I get the intent of the video, but if the delivery is taken in literal terms then it is very poorly executed. A race implies there are winners and losers, and in the context of the video it would appear that there is only one winner of a $100 bill. In that example there are no incentives for those who start with a disadvantage to even bother. They tried to generalize that concept too much in a way that it'd get picked apart by guys like appleomac.
In my opinion a better analogy would be: after all the steps have been taken, you give everyone 5 seconds to run as far as they can from the start line, and everyone gets a dollar for each meter they are from the start. In this case, those who are behind to begin with are still incentivized to run as far as they can, but they will have little to no chance of catching up to those who had big leads to start.
As an aside... if you did watch the video to the very end, you can see the guys who were at the very start and had hardly taken any steps, they blasted through those who had big leads very quickly

so much so that I'm almost certain the video had to get cut short so that the point could still be proven.