Passive Income Pilots

What does true diversification look like when you’re building wealth as a pilot? 

In this episode, Ryan Gibson sits down with his longtime colleague and friend, Ted Greene, to unpack how to define success with your spouse, avoid emotional investing, and create a portfolio that brings peace of mind. From surviving Wall Street lawsuits to building lasting wealth through real estate, Ted shares the hard-earned lessons behind his “NNN Principle”: Never, Never, Never invest by looking in the rearview mirror. Learn how to protect your assets, ladder your investments, and build a plan that lasts through every market cycle.

Ted Greene is the Investor Relations Manager for Spartan Investment Group. Ted is a third-generation Seattleite who married his high school sweetheart. Ted and Melissa have two children attending the same High School where they first met. After graduating from Seattle Pacific University with a BA in Finance, Ted spent 24 years in the financial services industry as an investment advisor and Fiduciary.

Download Ted’s Ebook here: https://go.spartan-investors.com/l/1038393/2025-09-17/39mf5b

Show notes:

(0:00) Intro

(1:30) Ted’s background: Merrill Lynch to Spartan

(3:10) Defining success through diversification

(5:22) Why Ted left Wall Street

(6:44) How to align with your spouse on money

(9:38) What “uncorrelated assets” really mean

(12:00) The 50-question eBook on financial alignment

(14:49) Concentration builds wealth, diversification protects it

(19:20) The NNN Principle: Never, Never, Never

(22:18) Smaller positions, smarter protection

(25:22) Laddering investments for flexibility

Connect with Ted Greene:

• LinkedIn: https://www.linkedin.com/in/ted-greene-iamnotafraid/

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If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/ 

—

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 [email protected] 

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.

Why do so many high-earning pilots struggle to build real wealth?

Hosts Tait Duryea and Ryan Gibson get candid about the habits, mindset, and blind spots that keep aviators from achieving true financial independence. They reveal the five biggest mistakes pilots make, from lifestyle creep and tax traps to ego-driven investing, and how to replace them with smarter, more sustainable wealth strategies. Whether you’re a first officer just starting out or a captain eyeing retirement, this conversation will challenge how you think about money, success, and the long game of building lasting freedom.

Show notes:

(0:00) Intro

(1:32) The pilot ego and knowing it all

(3:14) Why pilots don’t get rich

(7:01) The 401(k) balloon problem

(11:37) Multiple streams of pilot income

(18:25) #1 Lifestyle creep and paycheck trap

(19:21) #2 The investing knowledge gap

(20:31) #3 Ego over education

(21:46) #4 The silent thief: Taxes

(23:24) #5 Peer pressure and social influence

(29:37) Outro

Episode suggestions:

• #10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment: https://tinyurl.com/2kmd7y7z
• #14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate: https://tinyurl.com/4e2nex6d

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If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/ 

—

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 [email protected] 

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.

What do private placement memorandums really mean for you as an investor? 

Hosts Tait Duryea and Ryan Gibson sit down with attorney and real estate operator Seth Bradley to pull back the curtain on syndication documents, accreditation rules, and what truly protects investors. Seth shares his personal journey from med school to big law to entrepreneurship, and why his legal background gives him a unique perspective on raising capital and building passive income. Discover why trust in the operator matters more than projections, what to look for in waterfalls and fee structures, and the real truth about accredited investor requirements. Find out what every high-income professional should know before signing their first PPM.

Seth Bradley, Esq. is a securities attorney, entrepreneur, and real estate investor. After careers in both medicine and big law, Seth founded his boutique firm, Raise Law, where he advises syndicators and investors on structuring deals and protecting capital. As both an operator and investor, Seth brings a rare perspective, combining legal expertise with hands-on real estate experience.

Show notes:

(0:00) Intro

(03:06) Fired from big law, starting Raise Law

(06:04) Why PPMs exist and how they protect investors

(09:06) What it means to be an accredited investor

(12:53) Why projected returns can be misleading

(14:58) Understanding waterfalls and risk

(17:04) Are PPMs just boilerplate risk lists?

