The story sucks to be honest. First of all because of the percentage you mention, but is there that much difference between $5,000 and $27,000? If he had said that $5,000 got him $500,000, it would seem to me to be a considerable difference.
And besides, it was the only way he could get that $22,000 difference? I don't know, maybe taking a loan to invest in his company would have made more sense.
Maybe the meaning of the story is that he took a risk in the casino and won, it gave him the courage to continue to take risks in business - instead of a reliable bankruptcy after which he would still have a lot of capital, he decided to keep the business to the very end and eventually won the jackpot. In general, it is rather silly to confuse gambling with business, but sometimes such comparisons really make sense because in business there are many external factors that are beyond our control and can be perceived as random.