Masters of Scale

Join Brian Chesky, CEO of Airbnb, Sallie Krawcheck, CEO of Ellevest, and Franklin Leonard, founder of The Blacklist, as they reflect on the emotional challenges of entrepreneurship. They discuss overcoming self-doubt, the importance of trust within teams, and the power of storytelling in both business and film. Chesky shares his insights on creating connections with customers, while Krawcheck emphasizes the value of diverse networks. Leonard highlights how authentic narratives can transform the entertainment industry, driving home that successful entrepreneurship is rooted in genuine human connections.

John Doerr, a prominent venture capitalist and author of "Speed and Scale," discusses the imperative for businesses to combat climate change. He emphasizes that decarbonization is not just necessary but represents 'the greatest economic opportunity of the next century.' Doerr explores strategic approaches for various sectors to achieve net-zero emissions and underscores the importance of collective corporate action. He also shares insights on effective measures like transparent emissions labeling and the innovative 'Lobatical' initiative to boost employee well-being.

Marc Lore, a serial entrepreneur and founder of Diapers.com and Jet.com, dives into the exhilarating world of risk-taking. He discusses the importance of building a team and securing customer trust when making bold leaps in business. Lore shares humorous anecdotes from his journey, from starting e-commerce ventures to his vision for Telosa, a city built from scratch. He emphasizes that collaboration is key to success and explains how strategic thinking and innovative engagement are crucial when challenging industry giants like Amazon.

Marc Andreessen, an early internet pioneer and venture capitalist, shares his insights on the critical role of timing in entrepreneurship. He discusses how getting timing right can propel a startup while the wrong timing can lead to its downfall. Drawing from personal experiences, he highlights six key strategies for successful timing decisions. The conversation also touches on the lessons learned from innovative failures, the importance of supporting unconventional ideas, and how personal stories can shape actions and connect communities.

Barack Obama, the former president known for his grassroots organizing and transformative political leadership, shares insights with Reid Hoffman. He discusses the connection between politics and entrepreneurship, emphasizing the importance of strategic patience and belief in a better future. Obama reflects on his rise from community organizer to a national political figure, detailing the innovative strategies that fueled his 2008 campaign. Highlights include the birth of the 'Yes We Can' anthem and navigating the pivot from campaigning to leading a large government entity.

Janet Hayes, CEO of Crate & Barrel Holdings, has been at the forefront of modernizing the retail giant since 2020. In a world disrupted by COVID-19, she emphasized flexibility, valuing results over location, which transformed employee productivity. The discussion covers the challenges of supply chain issues and the importance of empathy in communication. Hayes also highlights the significance of integrating digital strategies, sustainable practices, and unique employee initiatives like the ‘Lobatical’ for enhancing customer experience.

In a lively strategy session, entrepreneurs tackle pressing issues like protecting against copycat businesses and seeking funding. There's a fascinating discussion on how the pandemic reshaped a cheese shop owner's business, emphasizing the adaptability required for survival. The podcast features a unique game show where participants devise creative pivot strategies, alongside insights into targeting the right investors. Lastly, the importance of employee well-being is highlighted with an innovative sabbatical program that links care to better customer experiences.

Tim Cadogan, CEO of GoFundMe, shares insights on how the platform has facilitated an astonishing $15 billion in giving. He discusses the spike in donations during the pandemic and the emotional bonds formed through crowdfunding. Cadogan emphasizes the importance of community support and the company’s unique focus on people helping each other rather than just transactions. He also touches on the need for adaptability within businesses and how asking for help can unlock new avenues for success.

Paul Polman, former CEO of Unilever, shares insights from his tenure where he transformed the company by emphasizing sustainability and long-term growth. He discusses the importance of redefining boundaries to invigorate teams and drive performance. Polman highlights how shifting corporate purpose from short-term profits to societal impact can lead to greater accountability and success. His experiences underscore that true change requires not just a focus on mission but also on the boundaries that shape behavior within organizations.

Fidji Simo, CEO of Instacart and former head of the Facebook app, dives into her journey transitioning from tech titan to grocery innovator. She discusses redefining Instacart’s mission amid evolving consumer expectations, highlighting the need for technology in grocery retail. The conversation covers challenges like ultra-fast delivery services and focuses on gender diversity in leadership. Additionally, Fidji emphasizes the importance of storytelling in leadership, along with plans to enhance accessibility and health initiatives in grocery delivery.