Update on this post in 2022… I wrote some posts around this time that were explicitly predicting things. This post wasn’t that. It was more what we’d call a ‘vibe shift’ take. But I think I actually called this pretty well! Original post… Like many tech minded people I viscerally hate prestige. We tend to want to view the world as a harsh meritocracy where only the best achieve success. It’s partly why we revere people who have the guts to drop out of school. They took the risk of losing the prestigious paper to hang on the wall. However, whether or not we choose to ignore it, prestige does matter. ...

“The first principal is that you must not fool yourself, and you are the easiest person to fool.” Richard Feynman Near the beginning of my time as an SAT tutor I had a client, who we will call “Steve.” When I first met Steve he seemed like a nice kid, perhaps a bit reluctant to work hard to improve his score, but amiable enough. My first few visits with each student began the same way- going through the basic strategies before tailoring the rest our time to the specific students needs. During this introductory period I gained a good idea of where I thought a student would score when we moved on to taking practice tests. ...

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 ...