Code with Jason

Latest Episodes:

299 - Eleni Konior, Senior Staff Software Engineer at Cisco Meraki Jan 01, 2026

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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.

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298 - AI-Assisted Rails Upgrades with Ernesto Tagwerker Jan 01, 2026

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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.

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297 - AI-Assisted Coding with Steven Diamante Jan 01, 2026

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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.

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296 - Software Design Principles with Andrea Laforgia Jan 01, 2026

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In this episode I talk with Andrea Laforgia about programming principles, why good code is code that's easy to change, and his motto: "write your code so it can be easily deleted." We discuss technical debt as an operating model, the fallacy of sacrificing quality for speed, and AI's impact on learning fundamentals.

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292 - Kendall Miller, CEO and Founder of Maybe Don't AI Jan 01, 2026

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In this episode I talk with Kendall Miller about MCP (Model Context Protocol) and why AI agents need third-party guardrails. His company Maybe Don't sits between AI agents and MCP servers to prevent disasters—because AI sometimes solves problems in creative and terrifying ways.

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291 - Joel Drapper Jan 01, 2026

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In this episode I talk with Joel Drapper about defect-free development—not just automated testing, but the full spectrum: linting, static typing, database constraints, and especially runtime assertions. Joel's library Literal lets you define type expectations that blow up immediately when violated, catching bugs before they spread.

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290 - Dead Man's Snitch with Chris Gaffney Jan 01, 2026

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In this episode I talk with Chris Gaffney about Dead Man's Snitch, a cron job monitoring service he's run full-time for six years after Collective Idea acquired it at a very early stage. We discuss the five-year path to profitability, SaaS being harder today, and dopaminergic personalities in tech.

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289 - Lio Lunesu, CTO at Defang Jan 01, 2026

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In this episode I talk with Lio Lunesu, CTO of Defang, about infrastructure as code, Docker, and Docker Compose. Defang compiles Docker Compose files into cloud infrastructure code.

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288 - Ryan Frisch and Brendan Buckingham, Co-Hosts of the Rails Business Podcast Jan 01, 2026

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In this episode I talk with Ryan Frisch and Brendan Buckingham from the Rails Business Podcast about whether info products are viable in the Rails community, how business ideas emerge from personal pain points rather than brainstorming, and I give an update on SaturnCI sales.

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287 - Jeff Casimir, Founder of Turing School Jan 01, 2026

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In this episode I talk with Jeff Casimir, founder of Turing School, about why AI is far down his list of reasons for the tech job market downturn—he points instead to macroeconomic policy, copycat layoff culture, and companies using layoffs to suppress worker organizing. We also discuss aptitude vs. belief, why school is mostly daycare, and his prompt injection resume experiment.

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