Passive Income Pilots

Tait Duryea and Ryan Gibson sit down with Money Insights wealth strategists Brenyn McConnell and Blake Brogan to explore how pilots can create more tax-efficient retirement income beyond a traditional 401(k). They break down how properly structured whole life insurance can provide liquidity, tax-free access to cash value, long-term care benefits, and estate-planning flexibility. Discover how this strategy can complement Roth conversions and alternative investments while helping high-income pilots reduce their dependence on taxable retirement accounts and build greater financial flexibility for the years ahead.

Brenyn McConnell and Blake Brogan are Wealth Strategists at Money Insights, where they help high-income professionals build more efficient wealth strategies using high-cash-value life insurance and alternative investments. Brenyn has worked in financial services since 2018, while Blake brings roughly a decade of industry experience focused largely on overfunded life insurance strategies. They teach how properly structured policies can support tax-free retirement income, long-term care planning, liquidity, and generational wealth.

Show notes:

(0:00) Intro

(0:13) Diversifying beyond the traditional 401(k)

(7:20) The 401(k) retirement tax problem

(11:12) Roth conversions and tax planning

(14:24) Creating tax-free policy income

(17:09) $2.5M cash value example

(21:55) Accessing money before retirement age

(23:49) Life insurance as a vehicle

(25:13) Designing a self-sustaining policy

(26:58) Avoiding poorly designed policies

(29:24) Planning for long-term care

(35:26) Estate and wealth-transfer planning

(41:46) Outro

Connect with Brenyn McConell & Blake Brogan:

• Website: https://insights.moneyinsightsgroup.com/pilots

Related Episode:

• #47 - Innovative Wealth Strategies and Alternative Investing with Christian Allen and Rod Zabriskie

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 https://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 at 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 close out the Passive Income Pilots Conference with a rapid-fire Q&A alongside experts Koy Harris, David Vanlandingham, Kurt Harris, and Adam Kintigh. Drawing on their expertise in estate planning, asset protection, business structuring, and tax strategies, the panel answers real-world questions about self-storage investing, tax withholding, privacy trusts, cost segregation, retirement conversions, and depreciation recapture. Pilots and high-income professionals will gain a clearer understanding of how to structure investments, protect real estate assets, avoid costly tax mistakes, and evaluate opportunities to generate passive income without adding unnecessary responsibilities to their already demanding careers.

Show notes:

(0:00) Intro

(3:27) Self-storage market outlook

(6:56) House hacking and privacy trusts

(7:34) Managing tax withholding strategically

(12:20) Replacing captain pay passively

(13:16) Homestead and privacy trusts

(16:10) Cost segregation on older rentals

(17:00) Investing without active real estate

(17:49) Naming trusts for asset privacy

(21:41) Leveraging paid-off rental properties

(27:28) Using real estate professional status

(32:28) Outro

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 https://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 at 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 host a live Q&A with Adam Kintigh, Kurt Harris, and David Vanlandingham covering the financial questions pilots face as their income and investments grow. From short-term rental tax strategies and Roth conversions to self-directed IRAs, 401(k) contributions, real estate leverage, and estate planning, the panel examines how different pieces of a wealth plan fit together. Pilots will leave with practical guidance on deploying capital more efficiently while balancing tax savings, liquidity, retirement planning, and long-term financial freedom.

Show notes:

(0:00) Intro

(1:56) Where to hold investment cash

(3:26) STR depreciation recapture strategies

(5:57) Moving beyond a scarcity mindset

(8:18) Short-term rental tax qualification

(11:58) When passive income becomes enough

(14:49) Traditional-to-Roth conversion strategies

(18:45) Choosing cash versus retirement funds

(23:12) Optimizing pilot 401(k) contributions

(32:28) Financing short-term rental properties

(36:43) Avoiding major estate planning mistakes

(45:31) Outro

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 https://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 at 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 sit down with veteran passive investor Jeremy Roll to discuss building wealth beyond traditional stocks and 401(k)s. Jeremy shares how more than two decades of alternative investing shaped his approach to market cycles, diversification, liquidity, and passive cash flow. They also discuss preparing for market corrections, creating life-changing income through a “get rich slow” strategy, tax advantages of alternative investments, and managing dozens of K-1s. For pilots looking to build additional income without relying entirely on the stock market, this episode offers a long-term investor’s perspective.

