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Passive Income Pilots

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Passive Income Pilots

Tait Duryea and Ryan Gibson

#159 - How Deferred Sales Trusts Work with Trevor Kuresa

June 30, 2026 10:00am 36 min

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 th...

#158 - Why the 10-30-30-30 Strategy Could Change How Pilots Invest

June 24, 2026 10:00am 30 min

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 investmen...

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

June 16, 2026 10:00am 57 min

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 equit...

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

June 09, 2026 10:00am 43 min

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, t...

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

May 20, 2026 10:00am 33 min

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 an...

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

May 13, 2026 10:00am 27 min

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 strat...

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

April 28, 2026 10:00am 55 min

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 le...

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

April 14, 2026 10:00am 49 min

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 pil...

#152 - Free Estate Planning and a Hidden Tax Strategy with Jenny Spradling

April 07, 2026 12:51pm 48 min

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 do...

#151 - Debt, AI, and the Next Market Cycle with Guy Adami

April 02, 2026 10:00am 48 min

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...

#150 - From Listener to Investor with John Wahrmund

March 27, 2026 11:52am 40 min

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 s...

#149 - Side Hustles Every Pilot Should Consider

March 11, 2026 6:16am 34 min

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 sha...

#148 - Traditional Vs. Roth IRAs: What Pilots Need to Know

March 04, 2026 10:05pm 45 min

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 ...

#147 - From Cap Rates to Cash Flow: Strategic Moves for 2026

February 17, 2026 9:32am 35 min

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 senio...

#146 - Aircraft Tax Write-Offs Explained by a Former IRS Auditor, Victoria Boon

February 09, 2026 10:00am 54 min

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 rea...

#145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia

February 04, 2026 9:54am 39 min

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 ...

#144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall

January 27, 2026 10:00am 1:00

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...

#143 - How High Cash Value Life Insurance Works for Pilots with Rod Zabriskie

January 20, 2026 10:00am 39 min

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 ...

#142 - Tax Planning for W-2 Pilots Without Complex Businesses with Gary Heldt

January 13, 2026 10:00am 44 min

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 fo...

#141 - How Pilots Can Use Business Structures to Reduce Taxes with Toby Mathis

January 06, 2026 10:00am 56 min

Tait Duryea and Ryan Gibson sit down with Toby Mathis to unpack one of the most misunderstood topics for high-income pilots: business structure and taxes. They explain when to use sole proprietorships, LLCs, S-corps, and...

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