Episode 549: ChicagoRuby with Anton Tkachov and Michelle Yuen

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

Episode 548: MCP + Generators with Andy Andrea and Rachel Wright-Munn

Sometimes the best conference conversations start with a weird idea. Rachel 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

Episode 547: Special Guest Andy Croll

Andy Kroll joins the podcast to talk about Brighton Ruby, the impact AI is having on software development, and how the changing technology landscape is affecting everything from conference budgets to engineering teams. Andy shares how tools like Claude Code have changed his day-to-day work, making previously neglected projects more achievable while putting even more emphasis on code review, judgment, and maintaining a sustainable Rails application. They also dig into one of the harder questions created by AI: how do you interview software engineers when take-home coding exercises and traditional technical tests are increasingly easy to hand off to a model? Andy explains how CoverageBook is approaching hiring by focusing on product thinking, decision-making, real-world code review, and conversations that more closely resemble actually working together. The conversation also turns to the challenges of organizing Brighton Ruby, why Andy is taking a year off from the conference, David’s interest in someday organizing a Ruby conference of his own, and why keeping financial risk under control may be the most important lesson for a first-time conference organizer. Finally, they look ahead to Rails World and reflect on one of the biggest reasons conferences still matter: getting Ruby developers out from behind their screens and into a room with people who understand what they do. Sponsor Judoscale: https://judoscale.com/

Episode 546: Gearing up for Rails World, with Amanda Perino

Rails Foundation Executive Director Amanda Perino joins David to preview Rails World 2026, the conference’s first year in the United States. Amanda shares how the team is bringing Austin’s personality into the event through live music, barbecue, sponsor experiences, a mechanical bull, the returning Buzzsprout podcast booth, and Rails World’s biggest lightning-talk stage yet. She also discusses the opening keynote livestream, the lightning-talk CFP, ticket availability, and what attendees should expect as the conference approaches. The conversation then turns to the Rails Foundation itself. Amanda explains how the rapid growth of AI has forced the organization to reconsider how it executes its mission across events, marketing, documentation, and education. They also discuss the challenge of building a conference program that serves developers interested in AI without neglecting everything else happening in Ruby and Rails. Finally, Amanda surprises David with an extra ticket to Rails World—and they decide to give it away to a podcast listener. Enter the Rails World ticket giveaway: https://forms.gle/LoLvTfJ2BFavpox69 Sponsor Judoscale: https://judoscale.com/

Episode 545: Post RubyConf conversation with Neha Abraham

Making new Ruby Friends is one of my favorite parts of attending conferences. Neha Abraham joins me to chat about RubyConf, Mental Health, Data Aggregation, and being my Nemesis

Episode 544: RubyConf 2026 Hallway Track

While at RubyConf, I caught up with several attendees and volunteers to discuss their experiences. These quick interviews have been collected for this episode. Our Guests Charles Nutter Miguel Filho Cameron Dutro Nico Roulston

Episode 543: Mike Dalton and Authentication Hell

Episode 542: Kyle D'Oliveira and the Fibonacci Funhouse

Episode 541: Markus Schirp and Mutation Testing

With AI seeming to generate more code every day, we need better tools to verify that it hasn't broken something. Maybe mutation testing can help us get there. Markus Schirp chats with us about the mutant gem and mutation testing. Show Notes https://github.com/mbj/mutant Sponsors Lots of teams out there are still overpaying for their hosting and getting tripped up by traffic spikes. If you’re on one of those teams, you need a better autoscaler. Judoscale uses better metrics, gives you more control, and reacts faster than any other autoscaler. Learn more at https://judoscale.com/

Episode 540: Jeremy Smith and Blue Ridge Ruby

Blue Ridge Ruby made a comeback in 2026 and Jeremy Smith joins the podcast to talk about how it went Show Notes https://blueridgeruby.com/ Sponsors Lots of teams out there are still overpaying for their hosting and getting tripped up by traffic spikes. If you’re on one of those teams, you need a better autoscaler. Judoscale uses better metrics, gives you more control, and reacts faster than any other autoscaler. Learn more at https://judoscale.com/

Episode 539: Travis Dockter and Blastoff Rails

Travis Dockter wanted a Ruby conference closer to home, so he made one. Today we chat about the ups and downs of putting together a brand new conference. Show Notes https://www.blastoffrails.com/ https://rubyconferenceproject.com/ https://game.blastoffrails.com/ Sponsors Lots of teams out there are still overpaying for their hosting and getting tripped up by traffic spikes. If you’re on one of those teams, you need a better autoscaler. Judoscale uses better metrics, gives you more control, and reacts faster than any other autoscaler. Learn more at https://judoscale.com/

Episode 538: A New Host Has Appeared!

