He owed $59,000 to credit card companies and $18,000 to his father. In one year alone, he had lost $30,000 gambling, court documents show. In January 2004, the 26-year-old filed for bankruptcy protection.Nearly two decades later, [he] rarely if ever mentions the bankruptcy. Yet he and his company ... are urging their tens of millions of followers to dive into the fast-growing and lightly regulated world of online sports betting.