At a retreat over the summer, one of the attendees was rather rich and rather famous in the technology space. Having made enormous sums of money in a variety of startups and corporate settings, this entrepreneur had started all over yet again.
My question to him was if he still had the energy to pursue the impossible when failure to achieve it would in no way shrink his own living standards, along with those of his family. He well understood the question, only to comment that one reason he accepted venture capital funding (despite not needing it) was to keep the outside pressure on him. It wasn’t exactly the same as being in full start-up mode, but as close as someone worth hundreds of millions could approximate.
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