Code with Jason

Latest Episodes:

306 - Steve Pike, Co-Founder of Infield Jan 23, 2026

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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.

305 - Sean Schertell, CEO and Founder of Codepilot Jan 14, 2026

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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.

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304 - Abstraction and Consciousness with Christian Genco Jan 13, 2026

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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.

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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

303 - Christian Genco, Founder of Fileinbox Jan 13, 2026

Show notes

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.

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302 - Miles Woodroffe, CTO of Mindful Chef Jan 12, 2026

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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.

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301 - Bekki Freeman, Staff Software Engineer at Caribou and Co-Organizer of Rocky Mountain Ruby Jan 01, 2026

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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.

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300 - TDD and AI with Paul Hammond Jan 01, 2026

Show notes

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.

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295 - Freelancing and Consulting with Wale Olaleye Jan 01, 2026

Show notes

In this episode I talk with Wale Olaleye about finding consulting clients through referrals and word of mouth. We discuss the "hunting vs farming" analogy for marketing, simplifying your pitch, filtering clients with deposits, and how genuine community relationships lead to business over time.

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294 - The Dubious Idea of Code Reuse with Dave Thomas Jan 01, 2026

Show notes

In this episode I talk with Dave Thomas about why code reuse is overrated, the economics of programming principles, and why we can't empirically test whether practices work—we have to scrutinize the arguments behind them. Dave also discusses his new book Simplicity and his "developer without portfolio" concept.

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293 - Cory Zue, Solopreneur Jan 01, 2026

Show notes

In this episode I talk with Cory Zue about his solopreneur journey building SaaS Pegasus, a Django boilerplate product. We discuss AI's potential impact on the business of selling code, the financial anxiety that persists even when things are going well, and content marketing strategies for technical products.

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