Bet on the Room
Why Some Checks Are Worth Writing
We'll say it plainly. This one is harder to write. Asking for money from people you respect is uncomfortable. It's personal. It's direct. It's a conversation you have with people who already know the work you do and are deciding whether to put their name behind it.
XO Ruby isn't run by a fundraising team. It's run by people who have demonstrated they care deeply about this community for the past 15 years through organizing events like Madison+ Ruby and participating in dozens of events around the world.
Without sponsors, XO Ruby doesn't happen.
Not because we're struggling to justify the idea. Last year proved the idea. Six events spread over a 9,000-mile route, with rooms full of people having conversations you don't get on Zoom, and leaving with something you can't put in a post-event survey.
One attendee said it best after a long day in Portland: "I literally forgot how good this was, getting together in person."
A glimpse inside the room at XO Ruby Portland
That feeling is exactly what Cisco bet on.
"I have had so many people come up to me and thank me for XO Ruby and I didn't do anything but write a check." - Alan Ridlehoover, Cisco
The largest Rails shop you've probably never heard of matched every dollar contributed to XO Ruby up to $30,000. Not because the ROI was obvious. Because Alan and the Cisco team have been in enough rooms to know the value doesn't need to be measured to be real.
JIM NANNEY - NEW ORLEANS, LA
"The XO Ruby organizers really understand the value of the smaller local community, and the powerful connections you make at the local level. I really enjoyed the speakers and getting to meet all the local folks. If you get the chance to go, don't miss it!"
KARL OSCAR WEBER - SAN DIEGO, CA
"XO Ruby exemplifies the Ruby community's dedication to uplifting diverse voices, and in cultivating our connections. It was the best. I'll be coming back. Were gonna throw one of these in SLC next year it was so fun.
JIM CALL ME!"
ALISON ACUÑA - PORTLAND, OR
"It was technically a Ruby conference...but it could've been for anyone who codes...l wish l'd dragged along all my non-Ruby dev friends. So much content applied across stacks."
ARIEL VALENTIN - AUSTIN, TX
"It was reinvigorating. I haven't gone to many meetups or conferences since the pandemic due to life changes so was glad to connect with folks in my community and meet new Rubyists in the Austin Area."
Jim has known that longer than most. Twenty years as a Ruby developer, program chair for RubyConf, founder of Madison+ Ruby. He's been building rooms worth being in long before XO Ruby had a name. This is the next version of that same bet. Bigger in reach, more intimate in practice, with more space for deeper, more challenging conversations.
The 2026 tour spans three regions: Pacific Northwest. Midwest. East Coast. Ten cities across the U.S. and Canada. Each stop is a decision someone made that their community was worth showing up for.
We've been making that decision for a year. We're asking if you want to make it with us.
If it's not the right fit right now, that's a real answer and we respect it.
But if you've ever left a room thinking differently about something because of a conversation you didn't plan to have, that's what we're trying to encourage and curate that same opportunity for others. A sponsorship is a bet that those rooms keep happening.
We think they should. We're asking if you do too.