See also The Bootstrapper's Bible by Seth Godin. Seth has a much better explanation of the benefits of bootstrapping than anything else I've seen. The eBook version is only three bucks on Amazon too.
don't know if this particular speech applies so much to consumer-facing internet companies-- his first mantra is "sales comes first", and he tells the story of how he sold a bunch of software before the product even existed.
Some of the other principles, though, such as not spending more than comes in, first things first (keeping the cash flow coming), etc, are more universal.
Yeah, it's probably not so applicable to consumer facing internet companies since the approach really needs a business to buy into the idea (much more willing to preorder, a single sale could fund the entire development).
Although maybe that depends on what you are creating. I could see something like Hotmail or Skype being bootstrapped with this method, because those services are useful to both individuals and businesses. Back then, email from any PC with the internet or free international voice calls would have been things that many businesses would have paid for (and still would, if there weren't so many free alternatives now). Even Reddit got its NYT deal soon after starting which pushed it into the black, did it not? (not rhetorical - I don't know much about their history so tell me if I'm wrong!)
There is the problem of loss of focus though. If a company like Hotmail started in '95, realised it could make millions selling their product to companies and focused on that (sales, turnkey servers for easy installation), they would probably only get a few years of that income at most before they are dethroned by a company that just focused on making the best web based email possible. So it would be a bit of a local maxmimum. Is this more dangerous than the loss of focus of doing something totally unhelpful/unrelated to the main product to bring in some cash (contracting, searching for investors) while simultaneously working on the final product? I'd like to know what everyone thinks.
Sorry, I decided not to tag it [MP3] since it linked to the site not the file directly, forgetting about the lack of a domain indicator. Harb suggested it under the feature requests but it didn't really get any attention - I think an upvote is in order.
http://news.ycombinator.com/comments?id=363
[edit: handily, though, there is an option to edit the title of a submission]