Jeremy Roll is the Founder and President of Roll Investment Group and a longtime passive investor in real estate and private businesses. Before becoming a full-time investor, he spent more than a decade in the corporate world, including roles at Disney and Toyota, and earned his MBA from The Wharton School. Jeremy is also a co-founder of For Investors By Investors (FIBI), a nonprofit investor education and networking community. Known for his disciplined, research-driven approach, he has participated in more than 200 managed investments over his investing career.

Show notes:

(0:00) Intro

(2:28) Jeremy Roll’s investing background

(4:21) Investing through market cycles

(7:21) Preparing for a market correction

(11:43) Market concentration and margin debt

(16:34) Diversifying beyond the 401(k)

(18:59) Building life-changing passive income

(23:38) The get rich slow strategy

(26:30) Tax advantages of alternatives

(30:44) Where Jeremy is investing today

(33:35) Managing multiple K-1s

(37:18) Outro

Connect with Jeremy Roll:

• Email: jroll@rollinvestments.com
• LinkedIn: http://linkedin.com/in/jeremy-roll-655107

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 https://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 at 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.

Join us on October 8–9, 2026, in Las Vegas, Nevada, for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference

Tait Duryea and Ryan Gibson examine the side of real estate investing that spreadsheets often miss, the return on life. Drawing from their own experiences with rental properties, they discuss when active ownership is worth the time, why so-called passive investments can start to feel like another job, and how pilots should think about short-term rentals beyond the tax benefits. They also cover cost segregation, bonus depreciation, depreciation recapture, 1031 exchanges, and why buying assets you are comfortable holding long term can matter. For pilots focused on tax efficiency and financial independence, this episode offers a practical look at what real estate ownership can actually require.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(0:54) Reality of active real estate investing

(2:24) Measuring your return on life

(6:50) Tait’s costly multifamily lesson

(11:10) Moving from active to passive investing

(13:24) Short-term rentals and tax benefits

(14:51) Grade the deal and lifestyle

(19:56) Short-term rentals are hospitality businesses

(24:28) Cost segregation and CPA planning

(28:43) Depreciation recapture when selling

(32:37) Buying assets for long-term wealth

(37:54) Outro

Related Episodes:

• #32 - Tax Savvy Investing: The Power of Cost Segregation with Yonah Weiss
• #85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver
• #144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall
• #145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia

Book Reference:

• Optimize YOUR Bnb

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 https://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 at 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.

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference

Tait Duryea and Ryan Gibson sit down with Larry Lemer and Mark Goldstein of Foliage to examine how a community of accredited investors approaches commercial real estate together without pooling money or making investment recommendations. They cover Foliage’s syndicator vetting process, its extensive due diligence questions, operator trust and execution, portfolio diversification, and lessons learned from deals that did not go as planned. For pilots and high-income professionals considering alternative investments, the conversation shows how surrounding yourself with experienced investors can bring additional perspectives to your own decision-making.

Larry Lemer and Mark E. Goldstein are co-founders of Foliage, a private investor education group that brings together accredited investors, including airline pilots, to evaluate commercial real estate opportunities. Larry brings roughly 20 years of real estate investing experience, while Mark draws on his corporate leadership and private equity background. Together, they emphasize rigorous due diligence, trusted operators, and the value of learning from a network of experienced investors.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(1:03) How Foliage vets syndicators

(5:23) How the group started

(9:11) Value of diverse investor perspectives

(14:05) Foliage is not a fund

(18:10) Education through the syndication playbook

(18:47) Case for alternative assets

(22:19) Lessons from investing mistakes

(25:01) Understanding deals and trusting operators

(30:38) Red flags when vetting syndicators

(40:44) Outro

Connect with Larry Lemer and Mark Goldstein:

• Website: https://www.foliageig.com/
• Larry’s email: larry@foliageig.com
• Larry’s LinkedIn: https://www.linkedin.com/in/larry-lemer-0503aa5/
• Mark’s LinkedIn: https://www.linkedin.com/in/mark-goldstein/
• Link to their Book: https://amzn.to/4rxzrn9

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 https://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 at 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.

