Episode 121
What if your first home turned into your first big win?
Tait Duryea and Ryan Gibson welcome Brad Hilton and Aubrey Carlson, a powerhouse pilot couple who turned a VA loan into a cash-flowing real estate business. From renovating a dated beach house to designing destination-worthy cabins in Julian, CA, Brad and Aubrey break down how they scaled a short-term rental empire—without any formal training. Learn how they source properties, design for ROI, automate operations, and balance business with marriage. This episode is packed with real-world strategies, software hacks, and tax tips for pilots and professionals ready to take action.
Brad Hilton and Aubrey Carlson are a husband-and-wife team with deep roots in aviation—Aubrey, a former naval aviator, and Brad, a private pilot and entrepreneur. Together, they’ve built a thriving short-term rental business in Southern California, blending design savvy, military strategy, and hands-on grit. Their portfolio now spans multiple markets, with a focus on high-return properties and automation-driven management.
Show notes:
(0:00) Intro
(04:08) STR loophole for W-2 offsets
(13:21) How they got into real estate
(19:00) The course that changed everything
(27:45) Finding high-return STR markets
(31:03) Design strategy and hot tub ROI
(38:00) DIY vs contractor tradeoffs
(46:13) Top software stack for automation
(51:03) Building once, automating forever
(53:23) Outro
Connect with Brad Hilton and Aubrey Carlson:
Links Mentioned:
Published on 1 month, 1 week ago
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