During the dotcom boom in the late 1990s, there was a high flying tech startup named FreeMarkets. They made quite a splash in my hometown of Pittsburgh. I remember meeting the two founders during a happy hour on a rooftop bar when they had a few dozen employees. Two years later the company occupied a prime downtown high-rise, had hundreds of employees and was valued in the hundreds of millions.
After Freemarkets went public, one of the cofounders resigned. At the time, he reportedly received $10M in cash and had stock worth $150M. He was in his mid 30s and said he wanted to spend more time with his family and had no desire to join another startup or be a CEO.
The other cofounder stayed on as CEO, grew the company and sold it for $500M several years later. He remained active in startups, venture capital and politics in Pittsburgh.
What was most intriguing to me about tis story, was the first cofounder who resigned. He seemed to have dropped off the earth. After he resigned, there were no articles in the local business journals about him. He wasn’t listed in the “Top 40 under 40” or the local “Who’s who”.
I recall reading a small blurb somewhere that he moved to Oregon or Washington State, bought a small winery ad became a hobbyist/gentleman winemaker.
I thought that was fabulous. Ever once in while, I’ll google him to see what he’s up to. There’s nothing on the web about him. He effectively disappeared from all tech and business news.
If I was on social media, I might be able to find out more on Facebook or Instagram. But I don’t care that much.
I’d rather admire the way he cashed out and moved on at a time when most other people I read about chose to work more, earn more and become more famous.
I’ll never have that type of cash out – my days of startups and IPOs have passed. But in my own much smaller way, I’ve followed in his footsteps.
Although I have good memories of those times, I don’t miss the thrill of the chase, the corporate world, the “power” or the excitement of work. Sometimes I miss the camaraderie and the people. I certainly miss some of the big commission checks. I occasionally miss being part of a mission.
But I’d rather spend my days writing, painting, drumming, swimming and working out.