Why is it said that “once an entrepreneur, always an entrepreneur”?

I think it varies whether this is the case, or not.

From my cohort of CEOs, I know several who had amazing exits and are … done. Simply done. Not doing angel investing, just done. At peace. Or at least seemingly so. Vacation homes. Time with the kids. Non-profits in different spaces (not not full time).

But most I’d say are always entrepreneurs.

Personally, when I sold my first start-up, I was done — and happy. I took a year off, and it was great! I never needed to do a start-up again. But we sold it for $50m after just 12.5 months. As tough as those 12.5 months were … I hadn’t yet gotten “entrepreneur” burned into my brain. My brain hadn’t yet been rewired.

My second start-up, EchoSign, was 5+ years to exit. Not as tough years as the first one, but still tough ones, and importantly, many more years. Those 5+ years rewired my brain.

After that, I again took a year off. I was miserable. I crashed my wife’s car up a bit. I clunked around the house.

For me I learned that now, after my brain has been re-rewired — I have to build. I may not be “happy” always building. But it what gets me up at 5am and thinking all weekend long. I am restless and unhappy if I’m not.

To paraphrase CEO of Box Aaron Levie, when Citrix offered to buy them for $600m+ well before the IPO … “But then what would I do?”

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Published on December 6, 2018

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