Why I'm Taking Events on the Road This Fall

I last interviewed for a job in 2007. Since then, each new opportunity in my career has come through my network. People who knew when I was ready for something new, who could vouch for my work, who said "here's a specific person with these traits, would you give them a shot?" instead of posting another abstract job listing. But here is what worries me: we've spent five years breaking the very systems that create these connections. The pandemic moved us online, regional meetups struggle with attendance, and conferences have become too expensive for many people. Meanwhile, an entire generation of professionals has limited access to the serendipitous, in-person moments that build careers. The conversations between talks, the discovery that someone shares your taste in music from a laptop sticker, the bond formed over sugar-free lattes at the coffee shop.

That's why we're organizing XO Ruby, a series of traveling events this fall. Not an expensive conference that requires a plane ticket and hotel stay, but smaller, regional gatherings designed to bring together the 60-100 people in your area who are rubyists or ruby-curious but haven't had a reason to meet. These aren't just learning events (though you'll definitely get inspired by great speakers). They're deliberately designed to recreate those side conversations that can't happen virtually without intentional effort. The moments when you discover that the person next to you has been working on exactly the problem you're trying to solve, or when a casual conversation leads to your next career opportunity. We want to connect people who live in the same city but didn't know the other existed until someone gave them a reason to put on their shoes and leave the house.

When I'd visit San Francisco, I'd inevitably end up introducing two locals who lived in the same city but had never crossed paths until a visiting friend gave them both a reason to show up somewhere. That's exactly what we're recreating, but systematically. You'll spend the day hearing from speakers who will challenge how you think–but just as importantly, you'll have time to connect with the other attendees through serendipitous moments. Maybe you'll meet someone who's hiring for exactly the role you want, or discover a potential co-founder, or simply find people who get excited about the same problems you do. These conversations happen naturally when you put thoughtful people in the same room. No awkward networking scripts required, just genuine curiosity and shared interests.

We're planning events across multiple cities this fall, keeping them intentionally small. Around 60 people, never more than 100, so every conversation matters and no one gets lost in the crowd. Each event will be a full day of speakers and structured connection time, priced to be accessible rather than prohibitive. Chicago kicks off September 6th, followed by Atlanta on September 13th and New Orleans on September 20th. Tickets are on sale now with upcoming dates coming for Portland, San Diego, and Austin in October. If you're not ready to commit but want to stay updated, you can subscribe to our low-traffic newsletter. We're also looking for sponsors who believe in rebuilding professional community and speakers who want to share their expertise with engaged regional audiences.

We're thankful for the commitments and interest we've already received from folks like Cisco, Typesense, and Sidekiq.

Do you want a job? Are you looking for a different job? Do you want to connect with other like-minded people who challenge the way you think? Are you hiring? Are you looking for a co-founder? Do you want work that energizes you while keeping your finances healthy? The answer to all of these starts with the same step: go out and meet people. These events are designed to make that happen.

Community fuels our fun, creates career opportunities, and provides connection. Let's rebuild it together.