Andrew Ross Sorkin on Oprah, Elon Musk, AI, and the Next Big Stock Market Crash

Andrew Ross Sorkin has spent his career following the money to understand everything — from Wall Street to Silicon Valley, from media to AI. A journalist who never set out to be one, Sorkin built DealBook into the Super Bowl of business journalism, turning curiosity into empire-building. In Boardroom's October Cover Story, he shares how an overheard word such as “internet” landed him at The New York Times, how he approaches interviews like a tennis rally rather than a serve, and why Oprah remains his white whale. Through stories of Too Big to Fail, the 1929 crash, and the coming AI reckoning, Sorkin unpacks how narrative drives markets, crashes, and comebacks alike. From Elon Musk’s many personas to the billion-dollar game of sports, streaming, and live entertainment, this is Andrew Ross Sorkin: journalist, storyteller, dealmaker — chasing what feels impossible, one conversation at a time.