I see my role much like a small-town praire banker in the 1880’s. My job is to project an aura of calm, solvency, and permanence in an industry where none of those adjectives applies. People are justifiably risk-averse when it comes to their bookmarks, and they are looking for stability. This means several things at once:
On the most basic level, the site just has to work.
On the design level, it means not futzing with stuff unnecessarily, except for bug fixes and basic improvements. Luckily there is so much work to do on Pinboard that I am immune to the temptations of a redesign. If there is a feature (or bug) you love in 2014, chances are excellent it will still be there, like a cherished friend, years from now when your trembling and aged hands go to make that final click.
Finally, there is stability on the business level. This means persuading people (including myself) that I am going to stick around, and then actually earning enough money to do that.
The money part turns out to be easy. People will pay for a decent service. As long as you stay small and don’t forget to have revenue, you too can build a bookmarking website. There is plenty of room to specialize!
My strategy of pre-emptively antagonizing anyone who might possibly have an interest in acquiring or funding the site has worked wonderfully. In five years, I haven’t received a single email from an investor or potential acquirer. The closest I came was a few months ago, when the new Delicious owners reached out to me about providing “vision”, but I think they were just unfamiliar with my oeuvre. They learned quickly.