I think he’s just kinda an ordinary person who grew up privileged. He has fairly standard techbro style libertarian beliefs, but he also has criticisms of some of the influencers he watches, and didn’t seem to like Peterson very much. He also seems to be an environmentalist, and I think he seemed to have become more anti-corporation based on the manifesto released (obviously assuming he did it).
Him being a privileged but ordinary guy who still got radicalized reflects a lot more strongly on the plight of everyone who isn’t one of the owner class. It doesn’t matter that he was relatively wealthy, he still wasn’t one of them.
I actually kinda feel that someone like Bernie may have had enough youth appeal to have a somewhat organic version of that happen. During the 2016 primaries, a decent amount of memes and online talk were spawned by him/his campaign.
Definitely agree that delivery is extremely important though, campaigning on helping workers while appearing elite and out of touch just makes people consider you a liar or to be looking down at people.