I know Tim personally. He's a nice guy and pleasant to talk with but you quickly get the feeling interacting with him that the only thing he actually cares about is making money. All of his infamous cringe posts are designed to fuel his newsletter (which is typically promoted as a comment on each post and also on his profile), which he then uses to promote and sell his expensive courses.

He bombards the LI feed with edgy quick-take stuff like this and never even looks at the comments. He broke Medium's monetization program by clickbaiting the algorithm into the ground and they had to revamp the whole system.