Best Pilot Wealth Management Podcasts (2025)

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279. What Should Parents of Children with Disabilities Know About Estate Planning? 31:15

1d ago31:15

31:15

Planning for the future of a child with disabilities is a complex and emotional journey, but taking proactive steps can help ensure a stable and fulfilling transition into adulthood. Families often face significant challenges when essential services suddenly end, making it crucial to have a well-structured plan in place. In this episode of A Wiser …

1
#107 - Take Control of Your Capital: Infinite Banking Strategy With Brent Kesler 38:43

7d ago38:43

38:43

Host Tait Duryea sits down with Brent Kesler, a seasoned life insurance strategist, to explore how pilots and high-income earners can build wealth by turning whole life insurance into a personal banking system. Brent breaks down the misunderstood "infinite banking" concept and how it can be used for real estate, debt payoff, or high-return lending—…

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278. Avoid These Common Mistakes After Receiving a Large Inheritance 34:09

9d ago34:09

34:09

Receiving a large inheritance can be both a blessing and a challenge. While it offers the opportunity to improve your financial future, it also comes with important decisions that can impact your long-term stability. Without a clear plan, it's easy to make costly mistakes. In this episode of A Wiser Retirement® Podcast, we discuss key consideration…

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#106 – Time Freedom and Cash Strategies with Brian Herriot 39:31

14d ago39:31

39:31

Hosts Tait Duryea and Ryan Gibson welcome financial strategist Brian Herriot for a thought-provoking conversation on redefining retirement and wealth. Explore the power of time freedom, why cash might be your most underappreciated asset, and how to build passive income streams that work for pilots and professionals alike. Brian shares practical tac…

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277. Tariffs, Trump, and Turbulence: Making Sense of Market Mayhem 52:13

16d ago52:13

52:13

Tariffs, fiscal policy, and market volatility have become growing concerns for many investors. In this episode of A Wiser Retirement® Podcast, we unpack what tariffs are, how they work, and how current market conditions may affect your investment portfolio. Related Podcast Episodes: - Ep 263: Trump’s Economic Policies: Tax, Tariffs, and More - Ep 2…

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#105 - Buying and Building a Profitable Aviation Business with James Spearman 46:05

21d ago46:05

46:05

In this episode, Tait Duryea and Ryan Gibson are joined by James Spearman, owner of Spearman Aircraft and Iconic Rides. James walks through his journey of acquiring and scaling an aircraft maintenance business through seller financing, boosting its value through streamlined systems and strategic marketing. He shares the mindset and steps that helpe…

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276. How to Make Sure You're Ready for Retirement 33:06

23d ago33:06

33:06

Join us on this episode of A Wiser Retirement® Podcast, where we break down the essential steps to help you prepare for a secure and fulfilling retirement. From creating a realistic budget and eliminating debt to maximizing Social Security and Medicare benefits, we cover key financial strategies to set you up for success. Related Podcast Episodes: …

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275. Crypto Update: The U.S. Bitcoin Reserve, SBF’s Prison Interview, and 24-Hour Nasdaq Trading 28:33

28d ago28:33

28:33

Join us for this episode of A Wiser Retirement® Podcast as we explore the U.S. government's growing Bitcoin holdings and the potential creation of an official Bitcoin reserve, a proposal now under legislative review. We also dive into the latest developments in crypto regulation, Sam Bankman-Fried’s unauthorized interview with Tucker Carlson, Binan…

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#104 - Active vs. Passive: Storage Strategies from the Flight Deck with Michael Meylor 49:01

28d ago49:01

49:01

In this episode, Tait Duryea and Ryan Gibson sit down with Michael Meylor, a seasoned pilot and self-storage investor who has built an impressive portfolio without raising outside capital. Michael shares how he transitioned from military to commercial flying, how he and his wife started investing in single-family rentals, and why they pivoted to co…

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274. Buying a Home in the Best School District: What You Need to Know 40:10

