Episode 550: XORuby with Jim Remsik

Jim Remsik, founder of Flagrant and organizer of XORuby, joins David to talk about what he’s learned from taking a Ruby conference on the road.

XORuby was designed around a simple premise: traditional conferences are valuable, but travel costs, time away from work, and family responsibilities put them out of reach for many developers. Jim explains how XORuby tries to lower those barriers with inexpensive, one-day regional events—and why he measures their success as much by first-time attendees, new speakers, friendships, and community connections as by the financial bottom line.

The conversation turns to Flagrant and the rapidly changing role of AI in software development. Jim discusses the company’s decision to invest more heavily in design, the difference between simply having access to AI tools and actually building an effective AI-assisted development workflow, and a recent project where careful preparation helped his team deliver roughly 700 cards in eight weeks.

Finally, Jim and David explore the increasingly difficult problem of building local developer communities. With meetups struggling, online communities fragmented across Slack and Discord, and developers finding technical content everywhere, they consider what actually motivates people to leave the house and spend time together—and where XORuby might go next.

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