Henry Blodget Creates Imaginary Staff of AI Personalities for His New Website and Hits on One of Them

Henry Blodget, who sold Business Insider to German publishing giant Axel Springer for $340 million a decade ago, has supposedly launched a new site, Regenerator, built on Substack. I was going to tack on an “alas” re: building on Substack, but maybe this is the sort of thing Substack deserves.

The gist of his debut post is that he used ChatGPT to create a small “staff” of teammates to work with, along with photos of these personalities, and he developed a crush on his new CEO. Really.

Do I think he’s serious? No, not at all. Do I think he wrote this to generate attention just like I’m giving him now? Yes, obviously. But I really do have to salute the absolute shamelessness of him playing this straight, painting himself as an utter buffoon, a tone deaf jackass, and downright weirdo, just for the attention. (Blodget has never been very smart even when he isn’t trying to make a fool of himself.)

★ Friday, 25 April 2025