Rails Business

Jim Remsik — founder of Flagrant, Madison Ruby and the traveling XO Ruby conferences — joins us for a wide-ranging conversation.  The discussion starts with the ups and downs of running a design-and-dev agency in the AI era.  Topics covered include:
- Why design has started outselling development at Flagrant.
- Why accessibility and UX are the parts people forget, and how Flagrant's hiring process mirrors real work to surface the thing that matters most: communication.
-  Plus the story of XO Ruby — small, one-day, city-to-city conferences built to make community accessible again.
LINKS
- Flagrant
- XO Ruby
- Ryan's Website
- Brendan's X/Twitter
- Brendan's Bluesky
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Nate Berkopec (Speedshop) returns to dig into what AI actually changes about Rails performance work — and it's not what the hype says. The through-line: stop conflating understanding code with verifying it, because the real leverage is building objective, tool-callable checks an agent can loop against — N+1s, characterization tests, jemalloc — instead of shipping more unreviewed slop. Nate makes the case that the future looks like Intercom's "software factory" (tiny, automatically-verified PRs, most merged with no human review) and asks why the rest of us are still hand-building 4,000-line monstrosities. Plus: why "intelligence" is the wrong word for what these models do, and a first look at Thread Pilot, his new automatic thread-pool tuner for Sidekiq and Puma.
LINKS
- Speedshop
- Nate's X/Twitter
- Threadpilot
- The Complete Guide to Rails Performance Book
- Sidekiq in Practice Book
- On Rails Episode with Brian Scanlan from Intercom
- Ryan's Website
- Brendan's X/Twitter
- Brendan's Bluesky
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Ryan Castillo returns to talk about pivoting Knowatoa from an SEO play into an AI-visibility tool — and why the analytics everyone wants to track are becoming impossible to trust in an AI-search world. The back half turns into a deep dive on Ryan's AI coding workflow: skipping the Claude chat interface entirely in favor of firing off cloud agents from Cursor, letting them run unsupervised, and reviewing PRs cold instead of living in the conversation. Plus: why "throw away the code, not the plan" beats hand-holding an agent through every step, and why the AI labs have zero incentive to ever let you leave the chat.
Links:
- Knowatoa
- Ryan Castillo's X/Twitter
- Ryan Castillo's LinkedIn
- Ryan's Website
- Brendan's X/Twitter
- Brendan's Bluesky
Questions or comments, email us at railsbusinesspod@gmail.com
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Ernesto Tagwerker (FastRuby.io / OmbuLabs) returns to talk through how AI is reshaping both sides of his business — speeding up Rails upgrades while simultaneously eating into revenue, and opening a new lane in AI strategy consulting for non-technical businesses. The group digs into the messiness of AI-generated tests, mutation testing, and how to know when your tests are actually testing anything.
  01:00 FastRuby's Open Source Claude Skill for Rails Upgrades
  03:30 How AI Has Eroded (and Grown) FastRuby's Revenue
  07:00 Engineering as Marketing — Why They Open Sourced the Playbook
  10:00 The Tooling Isn't the Problem — Engineering Culture Is
  12:30 Using Claude to Write Contract Tests and Improve Coverage
  15:30 The Problem with AI-Generated Tests
  17:00 Mutation Testing Explained
  19:00 Classicist vs. Mockist — Where Claude Gets It Wrong
  23:00 Playwright for Acceptance Testing in the Development Loop
  26:00 Who Watches the Watcher?
  28:00 Staff Augmentation and AI Strategy at OmbuLabs
  31:00 Working with Non-Technical Businesses in Philadelphia
  33:30 Engagement Sizes — AI Discovery vs. Rails Upgrade Projects
  35:30 CRM Summaries and One-on-One Prep with AI
  38:30 Observability and Guardrails — How Do You Know It's Working?
  43:00 LLM as Judge
  45:00 Event Scraping — AI Makes Scrapers More Maintainable
  50:00 Ryan's Universal Scraper — Using AI to Heal, Not Replace
LINKS
- Ernesto's LinkedIn
- Ernesto's Bluesky
- FastRuby.io
- OmbuLabs
- Ryan's Website
- Brendan's X/Twitter
- Brendan's Bluesky
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Colleen Schnettler and Joe Masilotti (Permission Not Required podcast) join Ryan and Brendan to catch up on what they're each building. Joe walks through Ruby Native — his platform for getting Rails apps into the App Store without touching Xcode or writing native code — and how AI has changed his development process. Colleen shares what AI automation consulting actually looks like in practice: more process mapping and integrations work than pure AI, and why developer credibility matters in a crowded market. The group also compares notes on how they're each using AI beyond coding — for business context, client management, and personal workflows.
  00:00 Introductions
  01:00 Ruby Native — Rails to the App Store Without Xcode
  05:30 What Changes When You're the Only One Reading the Code
  08:00 AI Automation Consulting in a Crowded Market
  13:00 Beyond Content and Sales — Where AI Actually Fits
  16:00 Cowork, Skills Repos, and Dropping OpenClaw
  18:00 Joe's Three-Agent Coding Workflow
  22:00 Projects You'd Never Have Tackled Before AI
  24:30 Ruby Native vs Hotwire Native Explained
  28:00 How the Preview Workflow Works
  33:30 Leveraging Existing Networks for New Businesses
  41:00 When Automation Doesn't Need AI
  44:00 The Command Center and Second Brain Thread
  49:00 Joe's Business Context in Claude — Powerful and Dystopian
  51:30 Colleen's Personal Agents (School Emails, LinkedIn Pipeline)
  54:30 Where to Store Context — Markdown, SQLite, and Avoiding Beads
  56:00 Joe at RubyConf in July
LINKS
- Permission Not Required Podcast
- Colleen's LinkedIn
- Colleen's Email: colleen@colleen.is
- Joe's Website
- Ryan's Website
- Brendan's X/Twitter
- Brendan's Bluesky
Questions or comments, email us at railsbusinesspod@gmail.com
Send us Fan Mail