As a fan and practitioner of bootstrapping I was interested in the part where pg says that the delay caused by bootstrapping can be fatal to many kinds of startups. Flipping that around, are there kinds of startups where the delay is not fatal? Taking Basecamp as an example, it was released probably decades after the first project management software. Is bootstrapping best if you're going after a mature class of soft…
You are probably in the lucky minority.
I can see that lucky things have happened to us and that the degree of success (especially the part about being able to afford more people than just myself) has been greatly influenced by luck. But I also think you're guaranteed to have some good fortune along the way.
If we weren't doing what we're doing we would be doing something else. In our case we're doing conferences but we could be doing intranets or adding integrations with other websites or building custom social networks.
I got an interesting take from one of the founders of Apperceptive, a just acquired Movable Type services company. He said that they intended to build a product company but that once they got started with services they found that the "world has an insatiable appetite for services."
That was my experience, once we'd built something that could be valuable we had a number of excellent service options.
I'll agree with anyone who says that bootstrapping to this stage is hard but I'd argue that it's quite repeatable. I'd like to take the company one stage further, to a point where we have stable non-services revenue and I won't make any claims about the repeatability or luck factor involved in doing that.