Joshua Schachter started the collaborative bookmarking
site del.icio.us in 2003. As often happens with startups,
del.icio.us began as something Schachter built for
himself. He needed a way of organizing his collection of
20,000 bookmarks, and he hit on the idea of “tagging”
them with brief text phrases to help him find links later.
He put del.icio.us on a server and opened it up to other
people, and it began to spread by word of mouth.
For the first several years, Schachter worked on
del.icio.us and other projects, like Memepool and
...

bookmarks. There were some 10,000 daily readers looking at my stuff. That was
interesting.
I did several other projects along the way. I did GeoURL. Something called
Reversible, that is long gone. Reversible was also like del.icio.us in many ways,
but different in a few key ways that made it fail.
In late 2003, I started working on del.icio.us, which is a multiplayer version.
I was actually trying to come up with a better Memepool—something between
Muxway and Memepool which was more vital somehow, and we ended up with
del.icio.us. I had...

to VCs if I didn’t have a great deal of user base and press to show. I think that
would have been a challenge. If I said, “Hey, I’m going to build a bookmarking
service,” I would have never been able to get off the ground.
Livingston: Because the idea was so new?
Schachter: No. There had been plenty of other startups that failed doing this.
Backflip and God knows what else. So it had been tried and failed in the past.
Livingston: Why did del.icio.us succeed?
Schachter: First of all, because it...

capital.
Livingston: And that’s because you didn’t want to take a huge amount of
capital?
Schachter: Well, there was a lot of risk. It was sort of hard to justify a large
valuation and so on, so we sold a small chunk for enough money to work for a
while and see if it turned into something. That was the plan: see where this
goes.
Livingston: Did you hire anyone?
Schachter:We did. There were eight employees total at the end.
Livingston: Were most of them shareholders?
Schachter:We gave shares to...

think we didn’t even go far enough. Whatever it is, question every single aspect
of conventional wisdom. “Is that the right way to do it or can we break that and
make it better?”
That’s also dangerous, because, if you are doing a lot of paradigm innovation,
call it—which is not a good word—but if you are breaking boundaries
elsewhere, maybe you need to be very within boundaries on other fronts.
Livingston: Do you remember a time when you were worried about something?
Schachter: Site’s down. Site’s slow. Table crash—MySQL corrupted a table....