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Charles M Wood

Our original panel podcast, Ruby Rogues is a weekly discussion around Ruby, Rails, software development, and the community around Ruby.

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Ruby Rogues

AI agents are no longer just tools we manually wire together—they’re starting to build themselves. In this episode of Ruby Rogues, I caught up with Valentino Stoll to explore a fascinating idea: autogenetic (self-generating) AI agents and what they mean for how we write software in Ruby.

We dig into Valentino’s experimental Ruby gem, agentic, and talk about plan-and-execute workflows, self-assembling agents, and how modern LLMs are reshaping everything from local development to production systems. Along the way, we zoom out to ask bigger questions about learning, career longevity, and what Ruby developers should really be focusing on as AI continues to accelerate.

AI isn’t eliminating the need for developers—it’s pushing us up the abstraction ladder. Understanding systems, concepts, and architecture matters more than ever, even as we write fewer lines of code by hand.

If you enjoyed this episode, please rate, follow, share, and review Ruby Rogues. It helps more developers find the show and stay ahead of where the industry is headed. Thanks for listening—and we’ll catch you next time.

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Autogenetic AI Agents and the Future of Ruby Development - RUBY 682

In this solo episode, I sit down to unpack my thoughts on DHH’s RailsWorld keynote and what it means for those of us building modern Rails apps. There’s a lot to love about Rails right now — from the push toward simplicity and reducing needless complexity to powerful new features landing in Rails 8.1 like Markdown rendering, offline mode, structured events, push notifications, and more. I also dive into some of the deployment and infrastructure ideas DHH shared, including Kamal, Omarchi, and the “broad toolchain” philosophy that’s shaping the future of Rails.

I also share my own experiences with deploying Rails apps using Kamal, my thoughts on the microservices vs. monolith debate, and why I’m seriously considering running more of my own infrastructure at home. Plus, I dig into some new projects I’m launching, including podcasts, video series, and SaaS work built using Rails 8.1’s latest capabilities.

🔗 Links & Resources • Kamal – 
https://kamal-deploy.org • Hotwire / Turbo Native – 
https://hotwired.dev

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

The New Era of Rails: Markdown, Offline Mode, and Smarter Dev Tools - RUBY 681

In this solo episode of Ruby Rogues, I’m unpacking one of the biggest stories in the Ruby world right now: the tension between Ruby Central and core RubyGems contributors. I share what I’ve learned from talking to people across the community and why this issue is more complex than it looks on social media. From the origins of Bundler and Ruby Together to the recent creation of gem.coop, I trace how we got here—and why both sides have valid points but also made serious missteps.

I also open up about what this means for the Ruby ecosystem going forward, why transparency and trust matter more than ever, and how we as a community can respond productively. Toward the end, I lighten things up with some picks, including a clever deduction card game and a heartfelt call for more understanding in our world—both in code and beyond.

🔗 Links & ResourcesRuby Centralgem.coop • – the new RubyGems mirror/community alternative
Top End Devs • – get involved or create your own dev content
 • Email Chuck: chuck@topendevs.com if you’re interested in co-hosting or authoring a series

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Inside the RubyGems Controversy: Transparency, Trust, and the Future of Ruby Central - RUBY 679

In this episode of Ruby Rogues, I sit down with Mike McQuaid, lead maintainer of Homebrew, to talk all about building and distributing CLIs. We dig into the practical steps for turning small scripts into reliable command-line tools, why Ruby is a great starting point, and when you might want to reach for Go or Rust instead.

We also explore the challenges of distributing CLIs across macOS, Linux, and Windows, why Homebrew remains one of the easiest ways to ship software, and the importance of testing CLIs from the outside in. Plus, Mike and I discuss how AI is transforming the developer workflow—from Copilot PR reviews to agent-based coding—and what that means for both seniors and juniors in today’s industry.

Links & ResourcesMike McQuaid’s Website • – Mike’s talks, articles, and contact info.
Homebrew • – The missing package manager for macOS (and Linux).
Bundler Inline • – Running dependencies inside a Ruby script.
Hyperfine • – CLI benchmarking tool.
Cursor • – AI-powered code editor.
GitHub Copilot • – AI pair programmer.

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Distributing Your CLI with Homebrew: Tips from Mike McQuaid - RUBY 678

Hey everyone, Charles Max Wood here! It’s great to be back behind the mic with Ayush Nawatia for another episode of Ruby Rogues. This time, we’re diving into the fascinating world of Ruby community resources with two amazing guests: Adrien Poly and Marco Roth. They’re the creators behind RubyEvents.org, an ambitious project that’s aiming to centralize and modernize access to Ruby-related videos, conferences, meetups, and more.

In this episode, we explore the vision and evolution of RubyEvents.org—originally RubyVideo.dev—and how it’s grown into a hub for the Ruby community. We discuss the technical stack (think SQLite, Tailwind, Vite, and Hotwire), how they’re leveraging LLMs to auto-tag thousands of conference talks, and what’s on the roadmap next. Whether you're a conference organizer, speaker, or just a Ruby fan, this one’s packed with insight and inspiration.

 Links & ResourcesRubyEvents.org • – Discover and explore Ruby conferences, talks, and speakers
Ruby Video GitHub Repo • – Open source code for web and mobile apps
 • StimulusUse – StimulusJS utility library created by the guests
 • Hotwire DevTools – Browser extension for debugging Hotwire apps
HYROX Fitness Race • – Hybrid CrossFit endurance competition mentioned by Adrian
 • Camel Up Board Game – Charles’ board game pick
The Overview by Steven Wilson • – Ayush’s music pick
 • Sword of Truth Series by Terry Goodkind – Fantasy book series
 • Catalyst (Web Components framework) – GitHub’s lightweight JS framework

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Indexing the Ruby World with RubyEvents.org - RUBY 677

Hey folks, in this week’s episode, I sat down with the incredible Ridhwana Khan — a South African technical writer for the Rails Foundation and lead engineer at Circle. We had a fantastic chat about all things Ruby on Rails, but especially the underappreciated art (and science!) of writing documentation.

