What does history say about how big the AI boom can get, and who will ultimately win out? When does a boom turn into a bubble that turns into a bust? On this episode of the podcast, we speak to Henry Blodget, the founder of Business Insider (and Joe's old boss there). In the late '90s, Henry was one of the most well-known Wall Street analysts covering internet stocks, before the crash and recriminations, which ended up in his lifetime ban from the industry. His new project is a publication called Regenerator, which will again focus on business and tech. We discuss the state of the AI boom, and what lessons we can draw from the dot-com era. We also talk politics, what's changed on Wall Street over the last 25 years or so, and a bit on the state of the media business.

Only Bloomberg.com subscribers can get the Odd Lots newsletter in their inbox — now delivered every weekday — plus unlimited access to the site and app. Subscribe at bloomberg.com/subscriptions/oddlots

See omnystudio.com/listener for privacy information.