The Midweek #77: Geekdom Looks Ahead to What's Next

Most people in San Antonio, even those who live or work downtown, have never set foot inside Geekdom, the startup incubator and co-working space established by Rackspace Co-founder Graham Weston and fellow Racker Nick Longo in 2011.

Yet its impact on San Antonio has been significant. Startups have attracted tens of millions of dollars in angel funding and venture capital, and the sale of the most successful companies born at Geekdom now amounts to hundreds of millions of dollars.

That’s impressive for a startup organization that began as an idea 15 years ago and quickly accelerated into something real where talent, vision and capital have come together and enabled aspiring entrepreneurs to turn ideas into profitable businesses.

Advanced manufacturing, rather than tech, has had a bigger impact on San Antonio’s economy in the last 20 years, but these days everything is driven by technology. Geekdom has helped non-tech startups launch as well.

Now, Geekdom finds itself undergoing its own reinvention as time, a pandemic, and new work boundaries redefine jobs and the workplace. Co-working space matters far less today than it did only five years ago. Many individuals now work remotely or in hybrid arrangements that allow them to operate outside a traditional office environment. Want affordable co-working space? Try your neighborhood coffee shop.

Geekdom’s coming changes reflect that new reality. Few people now use its offices at the historic Rand building on East Houston Street for co-working. Ending that aspect of the enterprise simply confirms the current reality. Geekdom’s future focus will be to serve as the place not only where startups are born, but also where they grow.

With this news of change in store for the hundreds of Geekdom members in the city, others have taken to social media with some nostalgia about their own transformative experiences at Geekdom. I’d like to challenge any assumption that Geekdom has outlived its usefulness by pointing to some of its success stories and the opportunity that now exists for meaningful reinvention.

Let’s look ahead before we look back.

The expansion of UT-San Antonio’s Downtown Campus with the opening of the university’s College of AI, Cyber and Computing at its San Pedro II building promises to bring thousands of students downtown, enrolled in 11 undergraduate programs, 12 graduate programs and six graduate-level certificate programs, including one of the nation’s only bachelor’s programs in Applied Data Analytics, “a dynamic academic program at the intersection of cybersecurity and data science.”

San Pedro II is situated on Dolorosa Street across from San Pedro I, home to the university’s School of Data Science, with the revitalized San Pedro Creek coursing between the two towers. It’s the latest development bringing back to life a historic downtown street within a two-minute walk to The Continental, the residential and mixed-use complex on West Commerce Street.

Students attending classes there are seeking the skills, tools and connections to find their way forward in an economy increasingly driven by continuing technology advances, notably the advent and application of artificial intelligence.

What better place to find mentors, capital, and experienced startup support than Geekdom, conveniently located in the historic Rand building a seven-minute walk away? UT-San Antonio is now recognized as a Tier One research university, but it lacks a record of successfully converting intellectual property into successful commercial applications. The university is growing and evolving in leaps and bounds under President Taylor Eighmy, but it isn’t Stanford and San Antonio is not Palo Alto.

Without a definitive partnership with Geekdom, I fear UT-San Antonio will find itself training the next generation of engineers and developers for future jobs in Austin, Denver and Dallas, where more tech-driven economies and lifestyle narratives serve to attract graduates. That partnership does not exist, at least not in the formal, defined way I imagine where students would be actively directed to Geekdom as a source of mentors, capital and access to the kinds of skilled associates every startup needs in order to convert a great idea into a good business.

His name isn’t on the building, but Graham Weston’s $15 million gift to UT-San Antonio more than a decade ago was the catalyst for opening San Pedro I. It now seems logical for the people around Eighmy and Weston to devise a program that initiates entrepreneurial students into the Geekdom universe and enables them to develop businesses in San Antonio. Students should not have to leave San Antonio to realize their dreams.

For anyone who regards my proposal as far-fetched, allow me to share some of the highlights from Geekdom’s first 15 years with you, assembled with the able assistance of Geekdom CEO Charles Woodin, who shares my view that while nostalgia is always worth indulging, the enterprise’s next chapter is equally full of opportunity.

"I would look at Geekdom as still in its adolescent stage, robust with a great development story, yet certain its best years lie ahead,” Woodin told me.

