The problem with bootstrapped businesses is scale. It can be very difficult to do big things like produce a LOT of high-quality original content and start an awesome family-themed DIY fair in the Bay area without money....
On the other side, one of the best bootstrapped DIY events is Defcon. I still remember when they didn't have air conditioning. I know it's not the same and it's not kids friendly- probably why it has succeeded.
My original point is, sometimes you just need to go big, so there is an opportunity to accomplish more. For an entrepreneur, failure is not always the biggest fear; Accomplishing too little can be a much bigger regret.