Andrew Ross Sorkin, founder of The New York Times’ DealBook and co-host of CNBC’s Squawk Box, joins Dylan for a candid conversation about the ins and outs of his media business. He walks through a typical day in his life, explains why he’s prioritizing quality over quantity (and skipping the media-empire chase), and breaks down his approach to high-stakes interviews. They also dig into the DealBook Summit—his toughest interview yet, his white-whale guest—and the advice he’d give to anyone trying to break into media in 2026.

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