When I was in high school, I got pretty intimidated right off the bat. I went to a scholarship school and I felt like I was the last guy they let in. As early as freshman year, everyone seemed to know what they were good at and had already found lots of interests. The best and brightest rose to the top quickly and I didn't believe I would ever break into that crowd.
I think the same thing happens in tech and startup communities. We put investors and the top entrepreneurs on a pedestal--and while that motivates some, I know it makes a lot of other people feel like they'll never attain that rank.
So when I actually thought about such "ranks" I wondered how accessable the Alley Insider 100 list was. Did the digerati have a stranglehold on it, preventing newcomers from rising through the ranks, or is this the kind of community that takes well to newcomers? Granted the Alley Insider list isn't the be all and end all explanation of who has accomplished the most in the communnity, it's the best we have, and it's a pretty decent directional proxy if you're tracking people who appear mutiple times.
As it turns out, only a dozen people have been on the list five or more times in the six year history of the list:
Ben Lerer
Brad Burnham
Eric Hippeau
Fred Wilson
John Borthwick
Tim Armstrong
Barry Diller
Charlie O'Donnell
David Karp
Ken Lerer
Michael Yavonditte
Nick Denton
If you lower the criteria to being on the list more than half the time, you're still only talking about 43 people. So that means that more than half the list is new in any given year--a huge opportunity to rise up.
Part of the reason for this is not only the speed at which startups can succeed--but also how fast they can fail. The community is extremely dynamic, and new opportunties give rise to new faces in the crowd. It also means that, given the odds of most companies succeeding, you've got to maintain your leadership presence no matter what the ground is doing beneath you.