I watched the full video ... I'm thinking that he made the 'large wheels first' comment only because the small wheels are the 'directional' wheels and may swivel as they go up the ramp making it more difficult to push up the ramps ...
I still can't imagine trying to push a full rig - kb, two spkrs, spkr stands, cart, and whatever, up those ramps ... in order to get the best leverage, one would have to be directly behind the cart, therefore being in between the two ramps ... would that even work?!?