Rachael interviews the new host of the show, David Hill, to discuss his history with Ruby, his love for podcasting, and how much he loves meetups and conferences. Show Notes https://www.odetorailsconf.com/ http://rubygemspodcast.com/ https://www.remoteruby.com/ Sponsors Lots of teams out there are still overpaying for their hosting and getting tripped up by traffic spikes. If you’re on one of those teams, you need a better autoscaler. Judoscale uses better metrics, gives you more control, and reacts faster than any other autoscaler. Learn more at https://judoscale.com/

Episode 537: Userlist with Benedikt Deicke

Benedikt used to be a freelance software engineer and co-founded Userlist in 2017 as a side project with his co-founder Jane Portman. They went full-time on it in 2020. Benedikt enjoys database query optimization just as much as pushing around pixels on the front-end Show Notes * https://userlist.com/ * https://slowandsteadypodcast.com/ * https://bsky.app/profile/benediktdeicke.com Sponsors Hosting for The Ruby on Rails Podcast is provided by Fireside.fm. If you want to start a podcast and are looking for hosting, visit fireside.fm/rails (http://fireside.fm/rails) to get started. Alright, let’s talk about deploying code without having a full-blown panic attack. You ever push something live and immediately regret it? Like, ‘Oh no, I just nuked the homepage’? Well, guess what—Flipper’s got your back. Ship your code whenever you want, roll out features on your schedule, and if something goes sideways? Boom. Roll it back. No redeploy, no drama. Plus, you get multi-environment sync, audit history, and fine-grained permissions, so you don’t wake up to a ‘WTF happened?’ Slack message. Best part? Sign up at http://flippercloud.io/rails (http:flippercloud.io/rails) and get 10% off your first year. Flip the switch and chill out.

Episode 536: Better With Becky with Becky Searls

Becky Searls is a teacher-turned-trainer, but her true passion is learning and continuous growth. She shares everything she learns through her business, Better with Becky, which recently launched its first product: a strength-training app called Build with Becky (which she built in collaboration with her husband Justin using Ruby on Rails) Show Notes * www.betterwithbecky.com * www.gram.betterwithbecky.com Sponsors Hosting for The Ruby on Rails Podcast is provided by Fireside.fm. If you want to start a podcast and are looking for hosting, visit fireside.fm/rails (http://fireside.fm/rails) to get started. Alright, let’s talk about deploying code without having a full-blown panic attack. You ever push something live and immediately regret it? Like, ‘Oh no, I just nuked the homepage’? Well, guess what—Flipper’s got your back. Ship your code whenever you want, roll out features on your schedule, and if something goes sideways? Boom. Roll it back. No redeploy, no drama. Plus, you get multi-environment sync, audit history, and fine-grained permissions, so you don’t wake up to a ‘WTF happened?’ Slack message. Best part? Sign up at http://flippercloud.io/rails (http:flippercloud.io/rails) and get 10% off your first year. Flip the switch and chill out.

Episode 535: Judoscale with Adam McCrea

Today we’re continuing our series of highlighting startups building with Rails. Every app eventually runs into scaling requirements. Whether that’s from a spike in traffic or persistent growth. That’s why we have autoscaling. Judoscale is a tool to make autoscaling easy. Adam joins us to talk about building Judoscale with Rails Show Notes * https://judoscale.com/ * https://www.linkedin.com/in/adamlogic/ * https://bsky.app/profile/adamlogic.com Sponsors Hosting for The Ruby on Rails Podcast is provided by Fireside.fm. If you want to start a podcast and are looking for hosting, visit fireside.fm/rails (http://fireside.fm/rails) to get started. Alright, let’s talk about deploying code without having a full-blown panic attack. You ever push something live and immediately regret it? Like, ‘Oh no, I just nuked the homepage’? Well, guess what—Flipper’s got your back. Ship your code whenever you want, roll out features on your schedule, and if something goes sideways? Boom. Roll it back. No redeploy, no drama. Plus, you get multi-environment sync, audit history, and fine-grained permissions, so you don’t wake up to a ‘WTF happened?’ Slack message. Best part? Sign up at http://flippercloud.io/rails (http:flippercloud.io/rails) and get 10% off your first year. Flip the switch and chill out.