30d ago40:10

40:10

Join us on this episode of A Wiser Retirement® Podcast, as Casey Smith and Paul Montaperto from Family2Family Relocation discuss tips for families looking to buy a home in a great school district. We explore how to evaluate school quality beyond online ratings, considering factors like administrative stability, private school options, and future zo…

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#103 - Multifamily Mastery: Building Cashflow and Legacy with Gino Barbaro 45:35

1M ago45:35

45:35

In this episode, Tait Duryea welcomes Gino Barbaro of Jake & Gino to unpack the mindset and mechanics behind building lasting wealth through multifamily real estate. Gino shares his journey from running a family restaurant to becoming a real estate investor with over 1,800 units. They explore topics like values-based decision-making, creating "happ…

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273. How Early Retirement Affects Pilot Benefits 30:29

1M ago30:29

30:29

Are you a pilot contemplating the possibility of retiring early? Join us on this episode of A Wiser Retirement® Podcast, where we explore the complexities surrounding the decision to leave the cockpit before the traditional retirement age. We dive deep into the unique emotional and financial considerations that come with this choice, focusing on th…

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#102 - Creating True Passive Income Through Note Investing with Tom Force 49:39

1M ago49:39

49:39

In this episode, Tait Duryea and Ryan Gibson sit down with retired airline captain and seasoned investor Tom Force to discuss a real estate strategy many overlook—note investing. They cover tax strategies, risk management, and how to get started in note investing. If you’re tired of tenant headaches and want to invest like a bank, this episode is f…

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272. Why should I pay a financial advisor to invest in low-cost ETFs? 40:56

1M ago40:56

40:56

Join us on this episode of A Wiser Retirement® Podcast, where we explore why paying a financial advisor to invest in ETFs may be worth the cost, even when providers like Vanguard offer these funds with low fees. Many investors wonder if they can simply do it themselves, but the real value of working with an advisor goes far beyond just selecting in…

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#101 - Airbnb for Aircraft: Hangar Investing & Aviation Real Estate with Trenton Ray 41:21

2M ago41:21

41:21

Hangar space is in short supply, but Trenton Ray is changing that. In this episode, Tait Duryea and Ryan Gibson chat with Trenton about Hangar Direct, his platform that’s like Airbnb for hangars—making it easier for pilots to find and rent space. They dive into the supply shortage, investment potential, and what to know about leasing, financing, or…

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271. How to Build Lasting Wealth in Your 20s and 30s: Tips for Financial Freedom 34:10

2M ago34:10

34:10

What steps should you take in your 20s and 30s to build sustainable wealth? In this episode of A Wiser Retirement® Podcast, we break down the key financial habits that can pave the way for lifelong security. Young adults today face unique financial hurdles such as rising living costs, student loan debt, and credit cards. Tune in as we share practic…

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270. Crypto Update: Meme Coin Resurgence, ByBit Hack & Crypto Taxation 27:26

2M ago27:26

27:26

Join us for this episode of A Wiser Retirement® Podcast, where we explore the latest changes shaping the cryptocurrency market. From the resurgence of meme coins to high-profile hacks and evolving tax regulations, we cover key trends that are influencing how investors, regulators, and global markets interact with digital assets in 2025. Related Pod…

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#100 - Getting to Know Tait & Ryan 51:12

2M ago51:12

51:12

In this special 100th episode of Passive Income Pilots, Tait Duryea and Ryan Gibson take listeners behind the scenes of the podcast, sharing how it all started and what goes into creating each episode. They also dive into their personal journeys in aviation, investing, and entrepreneurship. From buying their first rental properties to scaling multi…

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269. What College Expenses are Tax Deductible for Parents? 27:54

2M ago27:54

27:54

Managing college expenses can be overwhelming, but understanding available tax benefits can help parents reduce costs. Join us on this episode of A Wiser Retirement® Podcast as we discuss how these tax benefits work and what families need to know about deductions, tax forms, and financial planning for college. Related Podcast Episodes: - Ep 168: Ev…

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#99 - Turnkey Real Estate: Passive or Problematic? A Deep Dive with Zach Lemaster 52:24

