Remote Ruby

40 Episodes
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By: Chris Oliver, Andrew Mason, David Hill

Rubyists having conversations and interviewing others about Ruby and web development.

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Rails World Prep, Herb in Rails, Stacked PR Headaches and New Ruby Tooling
#366
Today at 12:00 PM

This week, Chris, Andrew, and David dig into a packed mix of Rails news, developer tooling, and the increasingly complicated role AI is playing in everyday coding. They talk about Herb making its way into Rails, the realities of Rails upgrades and stacked PRs, new approaches to Git hosting and object storage, and how Rails is being evaluated in the age of AI agents. They also get into improvements coming to Action Text, Podia’s approach to “flavored” Markdown, the never-ending frustrations of HTML email, and why tools like ArchSpec and Rubydex could become especially useful as more code is gen...


MCP Implementations and Rails World Preparations
08/28/2026

Andrew and David catch up on everything from wild weather and the upcoming Rails World conference to Andrew’s latest deep dive into MCPs (Model Context Protocols). Andrew shares what he’s learned while building an MCP for a Rails side project, including choosing the official Ruby MCP SDK, discovering the limitations of resources versus tools, and wrestling with OAuth and Doorkeeper authorization. They also look ahead to Rails World in Austin, highlighting talks on Active Search, Ractors, Herb, Action Text, Solid Cable, custom Rails generators, and appropriately enough MCPs. 

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Chris Oliver X

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Ernesto Tagwerker
#364
08/21/2026

Ernesto Tagwerker joins Chris, Andrew, and David, to talk about how AI is changing Rails development, consulting, and the way teams approach upgrades and maintenance. They discuss using Claude Code for Rails upgrades, the risks of relying too heavily on AI-generated tests and code, and why strong development standards are becoming even more important. The conversation also explores code quality, open AI models, team consistency, and how developers can use AI to work more efficiently without giving up the experience and judgment that good software still requires. Start listening now! 

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Chris Oliver XAndrew M...


Shipping Podia’s New Shop, AI Code Woes, and a Major Rails libvips CVE
#363
08/14/2026

In this episode, Chris, Andrew, and David dig into their latest experiences building with Claude, from massive diffs and unnecessary view specs to the challenge of catching subtle mistakes in AI-generated code. Andrew shares what went into launching Podia’s new Shop experience, Chris breaks down a serious Rails Active Storage security vulnerability, and David earns a developer rite of passage by accidentally bringing production to its knees. Along the way, they talk Redis 6, smarter Active Record queries, testing philosophy, and why sometimes the fastest solution is still jumping into the code yourself. Hit download now to hear more! 

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SF Ruby 2026 with Irina and Vladimir
#362
08/07/2026

Irina Nazarova and Vladimir Dementyev from Evil Martians return to preview the second annual SF Ruby Startup Conference and share what they learned from bringing the event to life for the first time. They discuss the conference’s new focus on ambitious builders, the importance of creating meaningful connections for attendees, and why Ruby on Rails remains a powerful foundation for startups tackling difficult, real-world problems. The conversation also explores open-source innovation, AI-assisted development, hidden pockets of Ruby adoption, and how the community can help the next generation of companies confidently build and grow with Rails. Hit download now!

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Big Wins For RubyConf and Grandma
#361
07/31/2026

Chris, Andrew, and David begin with summer heat, home cooling problems, and an IPv6 issue preventing Andrew from playing Battlefield 6. The conversation quickly heads down a Raspberry Pi rabbit hole, with projects ranging from smart-home automation and MagicMirror dashboards to local AI transcription. David then recaps RubyConf in Las Vegas before the group discusses design patterns, the changing conference landscape, and how AI is reshaping programming education, software development, and the economics of building products. Hit download now!

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Chris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftBrockovich AI Data Center ReportingRaspberry...


A Deep Dive into GitHub Actions
#360
07/24/2026

This week, Andrew and Chris swap stories from the front lines of Ruby development, from wrangling GitHub Actions and speeding up CI to keeping old Ruby versions alive on brand-new servers. They also unpack a tricky Sidekiq deployment issue, explore the promise of compiling Ruby apps into standalone executables, and reflect on how AI is making once-impossible infrastructure problems a little easier to solve. Hit download now to hear more!

