Episodes
#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 bonu...
#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 ...
#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 impa...
#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 fam...
#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 cons...
#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 al...
#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. The...
#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 ...
#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 ...