(From left) Circus Picnic's Natalie Tischler and Sabra Johnson perform during Geekdom's 7th birthday celebration held Friday Oct. 26, 2018 at the Weston Center.
Circus Picnic's Natalie Tischler (left) and Sabra Johnson perform during Geekdom's 7th birthday celebration Friday at the Weston Centre. Credit: Edward A. Ornelas for the San Antonio Report

It all started with Geekdom in 2011, which is why present-day members, alumni, and newcomers to the growing downtown tech scene along and around Houston Street gathered Friday evening to celebrate the co-working space and small-business incubator’s seventh birthday.

The Weston Centre lobby was transformed into Vegas casino, and as people picked up a T-shirt and a cocktail, the outside stage featured live music, feathered dancers, and just a tad of speechifying and lots of tech tribe socializing.

Some might challenge that first sentence and say “it” started Sept. 25, 2010, with the formal launch of SA2020, when 1,200 of us came together for a giant visioning effort. Engaged citizens took a hard look at San Antonio’s challenges and opportunities and worked together to set some goals and set the city on a path toward a healthier, more educated, more prosperous future.

Actually, we have to go even further back, if we are talking about “it,” to the successful recruitment of Rackspace Chairman Graham Weston by then-Mayor Julián Castro to serve as one of the tri-chairs for SA2020. Some were surprised he said yes.

Weston owned the downtown Weston Centre, the last office tower to be built in the city, but he was much better known as a co-founder of Rackspace. He was the guy who purchased the shuttered Windsor Park Mall along the unattractive Interstate 35 East corridor in Windcrest and proceeded to transform it into one huge, cool tech campus/playground for the fast-growing managed cloud computing company. It was a big investment, and it wasn’t anywhere near downtown.

Yet Weston is the common thread that runs through this narrative, so let’s go back a little bit further to a somewhat infamous email he received after Rackspace acquired Blacksburg, Virginia-based Webmail, co-founded by entrepreneurs and fellow Virginia Tech students Pat Matthews and Bill Boebel. Mathews agreed to move to San Antonio and become a senior Rackspace executive. Boebel did not.

In that now-infamous email, Boebel said there was nothing Weston could do or say to convince him to move to a city. San Antonio, he said, lacked a vibrant tech culture and startup scene, and a community of software developers. Its urban core lifestyle scene compared unfavorably with Austin, his new home base.

San Antonio was not (yet) a millennial magnet.

Boebel’s email hit Weston like the proverbial bolt of lightning hit Saul on the road to Damascus. Everyone he knew involved in shaping San Antonio’s future got a copy. Weston and fellow Rackspace founders Pat Condon and Dirk Elmendorf, both of whom had moved on to other ventures, knew how hard it was to recruit software developers to San Antonio. What was missing, Weston realized, was a tech ecosystem in a revitalized urban core. San Antonio was the Alamo City, its downtown designed for tourists and conventioneers. Beyond the River Walk and hotels, there was vacancy, blight, and a distinct lack of housing options. It was no mystery why so few people lived downtown.

Weston went on a multicity journey with Nick Longo, a fellow Racker who had turned a fairly unsuccessful coffee shop in Corpus Christi into a very successful web design and hosting company named CoffeeCup Software, which eventually split in two and was sold. The two toured co-working spaces on both coasts and birthed the idea that became Geekdom. Condon and Elmendorf were recruited to help get it off the ground.

Geekdom Co-Founders Nick Longo (left) and Graham Weston.
Geekdom co-founders Nick Longo (left) and Graham Weston discuss the growth of Geekdom and the state of San Antonio’s tech scene last month. Credit: Scott Ball / San Antonio Report

It started out in the Weston Centre, downtown’s most expensive commercial address at the time and the place Weston invited Monika Maeckle, my wife, and me to incubate the Rivard Report. The Weston Centre was home to major law firms, financiers, and others. The sudden arrival of geeks in hoodies and jeans and T-shirts who liked to play ping-pong in between writing code and developing apps was an uneasy marriage.

