Some thoughts on founding teams

Probably the second most frequently asked question I hear from aspiring entrepreneurs is “Should I have a co-founder, and how do I find them?” This seems especially common with folks who have a business idea, but don’t feel confident that they have the skills to build it themselves. As with other questions, most people have an intuitive hunch about what the answer is, but have a secret hope that there are other, easier options.

TL;DR: Yes you should have a co-founder, and you probably already know this person, so just reach out to them.

On having co-founders:

When faced with a complex or hard-to-solve situation, multiple co-founders are able to bring a broader perspective to bear, since they have different but complementary skillsets which can cover for each others’ blindspots.

While it’s possible, with enough time & effort, for one person to become a top 5% salesperson, product manager and technical developer (and thus have the perspective of a common 3-person founding team), I actually think that in the long run the 3-person team would make the better decisions. There’s something to be said for having a civilized debate between equals, rather than all important decisions being made by a single person in their head, and I think it leads to more rational & robust decision-making. This is especially true in the earliest days of the business, when you’re moving fast, taking lots of shortcuts, and rarely have the time to stop & think about big decisions from multiple perspectives.

As the business grows, the founders will need to grow with it, learning huge amounts to both broaden their knowledge, and usually developing really deep knowledge in a few areas. This is also easier for multiple people to do, since you can each specialize in your particular area and branch out from there. It’s true that your early hires (and ideally everyone on the team) will need to learn on the fly & grow themselves to keep up, but typically your lead SW dev will not need to learn GAAP & EU trade policy, but as CTO or CEO you might.

Lastly, when we look at really successful tech companies both locally and on the international stage, there is a remarkably small number that actually started with a single founder and are still thriving today. The best local example would be Pebble, but very shortly after starting at Y Combinator, Eric brought on Andrew Witte, who would stay as CTO until Pebble was sold to Fitbit.

Now, how the heck do you find those people?

Usually these are peopleyou already know, and ideally they’re people you’ve already done some work with. This is important because you’ll be going into the proverbial wilderness with these people, and your success will depend on their competence, ingenuity & resilience. Equally important is the fact that every so often there will be a plan or a decision that this person puts forward, which parts of your brain aren’t entirely comfortable with, and you’ll need to go along with it anyway. In short, you will need to have immense trust in these people, and that almost always takes time to build.

In the grand scheme of things, it doesn’t need to be a long time, but my gut feeling is that most successful co-founders knew each other at least 6 months before calling themselves co-founders. Some of them took 1–2 classes together, some worked together (either full-time or on a co-op). The ExVivo founders met through a Velocity brainstorming event, when each was working on their own idea part-time. Many co-founding teams had been classmates for their entire undergrad, or even high school together.

There aren’t as many obvious trends here, but I’ll add one caveat that you need to have immense, earned trust in each of these people. There is a strong mental pull, after meeting someone who sounds incredibly smart, to believe that they will make all your technical (or sales, or legal) troubles go away. That is a sign of a very persuasive person, but until you have done some amount of work with that person, treat those claims the same way you’d treat a blurb on someone’s dating profile: maybe they can live up to the hype, but don’t get too emotionally invested until you learn what they’re really like.

Think of it like dating…

Dating is a really great analogy to finding a co-founder: it’s important to make the right choice, not just the right choice out of 3 or 4 immediately-available candidates. In spite of this I often see aspiring entrepreneurs who ask someone they met 2 weeks ago to be their co-founder, and to me this is the equivalent of proposing to someone on the second date. Even if you did meet someone that you thought could be your long-time romantic partner, you wouldn’t say it right away! With romantic partners we play the long game, and see if our feelings are validated by reality. You will probably be spending a lot more time with your business partners, and have more heated “discussions” with them than with your romantic partner, so it is well worth applying the same level of patience & selectiveness to the process.

What skillsets should they have?

If you have a major technical component to your product, it is extremely beneficial to have at least 1 technical co-founder. There are very prominent voices in the startup community who have suggested that the CEO should have a strong technical skillset, since they believe that it’s easier to turn a hacker into a CEO or business person than vice versa. Velocity has seen a lot of great startups succeed that do not have technical co-founders, but I think they are the exception rather than the rule. Probably the biggest benefit of a highly-motivated tech. co-founder with enough knowledge to be dangerous is that they can help you rapidly get to a v1, which you can put in front of paying customers (and non-paying users) ASAP, and iterate on the the product as soon as possible.

If those technical hires are treated as a gate, where you feel like you can’t talk to customers until you’ve hired them & they’ve started building something, this can lead to either rushing the hiring process (and increasing your chances of making a mis-hire or finding the wrong co-founder) or avoiding talking to customers (and increasing your risk of putting a lot of time & energy into something people won’t want). Both of these are not-so-great outcomes. Be patient in finding the right people, and talk to customers before you have a demo-ready product.

A final point on equity splits:

This question often comes up a lot, and I’ll defer to folks who are very well-versed in this stuff. As they say, and I’ve tried to emphasize throughout this post: all the hard work lies ahead. I hope you are able to assemble the right team for that journey, and wish you the best of success on it.