Fred Wilson’s 2007 investment in Twitter Inc. drew a tough inquiry from the technology crowd at the time: How could a service that let anyone say anything in 140 characters be worth $20 million? Wilson was a believer.
“If you tried Twitter early on and found it useless, I suggest you give it a second try,” Wilson wrote in a blog post on Aug. 26, 2007, after making the investment in the previous month. “My bet (literally) is that you’ll find following your friends on Twitter to be habit forming. I certainly have.”