Scott Adams couldn't really find a new audience in the modern internet age.
Then he came up with the Trump master persuasion and Hillary Clinton campaign mole theory and got a following and a bunch of interviews on TV.
He doubled down on that smug persona explaining what was happening to the world and politics after the election.
He also mixed in his personal life of 'succes' such as chasing girlfriends much younger than him using the same 'linguistic kill-shots' and 'master persuasion' that Trump tapped into.
He essentially turned himself into a comic book character to sell more of his books and start-up ideas which all went surprisingly nowhere considering his master persuasion skills.
I think he tapped into something interesting at first but then it just became another repetitive grift.