Olmstead went on Millionaire on April 10, 2001. He managed to make it to the 15th question on the Millionaire Money Chart. However, he was not playing for a million dollars unlike the original format, but rather $2.18 Million. The reason why he was playing for that prize money is because it was bonus jackpot money. He managed to answer the million dollar question right away and took the money home with him. It has been known that Olmstead was the biggest winner in American Television history. He was also the seventh person to win the million dollars in Millionaire history.
Grand Slam Run
Six years after his Millionaire win, Olmstead went to play Grand Slam. Though he did not make it to the final round and won the $100,000, he still was able to make it through three rounds. Ken Jennings won the tournament.