Pros
The opportunity to work with some of the brightest, most creative people I had ever encountered, which I hadn't initially expected (given the reputation of the site in the era). Both witnessed and contributed to practices and methodologies, born out of necessity, that eventually became industry standards. Great environment to work in early on. Really felt like we were changing the world at the time...and we absolutely were.
Cons
Lack of vision, broken promises, and repeatedly ignoring the advice of the internal cultivators who correctly predicted trends that we failed to capitalize on. Acquisitions of products that weren't fully baked and didn't really fit with what we were doing would draw our attention away from things that users really needed. Management remained more concerned with implementing masses of poorly conceived features than addressing long-standing user concerns that were ultimately drawing users away to other sites. Many rounds of layoffs due to the above, ultimately killing team morale.