Few companies have had the meteoric rise — and impact — in San Antonio that Rackspace managed in the 2000s.
It was San Antonio’s own piece of the tech wave that swept the American economy. Rackspace brought wealth, expertise and life-altering opportunities for the hundreds the company has and continues to employ.
The influence of former Rackspace workers, the Rackers, has rippled far beyond the company’s walls. Its core values and culture of fanatical support have had a second life as its workers take on new opportunities in the private and public sectors.
Where are those Rackers now? And how did their time at Rackspace influence their journeys and San Antonio’s economy?
Rackspace, which was bought by a private equity company in 2016 and returned to the public market again in 2020, has now shifted its focus into artificial intelligence.
We spoke with some of the Rackers who were there for the company’s boom years and have stayed in San Antonio since. Their work has shaped business, culture and politics in San Antonio’s tech scene — and beyond.
From tech to City Hall
Talking about Rackers in the public sphere has to start with Marina Alderete Gavito, who worked at Rackspace in program and project management roles between 2010 and 2015 and was elected to San Antonio City Council’s District 7 more than two years ago.
“I loved Rackspace. It was such a fun place to be. I worked with really smart people,” Alderete Gavito said. “There’s so many principles from Rackspace I take with me.”
Many companies have slogans and values written on websites and in offices, but Rackers remember theirs like they were set in stone. Alderete Gavito said she has focused on servant leadership and promoting a collaborative workspace with her staff, two strategies she gleaned from Rackspace where workers were encouraged to learn, grow and contribute.
She keeps one of Rackspace’s core values with her during her work — substance over flash.
“Especially in politics,” she said. “People think ‘Oh, the nice, shiny thing.’ It’s lip service, people, I need the results.”
While at Rackspace, Alderete Gavito organized mayoral candidate forums and eventually stepped up as the first executive director of Tech Bloc, a nonprofit that is trying to grow the tech industry in San Antonio.
Alderete Gavito’s father had served on city council. That, combined with her increasing civic engagement work at Tech Bloc, encouraged her to take the next step and run for office.
She wants to make San Antonio into a place people want to be. It’s a common theme among Rackers — the desire to make San Antonio more appealing for skilled workers and, therefore, the companies that want to employ them.
Rackspace was a tech giant at the outset of the 2000s, but few large companies have followed in that industry. Groups like Tech Bloc are trying to change that and part of Alderete’s work she says is creating opportunities for innovation, growth and entrepreneurship in San Antonio.
Following the company’s founders
Lew Moorman was a leader at Rackspace for 16 years, serving as a board member, chief strategy officer, president and one of the company’s earliest leaders.
“I joined the company when it had roughly 30 people in 2000,” he said. “It was a fantastic experience. It was a unique experience.”
Moorman remembers Rackspace’s meteoric growth and key role in building the internet as we know it today. After he left the company in 2016, he took time to focus on his family and then co-founded ScaleWorks.
ScaleWorks is a San Antonio-based investment company that buys software companies looking to grow or change and, well, scales them up.
“We tend to try to buy companies that are trying to figure out their next step,” Moorman said. “It’s really just taking on a company that’s not a clear winner … and giving them some direction.”
That often includes bringing that company, its workers and its opportunities to San Antonio. Moorman grew up in San Antonio, he raised his kids here and he believes in San Antonio’s potential.
He’s been involved in efforts like Tech Bloc to help realize that. Moorman wants San Antonio to be ready for the next company that sprouts up in San Antonio’s backyard.
“We’d love for people to come here because there is opportunity,” he said.
Growing San Antonio’s tech sector
While Moorman has continued to work in the private sector and Alderete Gavito has shifted her focus to the public sphere, some Rackers have worked in between those worlds.
Lorenzo Gomez III grew up in San Antonio and spent a formative decade at Rackspace until he left in 2010. He joined the company without a college degree and rose into leadership roles.
“I was really indebted to Rackspace. I was an inner-city Hispanic kid,” Gomez said. “It really changed my life.”
We were watching and helping the internet expand,” he added. “It was exciting, as a young man, experiencing the internet in a whole new way.”
He enjoyed the mission-driven challenge; Rackspace was a company devoted to serving others. That mission felt slightly different to him when the company went public, Gomez said, and he departed in search of other missions to take on.
