Invest Like the Best with Patrick O'Shaughnessy
Barry Diller - Building An Entertainment Empire - [Invest Like the Best, EP.441]
23 Sep 2025
My guest today is Barry Diller. Barry is the former CEO of Paramount Pictures, Fox Broadcasting, and the founder of IAC. He has been at the center of every major media transformation over the past five decades, from creating the Movie of the Week format to building the fourth broadcast network to executing 150 internet-era deals. Barry reveals his "creative conflict" philosophy - pushing smart, opinionated people past their endurance point to generate breakthrough ideas. He also shares stories of working alongside media titans like Rupert Murdoch and Bill Gates. We discuss his current portfolio strategy, innovation in media, and how personal struggles can become professional superpowers. Please enjoy my conversation with Barry Diller. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:02) Early Career in Entertainment (00:06:33) Defining Moments and Fearlessness (00:09:18) Personal Reflections and Family Impact (00:12:37) The Magic of Interactivity (00:14:44) Creative Conflict and Instinct (00:19:24) Breaking Down Complexities (00:21:35) Innovations in Television (00:23:37) The Fox Network and Murdoch's Gamble (00:29:37) The Value of Money and Motivation (00:30:17) The Leap to Independence (00:32:28) QVC and the Internet Revolution (00:33:37) The AI Opportunist Approach (00:36:55) The Rise of Match.com and Tinder (00:38:57) The MGM Investment and Future of Entertainment (00:41:21) Negotiation Lessons from Lou Wasserman (00:43:47) The Simpsons: From Doubt to Success (00:44:25) The Changing Landscape of Media (00:51:53) The Kindest Thing Anyone Has Ever Done for Barry
Full Episode
The best operators have a relentless focus on leverage, finding ways to multiply their impact rather than just working harder. But here's what I see happening in finance teams everywhere. Brilliant people getting buried in expense management busywork. If you think about it, you become a finance leader because you love strategic work.
modeling scenarios, optimizing capital allocation, finding the insights that actually move the business forward. But instead, you're chasing receipts and categorizing transactions. It's the opposite of leverage. This is exactly why I'm so bullish on what the team at Ramp has built.
Kareem and Eric understood that every minute spent on manual expense management is a minute stolen from high leverage work. So they automated all of it. Automatic categorization, receipt matching, spending controls that actually work. Check out ramp.com slash invest and see what happens when you eliminate the busy work. Cards issued by Sutton Bank, member FDIC. Terms and conditions apply.
To me, Ridgeline isn't just a software provider, it's a true partner in innovation. They're redefining what's possible in asset management technology, helping firms scale faster, operate smarter, and stay ahead of the curve. I want to share a real-world example of how they're making a difference. Let me introduce you to Brian.
Brian, please introduce yourself and tell us a bit about your role. My name is Brian Strang. I'm the Technical Operations Lead, and I work at Congress Asset Management.
How would you describe your experience working with Ridgeline?
Ridgeline is a technology partner, not a software vendor, and the people really care. I get sales calls all the time and I ignore them. Ridgeline sold me very quickly. We went from 7 billion to 23 billion and the goal is 50 billion. Ridgeline was the clear front runner to help us scale. In your view, what most distinguishes Ridgeline? They reimagined how this industry should work.
It was obvious that they were operating on another level.
It's worth reaching out to Ridgeline to see what the unlock can be for your firm. Visit RidgelineApps.com to schedule a demo. One of the hardest parts of investing is seeing what's shifting before everyone else does. AlphaSense is helping investors do exactly that.
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