In $30 MILLION AND BROKE: If You Have It, Don’t Lose It forty-year investment veteran J. Ted Oakley explores the phenomena of going from rags-to-riches, then the unfortunate turn from riches-to-rags.  The book is filled with stories of entrepreneurs, heirs, athletes, artists, lottery winners, and settlement recipients finding themselves with enough wealth to “support them and their families in perpetuity.