On episode 54 of Generationship, Rachel Chalmers sits down with Vishakha Gupta to explore the hidden infrastructure challenges behind modern AI. They unpack why multimodal data systems are still fragmented, how graph and vector approaches can be unified, and what it takes to build production-ready AI pipelines. This conversation offers a systems-level perspective on scaling AI beyond prototypes.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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 that detect, patch, and remediate vulnerabilities automatically. This installment offers a mix of technical deep dives, AI optimism, and a vision of security that works more like an immune system than a fire alarm.

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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 traditional scraping tools, why Lightpanda is so much faster, and how AI is reshaping developer workflows. They also offer career advice to help new graduates stay ahead in the AI era.

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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-first design. From integrating hundreds of data sources to enforcing real-time compliance, Suzanne shares how her team is tackling the grunt work of data so humans can focus on innovation. Plus, her vision for turning every organization—big or small—into a data powerhouse.

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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 Netflix, Yelp, and Stripe, she explains how teams are bringing foundation models into production and what it takes to keep up. If you're grappling with LLMs, MLOps, or decision paralysis in GenAI, this one’s for you.

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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 “prompt injection,” the power of learning in public, and how he uses GitHub issues as an external brain to manage hundreds of projects. This quick-witted and humorous conversation offers a pragmatic look at leveraging today's tools for maximum productivity and impact.

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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 delivery, focusing on the crucial role of user experience in software development. Discover fresh insights on user autonomy, the pitfalls of uninvited AI, and how to bring empathy back into the software lifecycle.

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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 covers the practical benefits of fractional expertise, the importance of defining clear company strategies, and a thought-provoking exchange on the opportunities and pitfalls of artificial intelligence in shaping the future of entrepreneurship.

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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 building Nylas and discusses the practical applications of AI in business, as well as the ethical considerations surrounding its use. Lastly, they explore the social and cultural impact of AI, pondering its effects on human connection and the perception of reality.

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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 at Waymo and her current work at Coval, Brooke reveals how testing and evaluation are the key to staying ahead in a fast-moving AI landscape.

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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 software engineering, the role of platform engineering, metrics for assessing performance, and broader reflections on engineering culture and career growth.

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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 landscape. From coding with LLMs to evaluating trust in AI-generated outputs, they explore the future of developer experience and the enduring value of human intuition.

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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 challenges of founding a startup, and the future of generative AI in software development. Marcel also shares insights from his career journey and how AI is reshaping the way we work with multimodal data.

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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 Google Spanner inspired her mission to help businesses leverage live data for AI applications. Learn about the challenges of integrating AI, the myths of data unification, and the promise of generative AI.

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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 than automate them out of their roles. Ty unpacks his background, the motivations behind founding Continue, the trajectory of AI-driven software development, and the philosophy of open source technology.

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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 insights into transitioning from founder to CEO, aligning incentives for organizational success, and the transformative potential of AI. Don’t miss her practical advice for technical founders navigating leadership challenges.

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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 how her research connects the dots between neuroscience, AI, and our ability to collaborate, envisioning a future where technology amplifies collective problem-solving.

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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 role of developers to the challenges of building trust in AI systems, Melody shares her vision for a collaborative, human-centered future in tech.

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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 female tech leaders is helping boards navigate AI disruption while tackling global challenges like cybersecurity, climate change, and health tech. Discover actionable insights for the future of leadership and collaboration.

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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 considerations, Melinda shares how AI enhances productivity, democratizes analytics, and addresses the challenges of building trust in marketing. Discover actionable insights and the human side of AI innovation in this thought-provoking conversation.

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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 can be used to improve decision-making in sales and beyond, while discussing the potential benefits and risks of large language models. Tune in for a thoughtful conversation on the future of AI, human collaboration, and responsible innovation.

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In episode 23 of Generationship, Rachel Chalmers welcomes Timothy Chen, managing partner at Essence VC, for a deep dive into the startup ecosystem. Timothy discusses the challenges founders face when raising capital and why traditional VC support often falls short. He also explores the importance of culture in startup success, the overhype surrounding AI, and his philosophy of working closely with founders to guide them through critical early stages.

