Chris Brown (Pretty Boy) and T-Pain (Nappy Boy) consistently produce radio hits together

One of the most common problems I hear from friends looking to get into startups is the difficulty in finding a cofounder. While I was fortunate enough to stumble upon my own cofounders, I can empathize. It seems that the interests of business people are at odds with those of engineers. It's easy for one party to feel shortchanged or for visions to diverge. I've heard of plenty of cofounder disasters.

But if you look at successful startup founders, even the venerable Jobs and Wozniak, a pattern emerges. Every good pair of founders needs to have what I call a "Nappy Boy" and a "Pretty Boy".

The Pretty Boy is a dreamer and a visionary. He can make you fall in love with the future he has concocted. His foresight is unparalleled but his track record may be spotty. The Pretty Boy may sound like a douchebag "idea guy" but he's not. This persona does not necessarily imply a non-technical person. For example, an engineer Pretty Boy can convince you that a distributed, in-memory streaming database will change the way companies look at their data. The Pretty Boy looks beyond the status quo.

The Nappy Boy is a brilliant pragmatist. His performance is unflailing but he never seems to get the recognition he deserves. While the Nappy Boy may seem like the archetypal basement-dwelling engineer, he can also be a designer or a businessman. A business Nappy Boy finds the market for the Pretty Boy's state-of-the-art creations, finding the perfect messaging and positioning so that it will succeed. The Nappy Boy transforms visions into the new status quo.

Together, Nappy and Pretty can do amazing things. Pretty provides the strategy, the roadmap for the future, the "what could be". And Nappy chews down that vision with his keen practical attitude until it becomes something achievable. The key is that they support each other. The pragmatist helps build the vision and the visionary provides foresight and momentum.

This dynamic can become tense when times are tough at the startup. Like all relationships, some level of tension is perfectly healthy. The key to survival is mutual respect. Nappy should feel safe and trust Pretty's strategy. And Pretty should truly believe that Nappy tactics/expertise is what will make his vision happen. Magic happens when the Nappy Boy and the Pretty Boy want to tell the same story.

How do you know when you've found your perfect counterpart? The easiest way is to observe how you and your prospective founder behave during a brainstorm. The dialogue should cycle between periods of enthusiasm and "what-if" and periods of pragmatisms and "here-is-how". The rhythm feels like two steps forward and one step back every so often. If your trust and respect can withstand the tug of this push-pull mechanism, you might have found the one.