A podcast exploring the intersection of infrastructure and artificial intelligence, hosted by Rachel Chalmers.

Generationship

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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Generationship - Ep. #1, Building Future Infrastructure Sustainably with Catharine Strauss

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 fine-tuning and prompt engineering, and the privacy and security implications inherent to commercial LLMs.

Generationship - Ep. #2, Putting LLMs to Work with Liz Fong-Jones and Phillip Carter of Honeycomb

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.

Generationship - Ep. #3, A Contrarian History of AI with Steven Schkolne of MightyMeld

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.

Generationship - Ep. #4, Reimagining The Terminal with Michael Sawka of Wave Terminal

In episode 5 of Generationship, Rachel 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.

Generationship - Ep. #5, Live from DevGuild: AI Summit

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.

Generationship - Ep. #39, Simon Willison: I Coined Prompt Injection

Heavybit is the leading early-stage investor in enterprise infrastructure. Since 2013, we've helped launch and scale visionary technical startups—from DevSecOps and feature flagging to AI code generation and beyond. We go hands-on from day 0, backing founders as they turn code into companies and build the future of software from the bottom up to the top down.