In Depth

Anastasis Germanidis, Co-Founder & CTO at Runway, discusses the origins of Runway, limitations of being 'customer-driven' in AI, balancing research development with product development, goal-setting for AI products, and advice for early-stage AI founders.

Guillermo Rauch, CEO of Vercel, discusses his path into tech, the journey of building Cloudup and its impact on WordPress, the importance of simplification in business, finding the balance between developer and user experience, the benefits of using Red Panda, the value and positioning of the Vercel platform, AI code behavior, and the importance of simplification and saying no.

Ashley Kramer, CMO and CSO at GitLab, discusses how GitLab monetizes open source roots, marketing metrics, transparent company culture, serving enterprise customers, unique marketing lessons from open core company, and a recent marketing campaign.

Colin Zima, former Chief Analytics Officer and VP of Product at Looker, discusses lessons from Looker, investing in white-glove customer support, scaling high-touch customer support, intuition-based approach to product, Looker's goal achievement streak, founding story of Omni, and hot takes on startups and hiring PMs.

Wade Foster, Co-founder & CEO at Zapier, discusses the unorthodox decisions behind Zapier's success, their powerful distribution engine, and the impact of Veterans United. He shares insights on product market fit, fundraising, and people management. The podcast explores unconventional strategies, adapting to change, and the importance of intellectual honesty.

Laura Behrens Wu, Founder & CEO at Shippo, talks about the company's pivot-stricken origin story, finding product-market fit multiple times, unique take on founder-market fit, advice on talking to users, prioritizing resources using the 3 Horizons Framework, and the impact of unfiltered emails on team connection.

Dan Siroker, CEO at Rewind AI and co-founder of Optimizely, discusses Rewind's journey to Product Market Fit, lessons from Optimizely, his unique Twitter fundraising strategy, hot takes on the future of AI, and where to build in AI. They also explore the current state of AI and excitement surrounding large language models. The chapter on fundraising through Twitter explains the reasons and strategies used. Lastly, Dan shares future plans of Rewind AI and lessons on building a product people want.

Ryan Glasgow, CEO and founder of Sprig, and Kevin Mandich, Head of Machine Learning at Sprig, discuss key lessons from Sprig's founding story, product development in the pre vs. post-LLM world, how to overcome AI skepticism, evaluating new models, the importance of ML engineers, Sprig's 'AI Squad' team structure, and upskilling team members on AI.

Saumil Mehta, GM of Square’s flagship point-of-sale business, discusses the principles of effective org design, signs your company needs a re-org, Square’s GM-led org design, and lessons on incentive-design, pricing, planning, and decision-making at scale. He also shares the step-by-step process behind a recent re-org at Square and 5 lessons from Alyssa Henry, CEO at Square.

Guest Kellan Elliott-McCrea, Head of Engineering at Adobe, previously VPE at Dropbox and CTO at Etsy, discusses the changes in software engineering, the future of AI, achieving alignment, enabling engineering productivity, culture lessons from Adobe, Dropbox, and Flickr, tips for better management, and rituals for building business literacy throughout an organization.