Media mogul Barry Diller has built a career shaping some of the most influential leaders in business, and his approach to mentorship is as bold as the companies he’s helped build. As chairman of IAC and Expedia Group, Diller has worked closely with iconic names like Dara Khosrowshahi, now CEO of Uber, and former Disney chief Michael Eisner. But when it comes to developing young talent, Diller follows a sink-or-swim philosophy that pushes early-career employees far beyond their comfort zones. Speaking on the podcast "Invest Like the Best," Diller revealed that he intentionally hires people at the earliest stage of their careers often with no prior experience or specialized expertise and then gives them far more responsibility than their resumes warrant. His rationale is straightforward: under high pressure, natural leaders rise. “Then you give people more responsibility than they qualify for, because, in that forge, you find out who swims and who doesn’t,” he said. “If you have that kind of environment, out of it is going to come pretty good people.”
Diller’s approach comes from personal experience. He launched his own career with little more than determination and a willingness to learn. After dropping out of UCLA, Diller started in the William Morris Agency's mailroom in 1961. From those modest beginnings, he rose to become one of the most powerful figures in the entertainment industry. At Paramount Pictures, he helped deliver box-office hits like Raiders of the Lost Ark and Saturday Night Fever, and later co-founded the Fox Broadcasting Company alongside Rupert Murdoch. On the podcast, Diller reflected on how unprepared he was when he first entered the business world, admitting, “I was totally unprepared, and I had no reason for anyone to give me any responsibility, because I had no experience about anything.” But he succeeded precisely because his bosses gave him more than he could handle and expected him to adapt fast. “I got dropped in the deep end of the water, and I figured out how to swim,” he said.
This formative experience shaped how Diller evaluates potential today. He believes the best results come not from resumes, but from creating a pressure-cooker environment where true talent is forced to emerge. And when it comes to senior-level hires, Diller is famously skeptical. In fact, he’s on record as saying that hiring people externally into top roles is a failure of leadership. Back in 2018, he summed up his philosophy with a striking quote: “If you hire people at senior positions, you are a failure.” Instead, he encourages organizations to develop talent internally. “I have always believed to hire people, bring people into your organization who are young,” Diller said. For him, youth is not a liability it’s a blank canvas on which great leadership can be painted. The key is to find individuals who thrive under pressure, learn quickly, and grow into their roles, rather than waiting until they appear perfectly qualified on paper.
For young professionals entering the workforce or entrepreneurs trying to build strong teams, Diller’s philosophy offers a bold counterpoint to traditional corporate ladders. It’s not about earning responsibility slowly it’s about proving you can handle it when it’s thrown at you early. And for companies willing to trust the process, it’s a strategy that might just turn raw ambition into tomorrow’s industry leaders.
