On Rails

Robby is joined by Nikky Southerland, Lead Software Engineer at Shop-Ware — a cloud-based platform that helps independent automotive service shops run their businesses. Ruby on Rails has powered Shop-Ware since the first line of code was written back in 2013, and more than a decade later the codebase is still 90%+ Rails.
Robby talks with Nikky about what it actually takes to keep a mature Rails app moving with a team roughly half the size it used to be, including a frontend migration that's still in progress, the API decision they regretted almost immediately, and the LaunchDarkly kill switches that save them when a third-party integrator goes down.

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On Rails is a podcast focused on real-world technical decision-making, exploring how teams are scaling, architecting, and solving complex challenges with Rails. 
On Rails is brought to you by The Rails Foundation, and hosted by Robby Russell of Planet Argon, a consultancy that helps teams modernize their Ruby on Rails applications.

David Heinemeier Hansson, creator of Ruby on Rails and co-owner of 37signals⁩, joins Robby Russell the same week 37signals shipped Basecamp 5 to talk through the shift reshaping how software actually gets built today: why he reversed his "write every character by hand" stance, why he now considers taking AI seriously a professional obligation, and how cheap experimentation ("git reset and try again") is changing 37signals from the inside: designers and PMs working directly in code, and even the rigid six-week Shape Up cycle up for reconsideration. 

They also trace the history of Rails, including a backend so stable that a model file written today looks at home next to one from 2013, and take a peek at what's headed for Rails, from a Lexical-based editor ("Lexi") headed for ActionText to native passkeys and magic links. 

If you're curious where Rails is headed, have a listen.

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On Rails is a podcast focused on real-world technical decision-making, exploring how teams are scaling, architecting, and solving complex challenges with Rails. 
On Rails is brought to you by The Rails Foundation, and hosted by Robby Russell of Planet Argon, a consultancy that helps teams modernize their Ruby on Rails applications.

Tom Rossi, co-founder of Higher Pixels and the team behind Buzzsprout, joins Robby to talk about what it really looks like to stay "as Rails as possible", purely out of pragmatism. With over 472,000 podcasts on the platform and a team of fewer than ten people, Tom explains how sticking to vanilla Rails has been the foundation of Buzzsprout's ability to move fast, stay lean, and keep up with a rapidly evolving industry.
In this episode, Tom walks through Buzzsprout's migration from Paperclip to Active Storage (including what broke spectacularly in production), their recent shift from hand-rolled summary tables to ClickHouse for analytics, and how Hotwire made building the Buzzsprout mobile app surprisingly manageable. He also shares how Buzzsprout's real-world scale, including the monkey patching that resulted from it, led directly to contributions back upstream into Rails itself.
Higher Pixels: https://www.higherpixels.com
Buzzsprout: https://www.buzzsprout.com
Buzzsprout Blog: https://www.buzzsprout.com/blog
Tick (time tracking): https://www.tickspot.com
Donor Tools: https://www.donortools.com
StreamCare: https://www.streamcare.com
Higher Pixels joins the Rails Foundation: https://rubyonrails.org/2025/2/18/higher-pixels-joins-foundation
Send us Fan Mail
On Rails is a podcast focused on real-world technical decision-making, exploring how teams are scaling, architecting, and solving complex challenges with Rails. 
On Rails is brought to you by The Rails Foundation, and hosted by Robby Russell of Planet Argon, a consultancy that helps teams modernize their Ruby on Rails applications.

Jason Meller, founder of Kolide (acquired by 1Password in 2023) and now VP of Product at 1Password, joins Robby for a conversation about a career at the intersection of Rails, cybersecurity, and building.
They dig into why Rails has become one of the most token-efficient architectures for LLM-assisted development, and why that advantage matters as token costs increasingly shape what's worth building. 
Jason also shares what he's learned about keeping developer environments secure as agentic tools become part of everyday workflows, covering 1Password's open-source SCAM benchmark, how LLMs handle credentials when operating autonomously, and practical steps developers, founders, and engineering leaders can take to stay ahead of it.
Tools & Products
1Password (https://1password.com)
Kolide (https://kolide.com)
Cursor (https://cursor.com)
Claude / Claude Opus by Anthropic (https://anthropic.com/claude)
OpenAI Codex (https://openai.com)
Lovable (https://lovable.dev)
CrowdStrike (https://crowdstrike.com)
GitLab (https://gitlab.com)
Oh My Zsh (https://ohmyzsh.sh)
Wiz (https://wiz.io)
Projects & Benchmarks
SCAM Benchmark by 1Password (https://github.com/1Password/scam)
OpenClaw (open-source agentic AI tool)
Honest Security Manifesto (https://honest.security)
1Password Environments for Developers (https://developer.1password.com/docs/cli/secrets-environment-variables)
The Rails Foundation (https://rubyonrails.org/foundation)
Books
You Can Stop Stupid: Stopping Losses from Accidental and Malicious Actions by Ira Winkler & Tracy Celaya Brown (https://www.amazon.com/dp/1119566711)
Send us Fan Mail
On Rails is a podcast focused on real-world technical decision-making, exploring how teams are scaling, architecting, and solving complex challenges with Rails. 
On Rails is brought to you by The Rails Foundation, and hosted by Robby Russell of Planet Argon, a consultancy that helps teams modernize their Ruby on Rails applications.

In this episode of On Rails, Robby is joined by Brian Scanlan, Senior Principal Engineer at Intercom, where a 15-year-old Rails monolith with millions of lines of code sits at the heart of the business.
Brian shares how Intercom's philosophy of being "technically conservative" has kept their engineering organization productive and focused on shipping product rather than managing infrastructure complexity, and on Intercom's all-in bet on Claude Code as their singular AI tool, now generating over 95% of daily code, with over 1,000 weekly users across the company including non-engineers in sales, marketing, and finance. Brian explains their approach to automated code review and PR approvals, how they built a Rails console MCP that lets Claude run production queries (with non-engineers as the top users), their layered plugin and skills architecture, and where AI still falls short in open-ended debugging, using the metaphor of commercial airline pilots who know when to disengage the autopilot.
Tools & Libraries Mentioned
Claude Code — AI coding agent (mandated tool at Intercom) — https://docs.anthropic.com/en/docs/claude-code/overview
Rotoscope — Shopify's tool for identifying test subsets — https://github.com/Shopify/rotoscope
Honeycomb — Observability and tracing — https://www.honeycomb.io/
RuboCop — Ruby linting and static analysis — https://rubocop.org/
Snowflake — Cloud data warehouse — https://www.snowflake.com/
Datadog — Monitoring and metrics — https://www.datadoghq.com/
GitHub Dependabot — Automated dependency updates — https://github.com/dependabot
Console1984 — Rails console audit trail gem — https://github.com/basecamp/console1984
 Playwright — Browser automation (mentioned re: token consumption) — https://playwright.dev/
Books Mentioned
 Designing Data-Intensive Applications by Martin Kleppmann 
Blog Posts Mentioned
 Choose Boring Technology by Dan McKinley — https://mcfunley.com/choose-boring-technology

Send us Fan Mail
On Rails is a podcast focused on real-world technical decision-making, exploring how teams are scaling, architecting, and solving complex challenges with Rails. 
On Rails is brought to you by The Rails Foundation, and hosted by Robby Russell of Planet Argon, a consultancy that helps teams modernize their Ruby on Rails applications.