A friend of mine who'll remain anonymous is battling the demons of having a less than stellar co-founder. This person isn't sure what to do at this point: should they ride it out or part ways? They've asked me to write my thoughts on picking co-founders based on my experience. I've started half a dozen successful startups dating back to 1995, but will share stories of only my two most successful here.
Co-Founders of Convenience
I don't have any math to support my assumption, but based on my experience and the experience of many people I talk to, first time entrepreneurs tend to find themselves thrown together with co-founders of convenience. Meaning, they didn't go person-to-person with a specific checklist of co-founder requirements, expecting that somebody would turn out to be just the ticket. They simply stumbled upon one or more people — read Three's Company for why I think three co-founders is better than two — who were willing to try the experiment with them.
The same thing happens in love: You're not likely to marry your absolute dream girl or guy. Those paragons just don't happen to go to the parties you go to. You simply meet someone you connect with on a few basic levels and then as you get to know the person better you either stay with them for the long haul or you don't. Co-founders might as well be married, considering the amount of time we spend together arguing, planning, laughing, and staying awake nights, staring at the glow of our monitors.
So that's what it's like when you're starting out. But after you've started your second or third or fourth startup, you may now have a pool of people that you know and trust to start your next startup with. Until then it's simply blind luck. When you're on your first startup, you're untested and your network is small and anyone willing to take the chance of co-founding with you is probably in the same boat. Therefore, you're basically going into it with no idea whether your chemistry and complementary skills will align properly down the road. How well will you work together? Do you have all the skills between you to get things done? Time will tell.
I want to tell my friend, who is on his first startup, that there are guidelines for picking a good co-founder, that it's not simply luck. But, sadly, I believe that as with anything you do for the first time there's a lot of luck involved in the outcome. Sure, "beginner's luck" exists, but it's still luck. I don't know the success of online dating, but I have to imagine the odds are scarily low. What's really scary, though, is that it's undoubtedly better with online dating, where you're being presented with more information: photograph, description, likes, dislikes, work, characteristics, and even psychology test results if, for example, you're on OkCupid. I wish I had all that information when finding a co-founder for the first time.
During my freshman year of college (2002-2003), I was a computer science student at Case Western Reserve before transferring to Yale. During the end of my first semester I founded a company called NetFusion (still around today) that provided web hosting, game server hosting, and Ventrilo hosting for computer game players. I "met" both of my partners online in a game of Counter-Strike. The three of us founded a Counter-Strike team together before founding NetFusion.
This partnership didn't last long, mainly because of huge arguments we'd have during our Counter-Strike matches that would carry over to the business. Amazing, huh? We let a computer game dictate our business decisions. About six to nine months later our company (and Counter-Strike team) split in three, each of us taking a third of the company. My part was our web-hosting clients.
The three of us meeting was pure luck and we never vetted each other's skills before founding the company, but we were all ambitious and wanted to start something.
Anyway, I was kind of upset that I gave the Ventrilo hosting business to my partner and kept the slower growing web host. (Ventrilo is a VoIP service primarily used by computer gamers.) I soon sold that off to Atlantic Metro and looked for a partner to help found a new Ventrilo host.
I was now a sophomore at Yale, and still a computer science student, but I didn't really know many programmers there. I remembered that I had met a guy named David Grampa in my C++ Database class who I use to play Counter-Strike with. I had his AIM name lying around and reached out to him. I had no idea about his computer programming talents, but I knew he (1) liked computer games, (2) had used Ventrilo and (3) had to be at least a decent programmer.
I reached out in December, 2003 over AIM and was quickly able to convince him to start the company with me. I literally had met David twice or three times during our lecture class, but had never hung out with him outside of class and had no clue about what he was like as a person or his experience with web development.
Reaching out to David was like going on a blind date with a girl that you knew absolutely nothing about except that she was indeed a girl. This was the second time in my life where I'd gone into a co-founder relationship without vetting the other person beyond "Are you interested in doing this? Yes? OK, let's do it then." This relationship did last nearly five years, though.
Carbonmade was the first time in my life as an entrepreneur that luck wasn't 100% involved in picking my co-founders. It was still completely random that I met them, but we did at least build up a six-month working relationship before we agreed on becoming partners. However, we never saw each other face-to-face until after signing the papers.
I hired Jason and Dave, who were running a web design firm, to do a large project for me right after I sold TypeFrag. I actually reached out to Dave back when I was still working at TypeFrag and asked him to design some business cards for us — a job he rightly declined — through a mutual friend of ours, Matt Brett.
Luckily when I approached Dave and Jason again six months later, they had just wrapped up a project and were looking to sink their teeth into something big. I pitched them my idea and we ran with it for six months. During those six months we got to know each other rather well over e-mail and phone. We also chatted a lot about my past experiences as an entrepreneur and what I had accomplished.
Both of them were thinking about how to take their two-person design firm to the next level. They also had this little side project called Carbonmade that was rather neat, and asked for my thoughts about that. Then one day Dave approached me about being a one-third partner in nterface (their old design firm) and Carbonmade. We still hadn't met each other in person, but I accepted.
The circumstances of my ending up with these two co-founders were still pretty hit-or-miss, but even so, this was far and away the most vetted out of all of my relationships. We worked together for six months on a project, got along well, and we complemented each other's skill sets. I know that this relationship will last a long time, and maybe even result in another startup down the road.
If The Shoe Doesn't Fit
The good thing about starting an Internet company is that things happen at a relatively quick pace. You'll know within a few months — maybe even weeks — if the two or three of you aren't getting along. If things aren't going the way you hoped they would, you can always part ways, move on, and start something else. You may find yourself distraught and discouraged, but it's better to end things early and try again than to waste years of your life trying to patch things up.
I really lucked out with all of my co-founders at TypeFrag and Carbonmade. You may not be so lucky. However, it only gets easier with time and experience like so many things entrepreneurial. Just keep at it, try to meet as many people as you can, and in the long run, even though luck never stops playing a role, you'll be in a better and better position to combine luck with experience.