In the high-stakes world of corporate leadership, few figures embody unconventional wisdom quite like Barry Diller, the billionaire chairman of IAC and Expedia Group. Known for his sharp instincts in media and tech, Diller recently shared insights into his hiring philosophy, emphasizing a “sink-or-swim” approach that thrusts young, inexperienced talent into demanding roles. This method, he argues, separates those who can adapt and thrive from those who falter under pressure.

Diller’s strategy isn’t new, but it’s gaining fresh attention amid a cooling job market in 2025. He favors recruiting individuals without extensive resumes, placing them in positions that demand quick learning and high responsibility. “I like bringing in people without any experience,” Diller told Business Insider, explaining that this forces them to grow rapidly or reveal their limitations early.

Testing Resilience in a Competitive Job Market

This approach comes at a time when hiring has slowed significantly. Recent data indicates that the labor market is softening, with employers facing fewer pressures to fill roles aggressively. A report from the Society for Human Resource Management noted that September 2025 saw hiring hit a standstill, easing some recruitment worries but making bold strategies like Diller’s stand out.

Industry observers see parallels in Diller’s past successes. For instance, he promoted Anjali Sud to CEO of Vimeo at age 34, a move that exemplified his belief in accelerating growth through immersion. As detailed in a 2018 Business Insider profile, Sud’s rapid rise under Diller’s guidance turned Vimeo into a standout in IAC’s portfolio, proving that inexperience can be an asset when paired with mentorship.

The Philosophy Behind Promotion from Within

Diller boils his rule down to a simple maxim: promote inexperienced people into leadership to force adaptation. He reiterated this in a 2018 interview with Business Insider, where he described it as the best way to build resilient teams. In today’s environment, where one-third of workers are eyeing job changes according to a Manpower Group survey reported by The Hill, such tactics could help companies retain ambitious talent by offering swift advancement.

Critics, however, question the risks. Throwing novices into deep waters might lead to costly mistakes, especially in sectors like tech where errors can cascade. Yet Diller counters that “pretty good people” emerge from these environments, as he noted in a recent discussion echoed on BizToc. His track record, including building empires at Paramount and Fox, lends credibility to the idea that calculated risks yield innovation.

Broader Implications for Corporate Culture

Looking ahead, Diller’s model could influence how firms navigate economic uncertainties. With job seekers facing a muted fall hiring spike, as outlined in a September 2025 Business Insider analysis, strategies that prioritize potential over polish might become more common. Diller himself has evolved, advocating for flexible workweeks in a 2024 interview with the same publication, suggesting a blend of rigor and adaptability.

For industry insiders, Diller’s sink-or-swim test raises key questions about talent development. In an era of AI disruptions—Diller has warned legislators about its dangers in another Business Insider piece—fostering quick learners could be essential. His net worth, estimated at $5 billion by CelebMash in May 2025, underscores the financial upside of betting on unproven talent.

Lessons from a Media Mogul’s Legacy

Ultimately, Diller’s approach challenges traditional hierarchies, encouraging executives to rethink entry-level roles. As highlighted in a Harvard Business Review podcast from May 2025, his success stems from creating organizations that reward bold moves. While not every company can replicate his empire-building, the core lesson—embrace inexperience to ignite potential—offers a provocative blueprint for 2025’s evolving workforce dynamics.

This philosophy, refined over decades, positions Diller as a contrarian voice in boardrooms. As hiring managers grapple with global challenges noted in an Indeed survey via Business Insider, adopting elements of his test might just be the edge needed to cultivate tomorrow’s leaders.