I'll answer that for Dave - he was lucky for a short time. A good businessman would not have gotten himself involved in criminal deals. A good businessman makes his money legally, not illegally.
I think he was smart at one point. Made a lot of money. Then got greedy. I always thought he was creepy tho.
Backstreet Boys did a LOT more for him than N'Sync..but they both made him a fortune...BUT..the Boys signed a LOT away to get that break, and they were just some of the people that sued him in later years.