Rails Business

Jesse Hanley of Bento

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 railsbusinesspod@gmail.com Send us Fan Mail

Jim Remsik

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

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 Send us Fan Mail

Ryan Castillo

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

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

Colleen Schnettler and Joe Masilotti

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

Rolling Your Own APM with Claude: Real Wins, Real Tradeoffs

Ryan and Brendan talk through the growing pains of AI-assisted development — including fatigue, increased confidence in bigger code changes, and what happens when you stop paying for expensive APM tools and just build your own. Ryan walks through how he used Claude to identify memory pressure, fix N+1 queries, and cut his Heroku costs significantly in just a few days. They also dig into the real tradeoffs: maintenance burden, over-optimization, and why you still need to understand what Claude is telling you before you run anything on a live database. LINKS - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Scott Werner Returns

Scott Werner (Sublayer) returns to discuss how rapidly AI and agentic coding have is changing. The hosts and Scott dig into why niche tools are increasingly getting replicated by developers and hobbyists with "good enough" custom solutions — while complex enterprise platforms may actually have more staying power. Scott shares what he's seeing at the Artificial Ruby meetups. They also cover Stripe's "forward deployed" AI role, the reality of AI consulting, growing trust in AI-written code, and orchestration tools like Fabro for defining repeatable AI workflows. 01:03 Early Agentic Coding Days 04:49 SaaS Is Dead Debate 10:28 Enterprise vs Homegrown Systems 12:52 Forward Deployed Builders 15:20 Architects Still Matter 19:33 Personal Software vs Production 23:22 Stripe Forward Deployed AI Role 26:16 AI Adoption and Consulting Window 29:42 Games and What Software Becomes 33:20 Burnout and Pairing Lessons 36:06 Learning to Trust AI Output 38:57 Requirements Over Code Style 43:02 Multi Project AI Workflow 45:36 Software Factory Orchestration 54:40 Process Thinking and QA 56:41 Skills and Non Determinism LINKS - Sublayer Website - Scott's Blog (Works on My Machine) - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

• Transcript

Is Data the Moat for Your Business?

The hosts explore whether “data is the new moat” in SaaS and argues that data alone—especially customer data—is rarely defensible as extraction and migration get easier. Instead, moats increasingly come from clear product vision, differentiated approaches, integrated systems, and how well apps enable AI and humans to interact with structured data. They contrast niche SaaS with broad platforms like HubSpot and Salesforce, discuss pricing model changes driven by AI costs (moving beyond per-seat to metered/credits), and predict reduced reliance on traditional UIs as chat and CLIs become efficient interfaces for AI-to-backend communication. 00:00 Data as a Moat 01:52 Niche vs Platform SaaS 02:45 Integrations and UX Moats 05:31 AI Changes Pricing Models 06:48 Geocoding Data Example 08:35 When Not to Use AI 10:43 Why CLIs Are Rising 14:25 Future Without Interfaces 18:43 Data Product vs Customer Data 21:28 Opinionated SaaS Wins 23:19 AI Change And Strategy 23:48 Defensibility And Platform Risk 25:19 Building A Command Center 27:30 Top Tools In The Stack 27:52 Do You Still Need UIs 30:36 Second Brain For Priorities 33:37 Frameworks And Memory Systems 36:02 SaaS Moats In An AI World 39:23 AI Beyond Tech Businesses 41:35 Business Takeaways And Wrap LINKS Ryan's Website Brendan's X/Twitter Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Do Pull Request Reviews Still Matter in the Age of AI?

The hosts once again discuss the recurring theme of AI’s impact on development workflows. They discuss various topics, including: Increased PR volume from AI-assisted coding and whether traditional pull request reviews are still necessary. Should AI be used earlier for pre-PR review and stronger CI guardrails for performance and security. What is the role of automated testing, and are they even more important as code generation accelerates? 01:05 PR Reviews Under AI Load 02:38 What PR Review Is For 05:02 Human Review What Remains 08:36 AI Pre Review And PR Purpose 11:01 Guardrails CI Performance Security 12:39 TDD Tests As Behavior Spec 15:53 AI Versus Automation In Pipeline 19:17 Testing Evolution Unit Vs System 20:32 Feature Specs And Functional Review 21:35 Bugs vs Defects Focus 23:37 Smoke Tests for Upgrades 24:44 Controller Tests Debate 27:40 Test Pyramid and Frontend Gap 28:37 Refactoring for Unit Tests 30:57 AI Coding Raises Review Stakes 34:00 Claude MD Friction 35:54 Wrap Up and Testing Habit LINKS Justin Searls Podcast Working Effectively with Legacy Code Book by Michael Feathers Professional Rails Testing: Tools and Principles Book by Jason Swett Ryan's Website Brendan's X/Twitter Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Building with an AI Orchestrator Workflow

