Bill Gurley spent years on Wall Street, built his career as a partner at Benchmark, worked through Uber’s hypergrowth era, and now serves on the board of the Santa Fe Institute, where he studies complexity and systems thinking. Available Now: YouTube | Spotify | Apple Podcasts | Transcript | X In this episode, Bill shares …

Mark Pincus is the creator behind Farmville and Words with Friends. He built Zynga into one of the biggest gaming companies in the world and helped shape the early era of social products on the internet. Listen Now: YouTube | Spotify | Apple Podcasts | X | Transcript In this conversation, he breaks down how …

Chung Ju-yung built Hyundai because he refused to be stopped. He is known for turning Hyundai into an industrial force that helped transform South Korea. The company built highways, ships, cars, and entire industries. At its peak, Hyundai accounted for 16% of South Korea’s economic output. This episode explores how Chung built Hyundai, how he …

Winston Weinberg is the CEO and co-founder of Harvey, the AI platform built for the legal industry. Available Now: YouTube | Spotify | Apple Podcasts | Transcript In this episode, Winston explains how AI is reshaping legal work, why judgment becomes more valuable as routine work gets automated, and how to build the prioritization muscle …

The AI race, the future of AGI, and the inside story of OpenAI. Greg Brockman is the co-founder and President of OpenAI, the company behind ChatGPT and GPT-5. He was the first engineer at Stripe before leaving in 2015 to help start OpenAI. In this rare conversation, Greg goes inside the moments that built, and nearly …

Mario Harik is the CEO of XPO, one of the largest logistics companies in the world. For years, he was the protege of legendary entrepreneur Brad Jacobs (who built eight multibillion-dollar companies from scratch). Today, Mario leads 40,000 people with a management style shaped by what he learned. It’s a rare combination of smart capital …

Joe Liemandt is the principal of Alpha School and the founder of Trilogy Software and ESW Capital.  Liemandt dropped out of Stanford to build Trilogy, became the youngest member of the Forbes 400, then vanished from public life for 25 years. But he didn’t stop building. Through ESW Capital, he quietly became one of the most prolific …

Harrison McCain learned salesmanship by talking his way into a pharmaceutical job at 22, then spent five years under legendary entrepreneur K.C. Irving, absorbing lessons in vertical integration, relentless determination, and “management by suggestion.” When he quit, he had no plan, no income, and two newborn kids. His brother Bob noticed that New Brunswick potato …

Connor Teskey is CEO of Brookfield Asset Management, one of the world’s largest investors, managing about a trillion dollars across infrastructure, power, real estate, private equity, and credit.   In this exclusive interview, his first as CEO, we explore his approach to capital allocation, isolating variables, and building a business designed for long-term growth. Listen and …

The world’s largest hotel company spent its first 30 years without a hotel. It started as a root beer stand in 1927. The first room didn’t open until 1957. The man behind it was J. Willard Marriott. In this episode of Outliers, we explore how Marriott turned one root beer stand into a hotel empire, …