Auren Hoffman, Founder and CEO of SafeGraph, discusses all things data business including windfalls and net worth, reputational databases, and the failures and successes of LinkedIn. They explore the challenges of making informed purchasing decisions and the frustrations users face with slow performance on LinkedIn. They also discuss the complexities of matching individuals based on skills and compatibility, second-party data sharing, and the concept of incubators in building data businesses.

Greg Lukianoff, President of FIRE, discusses the current state of cancel culture, revealing surprising stats on schools with the best and worst free speech ratings. They also explore the broader significance of academia, alternative hiring criteria, and the origins of cancel culture in 2014. The conversation touches on the rise of shout downs, the value of elite schools, the decline of free speech on campuses, the varsity blues scandal, and the concept of unhappiness.

Mary Kay Henry, President of the Service Employees International Union, discusses the current surge in the labor movement, recent developments like Microsoft's agreement with unions for game developers, the evolving relationship between Republicans and labor, the effects of immigration on the labor market, and advice for CEOs. They touch on essential workers during the pandemic, the decline of union membership, union endorsements in presidential elections, leadership advice, belief in conspiracy theories, and the importance of taking risks and embracing failure.

Joe Lonsdale, co-founder of Palantir, Addepar and OpenGov, shares his vision for revolutionizing American healthcare and discusses the challenges within higher education. He also delves into the intersection of defense, geopolitics, and technology and redefines the qualities required to be a founder in the entrepreneurship world.

Sam Lessin, GP at Slow Ventures and former Facebook product manager, discusses the state of venture capital, the influence of megafunds like Tiger Global and Softbank, the best areas for investment in 2024, investing in AI, 'weird' investment ideas, and the changing global landscape of tech.

Brian Halligan, CEO of Hubspot, discusses the intricacies of boardroom politics and leadership transitions. He forecasts the future of marketing in the AI age and compares the tech scenes on the West and East coasts. They also touch on CEO transitions, the evolution of marketing, qualities of a good long-term investor, and the importance of writing and communication skills for CEOs.

Data expert Auren Hoffman discusses geospatial data and entity resolution. Topics include complexities of address matching, benefits of using Placekey, challenges of joining data sets, future goals of Placekey, and the importance of celebrating small wins.

Sam Corcos, CEO of Levels, a health tech startup, shares his strategies for delegation and leadership. He discusses the benefits of transparency and building in public. They also touch on personal topics like minimalism and intentional thinking. The podcast explores the role of executive assistants, challenges and benefits of delegation, tracking health data, optimizing diet, limitations of blood tests, connecting after events, and a conspiracy theory about insulin prices.

Jeff Lawson, CEO of Twilio, shares insights into the API economy, scaling successful businesses, and the future of the SaaS business model. They discuss the challenges of integrating communication features into digital products, the rise of the API economy, the evolution of the SaaS industry, collaboration and privacy, conventional wisdom, mastery, and following customers to drive company success.

Spencer Kimball, CEO of Cockroach Labs, discusses the future of open source companies, competing with giants like AWS and Oracle, and offers essential advice for first-time founders. They explore the evolution of open source and open core companies, the decline of Oracle's market share, and the advantages of cloud platforms for databases.