2M ago52:24

52:24

In this episode, Tait Duryea and Ryan Gibson connect with Zach Lemaster to explore the world of turnkey real estate and build-to-rent properties. They discuss the benefits and challenges of owning physical real estate, the tax advantages of rental properties, and how busy professionals can invest without becoming full-time landlords. Zach shares in…

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#98 - The Right Coverage: Property Insurance Strategies with Valerie Cusano 49:46

2M ago49:46

49:46

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Valerie Cusano, an insurance expert with a background in law and decades of experience in commercial and residential insurance. Val dives deep into the critical aspects of real estate insurance, particularly for condo and rental property owners. She explains the dif…

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268. Top Financial Mistakes and How to Avoid Them 44:51

2M ago44:51

44:51

Are you curious about the top financial mistakes people make, and how to avoid them? Tune in to this episode of A Wiser Retirement® Podcast as Grace Kennedy, Financial Planning Associate, shares insights on the most common financial pitfalls and how to steer clear of them. Related Podcast Episodes: - Ep 229: How do I avoid capital gains tax? Relate…

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#97 - Creative Deal Structuring: Smart Real Estate Strategies with Chris Prefontaine 53:27

3M ago53:27

53:27

In this episode, Tait Duryea and Ryan Gibson dive into creative real estate financing with Chris Prefontaine, founder of Smart Real Estate Coach. Chris shares powerful strategies like seller financing, subject-to deals, and lease purchases, revealing how investors can acquire properties without banks—even in today’s high-interest rate environment. …

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267. The 2025 Housing Market: Trends, Changes, and What to Expect 44:42

3M ago44:42

44:42

Curious about where mortgage rates and home prices are headed in 2025? Tune in to this episode of A Wiser Retirement® Podcast as Tom Townsend, Realtor at Townsend Realty Group, recaps the 2024 housing market and shares predictions and trends for 2025. We also discuss the state of the local market, inventory shortages, the cost of new construction, …

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266. Crypto Update: SpaceX Uses Stablecoins, Trump’s Meme Coin & Altcoin ETF Filings 33:36

3M ago33:36

33:36

Join us for this episode of A Wiser Retirement® Podcast as we dive into the latest developments in the cryptocurrency market. We explore new regulatory efforts, Bitcoin’s recent price swings, and the launch of a crypto task force aimed at bringing more clarity to the industry. Plus, we discuss the rise of President Trump’s meme coin, the growing in…

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#96 - Airplane Write-Offs, IRS Audits, and Smart Tax Planning with Ryan DeMoor 49:44

3M ago49:44

49:44

Have you ever wondered how you could write off an airplane? In this episode, Ryan DeMoor joins hosts Tait Duryea and Ryan Gibson to break down the tax benefits of aircraft ownership. Ryan shares how pilots and business owners can strategically use aircraft purchases for tax deductions, the IRS rules around business use, and why proper record-keepin…

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265. Roth 401(k) vs. Roth IRA: Which One is Right for You? 27:11

3M ago27:11

27:11

Curious about the difference between a Roth 401(k) and a Roth IRA? Join us on this episode of A Wiser Retirement® Podcast as we discuss key aspects of retirement planning, the importance of setting clear financial goals, and the distinctions between a Roth 401(k) and a Roth IRA. Discover valuable insights on maximizing your savings, navigating cont…

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#95 - Franchise Investing 101: Insights and Opportunities with Cliff Nonnenmacher 53:31

3M ago53:31

53:31

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson explore the world of franchise ownership with franchise expert Cliff Nonnenmacher. Cliff brings decades of experience as a franchise consultant and serial entrepreneur, sharing insights into how pilots and professionals can invest in or operate franchises to build wealth. T…

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264. Shaping the Future of Aviation: Key Leadership Skills for Pilots 47:38

3M ago47:38

47:38

Pilots, do you want to elevate your leadership skills? Join us on this episode of A Wiser Retirement® Podcast, where we dive into the essential role of leadership development for pilots. We’ll discuss the importance of emotional intelligence, effective communication, and adaptability in aviation. Joining us is Kyle Freiburger, CEO of First Class Le…