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In episode 22 of Generationship, Rachel Chalmers speaks with Elijah Ben Izzy, CTO at Dagworks. Elijah emphasizes the importance of streaming in chatbot interactions, highlighting how partial, real-time responses can significantly enhance user engagement. The discussion covers Burr, which simplifies AI workflows through state machines, and explores its use in debugging and complex AI/ML systems. Elijah also shares his thoughts on the sustainability of AI's hype and its energy demands, offering a balanced view on the future of this rapidly evolving field.

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In episode 21 of Generationship, Rachel Chalmers is joined by Dr. Maia Hightower of Equality AI. Dr. Hightower dives into the transformative potential of generative AI in healthcare, discussing both its promise for underserved populations and the risks of algorithmic bias. Discover how responsible AI can drive health equity and the importance of diverse perspectives in shaping technology's role in medicine.

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In episode 20 of Generationship, Rachel Chalmers is joined by Salma Mayorquin and Terry Rodriguez of Remyx AI. Together they unpack Remyx's mission to democratize machine learning by addressing common hurdles like data scarcity and resource limitations. The episode also highlights the critical balance between automation and human judgment, emphasizing the need for AI to handle repetitive tasks while humans focus on creativity and decision-making.

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In episode 19 of Generationship, Rachel Chalmers is joined by Stefan Krawczyk, co-founder and CEO of DAGWorks. They dive into Hamilton and Burr, shedding light on how they revolutionize data workflows and AI code auditability. From the genesis of these frameworks to their practical applications, Stefan shares insights on how they help data practitioners reason across complex functions and ensure transparency and accountability. Discover how Hamilton's graph structure simplifies auditability and why Burr's white-box approach is gaining favor.

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In episode 18 of Generationship, Rachel Chalmers sits down with Shawn "swyx" Wang to delve into AI Engineering. Shawn shares his journey from popularizing the term "AI Engineer" to navigating the rapid advancements in AI technology. Together, they explore the evolving demands and opportunities in AI, offering unparalleled insights into the future of this transformative field.

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In episode 17 of Generationship, Rachel Chalmers is joined by futurist and AI expert Mark Pesce to explore the complex intersection of AI-generated code and copyright law. Mark shares insights from his recent experiments with language models and discusses the flaws he uncovered in AI transformers. Tune in to hear about the challenges of reporting AI issues, the impact of AI hallucinations, and the future of this evolving technology.

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In Episode 16 of Generationship, Rachel Chalmers hosts Raiya Kind, PhD. Together they delve into the human-AI paradigm through the lenses of philosophy, psychology, and cultural anthropology. Discover how Raiya's work with language and consciousness sheds light on the mind-body connection and the environmental impact of AI.

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In episode 15 of Generationship, Rachel Chalmers sits down with Gülin Yilmaz of Rosette Health. This episode dives into the current state of healthcare in the US and discusses how large language models (LLMs) can play a crucial role in enhancing patient-provider communication and education. Gülin shares insights on mitigating the risks of AI hallucinations, the pros and cons of AI hype, and the transformative potential of AI tools in improving diagnostic speed and accuracy. Discover how technology is reshaping the role of healthcare professionals and empowering women to access top-tier care, regardless of their location or income.

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In episode 14 Generationship, Rachel welcomes Walter Roth, a distinguished sales coach and mentor. Walter discusses the transformative role of generative AI in sales, from altering buyer-seller dynamics to enhancing the founder-led sales flywheel. He shares lessons from his months-long immersive study of LLMs, offering key insights into using AI as a powerful assistant in coaching and accelerating sales impact. Walter also addresses the future of sales coaching in the AI age, the balance between automation and human connection, and his favorite AI learning resources. Tune in for a thought-provoking conversation about the exciting and challenging future of sales training.

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In episode 13 of Generationship, Rachel Chalmers and Archita Mandal explore the transformative effects of generative AI across creative industries. They explore the ways GenAI boosts productivity, democratizes creativity by lowering production costs, and is revolutionizing the film industry.

Archita continues to unpack her journey as a founder and CEO, sharing insights on the customer discovery process, product-market fit, and the challenges early-stage startups face, offering a unique perspective on the investor side of AI, including the hype and realities of fundraising. Join Rachel and Archita for a deep dive into the societal impacts of AI and its role as a co-pilot for innovation and storytelling.

