The Ruby on Rails Podcast

Chris Oliver and Collin Jilbert join David for a candid conversation about the changing economics of building products for the Ruby on Rails community in the age of AI.

Chris traces the history of GoRails from its beginnings as an attempt to fill the void left by RailsCasts, through to the creation of Hatchbox and Jumpstart, and explains how those products evolved together over more than a decade. But the rapid improvement of AI coding assistants has dramatically changed how developers learn and work. Instead of searching for a tutorial, watching a screencast, and adapting an example to their application, developers can increasingly ask an AI tool to work directly inside their existing codebase.

That shift has had a significant impact on GoRails and Jumpstart subscriptions, while at the same time making Chris and Collin dramatically more productive as developers themselves. They discuss using AI to research unfamiliar systems, refactor complex Rails code, prototype features, and build software in minutes that previously might have taken days.

Those changes also led to some difficult business decisions. Chris and Collin explain why Hatchbox has become increasingly important to the sustainability of their work, why they decided to raise its per-server pricing, and how they wrestled with balancing the needs of longtime customers against the reality of keeping a small bootstrapped company viable.

The conversation also looks beyond the immediate business changes to larger questions facing software development: what happens to developer education when AI can generate context-specific solutions on demand, how junior developers develop judgment when they no longer have to learn everything “the hard way,” and whether AI could ultimately change not just how developers write software, but what kinds of software they are able to create at all.

Jeremy Smith returns to the podcast ahead of Rails World to talk about his upcoming presentation, Practical Hotwire: Turbo and Stimulus on the Ground.

Jeremy shares how years of working with Hotwire in real Rails applications led him to identify a dozen recurring problems and pitfalls involving Stimulus, Turbo Drive, Turbo Frames, and Turbo Streams. He also walks through the surprisingly extensive process of turning those lessons into a 30-minute conference talk, including building a dedicated demo application, creating before-and-after examples, recording screencasts, researching edge cases, and using AI tools to help organize and refine the material.

They also discuss Jeremy’s decision to structure the talk around a Hot Ones-style progression of increasingly spicy Hotwire problems, the difficulty of deciding what to cut from an overstuffed technical presentation, and what actually makes a conference talk useful and memorable.

Finally, Jeremy previews one of the strongest opinions in the talk: that developers should often prefer Turbo Streams over Turbo Frames. He explains how Frames can introduce indirection and limitations as applications grow, why Streams can offer a more flexible approach, and how different Rails teams can arrive at very different—but equally valid—ways of using Hotwire in production.

Sponsor - Judoscale

Jim Remsik, founder of Flagrant and organizer of XORuby, joins David to talk about what he’s learned from taking a Ruby conference on the road.

XORuby was designed around a simple premise: traditional conferences are valuable, but travel costs, time away from work, and family responsibilities put them out of reach for many developers. Jim explains how XORuby tries to lower those barriers with inexpensive, one-day regional events—and why he measures their success as much by first-time attendees, new speakers, friendships, and community connections as by the financial bottom line.

The conversation turns to Flagrant and the rapidly changing role of AI in software development. Jim discusses the company’s decision to invest more heavily in design, the difference between simply having access to AI tools and actually building an effective AI-assisted development workflow, and a recent project where careful preparation helped his team deliver roughly 700 cards in eight weeks.

Finally, Jim and David explore the increasingly difficult problem of building local developer communities. With meetups struggling, online communities fragmented across Slack and Discord, and developers finding technical content everywhere, they consider what actually motivates people to leave the house and spend time together—and where XORuby might go next.

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Judoscale - https://judoscale.com/

Local Ruby communities don’t simply happen—they need people willing to create the connections that keep them alive.

David sits down with Chicago Ruby co-organizers Anton Tkachov and Michelle Yuen to talk about rebuilding and growing a local Ruby meetup. Anton breaks a meetup down into three essential pieces (attendees, speakers, and venues) and explains why, if you’re starting from scratch, the community itself matters more than anything else. He and Michelle share practical lessons from finding companies willing to host events, recruiting speakers, and creating opportunities for Rubyists to meet one another face-to-face.

That kind of personal connection may be more valuable than ever. The conversation explores how local meetups can help developers and companies establish real relationships in a job market increasingly complicated by remote hiring, AI-generated applications, and uncertainty about who is actually on the other side of an online interaction.

Anton also discusses his path from engineering into entrepreneurship, including the experience of being fired that ultimately pushed him into running his own consultancy. He talks about the less romantic realities of entrepreneurship, the challenge of balancing technology, sales, and marketing, and why becoming a founder isn’t necessarily the next rung on some professional ladder—it’s simply a different career path with a different set of problems to solve.

Finally, Michelle shares how years of involvement in the Ruby community opened an unexpected door: being selected as one of the MCs for Rails World. She walks through the application process, the community relationships that encouraged her to apply, and why getting the opportunity to introduce and celebrate people she already knows from the Ruby world makes the experience especially meaningful.

It’s a conversation about meetups, entrepreneurship, conferences, and the relationships that make the Ruby community more than just a collection of people using the same programming language.

Sponsor

Special thanks to this episode's sponsor: Judoscale

Sometimes the best conference conversations start with a weird idea.

Rachael Wright-Munn and Andy Andrea join me to revisit a moment at RubyConf when Andy's experiment with schemas and MCP tools collided with a problem Rachel had been trying to solve for Ruby Events: how to make Rails generators easily accessible to AI.

What started as an excited post-talk conversation quickly became an in-person pair programming session, and eventually working MCP tooling that Rachel now uses to maintain Ruby Events. The result has reduced some event updates from more than an hour of manual work to roughly 10–15 minutes.

They dig into how MCP tools work, why wrapping deterministic Rails generators can make AI workflows more reliable, and the tradeoffs between MCP, CLIs, skills, and letting models manipulate files directly. The conversation expands into harness engineering, metaprogramming, Git worktrees, dev containers, tool calling, and the strange reality that even developers deeply immersed in AI still feel like they're constantly trying to catch up.

It's a conversation about Ruby, AI, developer tooling—and the kind of serendipitous collaboration that still makes getting together at Ruby conferences so valuable.

** Sponsor **

Judoscale - https://judoscale.com