Boulder Ruby June 2026 Presentation Night
Join us at our monthly gathering where we present topics of interest to Rubyists and aspiring programmers.
Doors open at 6:00pm, where you can hangout and socialize with other Boulder Ruby members.
We also have a zoom at https://us06web.zoom.us/j/86988064634?pwd=RhnyR0iYNx47LASqjdOLQbAFxq9GX3.1 if you want to join online.
At 6:30, we do announcements before getting to our presentations.
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Talk 1: Death by a Thousand Endpoints: War Stories from an API-First Rails Rescue (Full Talk)
Description:
Picture a Rails app running three API versions at once, the frontend and backend teams pointing fingers, and integration bugs nobody could reproduce.
That was us. In this talk I'll share the (slightly painful) war stories from dragging a 15-year-old Rails codebase out of API-version sprawl and into an "API First" world — where a single OpenAPI spec finally got everyone speaking the same language.
I'll walk through what actually worked: treating the spec as a real contract, enforcing honest SemVer, and leaning on Anthropic's Claude CLI to crank out JSON schemas, stub endpoints, and draft Ruby in seconds instead of afternoons. Expect candid lessons, a few facepalm moments, and patterns you can take back to your own legacy app on Monday morning.
Beginner-friendly, but the war stories are for anyone who's ever inherited an API they didn't design.
Bio:
Chris Hough is a Ruby on Rails engineer and engineering leader with over 15 years of hands-on production experience building and modernizing complex Rails applications. He has pioneered AI-assisted Rails development — most notably using Claude and Cursor to build a production Rails 8 application featuring Rodauth authentication, Hotwire (Turbo + Stimulus), and Solid Suite background processing — achieving 10x faster delivery while upholding enterprise standards and best practices.
Known for his primary career superpower of simply "Getting Shit Done", he brings deep expertise in legacy modernization, scalable API design, RSpec optimization, and modern Rails tooling, alongside a strong commitment to community building: he founded and led a 155-member Ruby Guild, organized multiple Ruby meetups, and mentored students at Turing School of Software & Design. Passionate about clean code, fast tests, and empowering remote teams, Chris delivers practical, battle-tested insights from years of shipping high-impact production systems.
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Talk 2: Legacy Rails and the AI That Couldn't
Description:
Ruby and AI are supposedly a perfect match. In less-than-ideal legacy codebases, the reality is messier. Agents stumbled on the same things I had during onboarding: unnecessary complexity, conflicting patterns, and conventions that actively fought Rails. My PR review queue grew while I made the same corrections over and over - in my editor and then again on GitHub.
I hit a breaking point, unsure if this career was still for me. My coworker's advice seemed like a joke: "The antidote to too much AI is more AI." I didn't have time to become an AI expert; I would drown before I could get department consensus on strategy, so I ran a small experiment, changing only how I communicated with AI in my workflow.
What started as survival evolved into a flywheel. Whether you're skeptical, curious, or drowning in AI-generated code, you'll see how small experiments compound into real leverage — and how capturing your team's knowledge where both humans and agents can find it changes everything. No special title or pristine codebase required.
Bio:
Madison Sites is based in Lake Tahoe, CA and has been a professional Ruby developer for over 10 years. She believes that removing dead code is the sixth love language. When she's not building things with cool people on the internet, you can find her very much offline, hiking on or maintaining a trail.
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If you would like to present at this meeting, or at upcoming events, reach out to the organizers on this meetup, contact us in the #ruby channel on TechFriends, or ping us at @boulderruby or https://bsky.app/profile/boulderruby.bsky.social.