I agree that you need to be very confident, but you do not have to be egotistical.Ya see, you kinda Need an EGO to be Reilly Fricken Good at something, (you gOt it) !!
I do a lot of my riding is with the kid in the video. I am twice his age, but he is the one who taught me and keeps an eye out on everyone when we ride. I know it is only the East Coast, but believe it or not it can get kind of heavy here. He has taught a ton of people to kitesurf. He launches and lands everyone, and if someone goes down he is the first to kite by and check on them. I have never heard him once talk about how good he is, even though the rest of us cannot believe half the stuff he does.
I know it is the East Coast where according to Bob no real kiter can come from because we do not have any wind or waves. I know it is not real riding because it is not unhooked and the kite size is above 6m. Worst of all he will ride backside (normally into a few flat spins). But he keeps trying to be a real kitesurfer so give him credit. Bob appears to be a good rider, but this is what I consider to be style. I will let the forum decide if he can live up to Bob's riding.
I am not impressed by Bob's 2.5m riding. There are plenty of vids of guys kiting Hatteras at 40+ conditions, but the difference is that it is usually double overhead and exploding on the sand bars. Not just some white water riding.