Passive Income Pilots
By Tait Duryea and Ryan Gibson
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Image by Tait Duryea and Ryan Gibson
Category: Investing
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Subscribers: 6
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Episodes: 158
Description
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, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life.
Whether you're a seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.
| Episode | Date |
|---|---|
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#159 - How Deferred Sales Trusts Work with Trevor Kuresa
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Jun 30, 2026 |
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#158 - Why the 10-30-30-30 Strategy Could Change How Pilots Invest
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Jun 24, 2026 |
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#157 - Who Gets Paid First? How Real Estate Deals Are Actually Structured
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Jun 16, 2026 |
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#156 - From Active Deals to Passive Income with Chris Prefontaine
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May 20, 2026 |
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#155 - The New Reality of Aviation Hiring with Nik Fialka
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May 13, 2026 |
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#154 - The Pilot’s Guide to SDIRA Tax Traps with Mark Kohler
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Apr 28, 2026 |
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#153 - Tax Moves Every Pilot Should Know with Nathan Sosa
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Apr 14, 2026 |
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#152 - Free Estate Planning and a Hidden Tax Strategy with Jenny Spradling
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Apr 07, 2026 |
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#151 - Debt, AI, and the Next Market Cycle with Guy Adami
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Apr 02, 2026 |
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#150 - From Listener to Investor with John Wahrmund
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Mar 27, 2026 |
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#149 - Side Hustles Every Pilot Should Consider
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Mar 11, 2026 |
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#148 - Traditional Vs. Roth IRAs: What Pilots Need to Know
|
Mar 05, 2026 |
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#147 - From Cap Rates to Cash Flow: Strategic Moves for 2026
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Feb 17, 2026 |
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#146 - Aircraft Tax Write-Offs Explained by a Former IRS Auditor, Victoria Boon
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Feb 09, 2026 |
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#145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia
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Feb 04, 2026 |
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#144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall
|
Jan 27, 2026 |
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#143 - How High Cash Value Life Insurance Works for Pilots with Rod Zabriskie
|
Jan 20, 2026 |
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#142 - Tax Planning for W-2 Pilots Without Complex Businesses with Gary Heldt
|
Jan 13, 2026 |
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#141 - How Pilots Can Use Business Structures to Reduce Taxes with Toby Mathis
|
Jan 06, 2026 |
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#140 - From Goals to Execution: A Year-End Playbook
|
Dec 30, 2025 |
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#139 - How to Run Single-Family Rentals Like a REIT with Matthew Whitaker
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Dec 24, 2025 |
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#138 - How to Vet Deals, Operators, and Advisors the Right Way with Mat Sorensen
|
Dec 17, 2025 |
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#137 - Revocable Vs. Irrevocable Trusts: What Pilots Must Know with Adam Kintigh
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Dec 09, 2025 |
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#136 - What HGTV Won’t Tell You About Flipping Houses with Leka Devatha
|
Dec 02, 2025 |
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#135 - The Truth About Oil and Gas Investing with Tim Pawul
|
Nov 26, 2025 |
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#134 - Fatigue, Flight Deck Safety, and the Science of Sleep with Dr. Adam Shapiro
|
Nov 18, 2025 |
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#133 - Year-End Tax Moves Pilots Can’t Miss with Toby Mathis
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Nov 12, 2025 |
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#132 - How to Buy an Airport with Robert DeLaurentis
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Nov 05, 2025 |
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#131 - Reading the Economy: Insights from the Bowtie Economist, Dr. Elliot Eisenberg
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Oct 29, 2025 |
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#130 - From Wall Street to Real Wealth: Lessons from Ted Greene
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Oct 24, 2025 |