In this episode, the hosts discuss building a “universal scraper” for event calendars and a new AI-assisted workflow using a long-running orchestrator.md thread. 00:12 Why Change AI Workflow 01:29 Orchestrator File Setup 04:36 How Memory Persists 07:33 Platform Constraints WSL 08:45 Git Worktrees and Isolation 12:07 Scraper Build Approach 18:26 Incremental TDD Development 20:17 Making It Truly Universal 22:39 Universal Scraper Explained 26:03 Wrap Up and Next Steps LINKS - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

AI Coding at Scale: Managing PR Overload, Using Claude to Stay Organized and Rethinking SaaS for an AI-First World

The hosts discuss how AI-assisted coding has massively increased their output, creating a new bottleneck: cognitive load, PR review, testing, and getting work shipped. Ryan discusses splitting time between finishing near-complete work, advancing a few large architectural initiatives, and handling ongoing support. Brendan talks about his productivity system using Claude to manage his time using local markdown files to help stay on top of things. They also cover risks of AI automation, permission scoping, subagent/approval bugs, and conclude with a renewed optimism that AI raises abstraction, increases competition, and pushes SaaS to adapt via execution, moats, and AI-ready APIs. 00:27 AI Code Volume 02:17 Cognitive Load Shift 04:52 PR Buckets Strategy 07:22 Overwhelmed Yet Excited 10:36 Workflow Tools Check 11:51 Claude Productivity Setup 14:02 Second Brain In Practice 17:21 Simple Local Files 19:30 Automation Limits 22:13 Scheduled Script Automation 23:00 Claude Cowork vs Command Center 23:39 API Permissions and Safety 26:12 Claude Code Approval Friction 29:25 Subagents and Parallel Work 30:44 When Agents Pretend Work 34:34 AI Shifts SaaS Thinking LINKS - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Scaling AI-Assisted Development

Today we discuss lessons from our previous episode with John Nunemaker, focusing on the Conductor tool and how multi-workspace, multi-agent workflows can speed up coding and bug fixing. Brendan shares his experimenting with parallelizing six Rollbar error fixes at once by generating prompts and running them in separate Conductor workspaces. They compare this with a one-agent-at-a-time workflow and debate whether closed-loop setups (ports, databases, dependencies) could make parallel work trustworthy and reduce context-switching costs. They also cover using full Honeybadger/XML reports for faster debugging, using Claude Code from a phone to create PRs, challenges syncing session history, and broader AI product strategy like APIs/MCP, and RAG. 00:00 Catch Up And Recap 00:43 Conductor Workflow Overview 02:40 Parallel Rollbar Fixes 04:35 Manual Testing And Setup Hurdles 06:33 Debugging With Full Reports 08:46 Ports Docker And Dependencies 11:50 Parallelism Versus Focus 14:57 Closed Loop Trust And Context 18:24 Merge Conflicts And Acceptance Gaps 22:16 Review Bottleneck And Output Surge 25:26 Fixing Gallery Uploads 26:39 Multi Select Challenges 28:27 Branching Without Conductor 31:28 Claude Mobile Workflow 32:34 Session Sync Friction 34:44 AI Brain For SaaS 38:01 APIs And MCP Table Stakes 41:49 Internal AI Assistants 43:46 Access And Safety Concerns 46:31 Second Brain Revival 49:03 RAG Tooling Experiments 50:04 Wrap Up And Listener Feedback LINKS - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

