The fastest way to get this achievement is to start a single player game on medium difficult with AI and mini-games turned off. Get at least one question correct so you have a positive amount of money, then because it's a single player game, you can hit B to skip every remaining question after Alex reads it. (Skipping is optional, you could simply start the game and then walk away for 10 minutes, but hitting skip is faster.) Once the game is over, you will be the winner even though you had no competition, and the achievement shall be yours!
Per steveRPGmr: You can also do everything mentioned above on Hard difficulty and pop both achievements at once because they do stack