Gomez has worked closely with Graham Weston, one of Rackspace’s founders, on the 80/20 Foundation and Geekdom. Gomez, Weston and a group of former Rackers have focused on altering San Antonio’s urban landscape and downtown core.
“For about eight or nine years, I ran 80/20 and Geekdom at the same time,” Gomez said. “I didn’t realize how much I would fall in love with urbanism.”
80/20 donates to groups with an eye on fostering job growth and entrepreneurship. Geekdom started as a coworking space and has broadened its work as a startup incubator. Gomez said he saw lots of Rackers leave San Antonio when they left the company. He met other tech workers who would never consider coming to San Antonio.
“Anyone that was a hiring manager at Rackspace realized the futility of trying to recruit young single people to San Antonio,” Gomez said. “This is a problem. There should be a whole bunch of jobs that we should be able to go to for our next careers and that just never was there.”
After leaving 80/20 and Geekdom, he has worked as a writer and started Voice of San Antonio, a media platform where people can share their ideas and journeys in the city.
From entrepreneur to investor
Pat Matthews didn’t come to Rackspace, Rackspace came to him. His software company was acquired in 2007 and he moved to San Antonio to help run the Rackspace cloud.
“I planted roots here,” he said. “It was an incredible time at Rackspace.”
He stayed at the company until 2013. Rackspace was ambitious, he said, competing with large tech companies and obsessed with successfully serving customers. It was a winning formula that gave all its workers an opportunity to grow and be a part of that, Matthews said.
“I was always a very entrepreneurial guy and Rackspace always put me in the most entrepreneurial positions,” Matthews said.
He left Rackspace and ended up founding Active Capital. That San Antonio-based venture capital firm is similar to ScaleWorks, in that it helps firms learn and grow, but focuses on very early stage companies that are finding their feet.
“I wanted to be an investor, but I also wanted to be an entrepreneur, so I combined those,” Matthews said. “I’m totally in my sweet spot.”
Matthews is also part of a broader effort to grow tech in San Antonio and serves on Tech Bloc’s board. Tech, and the wealth that accompany it, foster other investments in restaurants and local businesses, Matthew said.
To him, a civic focus and giving back are parts of the tech industry’s ethos. It doesn’t surprise him that Rackers have stayed involved in San Antonio and want to make it better. It’s sentiment many Rackers share — wanting to see whatever comes next be wildly successful.
“Every parent wants their kids to succeed,” Matthews said. “I love catalyzing founders and entrepreneurs to go pursue their passion and their life’s work.”
The tech success story you didn’t hear about
Josh Odom was one the wildly successful tech stories that emerged from Rackspace and stayed in San Antonio when he and co-founder Will Conway sold their company Mailgun for $1.9 billion in 2021.
He joined Rackspace in 2007 as an intern and worked there for seven years before he left and then returned to help spin Mailgun out from under the Rackspace umbrella and into its own company.
For Odom, Rackspace’s period of rapid growth was where opportunity emerged.
“I could do different things. Every quarter, when the company is growing like that, you have to reinvent yourself,” he said. “That creates opportunity for people who just jump in and figure things out. Job titles almost didn’t matter.”
Odom has continued to work in that space. He enjoys the early days of tech companies and the problem solving that comes with it. He wants others to have the opportunity to learn and grow in the same way in San Antonio.
“I really aspire for people to have more options here,” he said.
It’s why he serves on Tech Bloc’s board of directors and he and Conway are locally focused for their next venture.
“We’re going to put a heavy emphasis on prioritizing hiring people locally in San Antonio,” he said. “We want to make sure we’re investing in the capability and talent of people here.”
‘All of this came out of Rackspace’
Conway is reflective when it comes to Rackspace. He joined the company in 2008 and eventually worked on Mailgun with Odom. The experience taught him valuable lessons.
“I’d always planned to go to law school, but when I got into Rackspace, it was growing,” Conway said. “When it was growing, my career grew.”
Rackspace’s boom years were an opportunity to be at the forefront of internet technology, Conway said. He started as an online sales specialist, but consistently got new opportunities.
“I probably changed jobs every year or so, but never companies,” Conway said. “The buzz was amazing.”
Some of that was lost, Conway said, when Google, Amazon and Microsoft started to compete with Rackspace. He found that entrepreneurial energy, though, when working with Mailgun in 2012 after it had been acquired by Rackspace.
Mailgun had a smaller team, Conway said, and he enjoyed making contributions to a tight-knit group spread between the West Coast and Texas.
