Larry Ellison bet big on AI. Will it pay off, or tank his legacy?

At age 81, why would Larry Ellison risk so much?   Show notes: For a moment earlier this year, Larry Ellison was the richest man in the world. Although the Oracle co-founder only briefly stole the top spot from Elon Musk, it was a high point in what was a huge — and risky — year for both Ellison and his legacy tech company.   Oracle’s stock price soared as it landed major deals with the biggest AI companies. It also took on a staggering amount of debt (a 500 percent debt-to-equity ratio, in fact), leading some to see Oracle’s dealings as proof of an AI bubble.   Meanwhile, Ellison has had his hands in everything: currying favor with President Trump, negotiating for a stake of TikTok in the U.S., and helping his son, David, become a media mogul.   Today on Circling Back, we have one of the best journalists to talk about this: Bethany McLean. She’s an award-winning business journalist and the author of five books, including one you’ve probably read, or at least seen the documentary, The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron.  Bethany recently dug into the big gambles that Ellison made in 2025 for an excellent Inc. story. She joined Inc. Editor-in-Chief Mike Hofman to go inside her reporting.