There were complaints about those of us jumping on to elevators with our bikes and crowding the guys in suits with briefcases. Monika didn’t help things when she started bringing our rescue dog, Cocoa, to the office. That led to a no-pets policy.

Weston and Longo quickly realized they had caught lightning in a bottle with Geekdom, which was growing rapidly and generating serious buzz but needed a new home.

Randy Smith, an attorney turned real estate specialist who had overseen the acquisition and conversion of the Rackspace mall, came on the scene as the CEO of newly formed Weston Urban. That led to the purchase and renovation of the historic Rand Building on East Houston, formerly Frost Bank’s back offices. The former 1911-era Wolff & Marx department store became Geekdom’s (and the Rivard Report‘s) new home in 2013.

Today the building is brimming with tech companies. What started at Geekdom has spread across downtown. Almost every available historic building on the market in the city center has been bought and renovated and filled with new companies or is in the process. Restaurants, coffee shops, and bars have followed.

The Rand building on East Houston Street prominently features the Geekdom logo.
The Rand building on East Houston Street prominently features the Geekdom logo. Credit: Scott Ball / San Antonio Report

Downtown’s most walkable street now has what it was missing: people. People walking, pedaling and scootering.

It took Monika and me a few months to get the Rivard Report designed, off the ground and into active publication. And, frankly, it took some time to move from our corporate pasts and mindsets to a more entrepreneurial way of thinking and acting. We underwent our own metamorphosis in and around Geekdom, learning a whole new way of creating and working by watching, talking, and hanging out with others doing their own startups.

In the early days, I would marvel as elected officials, business and civic leaders, and investors would take their first tour of Geekdom. Again and again, I watched people have an aha moment about this new way of working. The Longo startup era at the Weston centre gave way to the Lorenzo Gomez era at the Rand building when Geekdom reached critical mass and East Houston Street started to change before our very eyes.

The public-private proposal that brought Weston Urban, Frost Bank, and the City of San Antonio together for one of the most transformative real estate deals in city history in all likelihood would have never happened if Weston Urban and Frost Bank had not first done business with the Rand purchase, which would have never happened had there been no Geekdom. Across Soledad Street, former Rackspace President Lew Moorman has built ScaleWorks, a consortium of businesses which is leading the B2B software development sector of San Antonio’s tech economy.

In that respect, take a look at the new Frost Bank Tower anchoring the western reaches of downtown and remind yourself it wouldn’t be there if there had not been a Geekdom. And then imagine all that is yet to come.

Gomez, meanwhile, went on to write a book, The Cilantro Diaries, and is now engaged in other projects yet to reveal themselves. David Garcia is the third generation of Geekdom leadership.

We take it for granted now, but thousands of people in the urban core and even beyond can thank Geekdom for planting the seeds of something that grew and then went viral. Geekdom, like SA2020, helped set a new course for many of us in San Antonio.

Weston’s metamorphosis is the common thread in this big “it.” So it was only fitting that the Geekdom party was held in and around the Weston Centre, the building where it all started. Probably half the tech people in attendance trace their own attachment to Weston and to their time as Rackers. In fact, Jlen Events, the party planner for the evening, itself was founded by a former Racker. So maybe the “it” goes back even further.

A crowd gathers outside the Weston Centre during Geekdom’s 7th birthday celebration. Credit: Edward A. Ornelas for the San Antonio Report

The Rivard Report, meanwhile, turns 7 years old on Feb. 13, our first day of publication, but I always like to make it to Geekdom’s birthday bash. It still feels like home.

Postscript: You can help the nonprofit Rivard Report get an early start on our end-of-year membership drive by becoming a member now, or by renewing your lapsed membership, and help us earn a matching grant from the Newman Foundation. If you value our public service, independent journalism, move from reader to member today.

Robert Rivard, co-founder of the San Antonio Report who retired in 2022, has been a working journalist for 46 years. He is the host of the bigcitysmalltown podcast.