Generationship

On episode 56 of Generationship, Rachel Chalmers sits down with Mark Brocato, founder of Mockaroo and creator of Fabricate, to explore the evolution of synthetic data in the age of AI. Mark shares how a simple internal QA tool grew into one of the most widely used synthetic data platforms and discusses how agentic AI is transforming software development, testing, and data generation.

On episode 55 of Generationship, Rachel Chalmers sits down with Sunil Dhaliwal to explore how AI is reshaping developer infrastructure, venture investing, and computational biology. Sunil reflects on building Amplify Partners during the rise of cloud computing, why the best technical founders “live the problem,” and where he sees the next generation of AI tooling emerging. The conversation also di...

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.

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...

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.

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.

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 t...

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 joy...

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.

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.

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...

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.

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...

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...

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.

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 visio...

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, thi...

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...

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 sof...

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...

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...

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.

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.

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.

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.