Get ready to uncover the secrets of one of commercial real estate’s most resilient and misunderstood asset classes: self-storage. In this in-depth episode, Tait Duryea and Ryan Gibson explore why self-storage continues to outperform in uncertain times, how millennials are transforming storage use, and what makes it such a powerful wealth vehicle for passive investors. They share personal stories, break down tenant behavior, explain how to boost NOI with tenant insurance, and demystify cap rates and value creation. Plus, hear about their upcoming Houston tour where you can walk properties and learn the strategy firsthand.

Show notes:

(0:00) Intro

(4:07) A brief history of self-storage

(8:52) Sticky tenants and rent increases

(11:09) Millennials, boomers, and behavior shifts

(15:06) Business use cases and commercial demand

(18:43) Automation, kiosks, and virtual support

(23:02) Recession resistance and industry resilience

(30:20) Buying from mom and pops

(35:48) What actually drives cap rate compression

(43:10) Capital flows and REIT consolidation

(47:40) Outro

🎟️ LIVE EVENT — JULY 9, 2025

Want to see these strategies in action? Join Ryan and Tait for a half-day Self-Storage Bus Tour and happy hour in Houston. RSVP now at http://Passiveincomepilots.com/houston

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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/

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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.

In this episode, hosts Tait Duryea and Ryan Gibson sit down with attorney Amanda Wynalda from Anderson Advisors to unpack everything pilots and high-income earners need to know about trusts, wills, and asset protection. From revocable vs. irrevocable trusts to layering LLCs and avoiding the due-on-sale clause, this episode is a blueprint for protecting your wealth while staying legally compliant.

Amanda Wynalda is a licensed attorney and executive at Anderson Business Advisors, where she leads the land trust and deed department. With a background in tax law, estate planning, and a personal history in a multi-generational real estate business, Amanda brings practical and legal expertise to asset protection. She’s also a dynamic speaker, educator, and trusted advisor for high-income professionals looking to protect and structure their wealth.

Show notes:

(0:00) Intro

(04:51) Amanda’s legal and real estate background

(08:13) Key differences between wills and trusts

(12:41) Importance of funding your trust properly

(20:41) Choosing the right trustee and backup

(23:11) Real estate structure for everyday pilots

(32:58) Liability risks with and without entities

(46:17) Protecting your mortgage from acceleration

(54:28) Outro

Connect with Amanda Wynalda:

Website: https://andersonadvisors.com

LinkedIn: https://www.linkedin.com/in/amanda-fletcher-wynalda-a1a6373

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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/

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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.

In this episode, hosts Tait Duryea and Ryan Gibson talk with chief economist Dr. Peter Linneman to demystify interest rates, the national deficit, and how it all affects pilots, real estate investors, and entrepreneurs. Discover why U.S. debt may not be the threat it’s made out to be, how capital flows drive values, and what most people get wrong about inflation and treasury yields. They also unpack commercial real estate's current cycle, the impact of bonus depreciation, and why now might be the smartest time to invest if you know where to look.

Dr. Peter Linneman is a renowned economist, former Wharton professor, and founder of Linneman Associates. With a PhD from the University of Chicago and decades of experience advising major firms and boards, he is the author of the industry-standard textbook Real Estate Finance and Investments and publisher of the respected Linneman Letter. In this episode, he shares plainspoken economic insight tailored for high-income professionals and investors.

Show notes:

(0:00) Intro

(03:16) Peter Linneman’s background and credentials

(06:45) Why the deficit fear is overblown

(09:39) U.S. debt vs. national wealth explained

(13:18) The real issue: inefficient spending

(17:46) What pilots should focus on instead

(23:12) Why U.S. wealth keeps growing

(28:00) Are we headed into a recession?

(34:17) Where we are in the real estate cycle

(39:11) Bonus depreciation and capital flows

(42:27) Why treasury and Fed rates diverged

(45:53) Outro

Connect with Dr. Peter Linneman:

Website: https://www.linnemanassociates.com

LinkedIn: https://www.linkedin.com/in/peterlinneman

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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

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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.

In this episode, Tait Duryea and Ryan Gibson welcome CPA Thomas Castelli of Hall CPA to break down the latest tax developments affecting high-income earners. From the potential return of 100% bonus depreciation to how the real estate professional status works in practice, Tom shares key strategies to help you keep more of what you earn. Whether you're flying the line or growing your rental portfolio, this episode delivers practical advice for optimizing deductions, structuring entities, and deciding when to hire a pro vs. going DIY.

