Rails Business

Jesse Hanley joined us from southern Japan, where he runs Bento — an email marketing and transactional email platform — as a company of one. Topics covered include:
Why the bootstrapped dream now means picking big, hairy, competitive markets instead of cozy niches AI can replicate overnight.
Automating entire roles with agentic "employees" — Cursor Cloud Agents and Grok Bot wired into MCPs for support, compliance, infra, finance and dev.
Why most jobs are really just cron jobs, and how far one person can go if they build the tools deep enough.
Plus Heroku scale-to-zero, moving Postgres off to PlanetScale, and why he's eating his words on agents replacing labor.
LINKS
- Bento
- Tatami
- Ryan's Website
- Brendan's X/Twitter
- Brendan's Bluesky
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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
Questions or comments, email us at railsbusinesspod@gmail.com
Send us Fan Mail

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
Questions or comments, email us at railsbusinesspod@gmail.com
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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
Send us Fan Mail

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
Send us Fan Mail