This can be a little tricky to get. You have to win with exactly a lead of $100. Start a private Dollar Dash match with a guest signed in or with a friend and set the score limit to $3000 to win. Have the second player collect all the money they can and score it. Once the second player starts getting close to winning they will start to shine. At that point, melee player two ONCE so they drop $100, then have player two score for the last time, they will have a score of $2900. Now as player one complete the match.