Wale Olaleye

Wale Olaleye has run Rails Fever on his own for 12 years. His clients are companies at least 10 years old, earning up to about $5 million a year, with no full dev team, and running on a custom Rails app. We get into how he found clients through Philly meetups, Slack communities and now cold outreach, why two solid people (one on sales, one on engineering) probably beat going solo, and why he left hourly billing two years ago for outcome-based retainers.LINKS- Rails Fever (Wale's consultancy)- Wale's LinkedIn- Buy Back Your Time by Dan Martell- SPIN Selling by Neil Rackham- The E-Myth by Michael Gerber- MicroConf- Business of Software- Arkency- Ryan's Website- Brendan's X/Twitter- Brendan's BlueskyQuestions or comments, email us at [email protected] us Fan Mail

Jeremy Smith has worked as a fractional Rails developer for 13 years, and he says 2026 is the hardest year he's seen to start. We get into why companies are holding their wallets, what "good code" and good tests even mean when nobody writes code by hand anymore, and why running three agents at once leaves all of us fried by mid-afternoon. Then Jeremy makes his case for where consulting goes from here.LINKS- IndieRails Podcast- Blue Ridge Ruby- HYBRD (Jeremy's studio)- Jeremy's Website- Jeremy's X/Twitter- Jeremy's Rails World 2026 Talk: Practical Hotwire- Ryan's Website- Brendan's X/Twitter- Brendan's Bluesky--Sponsor--This episode is brought to you by Flagrant.  Your partners for delivering thoughtful products & applications from any stage in your project.Questions or comments, email us at [email protected] us Fan Mail

DHH's Rails World keynote barely mentioned Rails, and the internet decided that meant Rails is dead. We don't buy it. Ryan took one line from the talk as a direct order and had an agent building his CLI the same day, which raises a bigger question: how much of your working life do you hand to an AI agent, and where do you draw the line? Then we ask whether conferences are still worth the ticket, and when they are.LINKS- DHH's Rails World Keynote- basecamp-cli- Ryan's Website- Brendan's X/Twitter- Brendan's Bluesky--Sponsor--This episode is brought to you by Flagrant.  Your partners for delivering thoughtful products & applications from any stage in your project.Questions or comments, email us at [email protected] us Fan Mail

What do you do when the database is maxed out, the busiest day of your year is six months away, and you still don't know what's actually wrong? Andrew Atkinson joins us to talk through that exact scenario at Aura Frames - the Christmas Day 2024 outage that set it off, and how they made Christmas Day 2025 a success. LINKS- Andrew's Book- Andrew's Newsletter - Scaling Rails at Aura Frames: Splitting to 8 Primary DBs and Reaching #1 in the App Store- From Christmas Outage to #1 App Store Ranking: An Aura Frames Postgres Scaling Retrospective- Rails at Scale- Postgres Summit US- You can't spell Shard without the word Hard- Open Positions at Aura Frames- Ryan's Website- Brendan's X/Twitter- Brendan's Bluesky--Sponsor--This episode is brought to you by Flagrant.  Your partners for delivering thoughtful products & applications from any stage in your project.Questions or comments, email us at [email protected] us Fan Mail

No guest this week — just Brendan and Ryan working through several things they've been seeing lately. Topics covered include:  - Anthropic's skills: why both of us started by writing one giant skill instead of small composable ones, and why that's the same lesson object-oriented programming taught us years ago.  - Where skills end and agents begin — plus a surprise from Brendan's code review setup, where the sub-agents it spun up weren't using the skill at all.  - Ryan's spam war at Locable: 2,000 fake accounts before breakfast, 60,000 businesses stuck waiting on human review, and whether an LLM should get a vote on what's legitimate.  - Why the real blocker isn't the skill — it's the APIs, MCPs, and evaluation systems underneath it that nobody talks about.  - And the PR backlog problem: AI gets you 90% there in an hour, the last 10% is as hard as it ever was, and Intercom and Shopify keep their pull requests under 200 lines for a reason.LINKSAnthropic Developers Skill Usage VideoIntercom 2x Shipping Blog PostRyan's WebsiteBrendan's X/TwitterBrendan's Bluesky--Sponsor--This episode is brought to you by Flagrant.  Your partners for delivering thoughtful products & applications from any stage in your project.  Book an hour with Flagrant at beflagrant.com/callQuestions or comments, email us at [email protected] us Fan Mail

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--Sponsor--This episode is brought to you by Flagrant.  Your partners for delivering thoughtful products & applications from any stage in your project.Questions or comments, email us at [email protected] us Fan Mail

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 BlueskyQuestions or comments, email us at [email protected] 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 BlueskyQuestions or comments, email us at [email protected] us Fan Mail

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 BlueskyQuestions or comments, email us at [email protected] 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 ReplaceLINKS- Ernesto's LinkedIn- Ernesto's Bluesky- FastRuby.io- OmbuLabs- Ryan's Website- Brendan's X/Twitter- Brendan's BlueskySend us Fan Mail