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference

Tait Duryea welcomes Chris Naugle to discuss his unconventional path from professional snowboarding and Wall Street to real estate and privatized banking. Chris shares lessons from building businesses, surviving financial setbacks, owning dozens of rental units, and completing hundreds of flips before discovering the Infinite Banking Concept. They examine how specially designed whole life policies can support private lending, real estate investing, debt strategies, and greater control over capital while highlighting the discipline required to make the strategy work.

Chris Naugle is a wealth educator, entrepreneur, real estate investor, and former registered investment advisor specializing in privatized banking and the Infinite Banking Concept. A former professional snowboarder, Chris built multiple businesses before moving into financial services, real estate investing, and private lending. His experience includes managing investment assets, completing hundreds of house flips, appearing on HGTV’s Risky Builders, and building systems designed to help investors take greater control of their capital.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(8:00) Chris Naugle’s wealth-building journey

(13:54) Building a business at seventeen

(18:31) Transition from retail to Wall Street

(26:32) Building a financial advisory career

(29:24) First lessons in real estate

(36:20) Hitting the real estate debt wall

(41:51) From house flipping to HGTV

(44:05) Discovering privatized banking

(49:06) Rethinking traditional money strategies

(51:30) Infinite banking versus securities-backed credit

(57:25) Outro

Connect with Chris Naugle:

• Website: https://www.chrisnaugle.com/
• LinkedIn: https://www.linkedin.com/in/thechrisnaugle/
• YouTube: https://www.youtube.com/thechrisnaugle

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 https://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 at 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.

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference

Tait Duryea and Ryan Gibson sit down with Carollyne Carmichel and Kenya Hodson to discuss how a booking platform is changing the way pilots plan their getaways and owners market airport-adjacent properties. They share why general aviation travelers need more than a runway, what makes a stay truly pilot-friendly, and how Fly-Inn bridges the gap between landing and enjoying the destination. The conversation also considers the opportunity for pilots with short-term rentals, from meeting core hosting requirements to serving a highly specific guest base.

Carollyne Carmichel and Kenya Hodson are the mother-daughter founders of Fly-Inn, a short-term rental platform created for general aviation travelers. Built around pilot-friendly lodging, Fly-Inn connects guests with properties that offer nearby landing access, aircraft security, and ground transportation. Carollyne is a passionate general aviation pilot and property owner, while Kenya helps grow the platform through operations and technology.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(7:30) Fly-Inn’s pilot-first booking platform

(9:30) From boring destinations to business

(13:18) Private strips and nearby airports

(19:43) How hosts and Fly-Inn earn

(24:15) Landing permission at private strips

(26:14) Five promises for every host

(28:05) Short-term rental considerations

(31:03) What makes destinations perform

(33:28) Referring pilot-friendly properties

(38:24) Sync calendars across booking platforms

(39:02) Outro

Connect with Carollyne and Kenya:

• Website: https://www.fly-inn.com/
• Carollyne's LinkedIn: https://www.linkedin.com/in/carollyne-b-carmichel-833-i-fly-inn/
• Kenya’s IG: https://www.instagram.com/kenyahodsont/

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 https://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 at 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.

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference

The path beyond the cockpit can change everything. Tait Duryea and Ryan Gibson sit down with Dylan and Max for a crossover conversation on aviation careers, financial education, and building a platform that serves pilots. They discuss corporate versus airline flying, the realities of side gigs, and why pilots need reliable guidance on taxes, real estate, passive investing, and estate planning. The conversation also highlights how both podcasts help aviators make more informed decisions with their careers, time, and growing income.

Dylan and Max are the hosts of the 21.5 Podcast, a show for professional pilots covering aviation careers, training, industry updates, and unique flying stories. Both began their careers as flight instructors after attending Embry-Riddle, then built experience in regional and corporate aviation. Through more than 200 episodes, they offer practical perspective and help fellow pilots ask better questions about their careers and the industry.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(3:00) Max’s airline and corporate path

(7:12) Dylan on corporate flying careers

(10:46) Finding a corporate side gig

(14:29) Why the 21.5 Podcast began

(20:13) Financial education for high-income pilots

(27:01) Building a pilot-focused wealth strategy

(31:12) Why high earners need planning

(41:07) Active versus passive real estate

(53:14) Creating unbiased pilot financial education

(59:37) Outro

Connect with Dylan and Max:

• Website: https://www.21fivepodcast.com/

Related Episode:

• #10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis
• #14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis

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 https://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 at 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.

