173. Charlie Amato and Gary Dudley on Building SWBC — and Betting on San Antonio for 50 Years

This week on bigcitysmalltown, Bob Rivard sits down with Charlie Amato and Gary Dudley, co-founders of SWBC, to mark the company's 50th anniversary. What began in 1976 with $1,500, a third partner in Dallas, and car trunks for offices has grown into one of San Antonio's largest and most diversified private companies, with 2,500 employees, operations in all 50 states, and a growing presence in Monterrey, Mexico.They discuss:How two friends from the Gulf Coast reunited in college, learned the insurance business from the inside, and quit their jobs on the same day to start something betterWhy they chose San Antonio as their headquarters — and why a vote, a house sale, and a buyout sealed itHow surviving 17–19% interest rates in the 1980s shaped their philosophy on diversification and financial resilienceThe decision to expand into multifamily real estate development — and what the post-COVID softening of that market looks like nowWhy they joined the group that kept the Spurs in San Antonio in 1993, and what that $85 million bet looks like at a $3.5 billion valuationTheir operation in Monterrey — why they went, how H-E-B showed them the way, and how they're thinking about security during the World CupWhat 6,000 intern applications revealed about SWBC's reputation — and how they're thinking about AI across their businessesWhy San Antonio has work to do on corporate recruitment, workforce development, and staying top of mind for CEOsRECOMMENDED NEXT LISTEN:▶ 161. Former Assistant City Manager Lori Houston Reflects on 23 Years at City Hall and Her Next Steps — SWBC's growth mirrors San Antonio's own civic evolution. This episode examines the infrastructure and leadership decisions that shaped the city Charlie and Gary bet on.…..GET THE NEWSLETTER📰 If you enjoyed this conversation, sign up for Bob Rivard's Midweek — sharp takes on San Antonio's politics, culture, and civic life, delivered to your inbox every Wednesday. Independent, nonpartisan, and free to read.Subscribe here.-- --CONNECT📸 Connect on Instagram🔗 Join us on LinkedIn🎥 Subscribe on YouTubeSPONSORS🙌 Support the show & see our sponsorsTHANK YOU⭐ Leave a review on Apple Podcasts⭐ Rate us on Spotify