Wow. This is interesting on its own, as others mentioned, but it's really interesting to me personally, as the co-founder of a bootstrapped local real estate referral company.
One thing I didn't see mentioned much was the 2008 housing crisis, which was disastrous for us. We were in acquisition talks in late 2007 which were suddenly canceled, seemingly in anticipation of the horrors to come. Our revenues were devastated and I went back to consulting for several years. Basically, our site was on autopilot until January of this year, when the real estate market showed signs of long-term strength and we started our current development drive.
We're still bootstrapping off consulting revenue, so it hasn't exactly been fast-paced, sadly. Let me say, still running a business you started after Startup School 2005 gives you a much different perspective than the usual startup narrative. When you bootstrap, you can press pause instead of eject. You're not on fire, so you don't turn to ashes the instant you run out of fuel, but you sure do have to keep smoldering.
For those who aren't familiar, I would describe real estate startups as being similar to a closed game of chess. Lots of long-term possibilities and plans, but not a lot of good moves available. The market is sharded, guarded, scattered and smothered.
We haven't explored (or had an opportunity for) an agency conversion, so it's really interesting to read this account, thanks. Instead, we are trying to rework our regional site into a niche national site. I'll share how it goes, hopefully before our company's own tenth anniversary. Congratulations and thanks again for writing this history.