Unconventional advice for how to choose a cofounder for your startup

The cofounder checklists out there are fine for screening people out but they won't help you choose the right cofounder. Here's why, and what to think about instead.

What those "100 questions to ask a cofounder" lists are good for

There are a million and one guides for how choose a cofounder. Let me be clear: they are useful. Just in a very limited way.

There's some hygiene to cofounding that you should get out of the way up front. This includes things like:

• How long can you work without pay, if necessary?
• Are you full-time or part-time at first?
• What skills do you have?
• How should we divide equity? Don't be afraid to talk about splitting equity early in your relationship.

There you go, I guess I just created yet another checklist for you.

There may be a few more questions that make sense, but you get my point. This is basic hygiene.

Why cofounder questionnaires aren't all that useful

There are two reasons the checklist approach to cofounder selection doesn't work well:

1. Human relationships don't reduce to a spreadsheet
2. The process of cofounding changes you as a person

Spreadsheeting human relationships

You know how most dating apps have a bunch of filters? Filling out those filters isn't 90 Day Fiancee. You don't get matched with one person and then live in bliss forever.

And that's what I mean - people can't be spreadsheeted. If you have a romantic partner, and you think back to your initial set of go/no-gos for relationships, there are probably some things you accept that you never thought you would. My partner is a collector of things. I hate knickknacks, enough that this was on my list. I now live with little animal figurines covering too many surfaces. You don't get to build a person from your preferences.

The same is true for cofounders. No, you shouldn't match up with someone who has a history of lying. No, you shouldn't join a team of people with no skills. But the suitability of someone as a cofounder is some deeper human connection that nobody has the right questions to discern.

Discernment comes from life experience, not a spreadsheet.

Cofounding changes you as a person

Kind of like how parenting changes you. You go into it with so many things you're sure of: I'll never let the baby keep me up all night, we'll never stop going on this particular vacation, I'll never stop going to Tuesday night trivia. Then suddenly it's 3am on a Tuesday, you're still awake, and you can't fathom ever going on vacation again let alone eating a hot meal.

No exaggeration to say that cofounding is similar, especially if you both are first-time founders. You have no idea the depths of creativity, despair, excitement, flexibility, and just general startup weirdness you're about to experience. This is true even if you've worked for a startup before. Being responsible is totally different from being present.

Here are some things that changed for me in my first startup:

• I grew comfortable asking people for things (I'm an introvert, ok?)
• I learned to speak incredibly directly to my cofounder.
• I learned to push for a no in deals rather than a non-answer. I can do something with no, but not with ambiguity.
• I figured out how to hire with limited resources, and what can make a startup a great place to work in a totally different way than a corporation.
• I learned how to build relationships across the ecosystem rather than just with the people I work closely with.
• I learned how investors think and work, and exactly how much brain space to give them (very little)

Startups are a crucible. I grew so much over my first few years as a cofounder. You will too, and most of the things on your list of must-haves will change. Same for your cofounder. None of this is predictable.

What matters in choosing a cofounder

Some things do matter deeply, and I'd never cofound with someone who didn't meet these bars.

They're a fundamentally decent human being - If they're the least bit sus, run, don't walk. Too many things happen in startups that are ambiguous and confusing. Wondering whether your cofounder is playing you is not something you will have time or energy for.

You like them, a lot. You'll spend so much time together. You'll argue and celebrate and fight and feel pride together. Your gut had better be that you truly like this person, even if you don't know them all that well yet.

When one of you leaves your startup, they're not going to backstab you. This is the biggest smallest space, and reputation matters. Listen to how they talk about former bosses, old flames, past companies. They don't have to be all conversational roses and butterflies - gritty reality is ok. But if you're getting the sense they are bitter, that's not something you want in your life. And one of you will probably eventually leave.

Other people are drawn to them. If they're going to be CEO, they need some charisma and personal magnetism. Doesn't mean they need to be extraverted, but being able to rizz up a potential investor or key employee is important.

What else cofounder checklists can be useful for

One thing all these checklists do is drive you to talk to your potential cofounder about your life, your hopes, and your needs. Spending time together in conversation is what builds relationships.

Questionnaires can be valuable relationship-building tools, just not relationship-selection tools.

I'm not your lawyer, your therapist, your advisor, or your accountant. We're just internet friends, and these are just my experiences and personal opinions. Consult professionals for advice before you make any sudden moves in your startup.

You will see the occasional affiliate link. I do earn a commission if you buy the products I recommend. I appreciate you buying through the links if you're going to buy. This is a labor of love for my fellow cofounders, and I do love receiving a few coins to pay hosting costs if you like my work.