Join us on October 8–9, 2026, at the M Resort and Casino in Las Vegas for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit - https://www.passiveincomepilots.com/pip-conference

Tait Duryea and Ryan Gibson sit down with Adam Kintigh of Nevada Corporate Headquarters to explain how pilots and investors can use LLCs, trusts, and business entities more effectively. They discuss why forming an LLC is only the first step, the risks of commingling funds and poor recordkeeping, and when separate entities may make sense for rentals, investments, and active businesses. Adam also shares practical ways to keep compliance simple while building stronger asset protection.

Adam Kintigh is a Senior Coach at Nevada Corporate Headquarters, where he helps business owners and investors structure entities, protect assets, and maintain proper compliance. With 25 years of experience, including more than 18 years with NCH, Adam works alongside legal, tax, estate-planning, and business-credit professionals to help clients build practical entity strategies.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(3:54) A costly corporate recordkeeping mistake

(6:34) Corporate formalities and LLC structures

(9:31) Why DIY LLCs create risk

(12:34) What an LLC actually protects

(14:23) LLCs versus S-corps for investors

(23:25) Records, resolutions, and meeting minutes

(25:34) Keeping multiple entities manageable

(28:30) Compliance for S-corps and C-corps

(32:29) Asset protection for three investor levels

(40:08) Partnerships, short-term rentals, and K-1s

(48:13) Outro

Connect with Adam Kintigh:

• Website: https://nchinc.com
• Email Adam at: adam@nchinc.com and mention Passive Income Pilots to get started.
• NCH Consultation Phone: 1-800-508-1729

Learn more about:

NCH Consultation for Passive Income Pilots Investors: https://calendly.com/nchconsultation/nch-consultation-for-pipp?month=2025-12

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 https://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 at 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.

Join us on October 8–9, 2026, at the M Resort and Casino in Las Vegas for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit - https://www.passiveincomepilots.com/pip-conference

A practical path to business ownership. Tait Duryea and Ryan Gibson sit down with Brenda Gage, a pilot spouse who turned a long-time goal of business ownership into a growing café portfolio. Brenda shares how she found established, cash-flowing businesses, evaluated opportunities on BizBuySell, used SBA financing, and pushed through lender rejections. She also explains why culture, employee retention, and a respectful seller transition matter just as much as the numbers. This episode offers a grounded look at acquiring a business beyond franchises or real estate.

Brenda Gage is the owner of a growing chain of Washington cafés and Larson’s Bakery. Married to an Alaska Airlines pilot, she built a flexible career around family life before acquiring eight cafés through SBA financing. In three years, she helped grow annual revenue from approximately $16.7 million to $21 million. Brenda shares practical insights on finding established businesses, securing the right lending partner, leading employees through ownership transitions, and preserving the legacy of family-owned companies.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(3:54) Brenda’s path to business ownership

(6:46) Finding cash-flowing businesses online

(8:35) Growing the café business

(12:57) How BizBuySell works

(17:07) Criteria for legacy businesses

(21:07) Leading without industry expertise

(26:03) Funding an acquisition with SBA loans

(32:32) Finding the right SBA lender

(40:35) How a business purchase closes

(42:46) Leading staff through ownership change

(48:46) Outro

Connect with Brenda Gage:

• Website: https://www.cafesinc.com/
• LinkedIn: https://www.linkedin.com/in/brenda-gage-12796592/

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 https://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 at 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.

Watch this episode on YouTube to see the screen share: https://youtu.be/GjCnHgscdms

Join us on October 8–9, 2026, at the M Resort and Casino in Las Vegas for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit - https://www.passiveincomepilots.com/pip-conference

Tait Duryea and Ryan Gibson sit down with Captain Kit Darby for a detailed look at the airline industry in 2026. Kit breaks down pilot hiring, retirements, fleet delays, fuel costs, widebody opportunities, compensation, and retirement benefits. He also shares practical advice for aspiring pilots preparing for interviews and explains why pilots should build financial resilience outside their airline career. This episode offers a clear, data-driven perspective for pilots planning their next professional and financial move.

