Podcast · Business

Passive Income Pilots

by Tait Duryea and Ryan Gibson · English · Business

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,

New episodes: Weekly
Typical length: 46 min
Latest: 7 Oct 2026
Language: English

Latest episode

7 Oct 2026 · 40 min

#170 - The Get Rich Slow Strategy for Passive Investors with Jeremy Roll

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…

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Earlier episodes 28 most recent

E169 · 30 Sep 2026 · 41 min
#169 - When Passive Real Estate Isn’t Really Passive
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…
E168 · 25 Sep 2026 · 45 min
#168 - How Smart Investors Vet Real Estate Deals Together with Larry Lemer and Mark Goldstein
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…
E167 · 15 Sep 2026 · 58 min
#167 - From Wall Street to Infinite Banking with Chris Naugle
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…
8 Sep 2026 · 40 min
#166 - Fly-Inn Rentals for Pilots and Investors with Carollyne Carmichel & Kenya Hodson
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…
E165 · 18 Aug 2026 · 1 hr
#165 - Flight Decks, Financial Freedom, and the Pilot Community with Dylan and Max of 21.Five
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…
E164 · 5 Aug 2026 · 49 min
#164 - LLCs, Trusts, and Asset Protection for Pilots with Adam Kintigh
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…
E163 · 28 Jul 2026 · 50 min
#163 - From Pilot Spouse to Café Owner with Brenda Gage
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…
E162 · 22 Jul 2026 · 1 hr 41 min
#162 - The 2026 Airline Pilot Career Outlook with Kit Darby
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…
E161 · 17 Jul 2026 · 50 min
#161 - Aircraft Ownership, Insurance, and Liability with Scott Williams
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…
E160 · 7 Jul 2026 · 51 min
#160 - Insurance Strategies for High-Income Professionals with Rod Zabriskie
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…
E159 · 30 Jun 2026 · 37 min
#159 - How Deferred Sales Trusts Work with Trevor Kuresa
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…
E158 · 24 Jun 2026 · 30 min
#158 - Why the 10-30-30-30 Strategy Could Change How Pilots Invest
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…
E157 · 16 Jun 2026 · 57 min
#157 - Who Gets Paid First? How Real Estate Deals Are Actually Structured
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…
E156 · 20 May 2026 · 33 min
#156 - From Active Deals to Passive Income with Chris Prefontaine
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…
E155 · 13 May 2026 · 27 min
#155 - The New Reality of Aviation Hiring with Nik Fialka
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,…
E154 · 28 Apr 2026 · 56 min
#154 - The Pilot’s Guide to SDIRA Tax Traps with Mark Kohler
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…
E153 · 14 Apr 2026 · 49 min
#153 - Tax Moves Every Pilot Should Know with Nathan Sosa
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 around K-1s and explain when it makes sense to bring in a CPA. Nathan Sosa is a tax strategist…
E152 · 7 Apr 2026 · 48 min
#152 - Free Estate Planning and a Hidden Tax Strategy with Jenny Spradling
Tait Duryea and Ryan Gibson sit down with Jenny Spradling, co-founder of FreeWill, to explore how estate planning can be simpler, faster, and even free. Jenny explains why millions of Americans still lack basic estate documents and how that creates major complications for families. The conversation breaks down probate, wills vs. trusts, and why both are often needed. They also uncover powerful strategies around charitable giving, including how donating appreciated assets like stock or crypto can dramatically increase tax efficiency while maximizing impact. This episode offers practical…
E151 · 2 Apr 2026 · 49 min
#151 - Debt, AI, and the Next Market Cycle with Guy Adami
What happens when record debt, rising interest rates, and AI disruption collide in the global economy? Hosts Tait Duryea and Ryan Gibson welcome back market veteran Guy Adami to unpack the forces shaping today’s financial markets. From bond yields and inflation to the Buffett Indicator and AI’s impact on jobs, Guy offers a behind-the-scenes look at what professional investors are watching right now. The conversation explores why the market feels strong even while many stocks are down sharply, how passive investing has reshaped valuations, and why global debt and currency devaluation may…
E150 · 27 Mar 2026 · 41 min
#150 - From Listener to Investor with John Wahrmund
Hosts Tait Duryea and Ryan Gibson sit down with First Officer at Southwest Airlines pilot John Wahrmund to unpack how one listener turned podcast advice into real results. John shares how episode 10 pushed him to buy a short-term rental in Galveston, unlock major tax savings, and rethink how his family builds wealth. This episode highlights intentional investing, knowing your market, using the right team, and why tax strategy can be a powerful tool for high-income professionals who want more freedom, options, and time. John Wahrmund is a Southwest Airlines pilot and retired Air Force officer…
E149 · 11 Mar 2026 · 34 min
#149 - Side Hustles Every Pilot Should Consider
Hosts Tait Duryea and Ryan Gibson explore one of the most common questions among airline pilots: Should you start a side hustle? Drawing from Ryan’s early experience building income streams during layovers, the hosts share practical ideas pilots can pursue both inside and outside aviation. From consulting and drone photography to aircraft brokerage and real estate investing, they explain how extra income can become the fuel for long-term wealth building. They also discuss tax strategy, airline contract knowledge, and why passion matters when choosing a side hustle. If you’ve ever wondered…