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Chris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftSetting up code for your repository (GitHub Docs)Surviving rolling deploys when Sidekiq...


Dont Steal Our Business Idea
#359
07/17/2026

Chris, Andrew, and David dig into the practical realities of modern development, from building faster server images with Packer and untangling database schema problems to deciding when refactoring, code coverage, and quality tools are actually useful. They also share where AI coding assistants are saving real time, where they still create confusion, and why good judgment remains just as important as the tools themselves.  The episode wraps with the conversation going completely off the rails with a highly questionable plan to corner the personalized license plate market. Hit download now!

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Chris Oliver XAndrew M...


The Great Falcon Defense and CI Innovations
#358
07/10/2026

In this episode, Chris, Andrew, and David kick things off with a very Remote Ruby style detour through Costco, Blue Apron, leftovers, Blackstone grills, and cast iron pans. Then, Andrew explains his Stripe subscription migration scare and major GitHub Actions workflow improvements that sped up Podia’s CI by 20–30%. They dive into Apple’s new on-device AI tooling, container alternatives on macOS, and the state of conferences, GitHub, AI infrastructure costs, solar power, and even crows attacking solar panels. Hit download now to hear more! 

Links

Judoscale- Remote Ruby listener giftBlue Apron  (Andrew’s referral c...


Chris Is Back And Ready To Rant
#357
07/03/2026

Chris returns from Greece and catches up with Andrew and David on travel, conferences, movies, and the latest developments in the Rails community. They dig into the newly announced Rails World lineup, the possibilities of Active Search, alternatives to Elasticsearch, extending Action Text and Lexi, a tricky ruby-vips dependency update, and mise’s rapidly expanding machine bootstrap tools. They wrap up with open source funding, RubyConf preparations, rising tech prices, and the massive anticipation surrounding GTA VI. Hit the download button now! 

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Judoscale- Remote Ruby listener giftObsession Toy Story 5Porsche reveals three one-of-one 911 mode...


Blastoff Rails Recap and Ruby Central Revamp
#356
06/26/2026

Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter



Navigating Subscription Overhauls and Payments
#355
06/19/2026

Chris, Andrew, and David catch up after a missed week of recording and quickly dive into the kind of deeply practical Rails work that only comes from real production pain. Andrew shares the massive subscription and billing migration happening at Podia, including Stripe edge cases, legacy plan preservation, and stress-test tooling built from live scenarios. Chris then goes deep on a Hatchbox email cancellation flow that turns into a Rails internals rabbit hole around Action Mailer callbacks, mail delivery cancellation, and a tiny Rails PR born from production debugging. Hit download now to hear more! 

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[The lost episode 259]  All Right, Rant Time - Debugging
#259
06/12/2026

[This episode from February 2024 was never published and recently discovered]

In today’s episode, Andrew kicks things off with a rant about tackling developer experience tasks at Podia, wrestling with GitHub actions, and Heroku deployment woes. Then the conversation takes a turn to the importance of debugging, the power of bash scripting, and the challenges of naming in programming, with Chris mentioning DHH’s insights from a live stream. They discuss Chris’s travel plans for RubyConf in Australia, other conferences coming up, and reminisce about their childhood love for trains and Thomas the Tank Engine.  The episode...


Revise Auth and Podcasting Plans
#354
06/05/2026

Chris and David cover a lot of ground in this episode, starting with Chris’s experience teaching a Rails workshop for Frontend Masters in Minneapolis. Along the way, they dive deep into Rails authentication, Devise, Authlogic migrations, Chris’s ReviseAuth gem, password security, session handling, and the hard tradeoffs of maintaining open source tools. The episode wraps with big podcasting news: David is taking over The Ruby on Rails Podcast!  Hit download now to hear more! 

Links

Judoscale- Remote Ruby listener giftMinnebarRuby 4.0.5 Released ReviseAuthThe Ruby on Rails PodcastChris Oliver X/TwitterAndre...


