The dude's just trying to do self-promotion for his business, he's not so bad. I think shooting video without PPE was a bad choice because it defeats the purpose of discussing and promoting safe removal by professional arborists. Professional arborists wear PPE, he should've at least had the basics, preferrably along with chaps over those shorts.
Some people get weird when they're performing on video.
The reason Jesse doesn't seem any different in HIS videos is, he's always weird.
Now, about that dude with the pole pruner. What was he doing trying to guide the piece with a running saw head that close to a critical rope? It didn't need guiding to begin with and risking that rope could result serious property damage.
We can discuss ladders all day, I hate'em, especially in tree work but they do have a place. I wouldn't have done it that way but it seemed to work fine.