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.

Subscribe

Generationship - Ep. #47, The Tech Bros with Milette Gillow and Sedinam Simpson

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.

Generationship - Ep. #48, Trusting AI with Sarah Novotny

In episode 25 of Open Source Ready, Brian and John sit down with Rachel-Lee Nabors. They explore how AI agents are reshaping the web, from the decline of traditional browsers to the rise of agentic experiences powered by small language models and MCPs. Rachel-Lee explains why advertising models are collapsing and why the next web may depend on direct payments and open source innovation.

Open Source Ready - Ep. #25, Death of the Web Browser with Rachel-Lee Nabors

In episode 26 of Open Source Ready, Brian Douglas and John McBride sit down with Quinn Slack. They explore how Sourcegraph built Amp, why unconstrained coding agents represent a major shift, and why AI economics make traditional SaaS pricing impossible. Quinn also breaks down the rise of open source models, the future of developer tooling, and why ads might be the key to making AI accessible to everyone.

Open Source Ready - Ep. #26, The Economics of AI Coding with Quinn Slack

In this debut episode of Data Renegades, CL Kao and Dori Wilson dive into the unconventional paths that led them into developer tools, civic tech, and machine learning systems. CL recounts his experience building early open source infrastructure, mobilizing communities through data transparency projects, and now shaping how we design software around LLMs. This episode sets the tone for the show’s mission: celebrating builders who redefine the boundaries of what tools can do.

Data Renegades - Ep. #1, Introducing Data Renegades

In episode 2 of Data Renegades, CL Kao and Dori Wilson speak with Simon Willison. Together they dive into the origins of Datasette, the evolution of data journalism, and the surprising ways open source tools shape global reporting. Simon also explains how LLM-based agents will redefine data cleaning, enrichment, and analysis. A must-listen for anyone building or scaling data teams.

Data Renegades - Ep. #2, Data Journalism Unleashed with Simon Willison

On episode 3 of Data Renegades, CL Kao and Dori Wilson sit down with Maxime Beauchemin. They explore the origins of Airflow and Superset, the evolution of open source in the data ecosystem, and how today’s tooling reshapes the role of the data practitioner. Max also shares a forward-looking perspective on agentic workflows and how AI is accelerating everything from BI to pipeline development.

Data Renegades - Ep. #3, Building Tools That Shape Data with Maxime Beauchemin

On episode 27 of Open Source Ready, Brian Douglas and John McBride speak with Adam Hevenor, creator of Vibecheck. Together they explore the fundamentals of evals, how teams can run structured experiments across model variations, and why cost-efficient design matters more than ever. Adam also offers grounded perspectives on MCP adoption, Claude Skills, and the economics shaping today’s AI tooling ecosystem.

Open Source Ready - Ep. #27, Rethinking AI Evals with Adam Hevenor

In episode 4 of Data Renegades, CL Kao and Dori Wilson sit down with Micah Wylde. They trace his journey from building fraud detection at Sift Science to architecting massive real-time systems at Lyft and ultimately founding Arroyo. In this conversation, Micah breaks down the real complexity of streaming systems, why schema evolution is still the hardest challenge in data, and where the industry might move over the next five years.

Data Renegades - Ep. #4, Streaming Made Practical with Micah Wylde

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.

Generationship - Ep. #49, Dumpster Phoenix with Denise Koessler Gosnell and Kathryn Erickson

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.

This track is not available anymore.

Other tracks from Heavybit