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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, I open up about what’s been going on behind the scenes with Ruby Rogues and why you’ve been hearing more solo shows from me lately. Between new full-time work, family life, and shifting schedules among the panelists, it’s been a wild stretch — but I’m committed to keeping the show coming to you every week. From there, I dive into something that’s been on my mind for a while now: the health of the Ruby community and what Minaswan really means in 2024.

I reflect on the growing cultural and political tensions I’ve seen spill into technical spaces and why I believe our community is stronger when we focus on behavior, kindness, and collaboration rather than labels and ideological litmus tests. I talk about how we can disagree without dividing, maintain safe and welcoming spaces without gatekeeping based on worldview, and get back to what brought us all here in the first place: a shared love of Ruby, learning, and helping each other grow.

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

Keeping Ruby Welcoming: A Conversation We Need to Have - RUBY 680

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

In this episode, we had the absolute pleasure of sitting down with Carmine Paolino — an AI innovator, Ruby enthusiast, and all-around tech wizard. From his early days automating PC games at age five to building cutting-edge AI tools in Berlin, Carmine’s journey is as inspiring as it is impressive.

We dove deep into his latest creation: RubyLLM, a Ruby gem that simplifies working with large language models (LLMs) like GPT-4, Claude, and Gemini. Think of it as an intuitive, plug-and-play toolkit that lets Ruby developers tap into powerful AI features — chat, image generation, embedding, tools, and even multi-model support — with just a few lines of code. And yes, it’s as awesome as it sounds.

Key Takeaways: • RubyLLM is built for simplicity and power. Carmine wanted a tool that “just works” — one unified interface for chatting, streaming, tool use, image generation, and more. It abstracts away the API mess and keeps things Ruby-friendly.
 • Tooling support is next-level. RubyLLM allows for agentic AI by letting devs define tools (like checking the weather or sending a calendar invite). The gem handles when and how to use them — magic! 
 • Support for multiple models and providers. OpenAI, Anthropic, Google — RubyLLM makes it easy to switch between them seamlessly, even mid-conversation. Carmine also teased a future integration with a smarter model registry via an AI-powered API called Parsera.
 • Streaming and performance? Covered. Carmine shares clever architecture tricks using Turbo Streams and async Ruby for blazing-fast, lightweight responses — even when handling many concurrent users.
 • Real-world use case: ChatWithWork. Carmine’s app lets users “chat” with their docs from Google Drive, Notion, and Slack. RubyLLM is the backbone, and it’s got real startup traction. (Oh, and he DJed the night it went viral on Hacker News.)
 • Embeddings and image generation are just as easy. Need vector search or auto-generated podcast art? Just call .embed or .paint — seriously, that’s it.

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

The Magic of RubyLLM with Carmine Paolino - RUBY 676

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

01:37 - Greg Baugues IntroductionTwitter • 
GitHub • 
BlogRuby Rogues Episode @142: Depression and Mental Illness with Greg BauguesGreg Baugues: Devs and DepressionDevs and Depression02:51 - Twilio 05:27 - Two-factor AuthenticationCrash Override Network: So You’ve Been Doxed: A Guide to Best PracticesAuthy • 
Greg Baugues: Passwords are not Enough @ RailsConf 2015How Apple and Amazon Security Flaws Led to My Epic Hacking • 
13:42 - Implementing Security; Why Security is Important and EssentialDan Luu: Normalization of deviance in software: how broken practices become standard27:26 - Twilio Use CasesDoug Mckenzie • 
Ryan Leslie's SuperPhone: Beating Facebook To The Scalable Personal Messaging Table • 
mRelief • 
How I Taught My Dog to Text Me SelfiesArduino Yún34:16 - IP MessagingWebRTCiPhreaks Show Episode #129: WebRTC • 
Thomas Gorissen: jQuery for WebRTC @ JS Remote Conf 2015 • 
Talky.io38:02 - TwiML Burner 42:46 - Using Twilio to Enhance BusinessAppointment ReminderSMS Messaging48:50 - Twilio’s Tech StackFlaskAmazon Web Services (AWS)50:19 - Opt-outs and Phone Number Validation52:45 - LookupSIP55:46 - Developer Evangelism 
 Goodbye, Avdi. We will miss you <3
 Avdi's Newsletter 
 Who wants to be the next Ruby Rogue? Submit your video. Picks The CHECKS Pattern Language of Information Integrity (Avdi)
 Delegation (Avdi)
 CaJohns Ignite Hot Sauce (David)
 beach house (Coraline)
 CocoRosie (Coraline)
 The Misters of Circe (Sam)
 DesktopServer (Chuck)
 Advanced Custom Fields (Chuck)
 Convert Post Types (Chuck)
 Gravity Forms (Chuck)
 MemberPress (Chuck)
 SIGNAL Conference (Greg)Special Guest: Greg Baugues. 

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

258 RR Twilio with Greg Baugues

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