What was your first entrepreneurial adventure? What was your last? Which did you enjoy the most and why?

My first entrepreneurial adventure was in the crazy days of Web 1.0:

  • I joined one of my clients as a Director of Corporate Development in 1998. This was my first start-up job. It was a great job and I was very lucky to have it. Great founders and a super cool SOMA office. My “desk” was a door laid down between two file cabinets. I lunched in South Park (the South Park before the VCs moved in). I loved everyone I worked with. I had an excuse to use the Internet all day. We were a market/segment leader. It was great.
  • The first day on the job I had to fire someone on the management team who I’d never met before. That was crazy. I’d never fired or hired anyone.
  • The second week we had an offer from Amazon to invest in the company at a $100m-$150m valuation or more-or-less buy the company for $300m.
  • The third week we had a counter-offer from a pre-IPO company in the middle of its IPO roadshow to buy us for an effective $800 million – $1 billion. This was on about $1m in software revenue and maybe $2m in commerce revenue.
  • The fourth week this pre-IPO company halted its roadshow and bought the company. The stock price quadrupled and the acquisition price became $1,000,000,000. A unicorn!
  • By the sixth week or so the pre-IPO company had finished its IPO and I was worth $12,000,000 on paper in my 20’s.
  • The VCs negotiated an out from the lock-up and many were able to sell very quickly. But, the employees were locked up longer than usual, 9+ months.
  • 1 year later the IPO’d company was bankrupt and I’d only cashed in $60,000 of that $12,000,000. The rest of that paper gains were gone.

So, back to the drawing board!

[Boy we should have taken the Amazon offer.]

But a great learning experience.

Still, it probably took me a half-decade to get over it.

Maybe longer.

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Published on May 24, 2018

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