At the end of 2025, two things clicked for me at the same time. First, I was feeling a lack of professional network in Austin that had been building up for some time. I had been filling this void through Linkedin, but the increase of AI-generated communication had put a real damper on the connection it previously gave me. At the same time, we were seeing the success of our Tech Leader community meetup in London.
So I connected the dots, and recruited my Austin-based colleague, Dawn.
We had a vision from the get-go for the group to stay small and valuable–a curated room of folks who were actual tech leaders that would vibe and learn from each other. And we wanted to have fun doing it.
Defining who this community is for also meant being explicit about who it’s not for. It’s not for job-seekers, sales pitches, or folks early in their career without team or product oversight.
In January 2026, we held our first Austin Tech Leaders meetup for thoughtbot alumni, clients (past and present), and others in our product leadership orbit. It was intimate, it was meaningful, and the feedback was positive. The attendee filtering worked well too, and noted as such by the group.
Turns out I wasn’t the only one feeling the lack of connection these days, particularly in a city where so many of us work remotely.
Did you know: Austin has the highest percentage of the workforce that is remote in the country (at a whopping 23.6%)
We hosted again in February and were able to overlap with a conference Chad (our CEO and founder) was attending in town. Chad helped us invite even more former clients, Rubyists, and thoughtbot alumni who had made their way from other cities to Austin unbeknownst to us!
Session 1 folks returned. It was good.
The next month was March. March in Austin means SXSW, but surely we wouldn’t throw a SXSW event?
In March we threw a SXSW event.
We wanted to do “South By” (as we call it here) the thoughtbot way and lean on the tradition of old school, creative, and a little scrappy, Austin SXSW spinoff events.
We hosted it at an incredible art gallery and community space in East Austin, Riches’ Gallery, complete with a graffiti wall and make-your-own SXSW tote station.
We intentionally expanded the tent for this one–welcoming more founders, investors, designers, and community builders alongside our core tech leader group.
The larger event was exciting in a different way. The larger format created energy and new connections. But it also reinforced something important: the magic of this community is in the smaller, curated, consistent hang.
That’s the balance we’ll continue to strike. Intimate gatherings as the foundation, with occasional larger moments when it makes sense (Rails World 2026, I’m looking at you!).
Around SXSW, demand picked up fast. We ended up with nearly 100 people on the waitlist.
And that brings us to the April that happened 2 weeks ago, back to our roots (all four months of them). A smaller, intentional group having meaningful conversations.
As a wise person once said, pics or it didn’t happen. Here are a few more moments and friends from SXSW x Austin Tech Leaders:
