Barry Diller has a plan for monetizing legacy media in the AI age

Media titan Barry Diller, the chairman of publishing empire IAC, has built and rebuilt his career more than most executives, from network television to Hollywood studios to the earliest internet empires.

As part of Business Insider’s The Long Play, Diller talked to Peter Kafka, Business Insider’s chief correspondent covering media and technology, about what successful businesses require: good timing, nerve, and the willingness to walk away from what’s working.

During this conversation, titled “The Art of the Comeback: A Masterclass on Resilience,” Diller shares his perspectives on AI adoption. He also talks about why his MGM Resorts deal fell apart and how he’s leveraging legacy print publications like Southern Living to create new revenue streams.

The 84-year-old media and tech exec told Kafka he wants to keep working as long as he can be engaged and useful.