John Nunemaker on AI Development

John Nunemaker returns to discuss how fast AI tooling has changed and argues tech leaders should adopt Claude Max (defaulting to Opus), set up agent-friendly local environments, and roll that out to their teams. He shares how his company built an internal “brain” using LibreChat as a self-hosted interface, enabling non-engineers to query company data and generate insights like weekly support summaries from various sources. The conversation also covers worktrees and Conductor for parallel, isolated dev environments. 01:22 Tech Leaders Must Adopt AI 02:31 Why Opus Changed Everything 04:55 Claude Max Plans and Limits 07:41 Brain Idea and Safety Boundaries 09:03 Building the Stack with MCP 10:18 Ansible Automation and Deploys 12:53 Support Data Summaries in LibreChat 15:42 Scheduling Reports to Slack 20:17 OpenCode vs Claude and Mobile Workflow 23:54 What MCP Connectors Enable 26:20 Accessing Brain via Tailscale 30:48 Team Size and PR Volume 32:32 Claude PR Review Workflow 35:25 Conductor Daily Setup 38:36 Worktrees and Isolation 50:47 Conductor Limits and Pain 51:36 App Changes and Scripts 54:45 Caddy for Local Domains 57:10 Jobs Outlook and Wrap Notes - John's X/Twitter - John's Bluesky - John's post setting up conductor with Rails - John's Website - Ryan's Website - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Kyle Keesling

In this episode, Kyle Keesling, co-owner of PASS Testing and long-time solo Rails developer, shares how PASS grew from a college web design side project into a niche software and training business for the Underground Storage Tank (UST) industry. The conversation covers why they kept the products as two apps connected by a read-only private API, what makes compliance software hard, and how they modeled flexible equipment and inspection data—evolving from STI to Rails delegated types. Kyle also discusses early scaling pains around billing and payments, how feature requests are prioritized with help from their CRO and a contractor, and how tools like Claude Code are changing his workflow while maintaining PR-based review and safer deployment practices. 00:00 Meet Kyle Keesling& His Role at PASS Testing 00:29 From College Web Design to a Niche Opportunity in UST Compliance 02:31 Building Opus: A Custom LMS for Gas Station Training 03:34 Why Compliance Is Hard: 50 States, 50 Rulebooks 04:25 From Training to Past Tools: The Second Product Idea 08:06 Two Apps or One? Data Sync, APIs, and Customer Workflows 10:25 Would He Do It Again? Decoupling, Upgrades, and Acquisition Optionality 12:28 Why Past Tools Is More Complex: Data-Driven Inspections & Asset Inventory 16:13 Modeling the Domain in Rails: STI → Delegated Types (and Migration Strategy) 22:35 Versioning & “Point-in-Time” Inspections: Preventing Old Reports from Changing 24:13 Downtime, SLAs, and Recovering from Form/Data Bugs 26:40 Early Scaling Stories: Hardcoding States and Billing Growing Pains 29:39 Letting Customers Shape the Product (Beyond Compliance) 31:14 Integrations vs. Building Everything In-House 32:50 Feature Requests, Backlog Triage, and Adding Sales/Dev Bandwidth 37:41 Shipping Without the Never-Ending PR: Iterative Rollouts ("Visits") 40:39 Using AI Safely: PRs, Branch Protections, and Documentation Habits 46:14 Wrap-Up: Where to Find Kyle and Past Testing LINKS - PASS Testing - Kyle's X/Twitter - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Reflecting on Our First Year of the Podcast

In this episode, the hosts reconnect after a holiday break to reflect on their podcast journey over the last year. They discuss important milestones like their one-year recording anniversary, the various episodes from the past year, and sharing their favorite moments. 00:00 Introduction and New Year Greetings 00:34 Reflecting on the First Year of Podcasting 01:57 Memorable Moments and Guest Highlights 03:51 Popular Episodes and Themes 06:38 Looking Forward: Future Topics and Guests 07:42 Balancing Guests and Solo Episodes 09:15 Podcast Growth and Marketing Insights 10:16 Commitment to Consistency and Goals 12:18 Exploring Business and Technical Challenges 27:46 Concluding Thoughts and Call for Guests LINKS - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Striving for Ideal Code

