The San Antonio DevOps Meetup: A Retrospective

The San Antonio DevOps meetup is no more, so I wanted to document my thoughts and feelings on what was good, what was terrible, and if I did it again, what I would change.

The San Antonio DevOps Meetup: A Retrospective
Photo by Nam Hoang / Unsplash

The San Antonio DevOps meetup is no more, so I wanted to document my thoughts and feelings on what was good, what was terrible, and if I did it again, what I would change.

First of all, a huge thank you to Josh O’Brien, Chris Fidao, Tex Morgan, and Chase Hammock. You’ll see why in a bit.


San Antonio DevOps started in 2014 as San Antonio Chef Users at Geekdom, a coworking space in San Antonio. I started the group with Josh O’Brien, who had just left Rackspace for Chef (and still works there, unlike my ridiculous job-hopping since then).

Our original logo, really, the Chef logo

I was using Chef heavily at Rackspace at the time, and my personal goals for the meetup were pretty standard for a tech meetup:

  1. Go outside the Rackspace office walls to learn things from other people.
  2. Have our meetup be an influence in the “#CityOnTheRise” San Antonio New Tech Community
  3. Grow said community and level up other people.
  4. Teach people curious about Chef’s (and later, other DevOps-y stuff) best practices.

Our first few meetups we’re pretty well attended, I thought. Folks that were not Josh that also worked at Chef came to the meetup for support. The problem with being Chef-focused, which we learned after several monthly meetups, was just that we ran out of tech talk-worthy topics. You can only cover CHEF as a topic so many times, and we got feedback that folks liked other members but wanted to talk about Ansible, or Docker, or other things. TIME TO PIVOT!

New Hotness Logo

We changed to “San Antonio DevOps” to cover all the things, but to not alienate initial Chef-only interested parties we started a regular open-ended “Chef Coffee”. It was sparsely attended and eventually died. It was hard to get people up early to come to a morning “before work” tech meetup, although Josh and I definitely enjoyed hanging out together. I had a logo made. I put up a website. We tried random things (Facebook Groups! Online forum software! A Slack!). Meetup was home though.

Eventually I moved on from Rackspace (and Josh moved away from San Antonio) but I kept the meetup going. Tex Morgan volunteered to step up as co-organizer before running for Texas Land Commissioner. Somewhere in there Chris Fidao was a co-organizer for a bit (Chris: “I think I ordered pizza once”). Eventually I had to step back from the meetup completely - I was starting to travel a lot and couldn’t dedicate the time to organizing. Tex took it over for a while, then handed it to Chase Hammock. Everyone ran the group to the best of their abilities and I’ll always love them for it.

Chase recently stepped away as the organizer, and without another organizer willing to take it over, Meetup closed the group at the end of December 2018.

What Went Well

Did I accomplish what I set out to do? Sort of… we DEFINITELY got outside the Rackspace office and learned from others. We were an influence in the regional tech community. For example: I was able to talk about running a DevOps meetup at DevOpsDays Austin from my experience with this group. We also landed a spot in the TechBloc “Tech Deck”, used to try to pitch technical businesses on moving to or starting in San Antonio.

Look! We were in there!

I feel like we taught folks a thing or two as we went. I always got feedback from attendees that they learned something from San Antonio DevOps, and occasionally still hear from someone on how the meetup helped them.

A few people gave their first public talk ever at the meetup, which is THE BEST because I always wanted our group to be a safe space for that kind of thing. It always gives me warm fuzzy feelings when that happens, especially when they say “That wasn’t as bad as I thought! I kind of LIKED IT!” Our group did that for folks. High fives all around.

What Went Poorly

Venue selection for a tech meetup in San Antonio was… pretty awful. You need reliable internet, a projector, and seating. In San Antonio you also need parking, because even though one of our former organizers was on the VIA board, mass transit just isn’t a thing here. Geekdom has very nice conference rooms and a nice event space, provided you’re a member there or know someone who is a member. In the early days of the meetup, before there was a #TechDistrict, hosting at Geekdom also meant parking downtown (the worst, and not free). We also had issues occasionally with the Geekdom Event space being locked, with staff gone for the day on a scheduled meetup evening, which required frantic texting/slack to get someone to open the door for us. It didn’t happen often, but when it did it was brutal.

Even with those issues, meeting at Geekdom was much better than trying to use a corporate space. We tried to meet at a local tech company’s office ONCE. They required photocopies of organizer driver’s licenses, money from the meetup for security guards, and a list of attendees days prior to a meeting. People not on the list were not to be admitted. Local companies also sometimes require an organizer be someone that works for the company, because supporting local tech groups outside their walls is somehow unthinkable. I’d shame them here if I wasn’t worried about getting sued.

Last but not least: organizing a tech meetup in San Antonio is a chore. While we did have some great speakers (both pro and first timers, which again I am so proud to be a part of), every month seemed like a chase to find a speaker that I was always behind on. Our proximity to Austin was not a help here, but a hinderance. Austin meetups had great speakers I could not convince to also drive two hours south for an extra event. I was told by more than one travelling evangelist type they considered Austin “hitting South/Central Texas” before moving on. Organizers (myself included) spoke way too often. Too many members of the group were happy to consume content but not give back in the way of talks of their own. This got worse as my work travel increased, because I had less and less time to chase a speaker. I ended up cancelling events, or trying “Lean” style meetups where everyone just brings something to talk about. I think I personally leaned on that style too often, pun intended.

What Would I Do Differently?

Given the above issues, I don’t think a meetup in San Antonio in 2019 is the way to go. That’s not to say meetups are bad, or a waste of time. (I’m still a co-organizer for a local tech meetup!) I just think the dynamic of getting together in a community and learning from each other has changed in recent years, going more and more from meat space -> virtual space. The rise of podcasts, livestreaming, and social networks has accelerated it. In 2019, I want to accomplish the same goals I had for the meetup but in a new way.

This year, I’ll be working with a few friends on starting a podcast/stream on technology and working in technology in San Antonio. My employer has been wildly successful in building community with their YouTube channel, which I hope we can replicate a little with this project (we’ll record live, and publish the audio as a podcast). This will work as we all travel for work here and there, I don’t have to chase speakers (but I’m open to guests, especially first-timers!), and hopefully I can continue to put my mark on San Antonio’s tech community in my own way. Stay tuned for more info on the launch!