Masters of Scale

Fawn Weaver, founder of Uncle Nearest Whiskey and bestselling author who built a billion-dollar spirits brand, shares her journey. She reveals how uncovering a hidden story turned into a movement. She discusses choosing mentors, blending life with business, reframing fear of failure as public embarrassment, and how love fuels resilience.

Reid Hoffman, LinkedIn co-founder and AI investor, shares bold thinking on AI and leadership. He discusses making AI music to probe creativity. He talks about AI reshaping art, healthcare, and company strategy. He stresses the need for CEOs to speak up and for smart regulation, immigration policy, and energy planning to shape AI’s future.

Sean White, CEO of Inflection AI and human-computer interaction expert, discusses designing pro-social AI agents. He covers transparency so people don’t mistake AI for humans. He explores Socratic conversational designs that support ongoing exploration. He highlights AI’s role in education, attention and executive function, and broader system designs beyond foundation models.

Maya Shankar, a cognitive scientist and former behavioral advisor in the Obama White House, shares her journey from aspiring violinist to expert in change. She emphasizes reframing identity around core values rather than loss, leveraging behavioral insights to drive results in both government and personal life. Maya discusses practical tools for resilience, including tiny, identity-building actions and self-affirmation strategies. Her insights on awe and moral beauty highlight how witnessing kindness can rejuvenate our paths after adversity.

David Holt, the Mayor of Oklahoma City and president of the U.S. Conference of Mayors, offers insights into effective urban governance. He discusses the unique, less polarized role of mayors compared to federal politicians. Holt highlights Oklahoma City's growth strategies, like the transformative MAPS program. He emphasizes bipartisan approaches to problem-solving and the importance of collaboration with businesses. Holt also touches upon the necessity of controlled immigration for economic growth and how cities can combat societal polarization through pluralism.

Nicholas Thompson, CEO of The Atlantic and former editor at Wired, discusses his successful turnaround of the magazine from financial trouble to profitability. He shares insights on innovative paywall strategies and AI partnerships, emphasizing a pragmatic approach over legal battles. Thompson also connects lessons from long-distance running to leadership, highlighting the importance of mental resilience and coaching. His memoir, The Running Ground, explores family and personal growth, revealing how running shaped his perspective on ambition and potential.

Michael Miebach, the CEO of Mastercard, explores the latest holiday shopping trends revealing a 3.9% growth amidst changing consumer sentiments. He discusses the integration of AI in enhancing financial security, addressing risks like fraud and deepfakes. The conversation dives into the impact of crypto and digital wallets on traditional credit cards and the rise of agent-driven commerce. Miebach emphasizes the importance of trust and protection in payments, while also highlighting innovations like universal tokenization by 2030.

In this conversation, Co-CEOs Norah Weinstein and Kelly Sawyer Patricof of Baby2Baby share incredible insights on navigating the LA wildfires. They discuss their emotional and logistical challenges while mobilizing disaster relief efforts. From organizing community volunteers to packing essentials, their rapid response showcased the power of partnerships. With a focus on advocacy, they reveal their fight against diaper tax and how they manage ongoing demand. Listeners learn how they expanded beyond LA and transformed a gala into a significant funding engine.

Caitlin Smith, the founder of Simple Mills, shares her inspiring journey from apartment-kitchen experiments to a booming health food brand. She discusses her early days of cold-calling Whole Foods and bootstrapping packaging. Caitlin reveals the emotional weight of her parents mortgaging their home to support her vision and reflects on the challenges of scaling a startup. With an emphasis on clean ingredients and innovation, she explains why selling to Flowers was a strategic move for growth. Her insights on continuous learning are golden for aspiring founders.

In a forward-looking discussion, the host lays out intriguing predictions for 2026. Highlights include concerns over AI hype potentially stalling tech stocks, and how market pressures may lead to premature AI investments. Cybersecurity risks are set to escalate as AI lowers attack costs for hackers. Bob argues for a hopeful outlook on immigration policies that could attract talent and anticipates significant advancements in nuclear and fusion energy. The World Cup emerges as a prime opportunity for the U.S. to enhance its global brand.