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How do you find a badass co-founder?

Finding a co-founder is damn hard
In the last couple months, I’ve been keeping an open eye out on finding a high-quality co-founder for the startup I’m doing as part of my EIR gig. Ultimately, the scarcest commodity in the entrepreneurial community is NOT venture capital money – there are billions out there – but rather very high quality people. In particular, the highest quality people out there turn into co-founders, so that’s incredibly important.

In particular, a co-founder’s able to help balance you out, especially on mood. So if you are both in a room, the startup is on the rocks, and you say, “god we’re fucked!” then sometimes your co-founder will say, “well, why don’t we do X.” The same will happen vice-versa, which is great.

How many co-founders?
2-3 founders maximum. I think once you get beyond that, you’re diluting the group of talent in place. Ultimately, there’s a huge distinction between founders and employees, and you have to choose carefully. Beyond 3, the equity structure gets messed up too – you take a round or two of VC money and you own a very small piece of the company.

Of course there are exceptions like VMWare, which had 6 co-founders that all did well. But the norm seems closer to 2-3.

What defines a good co-founder?
Short answer is, I have no idea :)

Long answer is, I’ve done a lot of talking and thinking about the issue, and I think I know what is good for me (and maybe me only). Ultimately, you are looking for a guy with the following:

Complimentary in skills, but from the same cloth in attitude and culture

On the skills front, because I’m more of a business-y person, I’m looking for someone who is very technical. Also, because I’m more of an unstructured creative thinker, it might be useful to meet someone who is more structured and detail-oriented. A big piece of this is also a Mr. Inside versus Mr. Outside designation. Who’s in charge of talking to customers, partners, and potential investors? That might be one guy, whereas the other is more focused on internal operations. This might hold true even as the company scales up.

The other side, which is about attitude and values, is much more difficult. If you are looking to found a company, and you have an idea that you’re driving, that says a lot of things about you already. You’re probably driven, have a vision for where you want things to go, and are self-motivated enough to get things off the ground. You may also be someone who can convince people to follow you, or give you money, or whatever.

My questions for values/culture
For me, I’ve been thinking about a series of questions related to culture and values. Here are a selection of them:

  • Let’s say you wanted to start a new company? How would you do that?
  • Tell me about a major disagreement you had recently – describe what happened?
  • How would you approach hiring people?
  • What’s your long-term goal with your career? Where do you want to be in 20 yrs?
  • … and etc. Lots of questions you’d ask an employee, of course.

I think you’d also ask a couple questions as you observe the guy:

  • If you put them in a room with 5 peers, would they emerge with the 5 guys signed up to follow them?
  • Would you feel comfortable introducing them to everyone you know?
  • If you say something they disagree with, how long does it take before they push back? How hard do they push back?
  • If you guys disagree on their side of the complimentary skills, what happens? What happens if it’s on your side of the domain expertise?

Peoples’ views on this are going to be different, but in general I’m going to be looking for the guy who can sign up the 5 guys in a room, who’s great to introduce to everyone at all levels, who pushes back hard and immediately, and doesn’t care if its on your side of the skillset or theirs. I think all of these things define a strong leader who’s a peer, rather than an employee.

I’ll write more on this topic later, as it’s a critical one, but would appreciate comments in the meantime.

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