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#129 - Ego, Taxes, and the Paycheck Trap: Pilot Wealth Myths Exposed
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Oct 10, 2025 |
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#128 - Inside the Fine Print: PPMs, Trust, and Investor Protection with Seth Bradley
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Oct 01, 2025 |
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#127 - LLCs, Trusts, and K-1s: Smarter Asset Protection with Adam Kintigh
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Sep 25, 2025 |
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#126 - Early Real Estate Mistakes and Lessons Learned
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Sep 18, 2025 |
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#125 - Oil & Gas Investing for High-Income Pilots with Mark Fleming
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Sep 02, 2025 |
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#124 - $44 Trillion and the Future of Retirement Investing with Mat Sorensen
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Aug 26, 2025 |
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#123 - Market Cycles, Debt, and Real Estate Opportunities with Hunter Thompson
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Aug 19, 2025 |
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#122 - How Pilots Use Whole Life Insurance to Fund Investments with Rod Zabriskie
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Aug 12, 2025 |
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#121 - Short-Term Rentals, Long-Term Wealth with Pilot Couple Brad Hilton and Aubrey Carlson
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Aug 05, 2025 |
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#120 - How to Evaluate Markets, Properties, and Risks in Real Estate with Derrick Harris
|
Jul 29, 2025 |
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#119 - LLCs, Trusts, and Bulletproof Asset Protection with Adam Kintigh
|
Jul 17, 2025 |
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#118 - The Big Beautiful Tax Bill with Nathan Sosa
|
Jul 11, 2025 |
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#117 - How to Evaluate and Join Real Estate Syndications
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Jul 02, 2025 |
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#116 - Medical Checkride: Medical Myths, Truths, and Tips with Dan Monlux
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Jun 24, 2025 |
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#115 - Inside Self-Storage: A Hidden Powerhouse for Investors
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Jun 17, 2025 |
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#114 - Trusts, Taxes & Transfers: What Every Investor Should Know with Amanda Wynalda
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Jun 10, 2025 |
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#113 - The Fed, The Treasury, and Your Portfolio with Dr. Peter Linneman
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Jun 03, 2025 |
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#112 - The Tax Strategies Every Pilot Should Know in 2025 with Thomas Castelli
|
May 27, 2025 |
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#111 - Five Investing Strategies for High-Earning Pilots
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May 22, 2025 |
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#110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury
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May 13, 2025 |
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#109 - The Flight Plan for Syndications: Risk, Returns, and Real Wealth
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May 06, 2025 |
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#108 - Case Study: Real Estate Professional Status That Held Up in Court with Brandon Hall
|
Apr 30, 2025 |
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#107 - Take Control of Your Capital: Infinite Banking Strategy With Brent Kesler
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Apr 22, 2025 |
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#106 – Time Freedom and Cash Strategies with Brian Herriot
|
Apr 15, 2025 |
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#105 - Buying and Building a Profitable Aviation Business with James Spearman
|
Apr 08, 2025 |
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#104 - Active vs. Passive: Storage Strategies from the Flight Deck with Michael Meylor
|
Apr 01, 2025 |
|
#103 - Multifamily Mastery: Building Cashflow and Legacy with Gino Barbaro
|
Mar 25, 2025 |
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#102 - Creating True Passive Income Through Note Investing with Tom Force
|
Mar 18, 2025 |
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#101 - Airbnb for Aircraft: Hangar Investing & Aviation Real Estate with Trenton Ray
|
Mar 11, 2025 |
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#100 - Getting to Know Tait & Ryan
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Mar 04, 2025 |
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#99 - Turnkey Real Estate: Passive or Problematic? A Deep Dive with Zach Lemaster
|
Feb 25, 2025 |
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#98 - The Right Coverage: Property Insurance Strategies with Valerie Cusano
|
Feb 18, 2025 |
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#97 - Creative Deal Structuring: Smart Real Estate Strategies with Chris Prefontaine
