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PODCAST

Passive Income Pilots

Tait Duryea and Ryan Gibson

Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success. Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life.Whether you"re a

business investing

All Episodes

39:37

#170 - The Get Rich Slow Strategy for Passive...

Passive Income Pilots ·

2026/10/07

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

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39:38

#170 - The Get Rich Slow Strategy for Passive...

Passive Income Pilots ·

2026/10/07

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 alternative investments helped him leave the corporate world, why he believes investors should pay closer attention to market cycles, and how diversification can protect long-term retirement income. They also cover compounding passive cash flow, syndications, tax advantages, K-1 management, and why Jeremy is currently keeping substantial

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41:04

#169 - When Passive Real Estate Isn’t Really Passive

Passive Income Pilots ·

2026/09/30

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

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44:46

#168 - How Smart Investors Vet Real Estate Deals...

Passive Income Pilots ·

2026/09/25

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

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58:02

#167 - From Wall Street to Infinite Banking with...

Passive Income Pilots ·

2026/09/15

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

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39:36

#166 - Fly-Inn Rentals for Pilots and Investors with...

Passive Income Pilots ·

2026/09/08

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

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1:00:17

#165 - Flight Decks, Financial Freedom, and the Pilot...

Passive Income Pilots ·

2026/08/18

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,

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48:46

#164 - LLCs, Trusts, and Asset Protection for Pilots...

Passive Income Pilots ·

2026/08/05

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

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50:20

#163 - From Pilot Spouse to Café Owner with Brenda Gage

Passive Income Pilots ·

2026/07/28

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

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1:41:55

#162 - The 2026 Airline Pilot Career Outlook with Kit...

Passive Income Pilots ·

2026/07/22

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

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49:51

#161 - Aircraft Ownership, Insurance, and Liability...

Passive Income Pilots ·

2026/07/17

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

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50:35

#160 - Insurance Strategies for High-Income...

Passive Income Pilots ·

2026/07/07

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

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36:35

#159 - How Deferred Sales Trusts Work with Trevor Kuresa

Passive Income Pilots ·

2026/06/30

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

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30:06

#158 - Why the 10-30-30-30 Strategy Could Change How...

Passive Income Pilots ·

2026/06/24

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,

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57:27

#157 - Who Gets Paid First? How Real Estate Deals Are...

Passive Income Pilots ·

2026/06/16

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

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43:37

#157 - Oil, Gas, AI, and the Next Energy Boom with...

Passive Income Pilots ·

2026/06/09

Hosts Tait Duryea and Ryan Gibson sit down with Elena Melchert to examine how energy demand, fossil fuels, mineral rights, royalties, and infrastructure shape real passive income opportunities. Elena brings a grounded, technical perspective to a sector many investors hear about but rarely understand deeply. For pilots and high-income professionals looking at alternative investments, tax strategy, and long-term cash flow, this conversation offers a clearer way to think about energy as both a global

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33:23

#156 - From Active Deals to Passive Income with Chris...

Passive Income Pilots ·

2026/05/20

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

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27:23

#155 - The New Reality of Aviation Hiring with Nik...

Passive Income Pilots ·

2026/05/13

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

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55:40

#154 - The Pilot’s Guide to SDIRA Tax Traps with Mark...

Passive Income Pilots ·

2026/04/28

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

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49:23

#153 - Tax Moves Every Pilot Should Know with Nathan...

Passive Income Pilots ·

2026/04/14

How much money are you leaving on the table by waiting until tax season to start planning?Hosts Tait Duryea and Ryan Gibson talk with Nathan Sosa from Hall CPA to break down the latest tax updates that matter most to pilots and high-income professionals. Get ready to hear practical insights on bonus depreciation, the short-term rental strategy, oil and gas tax benefits, passive real estate losses, and why filing an extension may be smarter than rushing to file. They also clear up common confusion

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173 results

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