Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success.
Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life.
Whether you're a seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.
Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success.
Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life.
Whether you're a seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.
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:
—
You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry.
Remember to subscribe for more insights at PassiveIncomePilots.com! https://passiveincomepilots.com/
Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots
Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/
Follow us on X @IncomePilots: https://twitter.com/IncomePilots
Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/
Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com
See you on the next one!
*Legal Disclaimer*
The content of this podcast is provided solely for educational and informational purposes. The views and opinions expressed are those of the hosts, Tait Duryea and Ryan Gibson, and do not reflect those of any organization they are associated with, including Turbine Capital or Spartan Investment Group. The opinions of our guests are their own and should not be construed as financial advice. This podcast does not offer tax, legal, or investment advice. Listeners are advised to consult with their own legal or financial counsel and to conduct their own due diligence before making any financial decisions.