Code with Jason
On the Code with Jason podcast I discuss technical topics with interesting people. Guests include people from companies like GitHub, Google and Stripe.
Episodes
312 episodes
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...
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1:24:15
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.
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1:23:07
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...
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59:03
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:
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1:10:36
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...
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1:20:28
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...
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1:11:39
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...
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59:46
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...
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52:35
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...
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1:25:24
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...
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56:37
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:
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46:39
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, ...
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1:07:10
296 - Software Design Principles with Andrea Laforgia
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...
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1:08:22
295 - Freelancing and Consulting with Wale Olaleye
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 c...
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1:05:18
294 - The Dubious Idea of Code Reuse with Dave Thomas
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 hi...
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1:18:05
293 - Cory Zue, Solopreneur
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 g...
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57:31
292 - Kendall Miller, CEO and Founder of Maybe Don't AI
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 problem...
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1:02:17
291 - Joel Drapper
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 ty...
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1:23:21
290 - Dead Man's Snitch with Chris Gaffney
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 bein...
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58:48
289 - Lio Lunesu, CTO at Defang
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.Links:Defang
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51:46
288 - Ryan Frisch and Brendan Buckingham, Co-Hosts of the Rails Business Podcast
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 g...
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1:09:18
287 - Jeff Casimir, Founder of Turing School
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 ...
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1:24:24
286 - Darwin, Science and Programming with Kate Holterhoff
In this episode I talk with Kate Holterhoff, senior analyst at RedMonk, about her PhD research on Darwin's methods, speculation in science, and how 19th century evolutionary thinking influenced literature. We discuss epistemology, conjecture an...
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56:29
285 - Michael Ferranti, Chief Marketing Officer at Unleash
In this episode I talk with Michael Ferranti from Unleash about feature flags, trunk-based development, and why DevOps metrics alone aren't sufficient. We discuss FeatureOps—focusing on customer outcomes rather than just code delivery—plus the ...
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52:54
284 - Josef Strzibny, Author of Deployment from Scratch and the Kamal Handbook
In this episode I talk with Josef Strzibny about his books Deployment from Scratch and Kamal Handbook, the economics of info products in the Ruby space, his new project Lake AI, and his road trip through the Balkans. We also compare driving cul...
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59:15