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Desperate situations make people do objectively stupid things.
For example, Fred Smith, the founder of Fedex, gambled $5,000 in 1973 because he was unable to secure a loan from a bank and was desperate. In this case, his gamble paid off and he managed to win $27,000. Adjusted for inflation it is a much larger sum, roughly around $33,000, but blackjack has an expected negative net return.
It's hard to say how much this gamble is the reason he was able to turn fedex around considering the company was $11 million in debt at the time, but it's likely that if he lost that gamble the entire company would have 100% gone under.
Would the impact of the story be less if it was $5,000 in today's value? Maybe, but I think the intention and situation around the gamble make the story more interesting than the amount. I know you're asking specifically about the loss here, and maybe you're more interested in how the loss impacted/changed a person, but I think the situation/circumstances that led to the gamble are more interesting. I'd also argue that if the amount he gambled was much larger, say $500,000, it be harder for me to accept that it was a desperate situation versus a stupid impulsive decision, even if you win with that larger amount.
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