Building the City Our Kids Want to Call Home with Randy Smith | Ep. 1 episode artwork

EPISODE · Jan 25, 2026 · 49 MIN

Building the City Our Kids Want to Call Home with Randy Smith | Ep. 1

from Breaking Ground SA

In this episode, we sit down with Randy Smith, co-founder and CEO of Weston Urban, to explore his unexpected journey from attorney to developer and his vision for San Antonio's future. Randy shares how a breakfast at IHOP led him to Rackspace and eventually to transforming downtown San Antonio with projects like Frost Tower, the Milam Building, and the upcoming downtown baseball stadium. We discuss why downtowns matter, the importance of people over buildings, and how San Antonio's unique community spirit sets it apart. Randy also opens up about the challenges of capitalizing development projects, his passion for creating family-friendly spaces, and why he believes San Antonio does community better than anywhere else in America.Topics Covered:(00:34) - From Attorney to Developer: Randy's unexpected career journey(8:34 - Moving to San Antonio: Why Randy and Rachel chose San Antonio in 2005(13:41) - The IHOP Breakfast: Meeting Graham Weston and joining Rackspace(15:19) - Founding Weston Urban: "Building the city our kids want to call home"(23:00) - Frost Tower: Breaking San Antonio's 30-year office tower drought(25:09) - The Frost Tower Land Deal: Complex three-way swap with Frost Bank and the City(28:53) - Why Downtown Matters: Economics, community, and San Antonio's identity(37:55) - Downtown Baseball Stadium Update: Current status and challenges(42:05) - "Who Has It Better Than Us?": Randy's philosophy on gratitude and perspective(47:00) - The Power of People: Why humans matter more than buildings in San Antonio's futureResources:https://recsanantonio.com/https://westonurban.com/Podcast Production Services by EveryWord Media

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Building the City Our Kids Want to Call Home with Randy Smith | Ep. 1

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