My Lesson in Bootstrapping
John Nunemaker wrote up his experiences in bootstrapping Harmony with Steve Smith. He makes a lot of great points that have been working out for them. I just have one quick thing to add to it all:
Embrace Open Source
I helped bootstrap both Lighthouse and Tender Support, and noticed big gains after supporting open source projects. Obviously, these products are more developer focused than most, but we also take every chance to sponsor non profit organizations, educational use, etc.
When Lighthouse launched, I was apprehensive about supporting them. I worried that we'd get some project like Rails or Wordpress on there, melting my poor servers. Really, we were extremely fortunate to get some high profile OSS projects. Our servers didn't melt (yes, we love Engine Yard, our hosting partner), and put our product in front of a lot more eyeballs.
Write these opportunities off as advertising if it helps.