Tom Conrad, former CEO of Zero, discusses lessons from failures at Pets.com and Quibi, along with successful experiences at Apple, Pandora, and Snap. He shares advice on choosing where to work, understanding the math formula of a business, and how to avoid burnout. Tom emphasizes that not everyone needs to be a founder and talks about his current projects.

Paul Millerd, author and host of The Pathless Path Podcast, shares insights on redefining success, finding fulfillment, and taking unconventional career paths. He discusses the default path, signs of being stuck, and how to embrace the pathless path. He advocates for three-month sabbaticals and offers tips on overcoming fear. The podcast explores creating space in life, financial support options, and the importance of reframing. It also tackles the challenges of unenjoyable jobs, constant reinvention, and pursuing unconventional paths in career and life.

Melissa Perri and Denise Tilles, experts in product operations, discuss the role and benefits of product ops in organizations, including offloading certain tasks from product managers. They also highlight successful examples and provide insights on hiring for the role.

Brian Chesky, CEO and co-founder of Airbnb, shares his contrarian approach to product, growth, and leadership. He discusses how Airbnb shifted their thinking on product management, how they moved away from traditional growth channels, and their newly released features. Brian emphasizes the importance of founders diving into the details, setting ambitious goals, and improving reliability and trust on Airbnb. He also talks about the generous nature of successful founders in the tech industry and his journey from being an artist to an entrepreneur.

Ramesh Johari, Stanford professor and startup advisor, discusses marketplace design and optimization. Topics include building successful marketplaces, role of data science, implementing rating systems, and the impact of AI. Also mentioned are experimentation, the launch of the super host badge at Airbnb, and favorite products and life motto.

Maggie Crowley, VP of product at Toast, shares insights on building a broad-based PM skill set, crafting a product strategy, breaking into PM, simplifying writing, and the impact of content creation on her career. She also discusses the qualities of the best product managers and warns against being too data-driven. The podcast covers various topics including simplification, prioritization, feedback and support, the role of a product manager, experimentation, identifying bad ideas, and avoiding unnecessary rewrites.

Bill Carr, co-author of 'Working Backwards', discusses Amazon's unique ways of working including the concepts of working backwards, single-threaded leadership, disagreeing and committing. Other topics include input vs. output metrics, fostering a culture of risk-taking, and the role of a 'bar raiser' in hiring.

Eric Ries, creator of Lean Startup methodology, discusses the current state of Lean Startup, common misconceptions, thinking about MVPs, when to pivot, AI and uncertainty, structuring a company around core values, the Long-Term Stock Exchange, and more.

Paul Adams, CPO of Intercom, shares practical advice on integrating AI, tips for learning AI as a PM, hilarious stories from Google and Facebook, lessons learned from pricing at Intercom, and how Intercom implemented JTBD.

April Dunford, author and expert in sales pitching, shares invaluable insights and tactics on creating effective sales pitches. Topics include crafting a sales pitch for value, helping buyers overcome inertia, importance of differentiated value and insight, walking away from business that's not a good fit, category creation and extending boundaries, the Bowling Pin Strategy, aligning with the customer's point of view, refining sales pitches, exploring different frameworks, the value of writing skills in product marketing, and the perseverance in business.