Co-Founder Dating 101: Lessons From 60+ Founder Dates
By: Timothy, Chongz
Tags: Startup Lessons, Founders, Founder Stories, Cofounders, Startup

1. Do you vibe?

“I’m looking for a co-founder I can get fucked up with.” — Potential Co-Founder & Partner at an A-tier VC Firm 🍻

The founder above had an interesting idea, a good approach, and a strong background. When they mentioned what type of co-founder they were looking for, I had a good chuckle, but it was definitely off-putting. I’m not sure I’m ready to go the distance with someone who leads with getting fucked up as a requirement. Guess I’m lacking that big VC energy.

Also known more colloquially as the vibe check, for many this is the most important consideration in vetting a potential startup partner. If you plan on going the distance with a co-founder, you plan on spending more time with them than any other person in your life — 8 to 12 hours a day, every day, for the next 4 to 10 years. If you don’t enjoy your first conversation with them, you’re not going to make it to the thousandth.

Here are some key questions to ask yourself:

Am I excited to have a conversation with them?

Did we naturally go over the scheduled meeting time?

Do I respect what they have to say?

Is this someone I can talk to for hours without wanting a Xanax?

2. Does their technical skillset complement yours?

“I have an idea for an app. I can handle the business side, I just need someone to write the code.” — GSB, HBS, or Wharton MBA Graduates 🐍

While founders will be forced to wear many different hats throughout the startup development lifecycle, each should specialize in their own relevant skills. At a high level, this includes but is not limited to programming, design, business development, data science, recruiting, and sales. Your co-founders should cover your weaknesses — avoid doubling up on specific areas of expertise.

3. Does their personality complement yours?

“Kylie is a Leo and I’m a Libra, and it turns out these two signs are super complementary and good for each other.” — Kim Kardashian ♌️

There’s little to no chance you’ve made it this far in life without working on some kind of group project, be it a work epic, a university assignment, or a little league team. At this point you should be aware of what type of person motivates you to do your best work.

For example, I’m the type of person who’s fairly easy-going and tends to improvise when necessary, and my co-founder for my previous startup is similar in that regard. While this makes us great friends, it means that when someone needs to step up to define roadmap and planning, we’re both a little out of our element. The improvisers benefit greatly from the planners. Consider your own personality under this lens. Are you a real deep work type, someone who loves to be heads down developing? Perhaps look for someone with the extrovert energy to seek out conversations.

That’s not to say your co-founder should be totally different from you. There are many traits that benefit from alignment: approaches to conflict resolution, taste in hobbies & entertainment, stances on recreational drug use… you’re just Jobs looking for Wozniak (or vice-versa if that’s somehow more appealing to you).

4. Are they flexible?

“A tree that is unbending is easily broken.” — Lao Tzu ☯️

I’m cheating a little here, this one refers to flexibility on two dimensions. In some contexts, you’ll need to evaluate both, and in some you won’t need to evaluate either.

Are they full-time on the startup grind? Not everyone you meet is going to be in the unenviable position of searching for a co-founder full-time. For those who are thinking of making the leap, it often makes sense to spend some time proving concept before taking a startup leap of faith. I worked on my last startup with two part-time co-founders, to varying degrees of success —avoid this scenario if possible. Part-time co-founders don’t last too long, so in these circumstances, there are a few things to consider:

What would need to be achieved before they’re willing to take that leap?

How comfortable are you with them not being full-time, and for how long?

Are they a flexible thinker? The startup road is never straightforward; there are many twists, turns, and pivots along the way. If they have a specific idea in mind, they must be open to inevitably changing the details. You want them to love the problem not the solution. They should have strong opinions, weakly held.