Rails World Tickets, New JavaScript Package Managers, and Security Worries
#353
05/29/2026

Chris, Andrew, and David kick things off with a detour through Dungeon Crawler Carl, Rails World tickets, and conference travel before diving into developer tooling, package manager security, and the latest Ruby ecosystem updates. The conversation covers everything from Hotwire-style UI patterns and pnpm/Corepack setup to Jeff Dickey’s new package manager, the RubyGems malicious package attack, Ruby 4.0.4, Shopify’s Rubydex, Claude/Codex chatter, and the increasingly strange future of AI agents and delivery robots. Hit download now to hear more! 

Links

Judoscale- Remote Ruby listener giftDungeon Crawler Carl Dungeon Crawler Carl RPG + Unstop...


Blue Ridge Ruby Insights & Experiences
#352
05/22/2026

In this episode, Chris, Andrew, and David are back together with David starting out giving a recap of Blue Ridge Ruby and his renewed motivation to contribute to open source. The group discusses the value of smaller single-track conferences to hallway conversations, and lightning talks. The conversation then shifts into real-world Rails and Stripe lessons, including workshop prep, validation decisions, webhook recovery, subscription edge cases, and the growing complexity of payment integrations. Hit download now to hear more! 

Links

Judoscale- Remote Ruby listener giftGetting Started with Rails with Chris Oliver (Frontend Masters Live Interactive W...


Stripe Changes, File Upload Quirks, Scaling Sidekiq
#351
05/15/2026

Chris and Andrew catch up after Andrew’s whirlwind “vacation-ish” road trip before diving into Stripe’s latest announcements, usage-based billing, merchant-of-record pricing, Rails file upload quirks, Active Storage image handling, Sidekiq queue strategy, and the future of RubyGems. They also discuss browser form behavior, preserving and deleting attachments, image variant performance, and how to think more clearly about background job priorities. Hit download now to hear more!

Links

Judoscale- Remote Ruby listener giftDungeon Crawler CarlEverything we announced at Sessions 2026 (Stripe Blog)Scaling Sidekiq at Gusto (Medium)Scaling-Sidekiq -GitHubNate Berkopec post on LinkedIn-Running ContainersChris...


Direct Routes and Data Queries
#350
05/08/2026

On this episode of Remote Ruby, Chris, Andrew, and David kick things off with dentist trauma, gold star stickers, and fiber internet. The conversation centers on Rails direct routes, why they can be more powerful than helpers, the upcoming Rails World CFP and ticket rush, how AI is becoming more practical inside real engineering teams, a reminder to fill out the Rails survey, and Chris’s continued work expanding the Rails Getting Started Guide into a more realistic e-commerce tutorial with wishlists, reviews, ratings, and product images. Hit download now to hear more!

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Ju...


Behind the Scenes: Developing Podias New Version
#349
05/01/2026

Chris, Andrew, and David open with some classic confusion over what day it is then dive into Podia’s gradual rollout of a major new app version, including how the team is handling migration, feature flags, dogfooding, and eventual cleanup. From there, the discussion turns to underrated Rails routing features like direct routes and resolve routes, a newly merged Rails query command, observability improvements through Hatchbox’s AppSignal integration, and the ongoing pain of CSS build tooling in Rails apps. They also touch on conference season and their upcoming talks. Press download now to hear more! 

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Ruby Central Restructuring
#348
04/24/2026

This BREAKING NEWS episode is a candid reaction to Ruby Central’s latest shakeup, with Chris, Andrew, and David unpacking leadership departures, financial strain, the cancelled gala, and what all of it says about the organization’s direction. The conversation moves beyond the headlines into bigger questions about trust, transparency, community values, conference strategy, RubyGems sustainability, and whether Ruby Central can rebuild credibility by involving more of the community in what happens next. Hit download now to hear more! 

Links

Judoscale- Remote Ruby listener giftA New Chapter for Ruby CentralRubyConf 2026- July 14-16, Las Vegas...