My wife Monika Maeckle and I co-founded the Rivard Report, now the nonprofit San Antonio Report, at Geekdom in its earliest days when it occupied a vacant floor at the Weston Centre. I’ve been joined at the hip with Geekdom ever since, and a tenant of its offices for 12 of the last 15 years, including the present. The bigcitysmalltown podcast is produced at the Geekdom Podcast Studio each week.

In some instances, I watched young entrepreneurs burn through significant sums of cash while failing to convert their concepts into businesses. I’ve seen a parade of pretenders, people self-identifying as innovators who were non-productive hangers-on producing nada. And I’ve seen founders and investors ending up in court, fighting over the spoils.

The road to success, I learned, after leaving a 35-year career in newspaper and news magazine work, includes many off-ramps and dead ends. The books on winning tech ventures here and everywhere include chapters documenting early failure.

But, oh, those San Antonio success stories. There are more than people realize.

Woodin starts with “what was born at Geekdom.” That includes the ​Geekdom Fund,​ started by local tech leaders to provide $25,000 grants to early-stage startups, often representing the first round of funding that enabled founders to reach the stage where they could attract serious outside capital. By 2017, the Geekdom Fund had raised $17 million and its pool of local investors had grown to more than 50 people.

​Active Capital​, founded by former Rackspace executive Pat Matthews with Rackspace Co-founder Pat Condon and former Rackspace executive and Geekdom board chair Cat Dizon, closed a first fund of $21.5 million in late 2018 and a second fund of over $25 million by December 2020, and is now engaged in its third fund. Active Capital invests in seed and pre-seed B2B SaaS startups founded outside Silicon Valley. It counts about 50 companies in the portfolio as of 2020, and is now recognized nationally on rankings of VC funds.

​Alamo Angels​ launched in September 2016 under the name San Antonio Angel Network at Geekdom under executive director Chris Burney, another former Racker. Founding members included Michael Girdley (Geekdom Fund), Lew Moorman (former Rackspace president, TechBloc founder, and founder of ScaleWorks), Pat Matthews, Cole Wollak, Amit Mehta of Intrinsic Imaging, and former San Antonio Spur Brent Barry. It was set up as a nonprofit funded by member dues of $1,500 to $2,000 a year, with members committing to invest a minimum of $15,000 to $25,000 annually, targeting companies raising under $1 million across tech, healthcare, biomedical, energy, hospitality and consumer products.

Today it has grown to 140 accredited investors and has deployed more than $7 million across 50-plus startups. Its first exit was ParLevel. Its current portfolio includes Betty's Co., PrintNet3D, Darkhive, ASR Systems, and Axicle. The Alamo Angels web page states its creation occurred at ​VelocityTX​. That’s not true. It was born at Geekdom.

Geekdom also has served as host to different tech learning labs. One of the most widely known was CodeUp, founded in 2013 by Jason Straughan, Michael Girdley and Chris Turner, and continuing for a decade. At its peak it had 124 employees and offered certificates in full stack development, data science and cloud administration. It promised enrolled students a guaranteed job or their money back. By 2023 it had lost its director, endured rounds of layoffs and was the subject of widespread claims of false advertising.

In the end, it had to refund more than $760,000 returned to the U.S. Department of Veterans Affairs that the government agency had paid for veterans attending CodeUp who did not secure the expected jobs. Despite that ending, I encountered countless students along the way who told me CodeUp had given them a career path and changed their lives for the better.

Rackspace's ​Open Cloud Academy​ opened in the Rand building next to Geekdom in 2013, and trained about 900 graduates over seven years. Most early graduates went directly into good jobs at Rackspace itself. Rackspace was sold to Apollo Global Management for $4.3 billion in August 2016, which marked the decline of the company’s footprint in San Antonio and its workforce in Texas. Remnants of the program were consolidated into the company's current headquarters in the suburbs.

The Rivard Report, which ​changed its name and legal status​ to the nonprofit San Antonio Report in 2020, came to life at Geekdom in early 2012 after several months of development work there and at Rackspace. One of the first city-based digital media sites launched in the country, it became a voice for people from all corners of the community and an active journalistic promoter of a more prosperous, equitable city with a vibrant downtown and cultural and lifestyle amenities needed to keep and attract talented workers, including our own children.

