

Startup Sweethearts

Apparently, falling in love with your cofounder is more common than you’d expect.

It hasn’t happened to me, but let’s talk about what you can do if Cupid gets a little too involved in your startup.

(If this topic isn’t even remotely relevant to you, catch you on Monday!)

Someone sent me this post: Slowly falling in love with cofounder.

At first I thought it was a one-off situation but then I found these threads:

• _{Two co-founders dating}

• _{What to do if my cofounder and I develop feelings for each other?}

• _{I’m Dating My Co-Founder: The Good, The Bad, and The Preventable}

• _{Founders who are in a romantic relationship - problem for investors?}

• _{“I fell in love with my co-founder”: Do you mix business with pleasure?}

• _{I'm falling in love with my already involved cofounder, what should I do?}

• _{Do you think dating your startup co-founder can be bad for the company?}

• _{What do we do if we felt in love with each other after months working together?}

• _{I am a female co-founder at a startup. I have two male co-founders and they are both in love with me.}

Dozens of people chimed in and shared their own experiences on these threads.

I’m not surprised though. There’s plenty of reasons why you could fall in love:

• Mere exposure effect: you spend so much time together you either become attached at the hip or sworn enemies.

• Shared passion & goals: you’re chasing the same dream, at least for your career, and you’ll bond through repetition.

• Emotional dependency: the emotional highs and lows of startup life can mirror the rollercoaster of romantic relationships.

As you can imagine, the vast majority of the comments on those threads are cautionary tales and warnings against mixing romance and business. They have a point.

It can get complicated, messy. Dirty, and not in a good way.

The Heart of It

Here’s what I think.

• If you’re lovers first and want to become cofounders, do it.

• If you’re cofounders first and want to become lovers, don’t do it.

What’s the difference?

When you’re lovers first, your personal relationship has already been tested in emotional and unpredictable ways.

You’ve built a foundation of trust, communication, and mutual understanding — all critical skills for a successful cofoundership.

Becoming cofounders extends that bond into a professional space, with the personal relationship acting as a safety net when the inevitable startup storms hit.

The dynamic is different when you’re cofounders first.

The relationship is initially built on shared goals, professional collaboration, and a vision for the company — not emotional intimacy.

Transitioning into romance risks destabilizing this foundation. Personal conflicts can bleed into professional decisions. If things don’t work out romantically, the fallout can jeopardize the company as well.

But you know what else I think?

You’re going to follow your heart, regardless of what you read in any newsletter.

So go pursue your… passion projects.

How I Can Help

There are two parts to building your cofoundership:

1. Increasing compatibility and trust.

2. Decreasing tension and effort required.

I can coach you through both.

1. You’ll learn how to actually be comfortable with speaking your mind by creating a space where you feel heard and understood.

2. You’ll learn how to keep the company moving while addressing concerns that you thought would take too much time or energy.

Grab time here or simply reply to this email.

Thanks y’all,

Tim He

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