Reflecting on my life, as one does on later birthdays, I realize that my proudest professional achievements are recorded in a neat pile of embroidered casual clothes in my closet.

Looking back on each, I remember the optimistic ways I imagined “taking over the world” at these various stages. In most cases, I was especially proud of the early age at which I made the accomplishments — so now as a middle aged man (who has not yet taken over the world), there are times when I dwell on futures that could have been. But when I look at where I am, I’m overwhelmingly grateful that my choices led me where they did.

In chronological order:

Stuyvesant High School – Accepts the top 2% of applicants in NYC. Aced the test w/o prep, but surviving the years I spent there was a much bigger challenge. My pride comes not from gaining admission, but from making it through one of the toughest and most rigorous high school educations in the country. Graduated age 16.

One Technology, Inc — My first meaningful business, this Operations Research company used software I built around Genetic Algorithms to optimize business problems for Fortune 500s. Founded age 25. My stock value was in the millions by the time I was 30 years old, but the “dotcom” crash of 2001 sent the business for a tumble.

Young Entrepreneurs Organization (YEO) — This club required every member to be a business owner under age 40, with 10+ Full Time Employees, and revenue >$1M or funding >$2M. I joined when I was still under 30, and it was one of my proudest achievements. I wish I could say I met lifelong friends there, but it didn’t work out that way.

IMD Business School — The MBA I earned in my mid-30s helped a great deal in overcoming my Imposter Syndrome about being a business owner in technology with an undergrad in digital music, a few years as a software engineer, and no formal management credentials. I expected dry lessons about strategy and accounting, but I learned the most about the Psychology of Leadership.

This is why it was such a very special milestone to me, the day I got embroidered shirts for my new DRAM Conference. It’s still early, but I hope this new project earns me as much pride and joy as my other woven souvenirs.

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