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The Operator

Essays for senior executives building businesses they own.
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Cash Flow Beats Profit, and It's Not Close.
Profit is an opinion. Cash is a fact. And the day debt enters your business, bought or built, the two numbers split. My son is 27, a licensed personal trainer who genuinely loves the work and is good at it. He studied sports management, minored in entrepreneurship, and has wanted to run his own f...
Jul 30, 2026
Runway Is a State of Mind Until It Isn't
The strength of your runway was decided long before the day you look up and see how little of it is left. In December of 2020, a friend referred me into a startup in the Pacific Northwest doing genuinely exciting work in cloud security. Two ex-Microsoft product executives, Ivy League pedigrees, a...
Jul 30, 2026
What AI Made Cheap, and What It Made Priceless
Two years ago, I read Arthur Brooks's book β€œFrom Strength to Strength.” A friend had gifted it to me while I was considering launching a new online learning business. The last one I launched at 38, so doing it again at 56 was scary to say the least. The typical questions: What if I blow through a...
Jul 23, 2026

The Operator

Essays for senior executives building businesses they own.
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Library Writings
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