He should have leveraged the success of the album to get high paid work.

Jim Carrey was offered $350K for Dumb and Dumber, which he turned down (he wanted $400K). Then when Ace Ventura became a surprise hit, the offer for Dumb and Dumber was raised to $7,000,000, which he took. He made only $350K for Ace Ventura, but that opened the door to a bigger payday.

Based on the success of Dumb and Dumber, he was the first actor ever to be paid $20M, for Cable Guy, a flop at the box office.

You get paid for /previous/ success, and that's what the author's dad should have learned.

Edit: removed mistaken reference to Liar Liar, thanks