Jake is young, and has a presence online other than youtube. The internet generation has created a body of young people seeking to surround themselves with successful peers and to emulate them. Social media facilitates that to a degree previously unfathomable. It doesn't necessarily need to be someone in a similar field, but seeing someone put in the work, and become successful, is something a lot of folks want to see.
Because we climb, because we do the job, we often take for granted just how amazing and sometimes intimidating what we do really is. To us, it's endless monotony of dropping branches, to another, every cut may well be thrilling, or help to give a sense of the enormity of the task. Don't forget, the job you do is to climb into a tree, tie yourself off with a rope technically strong enough to pull a truck, and cut the tree down from the top.
Haven't you ever had a customer, and maybe their family and neighbors spectate as you make a huge plant disappear? Sometimes a veritable crowd forms, and you can't help giggling at their child like amazement, as you simply go about another Tuesday.
A lot of the comments on Jake's videos reflect this. There's a ton of tree workers of all stripes, offering thanks, advise, and criticism, and there's a ton of folks expressing sheer awe. He shows his mistakes, has a great sense of humor, and comes across as a guy I'd like to work with.