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Feb 11, 2025 |
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#96 - Airplane Write-Offs, IRS Audits, and Smart Tax Planning with Ryan DeMoor
|
Feb 04, 2025 |
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#95 - Franchise Investing 101: Insights and Opportunities with Cliff Nonnenmacher
|
Jan 28, 2025 |
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#94 - Fail Fast, Succeed Faster: Wealth-Building and Investment Strategies with Christian Schiller
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Jan 21, 2025 |
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#93 - Stock Market Insights and Tax Strategies for High-Income Earners with Brian Feroldi
|
Jan 14, 2025 |
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#92 - Opportunity Zones for Passive Income: Unlock Tax Savings and Growth with Nathan Sosa
|
Jan 07, 2025 |
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#91 - Interest Rates, Submarkets, and CRE's Future with Spencer Levy
|
Dec 31, 2024 |
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#90 - Balancing Flying, Business Ownership, and Financial Growth with Carl Valeri
|
Dec 24, 2024 |
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#89 - Air Traffic, Pilot Pay, and Airline Economics with A4A's Chief Economist John Heimlich
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Dec 17, 2024 |
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#88 - Flight Schools and Passive Income: Insights from Gordon Alvord
|
Dec 10, 2024 |
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#87 - The Mega Backdoor Roth and How Pilots Can Maximize Retirement Contributions with Timothy Pope
|
Dec 03, 2024 |
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#86 - Mapping the Skies: The Tech Behind Real-Time Flight Tracking with Ian Petchenik
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Nov 26, 2024 |
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#85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver
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Nov 19, 2024 |
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#84 - Tax-Free Growth & Infinite Loans: Whole Life Insurance Strategies for High-Earners
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Nov 12, 2024 |
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#83 - Market-Based Cash Balance Plans with Jesse Reed
|
Nov 06, 2024 |
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#82 - From LLCs and HSAs to Roth IRAs: Mastering Wealth Protection with Mark Kohler
|
Oct 29, 2024 |
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#81 - The Power of AI and Passive Income Strategies for Pilots with Jim Higgins
|
Oct 22, 2024 |
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#80 - Storm-Proofing Your Real Estate Investment with Jules Sneddon and Trevor Moss
|
Oct 16, 2024 |
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#79 - From Cockpit to Space: On Grit, Leadership, and Space Travel with Col. Eileen Collins
|
Oct 08, 2024 |
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#78 - Lifestyle Investments: Leveraging Seaside Property for Passive Income with Casey Roloff
|
Oct 01, 2024 |
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#77 - The Pilot's Flight Plan to Passive Income: Aircraft Leasing and Tax Benefits with Luke Lysen
|
Sep 17, 2024 |
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#76 - MOST POPULAR EPISODE: Reduce Taxes & Maximize Returns Using PROVEN Strategies with Toby Mathis
|
Sep 10, 2024 |
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#75 - Unlocking Real Estate Professional Status (REPS) with Brandon Hall
|
Sep 04, 2024 |
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#74 - The Inside Track: Mastering Real Estate Syndications for Long-Term Success
|
Aug 27, 2024 |
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#73 - From Market Cycles to REITs: What Every Pilot Investor Should Know with Glenn R. Mueller, PhD
|
Aug 20, 2024 |
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#72 - Cleared for Takeoff: Updated FAA Mental Health Regulations with Joe LoRusso
|
Aug 13, 2024 |
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#71 - 5 Creative Ways To Find Investment Cash
|
Aug 06, 2024 |
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#70 - Leveraging Life Insurance for Passive Income with Rod Zabriskie and Blake Brogan
|
Jul 30, 2024 |
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#69 - Sky-High Returns: Discover Off-Market Real Estate Gems with Sean O'Toole
|
Jul 23, 2024 |
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#68 - Cruising to Success: Optimizing Your Short-Term Rentals with Airbnb Insider Daniel Rusteen
|
Jul 16, 2024 |
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#67 - Protecting Your Wings: What Pilots Need to Know with Dr. Dan Monlux
|
Jul 09, 2024 |
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#65 - Cashing In on Convenience: The Secret Economy of Vending Machines
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Jul 08, 2024 |
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#66 - Frequent Flyer Health Hacks from Special Forces Coach Alex Racey
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Jul 02, 2024 |
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#64 - Shark Tank Pilot Episode: Nick Friedman's College Hunks Hauling Junk
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Jun 18, 2024 |
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#63 - Keith Rosenkranz: The Delta Captain Who Chartered His Own Retirement Flight
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Jun 11, 2024 |