Joined by John Athayde
#347
04/17/2026

Chris and David welcome guest John Athayde, who runs the branding and UX consultancy, Meticulous. They dive into John’s unusual path through the Rails world as a designer, front-end developer, consultant, author, and UX thinker. The conversation moves from early Rails history and The Rails View into a broader discussion about why designers need to understand implementation, how AI is changing product and UI work, where component-based design is headed, and why browser support is still one of the messiest parts of modern web development. Hit download now to hear more!

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John At...


Governance, Security Flaws, and AI Tools
#346
04/10/2026

This episode of Remote Ruby opens with stories of exhaustion from a sleepless week. Then, Chris, Andrew, and David spend most of the episode unpacking two big themes: trust and governance in open source, and the growing mess of software security and AI-assisted development. They dig into the new Ruby Central write-up on the RubyGems/Bundler fracture and question whether it actually clarifies the path forward, then pivot into the Axios npm compromise, supply-chain risk, and how fragile modern package ecosystems can feel. Then, they go into a wide-ranging discussion on AI coding, bloated production apps, image-performance headaches, CSS...


Memcached Mayhem
#345
04/03/2026

On this episode, Chris, Andrew, and David bounce from Ruby and Rails security updates into the messy realities of caching, UI architecture, and browser support. They break down the latest Zlib-related Ruby CVE, Dalli updates, Rails security and bugfix releases, and what maintenance windows mean in practice. Then, they swap stories about Redis, Memcached, observations about GitHub’s reliability amid massive Claude attributed code activity, and the kinds of performance problems that only show up at scale. The episode closes with a thoughtful Rails frontend discussion covering nested layouts, active sidebar links, CSS-powered empty states, pagination behavior, popovers, anchor po...


Conferences, AI Trends, and Sleepless Nights
#344
03/27/2026

Chris, Andrew, and David catch up on health, sleep deprivation, and the new Invincible season and Fallout. David shares some RubyConf CFP submissions news and this year’s broad conference themes. They discuss Andrew finishing difficult authentication work, touching on OAuth/SSO complexity and pricing, the idea of products built more for bots than humans, and where AI is proving useful, especially for debugging and research. The conversation eventually widens into a more skeptical look at the AI industry itself, touching on scraped code, deepfakes, surveillance, lobbying, and whether the promised productivity gains really match reality. Hit download now!

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Unraveling GitHub Actions & Modern Auth Challenges
#343
03/20/2026

On this episode, Andrew’s buried in messy authentication work spread across legacy code, Chris recounts a frustrating GitHub Actions debugging session, and David explains the mental drain of working across both Vue 2 and Vue 3 in the same application. They talk about using workflow run triggers, scheduled builds, and GitHub’s new Agentic Copilot workflows such as CI Doctor, Automatic Code Simplifier, and issue/PR management, while lamenting low-quality AI-generated PRs and paid AI code review tools. Andrew makes a special announcement about Blastoff Rails, they compare LazyVim, lazy.nvim, and Kickstart Neovim, we hear about Ruby 3.4.9 and its bug...


Heroku, Hosting, and the AI Era
#342
03/13/2026

Chris and David welcome back Adam McCrea from Judoscale, to discuss the uncertainty around Heroku after Salesforce’s announcement that it would stop taking new enterprise customers. Adam shares how the news landed in real time during a founder’s retreat, and the conversation expands into what Heroku’s apparent “maintenance mode” means for developers, pricing, autoscaling, platform alternatives, and the broader challenge of building durable developer businesses in the AI era. They also touch on Judoscale’s upcoming “platform tour” and the value of smaller Ruby conferences. Hit download now to hear more! 


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Jeff Dickey on Mise, Precompiled Rubies, and much more
#341
03/06/2026

Chris, Andrew, and David welcome special guest Jeff Dickey (jdx), creator of mise, discussing his background rewriting the Heroku CLI from Ruby to Node due to Ruby distribution/sandboxing issues.  The conversation digs into why language CLIs are hard to distribute, the tradeoffs between shims vs PATH-based version switching, why tasks can be the “clean” solution, and Jeff’s Rust-first tooling philosophy. They also dive into his other projects: usage (CLI docs/completions), Pitchfork (dev daemon runner that starts/stops services by directory), and fnox/Fort Knox (secrets management with encrypted files or remote stores like 1Password), and a big upc...


