The Bloodstone game is by far the easiest way to win this achievement. When you begin the game, go into the bank and take out about 3000 chips. Place you arch bet on 3, then each round place bets on 5, 4, 3, Trips, and all four specific triple rolls. The chances of a roll that low and triple are very low, and you'll pull in 80 chips a roll. This will give you 500 on your 7th roll. You can keep track of your progress on the stats page. Before you exit the game when you have 500, go into the bank and pay off your debt. Also, if by some rare chance you are hit with a triple roll, you'll find yourself somewhere around 2000 in the red. Being the achievement is for 1 session, it's best to exit the game and then start over fresh.