Update on this post in 2022… This is funny to read 11 year later. In review I’d say: 3 of 7 were directionally right (Facebook, NYC startups, and undergrads studying technical fields) 2 were underwhelming but reasonable (Enterprise Tablet, Hardware Startups) 2 were extremely wrong (AOL making a comeback! Phone’s getting viruses) It’s not that surprising that the three I got right were, basically, the things I understood best. I was a Facebook user in the target demo of the time. I was choosing to move to NYC to work in startups. And I was an undergrad in tech. The other ones were all trends I learned about by reading other people’s thoughts. Good reminder to do things you understand! ...

In early 1999, two students raised $100,000 to turn a research idea into a company. Young and risk-averse, they approached the market leader asking to be bought for $1 Million. They were negotiated down to $750,000 before the market leader finally decided not to make the purchase. The small startup asking to be acquired? Google, which IPO’d in 2004 and currently has a market cap of $192 Billion. The market leader that turned down the acquisition? Excite, which would merge with @Home Network before filing for bankruptcy in 2001.1 ...