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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

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

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.

Essential Tools, Updates, and Strategies in Rails Eight with Greg Molnar - RUBY_671

Welcome back to another episode of the Top End Devs podcast! Today, we have an exciting lineup featuring our host Charles Max Wood and special guests Robbie Russell from Planet Argon, along with panelists Ayush Nawatia and Valentino Stoll. This episode dives deep into the insights from the latest Ruby community survey conducted by Robbie Russell. We explore topics such as the rise of Stimulus JS in the Rails community, trends in deployment practices, popular tools and services in the software ecosystem, and the everlasting debate between monoliths and microservices. Robbie also shares the fascinating history and evolution of his widely-used open source project, Oh My Z Shell, and gives us a glimpse into his work with Planet Argon. Stay tuned as we uncover intriguing details and valuable insights from the world of Ruby and Rails development!

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

Rails Developers Survey: Continuous Deployment Trends and Emerging Tools - RUBY 670

In this episode of Top End Devs, host David Camira is joined by panelists Luke Stutters and John Epperson, along with special guest Jesse Spivak, a senior engineer at Ibotta. Jesse shares his experiences and insights from a challenging project at Ibotta, where he navigated through four critical mistakes. These included choosing the wrong technology, siloing work, falling into premature optimization, and making too many changes at once. Jesse explains how these mistakes jeopardized the project but ultimately led to valuable learning experiences. The conversation also touches on the importance of discussing and learning from mistakes openly, the complexities of transitioning to new technologies, and the significance of making systematic, verified changes. Additionally, they delve into the evolving landscape of developer interviews, aiming to create a more inclusive and positive experience. Join us as we explore the trials, lessons, and growth that come from navigating the highs and lows of software development.

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

Exploring Tech Choices and Team Dynamics with Jesse Spivak - RUBY 669

In this episode, Chuck, Ayush, and Valentino join Olly Headey as he shares his expansive career journey, from co-founding FreeAgent to navigating the intricate world of cloud migration and technology adoption. They dive deeply into the various challenges and decisions involved in choosing frameworks like React, tackling server costs with CDN solutions, and simplifying complex tech stacks. Olly also discusses his experiences with boot camps, emphasizing the importance of foundational knowledge over trendy frameworks.
They touch on the significance of dependencies in tech projects, the evolving landscape of Ruby usage beyond Rails, and the practicalities of AWS CloudFront integrations. Olly offers his unique insights into balancing established and new technologies, emphasizing a pragmatic approach to tech evolution.
Join them as they explore the nuances of engineering management, the real-world implications of tech choices, and the strategies for maintaining simplicity in a fast-evolving tech landscape. Let’s get started!

Socials
LinkedIn: Olly Headey
Picks
 • Charles - 
Challengers! | Board Game • Charles - 
The Book on Mental Toughness • Olly - 
Friendly.rb - Your friendy European Ruby conference • Valentino - 
PodcastBuddy 

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

Cloud Migration, Server Costs, and CDN Challenges - RUBY 650

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