Investing as an Angel or VC

He says that there was no demand at $12 million but almost infinite demand at $9 million. That rubs me as being a sign of herd behavior on the part of the investors. So all you would need to do is bid a little higher than everyone else and you would have been able to snap up a much bigger share of the company. Obviously you would still need to be able to determine which founders were more likely to succeed.

Hoffman: Probably my biggest regret on [a missed] investment is Twitter, mostly because it came out of Odeo. I never thought that its audio blogging would be the big area. When it spun out Twitter, I wasn’t anywhere close to the company. [NW: Huh?] The notion of how you create massive signal and attention and information through social media has been a constant investing thesis. [NW: Huh?]
Thiel: It’s always a question of how close one is to these investments at the time that you miss it. [NW: Huh?] We were both looking at YouTube, and we sort of missed that one.
Hoffman: Well, we would’ve invested, except that the [financing] round got away from us. [NW: Huh?]
Thiel: One of the big misses has been not investing more when companies worked. That’s when you often need to be doubling or tripling down. I probably invested in close to 200 companies over the last ten years. In every case where there was a significant up-round led by a top-tier venture capitalist, you should’ve always [invested more]. I don’t believe there was a single case where you lost money.