

Generationship
Heavybit
Exploring the intersection of infrastructure and artificial intelligence.
Episodes
Mentioned books

Mar 18, 2026 • 30min
Ep. #53, The Era of Reimagination with Dr. Mehdi Nourbakhsh
On episode 53 of Generationship, Rachel Chalmers sits down with Dr. Mehdi Nourbakhsh to explore how artificial intelligence is transforming the physical and digital worlds. They discuss the origins of generative design, why many AI initiatives fail inside organizations, and how leaders can move beyond experimentation toward real adoption. Mehdi also shares practical enterprise AI use cases and his perspective on how AI can augment human decision-making.The post appeared first on Heavybit.

Feb 18, 2026 • 21min
Ep. #52, Serendipity as a Service with Piyush Agarwal
On episode 52 of Generationship, Rachel Chalmers sits down with Piyush Agarwal to explore how developer behavior reveals far more about buying intent than traditional sales signals. They discuss why most dev tool GTM strategies fail, how to distinguish curiosity from real demand, and what it takes to engage developers at exactly the right moment.The post appeared first on Heavybit.

Jan 21, 2026 • 23min
Ep. #51, AI for Best Practices with Soya Park
On episode 51 of Generationship, Rachel Chalmers sits down with Soya Park of Akify to explore why an organization’s most valuable knowledge rarely makes it into formal systems. They discuss how leaders make excellent decisions every day without realizing it, and how AI can surface, reinforce, and scale those best practices without disrupting existing workflows.The post appeared first on Heavybit.

Dec 22, 2025 • 46min
Ep. #50, Defense Against Deepfakes with Joshua McKenty
In episode 50 of Generationship, Rachel Chalmers sits down with Joshua McKenty to unpack how AI-driven scams, deepfakes, and identity fraud are already reshaping our digital lives. From scam factories and nation-state actors to broken trust infrastructure, Josh explains why authenticity is the core problem, and what it will take to fix it. The conversation spans cybersecurity, public policy, and the future of human trust in an AI-saturated world.

Dec 10, 2025 • 35min
Ep. #49, Dumpster Phoenix with Denise Koessler Gosnell and Kathryn Erickson
On episode 49 of Generationship, Rachel Chalmers sits down with Denise Koessler Gosnell and Kathryn Erickson to unpack their new book Tech Confidential. Together they explore burnout, leadership, motivation, and the surprising ways our emotional wiring shapes tech culture. It’s a candid, deeply human conversation about transforming toxic systems into something resilient, sustainable, and even joyful.

Nov 26, 2025 • 40min
Ep. #48, Trusting AI with Sarah Novotny
In episode 48 of Generationship, Rachel Chalmers speaks with Sarah Novotny. They dig into why AI models fall short of true creativity, how the tech industry drifted into extractive incentives, and what real security and accountability might look like at scale. Sarah highlights lessons from Kubernetes, open source ecosystems, and political science to propose a more trustworthy technological future.

Nov 13, 2025 • 33min
Ep. #47, The Tech Bros with Milette Gillow and Sedinam Simpson
In episode 47 of Generationship, Rachel Chalmers chats with Dr. Milette Gillow and Sedinam Simpson, co-founders of The Tech Bros, about their mission to make tech more inclusive and inventive. They unpack lessons from their first accelerator cohort, debate the future of AI, and share what it takes to build confidence and community in an evolving industry.

Oct 30, 2025 • 40min
Ep. #46, Canned Monkeys with Don Marti
In episode 46 of Generationship, Rachel Chalmers and Don Marti trace a thoughtful arc from the open source protests of the 1990s to today’s AI-driven world. They explore how large language models blur truth and plausibility, debate ethics in benchmarking and market-based definitions of intelligence, and mourn the loss of the web’s early democratizing promise. Don discusses sustainable open source ecosystems, AI tooling, and practical advice for new graduates navigating an AI-saturated job market.

Oct 16, 2025 • 29min
Ep. #45, Perspective Density with Allegra Guinan of Lumiera
In episode 45 of Generationship, Rachel Chalmers speaks with Allegra Guinan of Lumiera about the trust dynamics and design ethics of voice-based AI. Together they explore how human tendencies to anthropomorphize voice systems can both build and erode trust, underscoring the need for responsible design and diverse perspectives.

Sep 22, 2025 • 24min
Ep. #44, Why Unikernels Are Cool with Felipe Huici of Unikraft
In episode 44 of Generationship, Rachel speaks with Felipe Huici, CEO and co-founder of Unikraft, about the powerful world of unikernels. Felipe breaks down how these lightweight, specialized VMs can achieve millisecond cold starts, enabling services to truly "scale to zero" without users noticing a delay. Learn how this efficiency is not just about saving money, but also about providing a secure and scalable foundation for the next wave of AI-generated applications.


