I dunno ... I think of gamblers as people who invest in things they don't understand, or take risks where they have no real way of knowing the odds. He clearly isn't a gambler therefore, otherwise he would have gone bust.
Everything in life is about risk and reward. Crossing the road, deciding whether to study hard or try and strike it out as a rock star, the decision to go to university or not to go, what to study etc. etc. Those who judge those risks right tend to do well, those who judge them badly tend not to. Of course, there are some people out there who are just extremely lucky/unlucky having done everything 'wrong'/'right'. Despite regarding ourselves as individuals, we are largely subject to the whims of fate.
Imo,
B