LiveComponent with Cameron Dutro
#340
02/27/2026

Cameron Dutro returns to the show to introduce LiveComponent, a new library that adds client-side state and targeted re-rendering to Rails ViewComponent using Hotwire + Stimulus with minimal JavaScript. Chris, Andrew, and Cameron dig into why he built it, how it serializes component state and models, how updates flow from events to fast server-rendered HTML morphs, where it shines compared to plain Turbo/Stimulus, and how optional React support can help with migration and interoperability. Hit download now to hear more! 

Links

Judoscale- Remote Ruby listener giftCameron Dutro GitHubCameron Dutro XRemote Ruby-Episode 134: Kubernetes, JSX for R...


Bridge Components, Swift UI and more with Joe Masilotti
#339
02/20/2026

Andrew and David hold down the fort without Chris and catch up on what they’ve been watching and reading, before welcoming back Joe Masilotti, the show’s most listened to guest from last year. They talk about Hotwire Native’s momentum, why “Bridge Components” are the unlock for truly native features, Joe’s push toward SwiftUI compatibility, the messy reality of in-app purchases, and how his “PurchaseKit” aims to simplify the whole Apple/Google webhook maze. We also hear about Joe’s new podcast with Colleen, the hosts’ AI tool usage (Claude, Augment, Codex), and Joe’s intent to submit a CFP to spe...


Kisses From Andrew, the Ruby Gala & Conference Workshops
#338
02/13/2026

On this episode of Remote Ruby, Chris, Andrew, and David dive into the newly released Claude Opus 4.6 and share their frustrations and solutions for debugging a turbo stream issue in Rails. They discuss a range of debugging challenges they've faced, including Rails credentials decryption errors and handling unexpected URL parameters in Pagy. The conversation shifts to the Ruby Gala, a fundraising event tied to RubyConf, highlighting its purpose, structure, and some notable people being honored. They reflect on their experiences with Hack Days at conferences, the challenges they pose, and suggest transforming them into structured workshops to maximize learning...


Kevin Newton on Ruby & Python, Prism, Psych-Pure, and Exreg
#337
02/06/2026

In this episode, Chris, Andrew, and David kick off with humorous stories about coding experiences across different languages, and then they welcome back guest Kevin Newton who shares his journey from Shopify to Meta. Then, Kevin discusses the intricacies of Ruby and Python, particularly the challenges and trade-offs in their runtime implementations. The conversation then shifts to the development and adoption of the Prism parser in Ruby, highlighting its impact on various projects. Lastly, Kevin shares insights on his work with a pure Ruby YAML parser and a regex engine, emphasizing the complexities and joys of coding and parsing...


Blue Ridge Ruby 2026 with Jeremy Smith and Joe Peck
#336
01/30/2026

In this episode, Blue Ridge Ruby organizers Jeremy Smith and Joe Peck join Andrew, Chris, and David to talk about the conference returning in 2026. They explain why it’s different (single-track, long breaks, and memorable community activities), what they’ve learned from running it, and how folks can help (speaking, sponsoring, and attending). The discussion also highlights the importance of community and in-person interactions in the tech industry, offering insights into how these events support professional growth and long-term sustainability in software development. Hit download now to hear more! 


Chris Oliver X/TwitterAnd...


Tool Standardization
#335
01/23/2026

In this episode, Chris, Andrew, and David dive into details about refactoring with SQL, updates on new Ruby versions, and share their views on various developer tools including Mise, Overmind, and Foreman. They also touch on standardizing tools within their teams, the benefits of using Mise for Postgres, and the efficiency of task scripts. The conversation also covers encoding issues, Basecamp Fizzy SSFR protection, and rich-text editors like Lexxy and its application in Basecamp. Additionally, there's a light-hearted discussion on the speculative future of AI and Neuralink.  Hit download now to hear more! 

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Ju...


Tech Resolutions and Tailwind Troubles
#334
01/16/2026

In this episode of Remote Ruby, Chris, Andrew, and David have conversations from New Year's resolutions and monitor specifications, to the sustainability challenges of open source projects like Tailwind CSS. They discuss the pros and cons of various hardware, upgrading to Ruby 4.0, recent issues in software projects, and the evolving landscape of AI's impact on productivity tools. They also touch on gaming experiences with Arc Raiders and the never-ending monitor hunt. Hit download now to hear more! 

