Speaking of cool strollers...
...check out this awesomeness from the Danes! The TrioBike is a bike, a stroller and a... stroller bike? It's designed with the highest of safety standards, good for the waistline, eco-friendly, and if you can't afford the $3K price tag, the Danish government will loan it to you. Unfortunately, you have to live in Denmark for that perk.
Oh those Scandinavians and their clever designs and social benefits... they never cease to amaze.
Thanks to shelterrific for the link!
Start by teaching him that it is safe to do so.