^{Forwarded this email? Subscribe for more.}

Hey, I’m Tim! ☕

In the 15th century, an engineer named Orban dreamed of creating a cannon unlike anything the world had ever seen.

He offered it to Constantinople, which was under siege by the Ottomans.

Lacking resources, they turned him down. Big mistake.

Orban turned to the Ottomans instead, who gladly accepted. He went on to create one of the largest cannons ever built.

It played a crucial role in the 1453 siege and breached the walls of Constantinople, ultimately leading to its downfall.

You’re Constantinople

Low on resources. Surrounded by competitors.

Yet you attract bold, ambitious talent. Quirky, unproven, but full of potential.

The question is: how do you, as cofounders, ensure they become your greatest allies, not your downfall?

I faced this challenge early in my startup days.

Our hiring process started with a quick call with me. If I liked the candidate, they moved on to a technical interview.

To speed things up, I began training one of my cofounders to run these calls too. But by pure chance, we stumbled upon something unexpected.

Doing these calls together worked even better.

It sounds inefficient, but it really wasn’t.

We recruited high-caliber talent, the kind we couldn’t afford on paper but somehow convinced to take a chance on us. The same happened with advisors.

Candidates got to see us banter and bicker, brainstorm, and build off each other. I think it eased everyone’s nerves.

More importantly, they got a glimpse of the company culture.

I saw something similar with OpenArt.

I chatted with an early team member who was so proud of her cofounders that she created a group text chat just to show me what she was talking about.

You can do the same.

Game-Changing

It’s moments like these unstructured, real-life interactions that reveal the true potential of your team.

I recently spoke with Alex Lee, cofounder & CEO at Truewind.

A few years back, Alex also did something unexpected: he spontaneously invited an (almost) stranger to spend Christmas with him and his family.

For a few days, they shared meals, played board games, and simply enjoyed each other's company.

He told me that the board games in particular revealed how everybody competes, collaborates, solves problems, and communicates.

A test of character, but more fun. That stranger, Tennison, went on to become Alex’s cofounder.

Too often people rely on rigid rules and formulas to assessing fit, whether it’s with cofounders or early team members.

Look at the endless “X questions to ask your potential cofounder” lists out there.

But sometimes, it’s the unstructured, real-life moments that reveal the most.

Alex and Tennison might’ve never become cofounders if:

• Alex had defaulted to a traditional interview, or

• Tennison didn’t show up to a random guy’s house for Christmas

Much like Constantinople’s missed opportunity with Orban, the key to finding the right people is recognizing potential when it presents itself, regardless of how.

How I Can Help

If you’re not sure how to evaluate someone, whether they’re a potential cofounder or early hire, I can help.

I’ve started several companies with about half a dozen different cofounders and hired many others along the way.

At the end of the day, you want to increase the likelihood that this person will drive the company forward in ways that you’ve never even imagined.

Enjoyed this? Copy your custom referral link and share Cherrytree with a friend.
^{Top referrers every month win a cash prize.}

Thanks y’all,

Tim He

_{Brought to you by:}