E148 · 5 Mar 2026 · 46 min
#148 - Traditional Vs. Roth IRAs: What Pilots Need to Know
Tait Duryea and Ryan Gibson break down one of the most important retirement decisions pilots face: Traditional vs. Roth IRAs. They explain how taxes impact withdrawals, why required minimum distributions matter, and how poor planning could leave your kids with a massive tax bill. The conversation also explores advanced strategies like Roth conversions, self-directed IRAs, and “Roth chunking” during low-income years. If you want to build wealth through real estate while protecting your retirement from unnecessary taxes, this episode offers practical frameworks to help pilots think long-term…
E147 · 17 Feb 2026 · 36 min
#147 - From Cap Rates to Cash Flow: Strategic Moves for 2026
Tait Duryea and Ryan Gibson sit down for a special hosts-only episode to break down where they see the biggest opportunities for 2026. From reshoring trends fueling industrial growth to the demographic wave driving senior living demand, they unpack the macro forces shaping real estate right now. They also explain why falling interest rates, reduced new construction, and renewed capital flows are creating a unique window for investors. Plus, they dive into debt funds, tax considerations, and why consistent cash flow can be a game-changer for high-income professionals looking to upgrade their…
E146 · 9 Feb 2026 · 54 min
#146 - Aircraft Tax Write-Offs Explained by a Former IRS Auditor, Victoria Boon
Hosts Tait Duryea and Ryan Gibson welcome former IRS auditor Victoria Boon to cut through the noise around aircraft tax deductions. Learn how bonus depreciation really works, why aircraft are treated differently from real estate, and what the IRS actually looks for during an audit. From Delta bonus taxation to leasebacks, qualified business use, and depreciation recapture, this episode is essential listening for pilots considering aircraft ownership as a tax strategy. Victoria Boon spent 22 years at the IRS as a subject matter expert, including leading national audits focused on aircraft…
E145 · 4 Feb 2026 · 39 min
#145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia
What if the IRS already allows you to write off far more of your real estate, but no one ever showed you how? In today’s episode, Tait Duryae sits down with Gian Pazzia to break down cost segregation in plain English and explain why it remains one of the most powerful tax strategies for real estate investors. Building on last week’s depreciation primer with Hall CPA, this episode covers how cost segregation works, when it makes sense, audit risk myths, and how pilots can apply it to everything from single-family rentals to commercial deals. You’ll also learn about a new, low-cost software…
E144 · 27 Jan 2026 · 1 hr
#144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall
Tait Duryea is joined by Brandon Hall to break down one of the most misunderstood tools in real estate investing: depreciation. From straight-line depreciation to cost segregation and 100 percent bonus depreciation, this episode explains how so-called “phantom losses” can legally reduce or even eliminate taxable income for pilots and other high earners. They also cover depreciation recapture, common investor mistakes, and why experienced investors think in decades, not tax years. Brandon Hall is the founder of Hall CPA, widely known as The Real Estate CPA. After working at Ernst & Young and…
E143 · 20 Jan 2026 · 40 min
#143 - How High Cash Value Life Insurance Works for Pilots with Rod Zabriskie
Could life insurance be a better cash-flow tool than a savings account? Tait Duryea and Ryan Gibson sit down with Rod Zabriskie from Money Insights Group to break down how high cash value whole life insurance can be used as a powerful cash-flow tool for pilots and investors. They cut through the confusion around “infinite banking” and explain how properly structured policies can improve liquidity, reduce friction when investing, and add meaningful long-term returns. This episode walks through real pilot use cases, common mistakes, and why this strategy has become a quiet cornerstone for…
E142 · 13 Jan 2026 · 44 min
#142 - Tax Planning for W-2 Pilots Without Complex Businesses with Gary Heldt
Are you paying for a high-powered CPA when your tax situation doesn’t actually require one? In this episode, Tait Duryea and Ryan Gibson sit down with CPA Gary Heldt to clarify what smart tax planning really looks like for high-income pilots with relatively simple financial lives. They break down how W-2 earners can optimize taxes without complex businesses, aggressive strategies, or unnecessary fees. Gary explains how often-overlooked fundamentals like benefits planning, estimated taxes, and coordinated advice can quietly compound into meaningful long-term gains. If you want clarity,…

About Passive Income Pilots

Passive Income Pilots is a English business podcast from Tait Duryea and Ryan Gibson. Melo plays each episode straight from the publisher's own feed — no ads added, no account needed — and remembers where you stopped, in this browser only.

Publisher: Tait Duryea and Ryan Gibson
Language: English
Category: Business
New episodes: Weekly
Typical length: 46 min
Latest episode: 7 Oct 2026
Feed: RSS — paste into any podcast app
Apple Podcasts: podcasts.apple.com/podcast/id1675913577

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