Capitalism, Chaos, Creativity & Why Weirdos Win | Rory Sutherland

In this episode of Branded Leaders, host Ben Kaplan sits down with Rory Sutherland, Vice Chairman of Ogilvy UK, to explore why safe, logical marketing often fails — and why embracing chaos, irrationality, and unconventional thinking can create the biggest wins. Rory explains why capitalism is less about efficiency and more like betting on long shots, how seemingly “bonkers” decisions (like Amazon betting on Prime) can redefine entire industries, and why reframing simple observations is the real engine of creativity. The conversation dives into politics, persuasion, and the psychology of risk-taking — from Donald Trump’s use of concrete language, to Elon Musk’s non-neurotypical way of seeing the world, to why opportunity cost is more important than cost-cutting. Packed with humor, sharp insights, and provocative reframes, this episode is a masterclass in why playing it safe may be the riskiest move of all.