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Judoscale- Remote Ruby listener giftKeychron M5 Wireless Ergonomic MouseBrandon Weaver BlueskyRan Craycraft LinkedInAdam Wathan XAdam Watham i...


Remote Ruby Wrapped
#333
01/02/2026

In this episode of Remote Ruby, Chris, Andrew, and David humorously discuss the rapid increase of 'wrapped' features in various apps, recount personal experiences with food apps, and then dive into their favorite conference moments of the year. They also explore the concept of UI affordances and its importance in web design and give a preview of upcoming conferences in 2026, and a brief discussion on modern CSS and JavaScript elements. Hit download now to hear much more! 

Links

Chris Oliver XAndrew Mason BlueskyDavid Hill BlueskyJudoscale- Remote Ruby listener giftRBQ Conf, March 26 & 27, 2026Tropical on Rails, A...


Ruby Upgrades & RAM Shortages
#332
12/26/2025

Chris, Andrew, and David are back together, and the conversation starts out with TV talk, Fallout hype, why some shows overstay their welcome (Prison Break), and the “season one magic” problem (Reacher). Then there’s a big shoutout to Marco’s Rails Luminary win, and a deep dive into AI rabbit holes: self-hosting LLMs, Mac minis, and the looming reality of both token costs and RAM shortages. They discuss the Ruby releases (3.4.8 + Ruby 4.0 preview3), highlighting practical fixes, previewing features like Ruby:: Box, new syntax tweaks, and core classes updates they’re excited about.  Hit download now! 

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Jumpstart Pro Evolution - Streamlining Rails Development
#331
12/19/2025

In this episode, Chris and David Hill catch up on wild winter temperature swings, then dive into what Chris has been refactoring in Jumpstart to reduce merge pain, cut dependencies, and make upgrades smoother. The conversation branches into AI-assisted coding pitfalls and where AI shines, new web security headers that could simplify CSRF handling, and a promising new “old school Heroku on steroids” platform from Evan Phoenix called Miren, plus a few Hatchbox deployment learnings along the way. Hit download now to hear more!

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Chris Oliver XAndrew Mason BlueskyJudoscale- Remote Ruby listener giftDavid Hill...


Joined by David Hill
#330
12/12/2025

Chris and Andrew kick things off with some weather whiplash and snowblower talk before introducing a new guest on the show, long-time Rubyist David Hill. They chat about fast food and favorite shows, David’s accidental path into Ruby and Rails, and various projects he’s worked on, including an AED management application. The discussion also touches on the new open-source release of Basecamp's Kanban board, Fizzy, and some innovative CSS techniques used in the project. The conversation wraps up with upcoming Ruby conferences in 2026 and how Claude's AI assistance is helping with coding tasks. Hit download now to hear...


Docker Disasters and Dev Container Journeys
#329
12/05/2025

Andrew kicks off at 8 a.m. with six Docker containers running, and he and Chris dive into what modern Rails development looks like inside dev containers—covering Rails’ own images and features, using Mise and Playwright instead of Selenium, and why OrbStack has replaced Docker Desktop on their Macs. They talk through the trade-offs of running services in containers, the quirks of Kamal’s new local registry, and how Chris is turning all of this into a practical SaaS building series that shows real-world deployment and scaling with tools like JudoScale. Along the way, they weave in life updates about...


San Francisco Ruby Conference Recap
#328
11/28/2025

Andrew returns from SF Ruby with a lot more than conference swag! He brings a clear snapshot of where Ruby, Rails, and AI are headed right now. In this episode, he and Chris walk through the most impactful talks from SF Ruby, share highlights of engaging discussions with other developers and friends, reminisces about nostalgic tech items, and explores insightful conversations on the future of Rails, startup culture, AI's impact on programming, developer anxiety, and they share product ideas from Chris new SaaS series on GoRails to Andrew’s concept for a serious GitHub Actions monitoring tool. Hit download no...