Just to make sure everything's clear:

Ashley posts [ Josh ] will do the Roadblock for [ Steve & Josh ].

Ashley will also need to post "[ Josh ] holds on." as many times as possible in the same minute (same time). Doesn't matter what minute that is. Say Ashley manages to make 5 posts in the same minute.

After all six teams has been posted for, for example Ashley's posts for Josh was 3rd overall, Josh will complete the Roadblock in 25 minutes.