Topsy-Turvy Cofounders

You've got it all backwards (& a special announcement)

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BIG NEWS BELOW (if you like coffee)

Hey, I’m Tim! ☕

Every Mon and Fri, I help you become a top 1% cofounder.

  • Actionable advice: Practical tips you can start applying today.

  • Relatable stories: Real-life experiences from people just like you.

  • Unique insights: Perspectives that you won’t find anywhere else.

PS — If you really want to answer the unGoogleable questions, book time with me. I’ve coached dozens of pre-seed/seed stage cofounders.

Friends Before Founders

The most FAQ I get is, “What can we do to improve our cofoundership?” (and, by extension, the company).

But that’s the wrong question to ask. It’s backwards.

When I taught university students, I could assign them to groups, but I couldn’t force them to become friends. In fact, some ended up hating each other.

Even when they chose their own teams, friendship wasn’t guaranteed.

Yet, without exception, the top teams were those who were actually friends. They saw the class as an excuse to have fun and hang out and get things done.

My cofounders and I did the same. For years, I couldn’t quite explain why it worked so well. It just did.

Only after interviewing hundreds of cofounders did I start to recognize the pattern. Once I saw it, I couldn’t unsee it.

They didn’t just work together.

They used the business to build their friendship.

So, the question should be how to use the company to improve the cofoundership, not the other way around.

Pablo Regalado and Santiago Jaramillo, cofounders of Twin Farms (marketplace for buyers and farmers), are the perfect example.

They grew up together. Their families are close. They’re practically brothers.

But life took them on different paths.

Pablo studied business and agriculture in Honduras while Santiago studied web design and development in Ecuador.

Still, some bonds (and some ideas) are too strong to fade.

After enjoying some fresh dragon fruit in the Ecuadorean Amazon, they started talking about connecting farmers to anyone who cares about shopping ethically.

Twin Farms was born.

Now imagine if they got it backwards.

Same Pablo. Same Santiago. Same dragon fruit.

But this time, instead of the business helping them reconnect, they tried to artificially rekindle their cofoundership for the sake of the business.

They try to force the friendship back. Every decision is wrapped in pressure. Every meeting feels like an attempt to rebuild what’s lost.

Soon, the cracks show.

  • They’re making decisions out of obligation, not excitement.

  • Their conversations are more transactional than authentic.

The business, instead of bringing them together, starts highlighting their differences.

Their business didn’t force them to become best friends again. It let them.

Especially for a business like theirs—with a mission grounded in trust—the character and camaraderie becomes the heartbeat of the culture and ethos.

Remember: great companies start with great company. 

That’s all for now,

Tim He

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