Evan grew up rich and has family money to fall back on if he fails, so perhaps he can afford to gamble for a bigger payday. The problem is that he is gambling with the financial futures of his investors and employees as well. In my opinion, a bet that Snapchat will ever be valued at more than $3 billion is a long shot, and there is a greater-than-zero chance that the company will be worth nothing two years from now.