(21:07) The blunt truth of a PPM: no control, all risk

(26:05) Due diligence on operators vs. documents

(29:37) How to prove accreditation: income vs. net worth

(39:32) Outro

Connect with Seth Bradley:

• LinkedIn: https://www.linkedin.com/in/sethbradleyesq 
• Podcast: https://passiveincomeattorney.com/seth-bradley

—

If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/ 

—

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 [email protected] 

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.

How protected is your wealth if something goes wrong? 

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with asset protection expert Adam Kintigh to share practical strategies every pilot and high-income professional should know. From real estate privacy trusts that cut transfer taxes to Wyoming LLCs that safeguard syndications, Adam explains how to structure your assets the right way. You’ll learn why a clean tax return matters, how partnerships and S-Corps simplify filings, and why umbrella policies aren’t enough. If you’re growing wealth through rentals, syndications, or brokerage accounts, this episode shows you how to keep it safe and secure.

Adam Kintigh is an asset protection strategist with over 24 years of experience, currently with Nevada Corporate Headquarters (NCH). He specializes in forming entities, estate planning, tax and accounting strategies, and business structuring for investors nationwide. Adam is an expert on practical, legally sound frameworks for protecting rental portfolios, drawn from decades of industry knowledge and client success.

Show notes:

(0:00) Intro

(02:32) Why asset protection matters now

(06:45) Real lawsuit examples and lessons

(10:40) The truth about anonymity and privacy

(13:44) First rental: when to start protecting

(19:02) Insurance basics every pilot needs

(27:33) Why true anonymity doesn’t exist

(30:08) Alternative structure to LLC stacking

(37:10) How partnerships clean up tax returns

(44:10) Correct way to hold syndications

(49:07) Moving brokerage accounts into LLCs

(51:27) Outro

Connect with Adam Kintigh:

• 📩 Email Adam at: [email protected] and mention Passive Income Pilots to get started.
• Website: https://nchinc.com

—

If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/ 

—

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 [email protected] 

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.

What separates pilots who want to invest from those who actually succeed? 

In this episode, Tait Duryea and Ryan Gibson share the real stories behind their first deals, the mistakes they made, and the lessons that still guide them today. From disastrous single-family rentals to managing multifamily properties, they explain why failure is often the best teacher and why no one should try to “lone wolf” their way through real estate.

They also highlight the power of networking and why being “in the arena” matters more than sitting on the sidelines. This is a practical, no-fluff conversation about education, community, and action for pilots and high-income professionals looking to create passive income.

Show notes:

(0:00) Intro

(03:42) Why in-person networking is essential

(07:03) The ballroom vs. hallway test for experience

(12:56) The reality of early rental property mistakes

(15:35) Why you can’t “lone wolf” real estate investing

(20:17) The “man in the arena” mindset for investors

(26:18) Turbine’s horizontal integration vs. Spartan’s focus

(30:19) Outro

Helpful Links: 

Houston Bus Tour Registration: https://www.eventbrite.com/e/houston-self-storage-portfolio-bus-tour-tickets-1591575237379?utm_experiment=test_share_listing&aff=ebdsshios&sg=ed19105646f93b16506dd629ad293a6953b60f4c21904c87d174147bc25617d71f6099f588a1abb3a895fbbeef2578e057d6effbb7d6e124cd35f68fece2d51827faa0c5beabab7ede30c93969



Turbine Capital Investor Weekend RSVP link: https://luma.com/8eryqndb 

—

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 [email protected] 

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.

Can oil and gas really be a smart play for high-income professionals? In this episode, Tait Duryea and Ryan Gibson sit down with Mark Fleming, petroleum engineer and Turbine Capital’s oil & gas advisor, to break it down. From the basics of how drilling works to the tax advantages that can offset W2 income, you’ll learn the realities of this often-misunderstood industry. The conversation covers political risk, environmental concerns, portfolio allocation, and many more. Whether you’re curious about non-op partnerships, cashflow timing, or long-term energy trends, this episode gives you the insider perspective every pilot-investor needs.