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In episode 12 of Generationship, Rachel Chalmers sits down with Lilly Ryan, an Information Security specialist based in Australia, to delve into the intricate world of generative AI and its potential misuses. Together they unpack the nuances of prompt injection and other adversarial attacks, shedding light on the dark side of AI technology. They discuss countermeasures to technological colonialism, strategies for maintaining a human-centered web, and the evolving role of AI in our workplaces. Tune in to explore the fascinating intersections of security, technology, and human interaction in the age of AI.

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In episode 11 of Generationship, Rachel is joined by Adio Dinika of The DAIR Institute to discuss ghost workers. This talk examines the challenges faced by platform laborers around the world, including unfair compensation, job insecurity, and data rights violations. Additionally, they explore the community-rooted AI research that's being done at The DAIR Institute.

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In episode 10 of Generationship, Rachel Chalmers and Dr. Marie Oldfield explore ethical benchmarks in AI. This conversation sheds light on professional accreditation for AI practitioners and offers unique insights on mitigating societal risks while building better AI models. Additionally, Marie shares lessons learned from her expansive career journey across Government, Defense, Legal, and Tech.

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In episode 9 of Generationship, Rachel Chalmers speaks with technology expert Michelle Yi. This conversation examines how generative AI will change the future of work. Together they explore topics like the philosophy of work and productivity, the advent of multi-agent systems, and what to consider when investing in AI.

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In episode 8 of Generationship, Rachel Chalmers speaks with Josh Furstoss of Incued about the promise of generative AI. This talk explores the considerations founders must make before incorporating generative AI into their products, and the potential impact AI will have on financial decision-making in the future.

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In episode 7 of Generationship, Rachel speaks with Wei Lien Dang of Unusual Ventures about the landscape of Generative AI and what it means from an investment standpoint. They analogize previous platform shifts to better understand what’s happening with LLMs today, and together they unpack the qualities investors seek out when investing in the world of AI.

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In episode 6 of Generationship, Rachel Chalmers speaks with Mark Wallace of Global Worldwide. The conversation kicks off with a deep dive on Mark’s philosophical stance that LLMs are actually thinking. Additionally, they explore the risks of using commercial LLMs, the difficulty of fine-tuning LLMs, and the crossroads of game infrastructure and generative AI.

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In episode 5 of Generationship, Rachel Chalmers shares interviews from Heavybit’s 2023 DevGuild: AI Summit on October 19th, 2023. This Open Space unconference brought together a community of 200+ to discuss how AI will change the face of software development. This episode features event highlights and insights from industry experts: Christine Spang of Nylas, Heidi Waterhouse of Sym, Paul Biggar of DarkLang, Raiya Kind of Code and Concept, and Seema Patel of Stifel Venture Banking.

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In episode 4 of Generationship, Rachel speaks with Michael Sawka of Wave Terminal (known as Command Line Inc. at the time of this recording). This talk focuses on the terminal, how easily it’s overlooked, and what’s missing from the terminals we use today. Other topics explored include the security implications of commercial LLMs, the risks AI poses to programming as an occupation, and the hard lessons Michael learned on the journey to building Wave Terminal.

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In episode 3 of Generationship, Rachel speaks with Steven Schkolne of MightyMeld. They discuss cultural myths surrounding AGI, theories on machine consciousness, philosophical insights on how humans might hybridize with machines, Steven’s literary influences, and how generative AI is helping humans advance their creative abilities.

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In episode 2 of Generationship, Rachel Chalmers speaks with Liz Fong-Jones and Phillip Carter of Honeycomb. Together they explore use cases for LLMs, insights on navigating AI hallucinations, the tradeoffs between prompt engineering and fine-tuning, and the privacy and security implications inherent to commercial LLMs.

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Generationship is a podcast exploring the intersection of infrastructure and artificial intelligence through a technical and philosophical lens. In this debut episode, host Rachel Chalmers is joined by special guest Catharine Strauss of Summerstir Solutions. Together they dive deep into the world of infrastructure capacity planning, sustainability in data centers, the future of AI in the industry, the importance of getting outdoors, and much more.

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