Over its 15 years of publication, the Report has employed dozens of journalists, raised millions of dollars via family foundations, philanthropy, individuals and business memberships, and community-building events. Earlier this year, Texas Public Radio and the San Antonio Report announced they were ​merging​ their two nonprofit organizations.

Other entities have come and gone, each having its own impact on Geekdom, the downtown business community, and the local economy, including Techstar Cloud, TechBloc, Google Fiber, WP Engine, Jungle Disk. Many companies and organizations housed at Geekdom, now or in the past, have been central to such on-site programs as Startup Week, 3-Day Startup, Venture Labs, Bunker Labs San Antonio and many Geekdom-sponsored events on the annual calendar. Interestingly, the ParLevel founders first met at 3-Day Startup weekend.

And that brings us to the many successful exits, or company sales by founders, most of which you have probably never heard of even as they created new business, smart jobs and wealth for their founders in the city. Many of these exits inevitably meant a company born in San Antonio left the city. Perhaps next-generation startups jointly created by UT-San Antonio and Geekdom will find the resources locally they need to thrive in their hometown.

​ParLevel Systems​, a 2013 startup founded by Luis Gonzalez and Walter Teele, was the Rivard Report’s neighbor in the Rand building when both of our startups fit neatly into small sixth-floor offices. How quickly that changed. The company, which automated remote management of vending machines updated for convenient credit card use by consumers, was sold for an undisclosed price said to be in the “tens of millions of dollars” to 365 Retail Markets in 2022. The company had 50 to 60 employees at the time.

The founders were former students who relied on free rent at Geekdom and Longo’s willingness to let them disassemble a vending machine in the building to demonstrate their proof of concept. They received $25,000 from The Geekdom Fund and around $2 million from investors after that. No other Geekdom startup better demonstrated how early mentorship and capital can convert a concept into a significant business and ultimate sale.

​DataRobot​, a Techstars Cloud success story, is another reminder that tech companies born here often attract outside investors who require the companies to move. Founded in 2012, DataRobot went through Techstars Cloud in San Antonio in the 2013 cohort, then relocated to Boston. The company went on to raise more than $1 billion and was valued as high as $6.3 billion in 2021.

​Threat Stack​, also in Techstar Cloud cohort in 2013, was acquired by F5 Networks for $68 million in 2021.

​TrueAbility​, from the same 2013 cohort, was acquired for an undisclosed sum by Aluminum, Inc. in 2023, founded by Dusty Jones, Frederick Mendler, Luke Owen and Marcus Robertson. It raised $2 million in 2013 and the Geekdom Fund was an investor.

​Keen.io​, from Techstar Cloud's 2012 cohort, was acquired in 2017 by ​ScaleWorks​, the San Antonio firm founded by Moorman and Ed Byrne. A Sequoia-backed company from the San Antonio accelerator ending up owned by a San Antonio firm is a tidy loop.

Two major exits occurred at companies with significant Rackspace DNA and indirect ties to Geekdom and the downtown tech community of investors. Mailgun was first acquired by Rackspace in 2010 and operated inside Rackspace until it was spun out in 2017 and eventually relocated to the nearby Weston Centre. A sequence of acquisitions eventually led to the ​$1.9 billion acquisition ​of Pathwire, the parent company of Mailgun, by Sinch AB, a Swedish communications technology company headquartered in Stockholm, in 2021.

More recently, ProsperOps founders and former Rackers Erik Carlin and Chris Cochran appeared in the ​bigcitysmalltown podcast​ to talk about their company’s acquisition by Chicago-based Flexera in January 2026. Chris Keel, the third co-founder and also a former Racker, wasn't on the episode. Active Capital and other Rackspace friends were early investors. The sale price was not officially disclosed, but people close to the founders said the sale price was for a nine-figure sum. ProsperOps was always considered an Austin company, despite never having a physical address. Its founders and investors all trace back to Rackspace and the startup community the company nurtured prior to its eventual sale to Apollo.

Many readers will not recognize the company names included here, but others who do know about individual success stories at Geekdom will appreciate the impact it has had on the city since its inception, and why a reboot now could and should lead to a new level of collaboration with UT-San Antonio and other economic development interests to keep San Antonio's 21st century economy growing.