Love everything that Pinboard is doing - both service and attitude wise. Great to have living examples of hackers doing what they love, without having to sell out to investors or a large company, all the while bringing in decent money.
All that said, I'm always surprised that Maciej racked in over $100k in revenue his first year. I was of the impression that your first 1-2 years are going to be in the red, unless you have something big to build on (existing business to promote your new one, big twitter following, etc.).
The fact that he has 10x the users now compared to the first year but only 2x the revenue is interesting. I assume that's due to moving the subscription fee to a small but ever incrementing amount to a larger, fixed one.
Any tips/prep advice for someone who has a business they want to launch but dread spending the first couple years making no money/having few users?