Sounds like a "cool story", if you know what i mean.
27 000 dollars for such company as FedEx this is nothing. Is like 27 cent for you. Will they help you? I doubt it.
The amount won does not help but the psychological impact does. It boosted his confidence in dealing with the company's problems resulting in more rational thinking which leads to an innovative way of solving the company's problems. As a result not only did he solve the crisis but even make his company even greater. Motivation at its finest.
And of course, Smith could lose his 5000 dollars and then jump out of the window. Much more probable outcome than such "success story".
True every story has its counterpart if the result is different. He might sell his company if he goes out of that Casino empty-handed and depressed.