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#62 - Pilot Math: Wealth Strategies for Aviators with Jason Depew
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Jun 05, 2024 |
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#61 - NFL Defensive Legend Cliff Avril: Crushing Real Estate After Crushing QBs
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May 28, 2024 |
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#60 - Cleared for Takeover: Collin Hathaway on the Boomer Business Buyout Boom
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May 21, 2024 |
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#59 - The Silver Tsunami: Dwayne Clark on the Future of Senior Living Investments
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May 14, 2024 |
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#58 - Tax Tactics: The TOP 5 Ways You Can Save with Toby Mathis
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May 07, 2024 |
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#57 - From Handshakes to High Stakes: The Best Ever Blueprint for Building Wealth Through Connections with Joe Fairless
|
May 01, 2024 |
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#56 - Black Box Wealth: Earning Passive Income On The Blockchain with PIVX DAO Advisor Hans Koning
|
Apr 23, 2024 |
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#55 - First Class Intro to Angel Investing with OfferUp Founder Nick Huzar
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Apr 16, 2024 |
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#54 - The Inner Game of Real Estate with Leka Devatha
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Apr 09, 2024 |
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#53 - Eyes On The Horizon: Real Estate Insights from Kathy Fettke
|
Apr 02, 2024 |
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#52 - Economic Tailwinds: How 1031 Exchanges Propel Real Estate Portfolios With Kyle Williams
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Mar 28, 2024 |
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#51 - Navigating Turbulence: Mental Health & Legal Safeguards for Pilots with Joe LoRusso
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Mar 13, 2024 |
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#50 - Real Estate Investing: Building Resilient Wealth and Financial Independence with David Phelps
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Feb 14, 2024 |
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#49 - Reflections & Revelations: A Look Back at our Favorite Episodes to Date
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Jan 31, 2024 |
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#48 - Mastering Goal Setting and Strategic Planning in 2024
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Jan 20, 2024 |
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#47 - Innovative Wealth Strategies: From Life Insurance to Alternative Investing with Christian Allen and Rod Zabriskie
|
Jan 06, 2024 |
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#46 - Investing in Oil, Gas, and Mineral Rights with Tax Advantages in Mind with Derreck Long
|
Dec 20, 2023 |
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#45 - Path to Financial Freedom: Real Estate, Mentorship, and Personal Growth with Alan Underwood
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Dec 13, 2023 |
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#44 - Mastering Year-End Tax Strategies: From IRA Conversions to Short-Term Rental Loopholes
|
Dec 06, 2023 |
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#43 - Exploring the Boom of Self-Storage and Its Investment Potential
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Nov 10, 2023 |
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#42 - Real Estate Investing: Tax-Saving Strategies and Best Practices with Billy Withers
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Oct 24, 2023 |
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#41 - Short-Term Rental Strategies To Maximize Your Passive Income with Dan Templin
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Oct 17, 2023 |
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#40 - A Deep Dive Into Flight School Financing with Anthony Geraci
|
Oct 10, 2023 |
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#39 - Decoding College Costs and Complex College Savings Plans with Brad Baldridge
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Oct 03, 2023 |
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#38 - Exploring Real Estate Investing, Work-life Balance, and Personal Growth with Rich Fettke
|
Sep 26, 2023 |
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#37 - Empowering Insights and Strategies On Short-Term Rentals with Alex Jarbo
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Sep 19, 2023 |
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#36 - Decoding the Untapped Potential and Complex World of Self-Directed IRAs with Derreck Long
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Sep 12, 2023 |
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#34 - Navigating Cash Balance Plans and Retirement for Airline and Corporate Pilots with Timothy Pope
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Aug 29, 2023 |
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#33 - Mortgages, Refinancing, and Home Buying with Expert David Temko
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Aug 22, 2023 |
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#32 - Tax Savvy Investing: The Power of Cost Segregation with Yonah Weiss
