This achievement can be done in the Thieves' Guild.
Max wager, hope that you get a anything but a 2, 3, or 12 in the first roll. If you get a 7 or 11, you win with a payout of 1 : 2.2. All others are chance, if on the second roll you get a 7, it's over. 4 or 10 get you a payout of 1 : 3.5; 5 or 9 get you a payout of 1 : 3 ; 6 or 8 get you a payout of 1 : 2.5.
It's all on chance, so be prepared to lose some florins.
Video courtesy of RoosterTeeth.