This week on bigcitysmalltown, we examine the story behind ProsperOps, a cloud cost optimization startup with roots in San Antonio and Austin. Founded by a group of former Rackspace employees—known as “Rackers”—ProsperOps has quietly grown into a significant player in cloud services, culminating in its acquisition by Chicago-based Flexera earlier this year.

Host Bob Rivard welcomes founders Erik Carlin and Chris Cochran for an in-depth conversation about the company's unconventional journey. Operating as a remote-first team with no fixed address, ProsperOps leveraged early support from the local “Racker family,” worked with minimal overhead, and never sought outside venture capital after its initial round. The company’s approach, shaped by the unique culture at Rackspace, stands out in the Texas startup landscape.

They discuss:

• How Rackspace’s culture of “fanatical support” influenced the creation of ProsperOps
• The impact of remote work—before and after the pandemic—on building a fast-growing company
• Navigating early funding, resisting acquisition offers, and why the founders waited for the right exit
• The challenges and opportunities for tech entrepreneurs in San Antonio and along the Austin-San Antonio corridor
• What the ProsperOps story says about the future of local startups, remote work, and the city’s efforts to build a lasting tech ecosystem

RECOMMENDED NEXT LISTEN:

▶️ #138. Alamo Angels: The Future of South Texas Startups – Building on the local founder journey explored in the ProsperOps episode, host Bob Rivard sits down with Sebastian Garzon of Alamo Angels to unpack how a thriving network of investors and entrepreneurs is shaping San Antonio’s next wave of tech success stories. Discover what it takes to grow a robust startup ecosystem and why early-stage investment is key to the city’s innovation future.

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