Throughout the 1990’s, the Microsoft stock price had an overall upward trend. Employees would sell their stock in order to make a major purchase, or to fund a vacation, or simply to cash in on the rise. But no matter when you sold your stock, you always sold it too soon. People joked about driving a $70,000 Honda Civic because they sold stock years earlier to buy the car at $10,000. The car depreciated quickly. The stock didn’t.
It was customary for a time for the Microsoft Company Meeting to hire a celebrity host, usually a comedian, to liven things up. Dana Carvey was the host for a company meeting in the early 1990’s, and one of the sketches he performed was a humorous interview with Bill Gates. The questions and answers were scripted, but Dana Carvey decided to ask a question that wasn’t on the script:
“Say, Bill, if I had bought a thousand shares of Microsoft stock 20 years ago, would I be a gazillionaire like you?”
I got the impression that Bill was not a fan of going off script, but he was ready with a comeback.
“Nah, you would have sold it too soon.”
That quip brought the house down.
I pity the fool who sold too late.
The funniest part I remember from that meeting was also ad-libbed, by Dana Carvey, after Steve Ballmer's usual amped-up speech. Steve actually retold it in Sports Illustrated at some point: "Funny story. We were doing a Microsoft company meeting. This was '89, '90, '91. I was either engaged to my wife or just married. I gave a speech, and I was wearing a dark blue shirt. The speaker after me was Dana Carvey, the comedian,...