I wouldn't call four bankruptcies and numerous defaults "lucky".
Over how many successes? Hundreds? Every business is a risk filled environment. Some of those were companies already in distress that were on their way out anyway. What he did was to retain that what was workable and to let the rest go by the way of the dodo bird. Essentially, he bought a house full of stuff and kept what he was after and let the rest go to the yard sale.
There's a big difference between Chapter 7 and Chapter 11.