I think someone with next-to-nothing risking everything demonstrates significantly more risk than a billionaire risking a fraction of his wealth. One person has everything to lose, and the other isn't really risking that much (I've personally risked more than 50% of my entire net worth on a single bet when I was already doing well - it's a ridiculously comfortable position to be in and doesn't really demonstrate anything other than privelege).

I think a more interesting question is comparing someone with $100 to someone with $1 billion risking their entire net worths - who has taken on more risk?