Kid bought an old crappy yacht. Years later he's caught in serial insurance fraud transactions for boats and planes. The dollar ripoff values go from $40k to $100k's rapidly within a few years, and a few years later he's in jail.

Guy is in this line of 'work' because he is an adrenaline junkie. It brings certain side benefits-- dealing in obscure obsolete aircraft and parts gives him means of leisure and more than a little swagger, without the pain of asset depreciation. Convinces himself, a romantic interest, and not many others, that he's James Bond.

Once his 'business' got big enough, it attracted the right attention and has given the guy an opportunity to remake himself yet again, this time from jail.