Episode 552: Hatchbox and GoRails in the age of AI with Chris Oliver and Collin Jilbert

Chris Oliver and Collin Jilbert join David for a candid conversation about the changing economics of building products for the Ruby on Rails community in the age of AI.

Chris traces the history of GoRails from its beginnings as an attempt to fill the void left by RailsCasts, through to the creation of Hatchbox and Jumpstart, and explains how those products evolved together over more than a decade. But the rapid improvement of AI coding assistants has dramatically changed how developers learn and work. Instead of searching for a tutorial, watching a screencast, and adapting an example to their application, developers can increasingly ask an AI tool to work directly inside their existing codebase.

That shift has had a significant impact on GoRails and Jumpstart subscriptions, while at the same time making Chris and Collin dramatically more productive as developers themselves. They discuss using AI to research unfamiliar systems, refactor complex Rails code, prototype features, and build software in minutes that previously might have taken days.

Those changes also led to some difficult business decisions. Chris and Collin explain why Hatchbox has become increasingly important to the sustainability of their work, why they decided to raise its per-server pricing, and how they wrestled with balancing the needs of longtime customers against the reality of keeping a small bootstrapped company viable.

The conversation also looks beyond the immediate business changes to larger questions facing software development: what happens to developer education when AI can generate context-specific solutions on demand, how junior developers develop judgment when they no longer have to learn everything “the hard way,” and whether AI could ultimately change not just how developers write software, but what kinds of software they are able to create at all.