One of my oldest personal rules is avoid little leagues.
Little leagues are places where you’ll develop more slowly, to an asymptote that’s lower than it might be elsewhere. The undergraduate investment club is a little league for being a professional analyst. TEDx is a little league for TED. Little leagues are relative: being an intern at a technology company at thirteen or taking non-AP Calculus at eight probably don’t count as little leagues.
When I went back to school after my first company, a friend tried to pull me into an “entrepreneurship” group he was putting together. They had some smart people working on some interesting things, and though I was concerned that it would suffer from the ordinary, boring infant diseases of undergraduate projects, what really pushed me away was the feeling that even if a member’s “startup” was successful in that context, it would still only be a student project. It attempted to recreate a hard, complex process that requires years of your life in a fleeting, riskless environment. No matter how well a student project did, it still wouldn’t be a company. Some might eventually become real companies, but the noise level is very high.
Instead of joining that group and being a highly sought out undergraduate, I focused on going to work for David Weekly at PBWorks to see a great manager of humans in action, and then Ryan Junee and Max Skibinsky at Inporia to learn from people who’d previously been successful (selling Omnisio to Google and Hive7 to Playdom, respectively) and have the opportunity to architect and build another large, complex production system.
The difference is that of an apprenticeship versus American college. In an apprenticeship, you start out the least useful person in a room of working professionals with real projects and business impact. By the end, you’re one of them.
When I arrived at Duke, my advisor asked me if there was any professor who I thought was interesting and I said, “Miguel Nicolelis’s brain-machine interfacing group,” to which I was told, “well, he’s hard to access, and is in the Medical Center. Anyone else?” It took time, but six months later I was the least useful person in Nicolelis’s primate lab, one of only three undergrads. The experience I had in that lab was hands down the largest educational component of my time at Duke.
While I was commuting during my last two years of college it was really interesting to see the difference in how I interacted with working professionals compared to other college students. The fact that I was still a student didn’t usually even come up. It was interesting to watch the conversations at summer Valley events; the conversations I had were qualitatively different than the visiting interns’. Being a student – or a member of any other boxed subordinate group – immediately changes the context. I had much richer interactions.
The key is to get yourself into a position where you’re the least useful person in the room, but work hard to quickly fix that. If you’re under 50 and the biggest fish in the room, either you’re doing many things incredibly right or you’re missing out on opportunities to develop yourself. Most of the time it’s a bad sign.