Episode Summary
Executive Summary: Michael Lewis moderates a candid conversation with Malcolm Gladwell and Jacob Weisberg about founding Pushkin Industries, balancing creativity with business discipline, and adapting podcast production during COVID-19. They discuss why they formed the company, how they divide roles, why storytelling matters more than “podcasting,” and how remote tools and a flexible team have kept production moving.
Main Topics: Why Pushkin Was Founded: Jacob explains that after Panoply shifted away from being primarily a content company, he and Malcolm decided to launch Pushkin to focus on shows they truly wanted to make. Friendship, Roles, and Decision-Making: The trio explores how long-standing friendships shape the business, with Malcolm as idea generator and Jacob as filter/operator, and Michael noting the depth of trust between them. Creative Business vs. Podcast Business: They argue Pushkin should be understood as a storytelling company using audio, not just a podcast company, which opens up larger ambitions similar to book publishing. COVID-19 and Remote Production: The conversation covers how the pandemic forced remote work, virtual meetings, at-home studios, and adaptation in reporting, while also revealing unexpected benefits of digital collaboration. Company Culture and Core Values: They emphasize fun, kindness, integrity, and diversity as foundational values, arguing that a healthy culture is essential to recruitment, retention, and quality work. Growth, Hiring, and Strategic Constraints: They debate whether to stay nimble and small or grow larger, noting that hiring quality people is crucial and that thoughtful constraints can strengthen creativity and focus.
Key Arguments: Pushkin was created to regain control over editorial direction after Panoply’s mission drifted toward technology. The company’s real identity is storytelling, not merely podcasting, which means it can scale like a publishing house rather than a niche media startup. Malcolm and Jacob’s friendship functions as a business advantage because they trust each other enough to divide labor based on strengths. Jacob’s role is to translate Malcolm’s abundance of ideas into executable decisions, preventing overexpansion and distraction. The pandemic did not stop podcast production because audio is adaptable, writers can rewrite around lost field reporting, and remote tools made collaboration possible. Fun, kindness, and ethical workplace behavior are not soft extras; they are central to making good creative work and keeping talented people. Hiring is existential for a small creative business because one great employee can transform a function and one poor hire can disrupt culture.
Data Points: Years of friendship: 35 years - Malcolm says he has known Jacob for 35 years and reflects on long-standing trust. Target company size vs. hypothetical expansion: 25 staff vs. 600 staff - Jacob contrasts Pushkin’s current size with how large it might become if they pursued all ideas. Office timeline: A week before COVID-19 closed it - Jacob says the company moved into its new New York office just before lockdown. Offices used: 5 offices in about a year and a half - Jacob notes frequent office changes, including home office and temporary spaces. Season progress: 5 of 7 episodes completed - Michael mentions he has nearly finished the second season but has one episode disrupted by travel restrictions.
Pivotal Quotes: "If we're not having fun, we shouldn't do it. It shouldn't be drudgery." — Malcolm Gladwell: Founding principle of Pushkin’s company culture and creative process. "We're not really in the podcast business. We're, you know, it's a cliche. We're in the storytelling business." — Malcolm Gladwell: Explaining Pushkin’s broader mission and why audio is just the medium, not the identity. "I handle more of the day-to-day, as they say. But honestly, at this point, more of the ideas come from Malcolm." — Jacob Weisberg: Describing the division of labor between operator and creative lead.
Implications: Pushkin’s model suggests audio startups can scale by prioritizing storytelling, culture, and adaptability. The conversation also shows how remote production and strong teams can preserve creative output during disruption.
About Against the Rules
Michael Lewis’s best-selling book The Big Short is now 15 years old. The Oscar-winning movie based on it came out a decade ago. To mark the occasion, Lewis has narrated a new audiobook of The Big Short. Here on his podcast, he and co-host Lidia Jean Kott are thinking about the legacy of the book, the movie, and the financial crisis of 2008. Michael catches up with the director of the movie, Adam McKay, as well as some of the real-life characters depicted by the likes of Ryan Gosling, Steve Carell and Jeremy Strong. He also calls up journalists, economists, and historians to make sense of the 2008 financial crisis and to understand how it still affects the world today.