Mailgun was spun out of Rackspace in 2017, Conway said. He and Odom worked to hire staff as investment and revenue grew quickly. Many of their new employees were Rackers who wanted to stay in San Antonio.
“It was so transformative,” Conway said. “It’s crazy to think all this came out of Rackspace.”
Conway took lessons from his time at Rackspace — some cautionary. He saw a need for a more performance-focused culture. Conway wanted people to be invested in the product’s success.
“We’re a business, we have to perform for others. If we can’t do that, we can’t exist,” Conway said. “Let’s not have this illusion that we have to be best friends, but let’s be human. Let’s be soft on the person, hard on the problem.”
Mailgun was smaller and focused on its market niche, Conway said. But it still took pages out of Rackspace’s playbook, including high-level support staff.
“I always saw it as an evolution of the Rackspace culture,” he added.
The Rackspace culture spreads
Erik Carlin, Chris Kiel and Chris Cochran met at Rackspace where they learned the ins and outs of building public clouds and cloud management.
Carlin worked at Rackspace from 2008 to 2018. Now, he’s the chief product officer for ProsperOps, a company founded by the three Rackers which manages $5 billion in public cloud infrastructure to help its clients save money.
“Rackspace gave us the context to really become experts in cloud computing,” Carlin said.
It wasn’t just the technical work that Carlin learned, though. Those core values of Rackspace — servant leadership, a focus on customer service — are things he works to emulate.
“Rackspace was a world-class culture. So much of what we’ve done at Prosper Ops we basically stole from Rackspace,” he said. “It’s not just a job, it’s kind of a mission.”
Many other Rackers have gone on to work at ProsperOps and tech companies across the industry.
“It’s had a big impact in San Antonio, it still does, but it’s had a big impact in other industries,” he said.
Solving problems with technology
John Engates worked at Rackspace for nearly 20 years, starting in 2000 and departing as chief technical officer in 2018.
Engates has served in multiple CTO roles since then, first at Japanese company Nippon Telephone and Telegraph (NTT) and later at CloudFlare, a multinational company that manages access and security for millions of websites. He also spends time in an advisory role at UT San Antonio and on boards for Frost Bank and his children’s school.
Rackspace took a different approach to the tech industry, he said.
“Rackspace was built a little differently. We knew we were a customer service-oriented company, so we hired people who had a good attitude, who were service-oriented,” Engaged said.
Rackspace’s offices, built in an old mall and in wide-open spaces, emphasized a collaborative environment. People were excited to come in and solve problems together.
“We were not there just to make money,” Engates said. “We were there to solve problems with technology.”
He’s continued to emphasize customer-facing work his work at NTT and CloudFlare. It’s important for him to meet customers in person, to build trust with them and to listen to their problems with his company when those do come up.
Rackspace’s leaders built that into the company’s culture. The company phone number was front-and-center on the website and there was always a person on the line, Engates said. Rackers bought into that mission.
“Everybody felt invested in and involved,” he said. “It was truly a unique company in that era. Even today, it’s hard to find success stories like that in San Antonio.”
‘It’s in your bones’
Prashanth Chandrasekar joined Rackspace in 2012 as a chief of staff to one of the company’s general managers. In his seven years with the company, his role morphed and grew. There were always opportunities to do more, and Chandrasekar worked to manage a major partnership with Amazon and the company’s foray into cloud computing.
At the time, he said, there were abundant opportunities to grow if you showed talent and promise.
“What I’m really grateful for at Rackspace was I had some great mentors,” Chandrasekar said.
In 2019, he was named CEO at Stack Overflow, a coding and software development platform.
It was a shift to a more business- and sales-oriented role, Chandrasekar said, but he still brought lessons from Rackspace to his new job. He’s tried to emulate Rackspace’s culture and its focus on customer service.
“What you learn at Rackspace is do everything you can for the customer,” he said. “If you’re there long enough, it’s in your bones.”
At Stack Overflow, Chandrasekar helped develop Stack Internal, a knowledge base or library platform. The company has added products and services for businesses and was bought by South African company Naspers for $1.8 billion in 2021.
He hasn’t forgotten Rackspace, though. Nor have many in the tech industry. Rackers have spread far and wide across the tech ecosystem, he added.
“The Racker network is really strong. Rackspace built this great reputation for service delivery excellence,” Chandrasekar said.
