On Rails

Jason Meller: Rails, Security, and the AI Advantage

On Rails

Show Notes

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 agen...

More from On Rails

Oct 22, 2026

Hussain Akram is an engineering manager at Donorbox, and Antonio Carlos de Souza (AC) is its chief architect, working on a Rails app that has helped nonprofits raise money online and in person for more than a decade. Robby, Hussain, and AC get into how Donorbox handles serious traffic with a deliberately boring setup, why the team moved CI back onto developers' machines, and how they're pulling older parts of the app back toward Rails defaults. They also talk about how they use agent docs to ...

Sep 1, 2026

Eddie Galindo is an engineering lead at Ascend and Kagen Hearn is a senior software engineer there, working on a Rails app that helps insurance agencies move and reconcile money. Robby chats with Eddie and Kagen about why Ascend still runs one Rails monolith five years in, what changed when much larger customers started arriving, and how the team went about finding the real limits of their data ingestion pipeline. They also get into feature flags versus database configuration, and where AI to...

Aug 18, 2026

Joanna Wang is a senior software engineer at Sixfold, where the team builds AI underwriting tools that help insurance companies gather data and assess risk. She came to Ruby on Rails after working across Java, Go, Python, and Node. Robby and Joanna get into why the homegrown orchestration they built on state machines and callbacks turned brittle, what moving to Hatchet changed, and the tradeoffs of leaning on a gem that is no longer maintained. They also talk about what happened whe...

Aug 4, 2026

In this episode of On Rails, Robby is joined by Aaron Patterson, better known online as Tenderlove, a senior staff engineer on Shopify’s Ruby infrastructure team and a longtime contributor to both Ruby and Rails Core. Aaron and Robby chat about how Ractors are finally bringing true multi-core parallelism to Ruby, the proposal Aaron has pitched to RubyGems.org for content addressable gems that could make bundle install dramatically faster, and the real reasons gems reach for native C extension...

Jul 8, 2026

In this episode of On Rails, Robby is joined by Bryce Harlan, a senior engineer at Phamily, the text-based chronic care management platform built by Jaan Health. Bryce has spent the last decade helping evolve Phamily's Ruby on Rails platform, which helps clinical practices coordinate between-visit care for patients with chronic conditions — sending and receiving roughly 100,000 Twilio SMS messages a day across hundreds of medical groups. Bryce and Robby trade stories about a long-lived Rails ...

See all episodes →