Code with Jason

In this episode I talk with Steve Pike, founder of Infield, about dependency management and automated Rails upgrades. We discuss the tradeoffs of taking on dependencies, authorization libraries like CanCanCan versus Pundit, open source maintainer obligations, and how AI is changing the upgrade automation landscape.

• Infield
• Once a Maintainer
• Nonsense Monthly

In this episode I talk with Sean Schertell about his return to Rails after many years in JavaScript, the pain of node module hell, Kamal for deployment, and Sean's new startup ZiaMap for land surveyors.

Links:

• Codepilot
• ZiaMap
• Nonsense Monthly

In this episode I talk with Christian Jenko for round two. We explore abstraction as the most important idea in software, Michael Singer's philosophy on consciousness and thoughts, whether AI can become conscious, and how our mental abstractions shape what we see in reality.

Links:

• Designing Object-Oriented Software by Rebecca Wirfs-Brock
• The Surrender Experiment by Michael A. Singer
• The Untethered Soul by Michael A. Singer
• Living Untethered by Michael A. Singer
• I Am a Strange Loop by Douglas Hofstadter
• A Thousand Brains by Jeff Hawkins
• Incognito: The Secret Lives of the Brain by David Eagleman
• The Emperor's New Mind by Roger Penrose
• Conjectures and Refutations by Karl Popper
• Being There: Putting Brain, Body, and World Together Again by Andy Clark
• On Looking: Eleven Walks with Expert Eyes by Alexandra Horowitz

In this episode I talk with Christian Genko, founder of Fileinbox. We discuss bootstrapping SaaS products, finding business ideas through openness rather than forcing, how LLMs have changed development workflows, TDD with Claude Code, and the enduring value of taste and abstractions in software.

Links:

• Fileinbox
• Christian Genco's personal website
• Christian Genco on X
• Nonsense Monthly

In this episode I talk with Miles Woodroffe, CTO of Mindful Chef. We discuss his music career touring with The Specials and working with Bob Dylan and Ray Charles, how he transitioned into tech, building great teams, and finding people who enjoy working together.

Links:

• mileswoodroffe.com
• Mindful Chef
• Nonsense Monthly

In this episode I talk with Becky Freeman, staff engineer at Caribou and co-organizer of Rocky Mountain Ruby, about legacy code, refactoring long-running applications, and the psychological skills required to get team buy-in for technical improvements.

Links:

• Bekki Freeman on LinkedIn
• Rocky Mountain Ruby
• Caribou
• Nonsense Monthly

In this episode I talk with Paul Hammond about TDD as a discoverable principle—something alien programmers would independently arrive at. We discuss my "specify, encode, fulfill" formulation, why programming needs theory instead of rules of thumb, and the business payoff of technical quality: Paul returned to a well-built project after 18 months and delivered months of planned work before Christmas.

Links:

• Scenarist
• Nonsense Monthly

In this episode I talk with Eleni Konior about her path from economics to graphic design to programming, and how creative skills benefit technical work. We discuss building customer-focused features, the importance of assuming the customer's role, and AI in products beyond chatbots—like proactively surfacing recommendations based on user behavior.

Links:

• datgreekchick.com
• Nonsense Monthly

In this episode I talk with Ernesto Tagwerker about using AI for Rails upgrades, AI as an unblocking tool rather than just a speeder-upper, and the dangers of AI-generated "speculative code" that adds liability without value.

Links:

• FastRuby.io
• OmbuLabs

In this episode I talk with Steven Diamante about coaching teams on XP practices and AI coding agents. We discuss why change is so hard (people have to want it), his success turning an underperforming team around through weekly learning hours, and how to use TDD with AI—including "predictive TDD" where you have the agent guess if tests will pass or fail.

Links:

• Diamante Technical Coaching
• Steven Diamante on LinkedIn
• Nonsense Monthly