I usually temper the amount of alcohol I consume when in a professional setting because when under the influence I tend to lose the split second of judgment that determines when a question is appropriate or not. On this occasion (this was while still with my previous employer), however, with a belly full of red wine and steak while in the presence of a young and well known internet entrepreneur, I decided to let myself go.
“So tell me the truth: we’re almost the same age. You’re running a multi-million dollar company. You have dozens of employees. You get over 30 million uniques a month. How the hell can you be so sure you’re not going to mess it up? Do you think about that much?”
He smiled as if I asked him how much he was worth and he was delighted to finally be able to let it out:
“Of…
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