I do not know if this is the case any longer, but I recall selling 1 Million Play Money chips at a time for $10 dollars. Also back in these 'golden' days Play Money were sellable. You could earn 2 dollars at a time pretty easily with a very bad placement in the tournament. I remember they had a special event freeroll going to celebrate 10 Billion hands being dealt, and they were giving away a ton of free money.
I made a bankroll from nothing many years ago when I was teen on pokerstars.