If it is a significant enough amount of money someone needs to go with him even if they have some eassist or a scooter. but one of the regular bike shop riders should be able to keep up. He'll need to keep up 10 mph the whole time. Definitely be a struggle on my hybrid. And even if you think it is a lot of money, a lot for a 12 hour ride, a lot for a bet but not a lot considering 2 months training. He's a GM, he should make 50 k a year which is 4 k per month without you guys. 2 months of dedication is worth almost 10 grand to him and i doubt the bet is for that much and then does he also lose money if he loses? Maybe pride will be enough motivation but it is doable but at the upper limits of doable. It seems a fairly matched contest that could go either way.