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Aug 15, 2023 |
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#31 - Discover Profitable Oil and Gas Investments and Expert Strategies with Ben Fraser
|
Aug 08, 2023 |
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#30 - Investing in Commercial Real Estate and Analyzing Economic Indicators with John Chang
|
Aug 01, 2023 |
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#28 - Real Estate Investing For Wealth And Purpose With The Right Mindset With Alex Felice
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Jun 27, 2023 |
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#27 - Commercial Construction Management: A Deep Dive Into Ground-Up Development with Aaron Saunders
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Jun 20, 2023 |
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#26 - Decoding Yield on Cost: Interpreting Numbers and Assessing Investment Risks and Returns
|
Jun 15, 2023 |
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#25 - From US Navy Pilot to Real Estate Expert: Unpacking 1031 Exchanges and DSTs with Trevor Flor
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Jun 13, 2023 |
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#24 - Passive Investing: Syndication 101 – Key Players, Documents, Due Diligence, and Liquidity
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Jun 06, 2023 |
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#23 - Counting the Cost: The Risks and Rewards of 401(k) Loans for Pilots
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Jun 01, 2023 |
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#22 - Economic Trends, Multifamily, Angel Investing, and Investment Strategies with J Scott
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May 31, 2023 |
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#21 - Flight Plan for Finances: Financial Planning and Strategies for Pilots with Jesse Reed
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May 25, 2023 |
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#20 - The Economic Landscape, Recession, Investing, and the Impact of AI Technology with Neal Bawa
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May 23, 2023 |
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#19 - Invaluable Insights: ASAP Reports on Passive and Active Investment Deals
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May 18, 2023 |
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#18 - Credit Unions vs. Banks: Choosing the Right Financing Partner with Charles Krawitz
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May 16, 2023 |
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#17 - Mastering Real Estate Investing: Key Systems and Processes with Tarl Yarber
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May 11, 2023 |
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#16 - Investing with Confidence: Asset Protection Strategies with Clint Coons
|
May 09, 2023 |
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#15 - Why Commercial Real Estate Trumps Residential
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May 04, 2023 |
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#14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis
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May 02, 2023 |
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#13 - Clean Profits: Building a Laundromat Empire with Sam Wilson
|
Apr 27, 2023 |
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#11 - How To Succeed In This High Interest Environment
|
Apr 20, 2023 |
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#10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis
|
Apr 18, 2023 |
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#9 - Demystifying IRAs: Transfers Vs. Rollovers with Carrie Cook
|
Apr 13, 2023 |
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#8 - Blockchain and Web3: Transforming Finance With Trustless and Decentralized Ecosystems with Ben Jorgensen
|
Apr 11, 2023 |
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#7 - The Pilot Network and Navigating the Aviation Industry with Adam Uhan
|
Apr 06, 2023 |
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#6 - Transitioning from Active to Passive Investing and Diversifying Investments with Jeremy Roll
|
Apr 04, 2023 |
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#5 - Live at the BEC 2023 (Where It All Started)
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Mar 30, 2023 |
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#4 - Build A Solid Investment Strategy Before Pushing The Throttle Forward with Alex Tapia
|
Mar 28, 2023 |
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#3 - Investments and Wealth Management for Aviators with Austin “Strobes” Hulbert
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Mar 21, 2023 |
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Special Episode: The Silicon Valley Bank Collapse
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Mar 15, 2023 |
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#2 - Invest Passively in DST and Opportunity Zones with Brandon Bruckman
|
Mar 14, 2023 |
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#1 - How Can Pilots Position Themselves for Success with CNBC’s Fast Money Trader Guy Adami
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Mar 09, 2023 |
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The Men Behind Passive Income Pilots
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Mar 06, 2023 |