The fact that Doug was trying a toe hold while wearing 16 oz boxing gloves on a guy wearing shoes (which help prevent toe holds but make heel hooks easy) demonstrates his experience level in MMA.
Watching that portion of the episode, what I noticed was Doug continually taking heel kicks to the ribs while trying to get a toe hold. To me, that spoke volumes. He didn't adapt to the situation, which is something Krav preaches (same situation in the Palm Grove, he continually wanted to go to ground instead of using the "weapons" freely available in the environment) and why Avivit continually yelled out he was dead.