Fred Wilson on Bootstrapping

Wednesday, May 07, 2008 by Dave Winer.

Fred's heart is in the right place. He puts money behind technology he likes. This is bootstrapping. Then he bothers the developers with features he needs. He's a bootstrapper and a hacker. Then Fred reads articles written by other people and listens to a Tim O'Reilly keynote and tries to get everyone into agreement. Reminds me of The Negotiator, William Shatner.  

Fred believes in triangulating, I do too. It's how you find the truth. Obviously I agree with Fred's conclusion -- just today I was working with Jay at Switchabit on a very small project. We spec'd it out, I went to work on it, and after I did it the way we discussed I realized there was a much more direct and simple way to do it, so I re-did it, and again I realized it was too complicated, and I re-did it, sent him a report, he integrated it into his project agreeing that it was much better than what we discussed. 

People who believe in big-bangs miss that you learn stuff while you're implementing stuff and that learning should be recycled back into the project, again and again. 

There was an excellent series on PBS a few years back called Connections; in each episode they take you through a series of developments how little pieces of one thing became something much bigger, you start with something small and every step of the way make small improvements and before you know it you're standing on the moon saying "One small step for man..." 

A journey of a thousand miles begins with a single step. 

I've heard bootstrapping described as "paving the cowpaths." 

Twitter was a bootstrap too. There were a lot of small things that needed to get solved before Twitter could work. It may look like it popped up out of nowhere if you don't know how the pieces came together, but if you do... 

One thing that's feeding epiphany for me is that I'm working with Scott Rosenberg on his history of blogging, which promises to be a great book, and reliving all the steps that got us to where we are.