How to Win the Cofounder Lottery

TL;DR

Hey, I’m Tim! ☕

Do you ever look at other cofounders and wish you had what they have?

Do you find yourself longing for that same deep connection? Do you feel a twinge of envy for the understanding they share?

What’s their secret? How do they bounce off each other so seamlessly? How are they always on the same page? Did they get lucky?

When it comes to the “perfect” cofoundership, does it feel like you either have it or you don’t?

DEEP DIVE

“Luck is believing you’re lucky.” — Tennessee Williams, considered among the three foremost playwrights of 20th-century American drama.

Luck Levers

Is luck replicable?

Paul Graham’s advice to increase your luck surface area is to meet new people, write online, and live in a major city — all ways to invite serendipitous opportunities.

In the same vein, building a strong cofoundership can feel like getting lucky. After all, some cofounders seem to just click.

But what if I told you there's a way to engineer that luck?

Simon Sinek outlines the 3+1 conditions for a great romantic relationship, and surprisingly, they apply just as well to cofounders:

1. Intellectual Compatibility (critical thinking, cognitive ability, “raw horsepower”)

2. Emotional Compatibility (trust, stress tolerance, “in it together”)

3. Sexual Compatibility (substitute with creative compatibility, “vision, innovation”)

What’s the +1?

TIM’S TAKE

Compatible Circumstances

The +1 is your circumstances.

You might meet someone who checks all 3 boxes but if they’re off to Stanford Business School next week or if they’re relocating from SF to London, the cofoundership might not work out.

We’ve spent a lot of time talking about the different types of compatibility. They dominate a lot of the early conversations around what to look for in a cofounder.

You can have a decent cofoundership if you’re all sorts of compatible. Maybe that’s where you are right now. But without engineering your circumstances, it’ll never be great.

Here’s how:

1. Awareness 
   Mindfulness of your current and near future circumstances sounds like a no-brainer but you’d be surprised how many cofounders neglect it.

   
   Your calendar from 3-6 months ago is a good predictor of where you’re at today. By extension, looking at your calendar today will give you a good idea of where you’ll be in 3-6 months.

2. Prioritization

   At some point, you have to adjust your external circumstances to align with your cofoundership. Where does it rank on your list of priorities?
   
   In the early days of my previous company, I decided that I didn’t need new friends. I went to a few birthday parties here and there but really didn’t do anything social for a while so I could focus on building the company.

A caveat.

Just because your circumstances aren’t perfect right now doesn’t mean the cofoundership isn’t worth trying. Sometimes, resistance is overcomable given the right workarounds — though it might require more sacrifice than you’d anticipate.

Another caveat.

I’m not here to glorify sacrifice for the sake of it. Sure, you might feel noble for a while, but that fades fast, and then life gets pretty miserable. Instead, focus on what you’re willing to commit to.

Go create your own circumstances.

Related Resources

• I’m a huge fan of biographies, and when I read them, it always blows my mind how much great work they produce. Here’s an essay to help you do the same.

• If you’re looking for a cofounder, check out StartHawk for an online platform and join LFC.DEV's in-person meet-ups in NYC for face-to-face connections.

• Missed a Cherrytree edition? Tsk tsk, but I’ll let it slide. Grab a coffee and hit the archive to get all caught up.

LAST LOOK

Make sure your cofounder sees this — either pass it along or get them to subscribe. A solid relationship takes everyone's effort.

Looking for a cofounder coach? Hit reply.

PS: good luck.

Tim He
Founder & CEO