Making the jump — how to decide on your cofounder

Hello! 👋

This article assumes that you’ve already talked to a couple of folks, and are looking to make the final decision to commit to a cofounder.

If you’re looking for help on how to find a cofounder, click here: https://medium.com/p/3827a1a51535

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First off, congrats on getting this far! 🍻 If you’re anything like me, you’ve probably spent ~300 hours sourcing and talking to 60+ potential cofounders.

Now it’s time for the big decision. Here are some questions that will help you make that big leap:

Question 1: Who is the person that I want to be working with at the lowest lows?

At some point in the startup journey one or both of you will think about quitting, one or both of you will become depressed, and one or both of you will want to strangle the other person. Most startups fail because the founders give up, not because they run out of money.

At that point, the question becomes — is this the person I want to be going through those things with? And who is the person that I can see myself being patient with, if they are the ones struggling?

One proxy that VCs use to evaluate cofounder pairs is length of relationship. This is because the longer two people have known each other, the more likely it is that they have experience working through conflicts together. This is also why people typically advise to source cofounders from your own network.

Question 2: Who is the person that frees me up to bring the best version of myself to work every day?

I’m assuming most of you reading the article don’t yet have a product or a significant user base. That means that the startup’s primary assets are human capital — you, and your cofounder.

To maximize your startup’s chances of success, you should maximize that human capital. You are half of that human capital, so who is the person who free you up to bring the best version of yourself to work every day?

This could mean many things, including:

• A cofounder who you can be intellectually and emotionally honest with
• A cofounder who inspires you with their work ethic or conflict resolution skills

Question 3: Who is the person who makes me feel like I can do anything?

Let’s face it — most of us will probably fail. We are embarking on something incredibly hard, filled with nebulous, difficult choices, and days of tedious, boring work.

If you get really lucky, you find product market fit early. For the rest of us, you have to get ready to wake up every day to “nos” — from people you’re trying to sell to, from your software breaking, from VCs who don’t want to fund you.

It’s an almost impossible task. So ask yourself — who is the person who makes me feel like I can do anything?

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Bonus! How NOT to choose your cofounder:

!not! Resume

As a recovering resume addict, it can be tempting to choose your cofounder based on a beautiful resume. Who doesn’t want a cofounder who went to Stanford, MIT, or Harvard?

But going to those schools (in isolation) does not necessarily guarantee a strong founding partner. Key factors that make a good founding partner include risk tolerance, willingness to grind, flexibility, and maturity in the face of repeat rejection.

Unfortunatly for us, these attributes are almost impossible to capture on a resume. The best way to gather data on these attributes is to have worked with and spent time with someone in the past.

(This is why it’s typically best to source from your own network, or your network’s network. Linkedin won’t know if someone has the right risk appetite, but their friends will. So ask your friends. And ask their friends.)