Thomas Castelli is a CPA and partner at Hall CPA, specializing in strategic tax planning for real estate investors and business owners. With deep expertise in real estate professional status, bonus depreciation, and entity structuring, Tom helps high-income earners legally reduce their tax burden. In this episode, he brings timely insights on new legislation and actionable strategies tailored for pilots and investors.

Show notes:

(0:00) Intro

(02:52) Why this tax bill matters

(03:39) Return of 100% bonus depreciation

(06:38) Key highlights from the 2017 tax act

(10:32) Real estate professional status explained

(15:07) MAGA accounts and standard deduction

(19:51) Overtime and tip tax exemptions

(21:51) QBI deduction and entity structuring

(28:41) When to use a CPA vs TurboTax

(38:01) Outro

Connect with Hall CPA: https://bit.ly/HallCPA

Hall CPA - Passive Income Pilots 1-1 Tax Strategy Call: https://calendly.com/tax-smart-rei-plus/pip

—

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.

In this episode, hosts Tait Duryea and Ryan Gibson welcome Ramez Fakhoury from IRA Club. This episode dives into how pilots can unlock old 401(k)s, TSPs, and HSAs for real estate and other alternative investments. Hear a detailed story of a Southwest pilot transitioning to American Airlines and learn what decisions made the biggest impact. Whether you're changing airlines or just seeking better returns, this episode is packed with actionable insights.

Ramez Fakhoury is the Vice President of IRA Club, a leading self-directed IRA custodian. With a background in hospitality and entrepreneurship, Ramez discovered a passion for alternative investing and now helps individuals unlock their retirement capital for real estate and other private assets. His practical approach and deep knowledge make complex financial strategies accessible for pilots and high-income earners.

Show notes:

(0:00) Intro

(01:07) Introduction to Ramez and IRA Club

(04:49) Three options when leaving an airline

(06:11) True vs. false self-direction explained

(10:27) Why you shouldn't rush rollover decisions

(14:39) What you can't invest in with IRAs

(20:48) Why IRA Club's structure stands out

(27:42) Contribution limits vs. rollover power

(38:56) Partnering personal and retirement funds

(46:59) Real estate in IRAs: tax pros and cons

(51:20) Outro

Connect with Ramez:

Website: https://www.iraclub.com/

LinkedIn: https://www.linkedin.com/company/the-ira-club/

—

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

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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.

In this episode, hosts Tait Duryea and Ryan Gibson deliver an in-depth, pilot-friendly primer on syndications and passive real estate investing. They break down the risk spectrum from core to opportunistic deals, while sharing real-world analogies and experiences from their own projects, like the Canyon City land entitlement.

Learn how to properly evaluate risk-adjusted returns, the importance of DSCR vs LTV, and what preferred return really means in a syndication waterfall. This episode is a must-listen for high-income professionals looking to navigate passive investing with clarity and confidence.

Show notes:

(0:00) Intro

(02:23) Active vs passive investing explained

(04:03) Is syndication risky? Understanding real risk

(05:22) Core, Core Plus, Value Add, Opportunistic defined

(10:11) Operational vs physical value-add

(13:35) What are risk-adjusted returns?

(17:19) How leverage impacts risk

(20:02) DSCR vs LTV: What's more important?

(22:59) Preferred return vs cash flow

(33:50) What is an accredited investor?

(38:55) Outro

—

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

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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.

In this episode, Tait Duryea flies solo to spotlight a powerful tax strategy many high-income earners overlook: real estate professional status. Featuring Brandon Hall from Hall CPA, this episode breaks down a real tax court victory by a harbor pilot who leveraged a flexible W-2 job schedule to claim REP status and unlock massive tax savings. Discover the legal requirements, the importance of documentation, and how pilots are uniquely positioned to take advantage of this IRS loophole—a must-listen for anyone serious about turning real estate into real tax strategy.

Brandon Hall is a CPA and the founder of Hall CPA, a firm specializing in real estate tax strategy. Known for his deep understanding of IRS code and investor-focused guidance, Brandon walks through a landmark tax court case that underscores how full-time professionals, including pilots, can successfully claim real estate professional status.

Show notes:

(0:00) Intro

(01:13) History of passive activity rules

(02:49) Short-term rentals vs. REP loophole

(04:33) Why pilots are uniquely eligible

(05:29) REP for married couples explained

(06:49) Brandon Hall sets up the case study

(09:12) Mr. Miller's job and schedule details

(13:18) Proving material participation

(16:31) The grouping election mistake to avoid

(19:24) Outro

Connect with Brandon:

• https://bit.ly/HallCPA - Recommended CPA for real estate-focused tax strategy

—

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.