Captain Kit Darby is a retired United Airlines pilot, aviation consultant, and president of KitDarby.com. With decades of experience across military, commercial, training, and airline operations, he specializes in pilot hiring trends, career planning, compensation analysis, application reviews, and interview preparation.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference

(4:50) Kit Darby’s aviation career

(15:08) Today’s pilot hiring environment

(19:12) Investing wisely to get hired

(21:29) Why interview preparation matters

(29:24) Airline recovery and fuel outlook

(45:47) Retirements and future pilot demand

(51:11) Fleet shortages and grounded aircraft

(1:01:00) Pilot demand through 2034

(1:26:03) Career value, pay, and retirement

(1:40:16) Outro

Connect with Kit Darby:

• Website: https://kitdarby.com/wp/

Related Episode:

• #34 - Navigating Cash Balance Plans And Retirement For Airline And Corporate Pilots With Tim Pope
• #83 - Market-Based Cash Balance Plans with Jesse Reed

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 https://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 at 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.

Buying an airplane can create opportunities and legal exposure that pilots may not see until something goes wrong. Tait Duryea and Ryan Gibson sit down with aviation attorney and pilot Scott Williams to cover LLC structures, dry leases, co-ownership, and the limits of depreciation for passive real estate activity. Scott also explains key insurance terms, including smooth coverage, open pilot warranties, and waivers of subrogation. A practical conversation for pilots who want to protect their aircraft, finances, and future.

Scott Williams is the founding principal attorney of the General Aviation Law Firm and a pilot with 38 years of flying experience and roughly 4,000 flight hours. He helps Part 91 aircraft owners buy, sell, structure, and operate aircraft while avoiding unintended legal and regulatory risks. Scott is also a Cirrus SR22 owner and former president of the Cirrus Owners and Pilots Association.

Show notes:

(0:00) Intro

(5:19) Why aircraft belong in LLCs

(7:01) Structuring aircraft co-ownership

(12:30) Passive real estate tax limits

(18:21) Dry leases and operational control

(24:08) Named insureds Vs. Named pilots

(29:54) LLC setup and aircraft domicile

(33:47) Using a trust for ownership

(36:34) Insurance as first-line protection

(40:52) Smooth Vs. Sublimit coverage

(43:39) Passenger waivers and liability

(49:34) Outro

Connect with Scott Williams:

• Website: https://www.generalaviationlaw.org/

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 https://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 at 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.

Insurance may not feel exciting until it becomes the thing protecting everything you’ve built. In this episode, Tait Duryea and Ryan Gibson sit down with Rod Zabriskie to unpack the coverage high-income professionals often overlook, from income protection and asset defense to long-term planning and liquidity. For pilots, physicians, business owners, and investors, this conversation offers a timely look at how the right insurance strategy can support wealth building, passive income goals, and family security before life forces the issue.

Rod Zabriskie is the President and Co-Founder of Money Insights Group, a financial strategy firm that helps high-income earners think beyond conventional planning and build wealth with greater control and protection. Known for his education-first approach, Rod helps clients connect insurance, alternative assets, tax strategy, and legacy planning into one cohesive financial system. He brings a practical lens to insurance, helping clients understand the coverages that can protect their income, family, assets, and future opportunities.

Show notes:

(0:00) Backcountry flying and insurance

(3:58) Ten insurance categories

(5:05) Health insurance essentials

(10:25) FSA Vs. HSA

(12:07) Homeowners and renters insurance

(17:18) Protecting personal assets

(24:31) Disability insurance basics

(29:07) Loss of medical coverage

(36:00) Long-term care insurance

(41:02) Term and whole life insurance

(50:27) Outro

Connect with Rod Zabriskie:

• Website: https://www.moneyinsightsgroup.com/
• LinkedIn: https://www.linkedin.com/in/rodzabriskie/

Related Episode:

• #82 - From LLCs and HSAs to Roth IRAs: Mastering Wealth Protection with Mark Kohler
• #67 - Protecting Your Wings: What Pilots Need to Know with Dr. Dan Monlux
• #47 - Innovative Wealth Strategies: From Life Insurance to Alternative Investing with Christian Allen and Rod Zabriskie

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 https://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 at 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 sit down with Trevor Kuresa to unpack the Deferred Sales Trust, a lesser-known strategy for deferring capital gains after selling a business or highly appreciated asset. Trevor explains how the structure works, why it differs from a 1031 exchange or monetized installment sale, and when the costs, timing, and compliance rules make sense. For pilots, real estate investors, and business owners thinking about a future exit, this episode offers a practical look at tax planning before a major transaction.

