...likely to waste $2,000 of his hoped-for winnings with the 100 push-up bet. I sincerely hope he pulls off the 100-mile ride, wins the money, and finds a sustainable lifestyle that helps him stay healthy and maximize the benefits of that incredibly generous gift from his friends.

Good for him, and good for you in helping to organize, motivate, and push him to reach his goals and change his life. Kudos and well wishes!