Code with Jason

Latest Episodes:

276 - Todd Kaufman, Agent #001 at Test Double Nov 22, 2025

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In this episode I talk with Todd Kaufman about founding Test Double, focusing on hiring senior consultants who excel at communication and empathy. We discuss how consulting is 90% psychology, the importance of seeking to understand before being understood, and why most software projects still fail due to organizational rather than technical issues.

Links:

Test Double
todd@testdouble.com
Nonsense Monthly

275 - Irina Nazarova, Organizer of SF Ruby Conference Nov 18, 2025

Show notes

In this episode I talk with Irina Nazarova about the San Francisco Ruby Conference happening November 19-21. She explains why SF needs a Ruby conference, the focus on connecting Ruby startup founders with engineers, showcasing new companies building with Rails, and fostering a pragmatic community centered on growth and innovation.

Links:

274 - Matthew Ford, CEO/CTO at Bit Zesty Nov 09, 2025

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In this episode I talk with Matthew Ford about AI-assisted coding at BitZesty. We discuss how AI speeds up development while requiring human oversight, the risks of "vibe coding," why automated testing remains critical, and how AI changes but doesn't replace fundamental software development practices like version control and architecture decisions.

Links:

273 - Steve Ruiz, Founder of tldraw Nov 04, 2025

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In this episode I talk with Steve Ruiz about creating TLDraw, an open-source canvas SDK. We discuss the intersection of design and engineering, managing complexity through abstractions, state machines, and how multiple rewrites helped him discover the core problems. Steve shares insights on building developer tools and solving difficult UI challenges.

Links:

272 - Anthony Eden, Founder of DNSimple Oct 24, 2025

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In this episode I talk with Anthony Eden about building DNSimple, a DNS provider and domain registrar. We discuss his 25 years in the domain industry, technical challenges, and why specialized niches create natural competitive moats.

271 - Hotwire with Radan Skorić Oct 07, 2025

Show notes

In this episode I talk with Radan Skorić about his book Master Hotwire, the challenges of Hotwire documentation, blogging in the AI age, how AI affects content creation, the Chinese room thought experiment, consciousness and computation, trust versus critical thinking, and why quality content that goes deeper than AI can produce still matters.

Jason's stuff:

270 - AI with Daniel Nastase Sep 29, 2025

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In this episode, I discuss AI with Daniel Nastase, covering Daniel's journey from building neural networks from scratch to understanding embeddings and vector databases. We explore the limitations of current AI learning models versus explanation-based reasoning, and discuss practical AI applications including agents and voice interfaces for programming.

269 - Cody Norman, Founder of Spot Squid for Tattoo Shops Sep 26, 2025

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In this episode I talk with Cody Norman about his journey from economics to programming, his tattoo shop management software SpotSquid, and lessons from building products for non-technical users. We discuss market challenges, customer development strategies, and Cody's path to conference speaking.

268 - Joel Drapper Sep 22, 2025

Show notes

In this episode I talk with Joel Drapper about open source development, the joy of coding without constraints, AI tools like GitHub Copilot, and our shared discomfort with the phrase "duplication is better than the wrong abstraction." We explore abstraction, technical debt versus "technical poison," and our mutual search for high-quality work environments.

267 - Upcoming Ruby Events with Jim Remsik, Founder of Flagrant Sep 19, 2025

Show notes

In this episode I talk with Jim Remzick about how AI has affected the job market, the value of in-person networking, and XO Ruby, Jim's series of regional Ruby conferences happening across the US.

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