Trevor Kuresa is a corporate and tax attorney specializing in mergers and acquisitions, fractional general counsel, and advanced tax strategies for business owners and high-income professionals. With experience in tax structuring, legal transactions, and corporate counsel work, Trevor helps clients evaluate strategies for reducing or deferring capital gains and income tax.

Show notes:

(0:00) Chamonix race recap

(2:14) Deferred Sales Trust intro

(4:47) Trevor’s legal background

(6:10) Tax strategy for pilots

(9:37) Deferred sales trust explained

(13:50) Rental property example

(17:26) Best use cases

(21:10) Tax deferral mechanics

(25:15) IRS rules and risks

(36:28) Outro

Connect with Trevor:

• Website: https://hibiscuslegal.com/
• Email: tkuresa@hibiscuslegal.com
• Phone: 801-577-3445
• LinkedIn: https://www.linkedin.com/in/trevor-kuresa-36b59339/

Related Episode:

• #10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis

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 https://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 at 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 your wealth strategy working together or pulling in different directions? Hosts Tait Duryea and Ryan Gibson unpack the 10-30-30-30 strategy for balancing cash, 401(k)s, real estate, tax benefits, and passive investments. They explain why liquidity, control, and tax strategy all matter, and how short-term rentals, syndications, oil and gas, and self-storage can fit into a pilot’s portfolio. Plus, they preview Passive Income Pilots Live in Las Vegas, a new event focused on financial education, estate planning, due diligence, and community.

Show notes:

(0:00) Intro

(2:15) Diversifying pilot investments

(3:33) The 10-30-30-30 strategy

(7:23) Managed money and 401(k)s

(9:21) 2026 401(k) limits

(12:14) Tax-advantaged real estate

(15:06) Short-term rental episodes

(16:50) Passive investments and syndications

(18:13) Oil and gas tax benefits

(26:51) Passive Income Pilots Live

(29:52) Outro

Related Episodes:

• #87 - The Mega Backdoor Roth and How Pilots Can Maximize Retirement Contributions with Timothy Pope
• #14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis
• #37 - Empowering Insights and Strategies On Short-Term Rentals with Alex Jarbo
• #41 - Short-Term Rental Strategies To Maximize Your Passive Income with Dan Templin
• #68 - Cruising to Success: Optimizing Your Short-Term Rentals with Airbnb Insider Daniel Rusteen
• #110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury

Event Mentioned:

Passive Income Pilots Live Conference - Location: Las Vegas, Dates: October 8–9.

For updates on tickets and details, keep an eye out for the official announcement from Passive Income Pilots.

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 https://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 at 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 break down one of the most important but often misunderstood parts of real estate investing: the capital stack. They explain how senior debt, mezzanine debt, preferred equity, and common equity shape risk, returns, and who gets paid first. For pilots and high-income professionals evaluating passive income opportunities, this episode offers a practical framework for understanding leverage, deal structure, DSCR, private credit, and why projected returns do not tell the whole story.

Show notes:

(0:00) Intro

(1:10) Ways investors get paid

(3:08) Capital stack basics

(4:11) Debt drives real estate risk

(7:32) All-cash versus leveraged deals

(10:31) Common equity explained

(18:50) Preferred equity position

(21:10) Checking debt ahead

(27:39) Rescue capital versus healthy deals

(35:36) Operator view on structure

(42:05) DSCR and cash flow cushion

(57:18) Outro

Related Episode:

• #2 - Invest Passively in DST and Opportunity Zones with Brandon Bruckman

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 https://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 at 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 back Chris Prefontaine for a practical conversation on active investing, creative deal structures, and using real estate to build capital for future passive income. Built for pilots and high-income professionals, this episode looks at what it takes to move beyond simply writing checks into deals and start understanding how opportunities are created. Chris brings a seasoned perspective on today’s market, traditional bank limits, and the skills investors need before getting more hands-on. If you have ever wondered whether active real estate could help fuel your long-term wealth strategy, this episode is worth your attention.

