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If you owe a little money, you have a problem. If you owe a lot of money, your bank has a prob,em. If you run one company, you have a problem. If you run 2 or more, your investors have a problem.
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Otoh… True startup types rarely run more than one company at a time. Jack Dorsey is a rare exception. True PE turnaround types rarely fewer than 3-4 companies (via holding companies with some shared executives and strong investor control) 🤔
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I think there’s an interesting 2x2 here. Investor control vs founder control, serial vs parallel entrepreneurship. Parallel+investor control = PE Serial+founder control = fat startups Serial+investor control = lean startups Parallel+founder control = Dorsey ops Origin: Musk