Generationship

In episode 43 of Generationship, Rachel explores the frontier of AI-driven cybersecurity with John Amaral, co-founder of Root.io. Together they unpack the promise and challenges of agentic systems th…

In episode 42 of Generationship, Rachel Chalmers speaks with Katie Hallett about why she and her team decided to build a web browser for machines, not humans. Katie explains the inefficiencies of tra…

In episode 41 of Generationship, Brighthive CEO Suzanne EL-Moursi joins Rachel Chalmers to unpack the “three-layer cake” of modern data architecture: composable stacks, agentic AI, and governance-fir…

In episode 40 of Generationship, Salma Mayorquin of Remyx AI unpacks the shift from traditional MLOps to ExperimentOps—a framework for scaling insight in modern AI development. With stories from Netf…

In episode 39 of Generationship, Rachel speaks with Simon Willison, founder of Datasette and co-creator of Django. Simon discusses the surprising resurgence of blogging, his coining of the term “prom…

In episode 38 of Generationship, Rachel Chalmers sits down with Heidi Waterhouse, co-author of "Progressive Delivery." They unpack what Progressive Delivery means as an extension of continuous delive…

In episode 37 of Generationship, Rachel Chalmers chats with Latrice Barnett and Kanika Chander from Majority Collective about their mission to empower underrepresented founders. The conversation cove…

In episode 36 of Generationship, Rachel Chalmers speaks with Christine Spang about the past, present, and future of enterprise software, with a particular focus on AI. Spang shares her experiences bu…

In episode 35 of Generationship, Rachel is joined by Brooke Hopkins to explore what it takes to make voice AI agents reliable, robust, and ready for real-world deployment. Drawing from her experience…

In episode 34 of Generationship, Nathen Harvey brings data, humor, and heart to a conversation about AI, DevOps, open source, and developer experience. He and Rachel dive into how AI is influencing s…

In episode 33 of Generationship, Rachel Chalmers is joined by Nicole Forsgren—developer productivity researcher and co-founder of DORA—to discuss how AI is reshaping the software development landscap…

In episode 32 of Generationship, Rachel speaks with Marcel Kornacker, creator of Pixeltable and a pioneer in database technology. They discuss how AI engineers can streamline data management, the cha…

In episode 31 of Generationship, Rachel Chalmers welcomes Deepti Srivastava, a trailblazer in enterprise technology and founder of Snow Leopard. Deepti discusses how her experiences with Oracle and G…

In episode 30 of Generationship, Rachel welcomes Ty Dunn to explore his journey and insights as the Co-founder and CEO of Continue, a company focused on creating AI tools to amplify developers rather…

In episode 29 of Generationship, Rachel chats with Leslie Fine, managing partner at Enjoy The Work. With a background in game theory, behavioral economics, and startup leadership, Leslie shares insig…

In episode 28 of Generationship, Rachel Chalmers speaks with Emily Mackevicius about intelligence in all its forms—from songbird learning to group cognition in subway rats and humans. Emily explains …

In episode 27 of Generationship, Rachel is joined by Melody Meckfessel, an industry veteran and CTO of Jasper AI, to discuss the rapidly changing landscape of AI-driven development. From the evolving…

In episode 26 of Generationship, Rachel Chalmers speaks with Rita Scroggin, founder of FirstBoard, to discuss the pressing need for diversity in leadership. Rita shares how her curated collective of …

In episode 25 of Generationship, Rachel Chalmers speaks with Melinda Byerley, founder and CEO of Fiddlehead, about the transformative role of AI in marketing. From practical applications to ethical c…

In episode 24 of Generationship, Rachel Chalmers speaks with Dr. Desiree-Jessica Pely and Jacqueline-Amadea Pely, co-founders of LoyeeAi. The sisters share insights on how AI and behavioral economics…