I'm not sure I've ever seen such a compelling "rationality success story". There's so much that's right here.
The part that really grabs me about this is that there's no indication that his success has depended on "natural" skill or talent. And none of the strategies he's using are from novel research. He just studied the "literature" and took the results seriously. He didn't arbitrarily deviate from the known best practice based on aesthetics or intuition. And he kept a simple, single-minded focus on his goal. No lost purposes here --- just win as much money as possible, bank the winnings, and use it to self-insure. It's rationality-as-winning, plain and simple.