I really like the paint chip idea, but if you over do it, you'll just put him back in a car, driving 90, doesn't matter where the road goes.
I can relate a bit about riding being "hard." Some time ago, I took my old Schwinn off the garage wall and went for a spin for the first time in years. When I finished the 4.5 mile loop, I could barely stand up. My legs were like rubber. I wasn't in super bad shape, I had been roller blading quite a bit, and I always walked to the train station to get to work. The muscles used for those activities, apparently, are not the same as cycling muscles.
Now, thousands of miles later, I don't have any problem knocking off my 16 mile each way commute, or longer rides on the weekend. But that first bike ride nearly killed me.