In this episode, the hosts discuss reflect on the high-quality, maintainable code found in various videos and books and their own aspirations to emulate such coding standards. The conversation covers the challenges of maintaining good coding practices over time and under business pressures. They explore the concept of 'good enough' code based on the maturity stage of a business, and debate how AI impacts coding quality. The hosts consider how AI can assist in writing tests, potential pitfalls, and the complexity of integrating AI into development while maintaining high standards. Lastly, they touch upon the concept of agentic coding and the importance of well-defined code boundaries in future development strategies. 00:00 Introduction and Catching Up 00:34 Exciting News from 37 Signals 02:11 The Urge for Clean Code 03:33 Challenges in Maintaining Code Quality 06:45 Reflections on Code Quality and Team Dynamics 16:12 The Role of AI in Coding 18:18 AI's Role in Code Architecture 18:33 AI in Controller and View Design 19:42 AI's Limitations in High-Level Decisions 21:13 Using AI for Writing Code and Tests 25:09 The Future of AI in Code Readability 29:49 Challenges and Hypotheses in AI-Driven Development 33:54 Final Thoughts and Future Topics LINKS - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Mateus Pereira

In this episode, we chat with Mateus Pereira from Ombu Labs about the nuances of Rails upgrades and how AI is revolutionizing the process. From tackling gem dependencies to client collaboration, Mateus shares valuable insights and tips for executing seamless upgrades. Perfect for developers looking to streamline their Rails projects and leverage AI tools effectively. 00:00 Introduction and Casual Chat 00:25 Meet Mateus: Senior Rails Engineer 01:29 Mateus' Journey into Programming 02:17 Joining Ombu Labs: Trials and Triumphs 03:33 Lessons from Rejection and Persistence 04:35 Challenges in Rails Upgrades 08:12 Tackling Gem Dependencies 20:04 The Role of AI in Rails Upgrades 30:47 Discussing Ruby Critic and Rails Bump 32:07 AI in Code Refactoring 33:58 Client Relationships and Project Management 44:14 Challenges with Test Coverage 45:32 Manual Testing and QA Processes 49:18 Using AI for Writing Tests 55:37 Final Thoughts and Sign-Off LINKS - Mateus' Blog - Mateus' X/Twitter - Mateus' LinkedIn - 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

In this episode, Nate Berkopec, the proprietor of Speedshop, a Ruby on Rails performance consultancy, author of several books including the Complete Guide to Rails Performance, and a maintainer of Puma, joins the podcast. Nate discusses his journey into Rails performance optimization, starting from his early career at startups and his breakthrough talk at the Gotham Ruby Conference. He outlines his 'Three S' framework—Speed, Scalability, and Stability—for tackling performance issues. The discussion includes practical advice for Heroku users on optimizing 'dynos' for better request queuing and performance, as well as insights on using tools like JudoScale and PG Analyze for better Sidekiq job management and database optimization. Nate also touches on the importance of setting proper performance thresholds to balance system efficiency and operational costs. 00:00 Introduction to Nate Berkopec and Speedshop 00:45 Nate's Early Career and Interest in Performance 03:36 The Impact of Nate's Conference Talk and Book 04:40 Challenges in Diagnosing Performance Issues 10:22 Framework for Tackling Performance Problems 17:27 Understanding Heroku's Load Balancing 27:39 Understanding TCP Open Failures 28:10 Optimizing Dynos on Heroku 29:16 Setting Performance Thresholds 31:12 The Importance of Monitoring and Automation 34:25 Challenges with Sidekiq and Data Processing 36:24 Best Practices for Sidekiq Queues 44:48 Ensuring Job Idempotency and Efficiency 49:26 Rapid Fire Tips for Indies 52:41 Conclusion and Final Thoughts LINKS - Speedshop - Nate's X/Twitter - The Complete Guide to Rails Performance Book - Sidekiq in Practice Book - High Availabillity Wikipedia Article - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail

Communicating Project Requirements

In this episode, we tackle the nuances of communicating project requirements within development teams. From managing user stories and acceptance criteria to balancing control and flexibility, we explore best practices for ensuring clarity and efficiency. We share real-world experiences, including the effectiveness of detailed videos and spikes in guiding team members. 01:24 Communicating with Different Levels of Expertise 06:06 The Role of Videos in Communication 14:45 Challenges in Estimating and Scoping Projects 30:52 Using AI to Assist in Writing Tickets LINKS - Ryan's Website - Brendan's X/Twitter - Brendan's Bluesky Questions or comments, email us at railsbusinesspod@gmail.com Send us Fan Mail