I worked at Formspring for a short period a little more than a year ago, and I left as they began to experience runway issues that were, more obviously each day, not going to be solved by another big funding round.

The talent assembled there was very impressive. They were a small team but full of fantastic engineers.

I also learned a lot about how expensive and challenging very large EC2 deployments are (but I also know how expensive and challenging very large colo deployments are. There's no free lunch.). I learned a lot from the Cassandra and Redis heavy design, and I got to play with tons of fun Amazon services (SQS, SimpleDB, etc).

I don't have the long-view of what went wrong aside from the fact that:

1) The site gained traction with young people who are fickle and eventually left. Maybe you could say the site didn't grow up with them. A lot like Myspace in that respect.

2) Everybody wants to answer questions about themselves, not enough people ask good questions.

3) There is no better place to ask all my friends "Where should we get sushi when we go to NYC next week?" and other types of Q&A, as well as the bread-and-butter questions like "What's the last dream you remember" and "If you were stuck on an island..." That sorta thing.

4) People always compare it to Quora, suggesting Quora is more successful. Well, they are in that they are still funded and alive. But the DAU numbers? I bet Formspring STILL, TODAY, weeks before shutting down, has more DAUs than Quora

On closing, I'll share my favorite Formspring story. It was my first time working on a popular Consumer product. When I released a feature (continuous deployment ftw), it went to millions of users. Well, one release was memorable to me. I think it was a redesigned Inbox or something, and immediately after the release you'd watch your instrumentation and Twitter for any hint of something going wrong. That was cool to me, that we have so many users of this social product that we can use Twitter as a real-time QC feedback mechanism. Anyway, a group of teenage friends on Twitter started discussing how they thought the update was lame, a waste of their time, and would Formspring please just give them something actually useful to them. Like what? One friend asked. The other replied "You know what would be bad ass, just a big fire breathing dragon on my inbox."

When the Founder saw these, a scheme was brewed. Through a bit of sleuthing and some good guess work, we found the Formspring accounts for these Twitter users. Somebody found a fire breathing dragon straight out of Ultima and a release was whipped-up that would display this dragon on these girls Formspring Inbox. We went from conception to release in 45 minutes. Then we just all sat in the office and waited. Needless to say, the girls shrieked with delight and I swear they were converted into Formspring lovers for life after that. It was a great little easter-egg just for these few users.

Anyway, it's not that riveting of a story, but it was a great moment to be on that team. I was new and mostly a bystander for that but it felt great to be a part of it all.