Profitable and proud: Campaign Monitor
37signals.com
37signals.com
Campaign Monitor is a great service too, I frequently reference and share their Guide to CSS support http://www.campaignmonitor.com/css/ to coworkers who have questions on what can and can't be done with styling in emails.
When Basecamp launched, we had something like 4,000 readers of SvN. Now that's a fair chunk, but certainly not unobtainable.
How many people/companies start blogs and don't succeed like you guys did?
Trying to be the next google or younameit is playing the lottery, no argument there. Bootstrapping to $10-100MM strikes me about as unlikely as being the next google.
That's not even a contest. $10MM+ bootstrapped companies are far more common than "being the next Google." More stories on the way.
This 37Signals post, and subsequent ones, should inspire you, not discourage you.