Episodes
#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 ...
#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 elim...
#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 con...
#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 ho...
#141 - How Pilots Can Use Business Structures to Reduce Taxes with Toby Mathis
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 C-corps, how losses and profits flow to your personal return, and why entity ch...
#140 - From Goals to Execution: A Year-End Playbook
Tait Duryea and Ryan Gibson close out 2025 by pulling back the curtain on how high performers actually plan, execute, and stay intentional across money, business, and family life. From Spartan’s acquisition pace and Turbine’s investor roadmap to family board meetings, goal frameworks, and habit form...
#139 - How to Run Single-Family Rentals Like a REIT with Matthew Whitaker
What if managing rentals like an institution is the key to higher returns and less stress? Hosts Tait Duryea and Ryan Gibson talk with Matthew Whitaker, founder of Evernest, about scaling property management with systems, data, and AI. From HELOC-driven growth to managing 20,000 homes nationwide, th...
#138 - How to Vet Deals, Operators, and Advisors the Right Way with Mat Sorensen
Tait Duryea and Ryan Gibson sit down with Mat Sorensen of Directed IRA to tackle one of the most common investor questions: Who do you actually trust when investing in alternative assets? The conversation breaks down how to vet operators, assess risk, understand leverage, and use self-directed retir...
#137 - Revocable Vs. Irrevocable Trusts: What Pilots Must Know with Adam Kintigh
Clarity and control for the wealth you’re building. Tait Duryea and Ryan Gibson sit down with asset protection expert Adam Kintigh for his third appearance to break down one of the most misunderstood pieces of a pilot’s financial plan: the revocable living trust. Discover how to structure your trust...