Chris Prefontaine is the Chairman and Founder of Smart Real Estate Coach®, a best-selling author, and host of the Smart Real Estate Coach® Podcast. With nearly 35 years in the industry, Chris has helped investors better understand creative real estate strategies through changing market cycles. His work gives listeners a practical look at how experience, education, and smart deal structure can shape a more resilient investing path.

Show notes:

(0:00) Intro

(0:44) Active income to passive wealth

(4:36) Chris’ real estate background

(9:23) The three-payday strategy

(11:51) First steps for active investors

(16:44) Creative financing trends

(19:04) What does creative financing mean

(23:28) Personal guarantee risks

(27:03) Buying short-term rentals

(33:03) Outro

Connect with Chris:

• Website: https://3paydaysbooks.com/pip
• LinkedIn: https://www.linkedin.com/in/chrisprefontaine/

Related Episode:

• #97 - Creative Deal Structuring: Smart Real Estate Strategies with Chris Prefontaine

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 https://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 at 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 happens when the aviation job market shifts faster than pilots are prepared for?

Live from TPNX in Dallas, Tait Duryea sits down with Nik Fialka for a timely look at pilot hiring, airline interviews, and career strategy in a changing aviation market. From major airline hiring trends to the pressure facing Spirit and regional pilots, this episode gives pilots and aviation families a clearer view of what is shifting, what still matters, and why preparation can make or break the next opportunity. If you know an aspiring pilot, military transition pilot, regional pilot, or airline hopeful, this is the conversation to send them before the next interview window opens.

Nik Fialka is a major airline pilot, former U.S. Navy pilot, aviation mentor, and host of Ready 4 Pushback. As part of Spitfire Elite, he helps pilots prepare for high-stakes airline interviews with a focus on confidence, communication, leadership, and cultural fit. With experience across military aviation, airline operations, and pilot coaching, Nik brings a practical, no-fluff perspective to the career decisions that shape a pilot’s future. His work supports aviators from flight training to major airline interviews and beyond.

Show notes:

(0:00) Intro

(1:48) Nick’s aviation background

(3:36) Inside Spitfire Elite

(5:11) Why interview prep matters

(7:08) Authentic interview answers

(8:49) Ready for Pushback podcast

(12:13) State of aviation hiring

(18:04) Major airline hiring numbers

(19:37) Advice for Spirit pilots

(22:59) Standing out beyond flight time

(27:16) Outro

Connect with Nik Fialka:

• Website: https://spitfireelite.com/
• Email: podcast@spitfireelite.com
• LinkedIn: https://www.linkedin.com/in/sir-nik-fialka-86b16515/

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 https://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 at 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 back Mark Kohler to unpack one of the most misunderstood topics in self-directed IRA investing: UBIT and UDFI. Mark explains how these taxes show up in real estate syndications, why leverage can trigger tax inside an IRA, when C corp blockers may help, and what pilots should watch for on K-1s and 990-T filings. This episode gives high-income professionals a clearer way to evaluate SDIRA deals without letting tax fear cloud the bigger investment picture.

Mark Kohler is a CPA, attorney, tax strategist, and longtime advocate for small business owners and investors. With decades of experience in tax law, entity structuring, retirement planning, and asset protection, Mark is known for making complex tax strategies easier to understand and apply. He brings practical clarity to the rules that affect pilots and high-income professionals using retirement dollars to invest beyond Wall Street.

Show notes:

(0:00) Intro

(0:48) UBIT and self-directed IRAs

(4:32) Understanding UBIT, UDFI, and 990-Ts

(5:36) Why UBIT exists

(10:05) How C Corp blockers work

(14:37) Reading K-1 warning signs

(18:57) How leverage creates UDFI

(23:09) Comparing SDIRA and cash investors

(31:18) Trust tax rates explained

(37:41) When IRAs need an EIN

(41:37) Real numbers on UDFI taxes

(55:30) Outro

Connect with Mark:

• Website: https://markjkohler.com/
• LinkedIn: https://www.linkedin.com/in/markjkohler/

Related Episodes:

• #110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury
• #36 - Decoding the Untapped Potential and Complex World of Self-Directed IRAs with Derreck Long
• #82 - From LLCs and HSAs to Roth IRAs: Mastering Wealth Protection with Mark Kohler

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/

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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.