Yes, this could be more accurately described as "investing his fortune", or if you want to focus more on the risk (as game development is a risky business), "bet his fortune."
Loved Braid, quite interested in trying out The Witness; hope it doesn't take too long to come to a platform I can play it on, as I have neither a Windows machine, nor any consoles, nor an iOS device.
I think part of the reason they consider he is "betting" or "risking" his fortune, is because it probably has a lot more risks than a "simple investment". i.e. he's not taking his money and putting it in a Fidelity investment account, he's spending money to create a game that might very well not sell more than a few copies and not make the money back.
I guess people see him as "winning the lottery" with Braid, so now spending that "lottery money" is seen as a foolish move. However I think that spending/investing your hard-earned money in something you enjoy (developing games) is the best investment one can do, even if you do lose all your money.
Loved Braid, quite interested in trying out The Witness; hope it doesn't take too long to come to a platform I can play it on, as I have neither a Windows machine, nor any consoles, nor an iOS device.