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...

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 seg...

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 toget...

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...

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 ca...

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 discu...

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 pool...

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...

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-adja...

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...

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 mo...

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 gro...

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 th...

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 warra...

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...

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...

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...

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 unde...

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...

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 vi...

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 clea...

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...

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 str...

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 no...

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 rig...