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Would you feel this way if he'd won big after buying a lottery ticket, or received an inheritance from a family member?

He took a risk (potentially, maybe he's the founder, maybe it's equity) and it paid off. It could just as equally not have.

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Inheritance I wouldn't care about because there's nothing I can do to change what I inherit. Lottery I'd probably care about, though. I've always looked down on people who buy into lottery but I think if I saw someone close to me win big I might feel like I missed out for not playing. It's a good comparison because I remember the early years when his business success was really far from certain - he bought a lottery ticket that was probably worth several hundred thousand dollars in the first years (income he would've easily made if he'd been an employee instead of being a business owner without any customers).

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