Ryan Petersen (@typesfast) is the founder and CEO of Flexport, the platform that coordinates global logistics from factory floor to customer door. In this conversation, he’s refreshingly transparent about the mistakes and painful lessons he’s learned building several companies.  He opens up about stepping down as CEO, his struggles with self-confidence, and what happened when …

When Katharine Graham took over the Washington Post in 1963, she was a shy socialite who’d never run anything. By retirement, she’d taken down a president, ended the most violent strike in a generation, and built one of the best-performing companies in American history. Graham had no training, no experience, not even confidence. Just a …

Daniel Kahneman (1934 to 2024) won the Nobel Prize for proving we’re not as rational as we think. We discuss how to think clearly in a world full of noise, the invisible forces that cloud our judgement, and why more information doesn’t equal better thinking. Kahneman also reveals the mental model he discovered at 22 that still guides elite …

Charlie Munger once asked me: ‘How can someone give away fifty percent of profits and make billions more than if he’d kept it all?’ Before I could answer, he told me about Les Schwab, a tire shop owner who understood incentives better than almost anyone.  What Schwab discovered will change how you think about business. …

What does it mean to live – and lead – with intention?  Shopify President Harley Finkelstein explores what happens when you treat every role in your life—father, husband, leader—as something you have to requalify for, every single year.  It’s a candid look at ambition, identity, and the challenge of holding yourself to a higher standard—everywhere …

At 96 years old, Jimmy Pattison still runs his $16 billion empire personally. He’s built it over 63 years without outside capital or a college degree. He owns 100% of car dealerships, billboards, radio stations—even Ripley’s Believe It or Not—with a philosophy of: “No partners, no shareholders, no relatives.” This episode is based on Jimmy: …

On her first day as CEO of PepsiCo, Indra Nooyi fired her general counsel. Then rehired him before dinner. It wasn’t a stunt. It was a signal. She ran a $200 billion empire the same way she ran her life: with surgical precision, uncompromising standards, and an allergy to corporate theater. But here’s what separates this conversation from every …

The job was editor-in-chief. The goal was to become the platform. And she did. Once she made it to the top, she didn’t just edit Vogue. She reinvented the power structures beneath it. This episode unpacks how a British girl who couldn’t type built the most bulletproof career in media, survived five decades of disruption, …

How do you build a high-performance culture without turning your company into the Hunger Games? Reed Hastings, co-founder and former CEO of Netflix, shares lessons from a career spent rewriting the rules—from severance as a management tool to “big-hearted champions who pick up the trash.” In this episode, he reveals how Netflix scaled trust, made …

Harvey Firestone built one of America’s great industrial empires from scratch, transforming from a farm boy to Henry Ford’s key partner. This episode reveals timeless principles about building businesses through booms, busts, and technological disruptions. Available now: Apple Podcasts | Spotify | Transcript The episode is based on his biography: Men and Rubber: The Story …