When I was in financial trading, I think that's what we called a "Texas hedge".
(A hedge being where you take some of your money and buy protection against downside risk. For example, since I'm in tech, it's in my interest to sell some of my company stock and buy something that is uncorrelated with tech. That way if my company blows up, I won't be totally broke. The Texas hedge is doing the opposite, so that you're even more screwed if the bet doesn't go your way.)
This could indicate confidence, but it could also indicate a double-or-nothing mentality. You can only be so bankrupt, after all.