A: Well, I spoke to Mark Pincus probably a month before he started Zynga. He grew up with a close friend of mine who introduced us. I was playing professional poker at the time. Mark discussed starting a Facebook poker game company, I thought it was silly. Not sure I could have invested in Zynga, but I didn’t even try… silly me.
A: I think before investing in a company, the last thing you want to hear is doubt. Doubt about starting a company. Doubt about the vision. Doubt about the team. Founders should clearly articulate the challenges ahead, and what keeps them up at night, but they should not doubt their ability to conquer those challenges.
A: Avoid: “Check-in for ‘x.'” I think FourSquare will or should eventually own most of this space…
Invest: Thriving communities. If you can build an active, engaged and social community early on around anything, you have the beginnings of something special. The ability to build passionate users around your product at the earliest stage is a great indicator of things to come.
A: I met a guy who had built a pretty cool virtual world screening room–watch movies/videos with others (avatars), it was five years ago, and I asked him if it was standalone thing, or part of Second Life, and he replied “What is Second Life?” It showed an utter lack of market awareness.
A: I have never rode out a bubble, so making this up. I think investing in great entrepreneurs, great teams is a good strategy no matter what the economic conditions. A ton of amazing companies were started in 2005/2006 when things were very quiet in NYC.