Ridhwana took us behind the scenes of the official Rails Guides — how they’re updated, expanded, and reviewed — and gave us a real sense of the thoughtful, collaborative work that powers one of the best-documented frameworks out there. She also shared her personal journey: from freelancing into Rails doc writing, to her passion for building inclusive communities like Rails Girls South Africa and Black Girls Code.

Some standout takeaways:
 • Metaprogramming = Superpower: We talked about the "magic" in Rails internals — especially metaprogramming — and how understanding it can make you a better developer. Ridwana gave a real-world use case from her time at Dev.to where metaprogramming enabled highly flexible custom profile fields. Elegant and practical!

 • Docs as a Gateway to Contribution: Whether you're new or experienced, contributing to Rails docs is a great way to get involved. Ridwana encouraged folks to read the source code, dig into tests, and not be afraid to open a PR — even if it's small.

 • Working on Circle: Ridwana’s team focuses on Circle's marketing and email hub features — think broadcasts, workflows, and analytics. She's leading the team (and hiring!), and we geeked out over async work, remote culture, and what makes for a great engineering org.

 • Life in Cape Town: From houseplants to penguins, we veered off into Ridwana’s love of nature, her Arduino hobby projects, and even how Shark Week got us thinking about visiting South Africa someday.

This episode was equal parts inspiring and insightful — especially if you’ve ever looked at the Rails codebase and thought, “how the heck does this work?” Ridwana makes it feel accessible, and she’s proof that curiosity and community-building go a long way in tech.

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Demystifying the Rails Codebase with Ridhwana Khan - RUBY 675

In this episode of Ruby Rogues, Charles Max Wood and Ayush Nwatia welcome back guest Stephen Margheim to dive deeper into the evolving world of SQLite. Stephen explains that with Rails 8, SQLite has reached a major milestone: it now supports a fully production-ready, server-driven web application experience with no compromises. He walks us through the big improvements, like better transaction handling and SQLite’s integration with Rails, which now supports background jobs, caching, and WebSocket messaging—all powered by SQLite without additional configuration. These enhancements mean that deploying a Rails app backed entirely by SQLite is not only possible—it’s efficient, stable, and simple.

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

How to Optimize Your Rails App Using SQLite - RUBY 674

In this episode, we dove into a topic that’s been on our minds — how to navigate change with purpose instead of fear. Whether it's personal transformation, career pivots, or unexpected life shifts, we talked about what it takes to stay grounded and aligned during times of transition.

We opened up about our own experiences with change — the messy middle, the doubts, the resistance — and how we’ve learned to see it as a creative force rather than something to avoid. A big takeaway? Growth doesn’t always look graceful, but it’s often where the magic happens.

One of the key points we emphasized was the importance of self-trust. It’s easy to look outside ourselves for permission or validation, but true clarity comes from tuning inward. We shared tools that have helped us build that inner compass, like journaling, setting intentional pauses, and letting go of perfectionism.

We also touched on how community plays a huge role in transformation. Change can feel isolating, but when we open up and connect with others who’ve walked similar paths, it reminds us we’re not alone.

Key Takeaways: • Change is a creative process, not just a disruption.
 • Self-trust is your greatest guide through uncertainty.
 • It’s okay to not have all the answers right away — clarity often follows action.
 • Community and vulnerability are antidotes to isolation during transformation.
 • Letting go of control creates space for something better to emerge.
We wrapped up with a little reminder: whatever shift you’re in right now, you’re not behind — you’re becoming.

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Why Change Feels Scary—And How to Make It Work for You - RUBY 673

In this episode of the Ruby Rogues podcast, we dive deep into the world of Hotwire Native with our special guest, Joe Masilotti. Hosted by Charles Max Wood, along with panelist Ayush Nwatiya, we explore the evolution from Turbo Native to Hotwire Native and the exciting new features and improvements that come with this transition. Joe shares insights from his journey of writing "The Rails and Hotwire Codex" and collaborates with Pragmatic Bookshelf to make the integration of web and mobile technologies more seamless for Ruby on Rails developers. Whether you're considering mobile applications for your Rails projects or pondering the benefits of working with a publisher versus self-publishing, this episode is packed with valuable advice and motivation. Tune in to learn about the intricacies of launching mobile apps with Hotwire Native and gain behind-the-scenes knowledge from Joe's experience as an author and developer in this ever-evolving tech landscape. Don't miss out on this compelling discussion that bridges the gap between Rails and mobile app development!

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

Joe Masilotti on Hotwire Native Updates, Challenges, and Opportunities - RUBY_672

In this episode of Top End Devs, we dive deep into the realm of security within the Rails ecosystem with our guest, Greg Molnar. Known for his expertise in this field, Greg joins our panelists Valentino Stoll and host Charles Max Wood to unravel the intricacies of security measures and updates in Rails 8 and 7.2. From exploring built-in features like rate limiting, authentication generators, and parameter filtering to discussing the importance of tools like dependabot and Brakeman, this episode offers a comprehensive look at how developers can maintain high-security standards in their Ruby on Rails applications. We also touch on practical strategies for handling authentication, authorization, and the evolving nature of security challenges developers face today. Whether you're a Rails veteran or new to web development, tune in to gain valuable insights into creating secure applications with ease.

Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.

How to Optimize Your Rails App Using SQLite - RUBY 674

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