Mark Fleming is a petroleum engineer and oil & gas advisor with over 20 years of experience across Chevron, Hess, and EOG. He has also advised major banks on energy lending and helped startups navigate the public markets. Today, Mark serves as Turbine Capital’s oil and gas advisor, guiding strategy and due diligence for private funds. His expertise spans drilling technology, unconventional plays, energy policy, and risk assessment, making him a trusted voice for investors seeking clarity in this complex sector.

Show notes:

(0:00) Intro

(00:41) Why oil & gas still matters

(05:20) Oil investing is long-term, not quick

(08:16) Politics and pricing shape investor returns

(11:42) Game-changing advances in drilling & fracking

(13:03) ESG, environment, and energy reality

(16:47) Oil plays vs. gas plays explained

(19:26) Three ways to invest privately

(24:21) Upstream, midstream, and key tax benefits

(30:58) How to vet operators & reduce risk

(45:05) Oil cashflow vs. real estate returns

(49:22) Outro

Helpful Links: 

LinkedIn: https://www.linkedin.com/in/mark-e-fleming

Turbine Capital: Iron Horse Energy Fund

Guide to U.S. Tax benefits for Direct Oil & Gas Drilling Investments: https://drive.google.com/file/d/1DZBu5zH8dpotRFijs6-VmJo1HF4EvIIu/view?usp=sharing 

Bettering Human Lives Liberty Energy: https://drive.google.com/file/d/1BqCoKUbcWBiaeY6g9l1DDsQFUY8Y8y82/view?usp=sharing 

The Prize: The Epic Quest for Oil, Money & Power: https://a.co/d/bwwLzZq 

—

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 [email protected] 

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.

Tait Duryea and Ryan Gibson welcome Mat Sorensen, CEO of Directed IRA, for a powerful discussion on how pilots and high-income professionals can unlock private investment opportunities through retirement accounts. From self-directed IRAs to Solo Ks, Mat explains the mechanics of rolling over old 401(k)s, navigating recent regulatory changes, and tapping into lucrative private markets that were once out of reach. 

Mat Sorensen is the CEO of Directed IRA and Directed Trust Company, where he oversees thousands of self-directed retirement accounts including IRAs, Roth IRAs, HSAs, and Solo 401(k)s. He is also a senior partner at KKOS Lawyers and the bestselling author of The Self-Directed IRA Handbook. A recognized leader in the self-directed investing space, Mat has helped countless professionals leverage retirement accounts to access private investments and alternative assets.

Show notes:

(0:00) Intro

(4:15) $44 trillion in U.S. retirement accounts

(5:06) Trump’s executive order on 401(k)s

(10:03) Fewer public companies, more private options

(20:13) IRAs vs. 401(k)s for private investing

(26:05) Pilot story: confusion with mutual funds

(28:37) Tax implications of IRA vs. cash

(35:29) How Mat vets private deals

Helpful Links:  

Website: https://matsorensen.com 

Mat’s Podcasts

• Directed IRA Podcast → https://directedira.com/education/#category-podcasts
• Main Street Business Podcast → https://www.mainstreetbusiness.com 



Alternative Asset Summit → https://www.altassetsummit.com (October 16–17 in Scottsdale, AZ)

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Houston Bus Tour Registration: https://www.eventbrite.com/e/houston-self-storage-portfolio-bus-tour-tickets-1591575237379?utm_experiment=test_share_listing&aff=ebdsshios&sg=ed19105646f93b16506dd629ad293a6953b60f4c21904c87d174147bc25617d71f6099f588a1abb3a895fbbeef2578e057d6effbb7d6e124cd35f68fece2d51827faa0c5beabab7ede30c93969

—

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 [email protected] 

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.

