Code with Jason
Episodes
325 episodes
322 - Joe Masilotti
In this episode I talk with Joe Masilotti about his new podcast with Colleen Schnettler, 'Permission Not Required.' We discuss how two independent consultants navigate the challenges and opportunities in business today, especially regarding the...
321 - Uncle Bob Martin
In this episode I talk with Bob Martin about his work with programming languages using AI, the essence of software engineering, and why understanding epistemology matters for developers. We also explore dependency inversion and the benefits of ...
320 - John Nunemaker of Fireside.fm, Box Out Sports and Very Good Software
In this episode I talk with John Nunemaker about his journey with Ruby, acquiring Fireside.fm, and his ventures in software focused on podcast hosting and feature flag services. We also explore the potential impacts of AI in the development spa...
319 - Kellen Presley of Rhizome Compliance
In this episode I talk with Kellen Presley about Rhizome Compliance, an anti-money laundering platform. We discuss the challenges of gaining initial customers, leveraging AI with Ruby on Rails, and the evolving role of developers in the AI age....
318 - Adam Dawkins, CTO of Dragon Drop
In this episode I talk with Adam Dawkins, CTO of Dragon Drop, about building internal tools using Ruby on Rails, the challenges of growing codebases, and how to effectively manage design and technical debt. We explore abstractions, code quality...
317 - Edward Tewiah, Creator of PropertyWebBuilder
In this episode I talk with Edward Tewiah about his journey with PropertyWebBuilder, a Ruby on Rails toolkit for real estate websites. We discuss the challenges of building a flexible UI, meeting client needs, and how AI is revolutionizing Edwa...
316 - Adapting to AI in the Agency World with Errol Schmidt
In this episode I talk with Errol Schmidt from reinteractive about the evolving role of development agencies amid rapid AI advancements. We explore the impact of AI tools on productivity and the future of software development, as well as the cu...
315 - Dave Thomas, RubyConf 2026 Keynote Speaker
In this episode, I talk with Dave Thomas about RubyConf 2026, the essence of a good conference, and the philosophy of programming, including abstraction and the art of using AI in coding.Links:
313 - David Santoro, CTO of Carwow
In this episode I talk with David Santoro, CTO of Carwow, about his journey from startup co-founder to leading a large engineering team. We discuss carwow's evolution, their focus on scalability, and how they tackled growth challenges across di...
312 - AI, Observability, and Entrepreneurship with John Gallagher
In this episode I talk with John Gallagher about changes in AI over the last 18 months and the impact of luck on success.Links:John's Linktree
311 - Tyler Ewing, Creator of Ductwork
In this episode I talk with Tyler Ewing about Ductwork, his innovative workflow framework for Ruby and Rails. We explore its unique position between background job libraries like Sidekiq and heavier solutions like Temporal, and how Ductwork aim...
310 - Brad Taylor, Fractional CTO
In this episode I talk with Brad Taylor about his journey as a fractional CTO and advisor for various companies. We discuss his experience with open source medical records, the importance of business objects, and navigating complexity in softwa...
309 - How I Built SaturnCI (Starring JP Camara)
In this episode I talk with JP Camara about RubyConf 2026, submitting CFPs, and why everyone should give talks. JP shares his experience using SaturnCI on the Mastodon project, and we dig into Saturn CI's Docker-based setup, Kubernetes architec...
308 - Christian and Jason Fail to Talk About AI
In this episode I talk with Christian Genco about IQ, the pros and cons of high intelligence, the Big Five personality traits, evolutionary differences between men and women, hypergamy, the origins of money, and whether Yuval Harari's "shared f...
307 - Kody Kendall, Co-Founder and CEO of LlamaPress AI
In this episode I talk with Cody Kendall about building software for his dad's HVAC business, learning usability testing, pivoting from contractor software to AI-generated code, and why he built LlamaPress.
306 - Steve Pike, Co-Founder of Infield
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 maintain...
305 - Sean Schertell, CEO and Founder of Codepilot
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:
304 - Abstraction and Consciousness with Christian Genco
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 abstraction...
303 - Christian Genco, Founder of Fileinbox
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 e...
302 - Miles Woodroffe, CTO of Mindful Chef
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 enjo...
301 - Bekki Freeman, Staff Software Engineer at Caribou and Co-Organizer of Rocky Mountain Ruby
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 impro...
300 - TDD and AI with Paul Hammond
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 thu...
299 - Eleni Konior, Senior Staff Software Engineer at Cisco Meraki
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 ro...
298 - AI-Assisted Rails Upgrades with Ernesto Tagwerker
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:
297 - AI-Assisted Coding with Steven Diamante
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, ...
