This is the most luck based achievement in the game. As you play the game, there are some spaces (that are yellow and blank) that if you land on, you are able to play Spin to Win. Basically it lets you choose one number, bet some money, then spin the wheel to see if it lands on it. To unlock this achievement, you need to make sure you place the max bet ($50,000) and then land on your number. There are several Share the Wealth cards that can increase your odds of getting this achievement. They allow you to either pick 2 or 4 total numbers on the wheel at once, instead of the usual 1 number, greatly increasing your odds of winning.
Just play the game and spin as normal. If you want to bother, you can keep restarting games until your players get the cards that increase your chance of winning. Also, make sure you take the "Risky" path near the end of the game. While grinding to ten victories in 2-player games, you will likely get 1-2 chances each game on Spin to Win.