Is now the right time to buy real estate or to hold cash? 

In this episode, Tait Duryea and Ryan Gibson sit down with Hunter Thompson, founder of Asym Capital and host of Cash Flow Connections, to unpack today’s real estate market. They cover cycles, debt structures, the COVID impact, rising interest rates, and why current distress is more about financing than fundamentals. Whether you’re an LP wondering how to vet a deal or a high-income professional looking for the next big move, this conversation offers clarity on where we stand in 2025 and what smart investors should do next.

Hunter Thompson is a real estate investor, author, and host of the Cash Flow Connections podcast. With 15 years of experience and billions in transactions, he’s built a reputation as a sharp student of economics and a hands-on operator. From launching Asym Capital to navigating the toughest market cycles, Hunter shares how debt, demographics, and timing shape opportunities for passive investors and active operators alike.

Show notes:

(0:00) Intro

(2:32) Early career and 2010 lessons

(6:30) Becoming a capital allocator

(8:01) Evaluating operators and first deals

(14:02) Understanding real estate market cycles

(19:30) Interest rates and inflation impact

(26:09) Debt costs driving distress

(30:00) Buying opportunities in strong markets

(43:34) Fixed vs floating rate debt

(47:14) Outro

Cash Flow Connections - Real Estate Podcast: https://podcasts.apple.com/us/podcast/cash-flow-connections-real-estate-podcast/id1193877994 

—

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 [email protected] 

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.

What if your life insurance could help you invest without selling a single asset?

Tait Duryea and Ryan Gibson welcome back Rod Zabriskie of Money Insights to demystify how whole life insurance can be used as a wealth-building tool. They break down the differences between term and whole life, how cash value grows, and why this strategy avoids risks like margin calls. You’ll hear how pilots are using these policies to fund real estate, reduce taxes, and create a perpetual source of investment capital.

Rod Zabriskie, president of the Money Insights Group, specializes in advanced wealth-building strategies using life insurance as a financial tool. With a pragmatic, education-first approach, Rod helps high-income professionals, especially pilots, understand how to leverage whole life policies for liquidity, tax advantages, and long-term returns.

Show notes:

(0:00) Intro

(01:06) Four ways to leverage capital

(02:01) Why life insurance can be exciting

(05:09) Term vs whole life basics

(10:35) How cash value policies work

(16:26) Risks of securities-backed loans

(20:01) Why whole life avoids margin calls

(27:30) How life insurance companies invest

(33:16) Using policies as your “cash chamber”

(39:02) Paying off loans vs max funding

(46:43) Funding ranges and contribution flexibility

(49:01) Outro

• For a free consultation with the Money Insights Group, go to https://moneyinsightsgroup.com/pilots/ 

Episodes Mentioned:

•  #47 - https://passiveincomepilots.com/episode/47-innovative-wealth-strategies-from-life-insurance-to-alternative-investing-with-christian-allen-and-rod-zabriskie
• #70 - https://passiveincomepilots.com/episode/70-leveraging-life-insurance-for-passive-income-with-rod-zabriskie-and-blake-brogan 
• #84 - https://passiveincomepilots.com/episode/84-tax-free-growth-infinite-loans-whole-life-insurance-strategies-for-high-earners 
• #23 - https://passiveincomepilots.com/episode/23-counting-the-cost-the-risks-and-rewards-of-401k-loans-for-pilots 



—

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 [email protected] 

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.

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:

• Instagram: https://www.instagram.com/saltandskylodgingco 
• Website: https://www.saltandskylodgingco.com 

Links Mentioned:

• Minoan: https://minoan.com/join-us?referral_code=2YW3J1CP4876&aid=I0KVIF 
• Hostfully: https://get.hostfully.com/xtb3o3sa28ea 
• Breezeway: https://referral.breezeway.io/l/AUBREYCARL48 
• White Feather Investments: https://whitefeatherinvestments.com/training 

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*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.