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#94 - Fail Fast, Succeed Faster: Wealth-Building and Investment Strategies with Christian Schiller 47:51

3M ago47:51

47:51

In this episode, Tait Duryea and Ryan Gibson sit down with Christian Schiller, an accomplished investment banker with a wealth of experience buying, selling, and evaluating businesses. Christian shares his investment journey, including lessons from early failures, how he refined his investment strategy, and why knowing your limits is key to success…

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263. Trump’s Economic Policies: Tax, Tariffs, and More 39:14

3M ago39:14

39:14

Curious how Trump’s economic policies will impact your portfolio? Join us on this episode of A Wiser Retirement® Podcast as we talk about strategies for navigating market volatility, emphasizing the importance of long-term investment approaches and systematic decision-making to capitalize on opportunities during economic transitions. Related Podcas…

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#93 - Stock Market Insights and Tax Strategies for High-Income Earners with Brian Feroldi 55:19

3M ago55:19

55:19

In this episode, Tait Duryea and Ryan Gibson welcome Brian Feroldi, author of Why Does the Stock Market Go Up? to unpack the fundamentals of the stock market and explain strategies tailored for pilots and high-income professionals. Brian demystifies the difference between Roth and traditional 401(k) contributions, shares insights into dividend inve…

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262. Optimizing Your Tax Plan for 2025: Key Moves to Make 34:10

4M ago34:10

34:10

Curious about how to optimize your tax plan for 2025? Join us on this episode of A Wiser Retirement® Podcast as we share key tax moves to make this year. We cover key topics like charitable giving, the SECURE Act 2.0, upcoming legislative changes, monitoring AGI, and optimizing business deductions. Related Podcast Episodes: - Ep 239: How can I redu…

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#92 - Opportunity Zones for Passive Income: Unlock Tax Savings and Growth with Nathan Sosa 51:28

4M ago51:28

51:28

Dive into the intricacies of Opportunity Zones with this episode of Passive Income Pilots. Hosts Tait Duryea and Ryan Gibson are joined by CPA Nathan Sosa of Hall CPA, who demystifies Opportunity Zone (OZ) investments and their potential for tax deferral and appreciation. Whether you're an active investor or prefer passive opportunities, learn how …

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261. 2025 Market Outlook: Navigating the Year Ahead 36:23

4M ago36:23

36:23

Curious how to navigate the stock market in 2025? Join us on this episode of A Wiser Retirement® Podcast as we share our 2025 market outlook. We cover key topics like market performance, predictions, diversification strategies, emerging technologies, economic challenges, and how to navigate external factors shaping the financial landscape. Related …

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#91 - Interest Rates, Submarkets, and CRE's Future with Spencer Levy 49:12

4M ago49:12

49:12

Spencer Levy, a leading expert from CBRE, joins Tait Duryea and Ryan Gibson to break down the current state of commercial real estate (CRE). He explains how rapid interest rate changes are reshaping the market, highlights key megatrends like reshoring and live-work-play neighborhoods, and offers advice on navigating submarkets. Whether you’re a sea…

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260. 10 Financial Habits That Lead to Long-Term Success 41:47

4M ago41:47

41:47

In this episode of A Wiser Retirement® Podcast, we discuss 10 financial habits to help you take control of your finances, from setting a clear vision and building a budget to avoiding debt and maximizing employer benefits. Learn practical strategies to automate your savings, build an emergency fund, and align your spending with your long-term goals…

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#90 - Balancing Flying, Business Ownership, and Financial Growth with Carl Valeri 49:22

4M ago49:22

49:22

In this action-packed episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Carl Valeri, an airline captain and experienced entrepreneur, to share actionable strategies to balance a flying career with building a passive income. Carl dives into creative ways to start or buy a business, reduce your tax burden, and even transitio…

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#89 - Air Traffic, Pilot Pay, and Airline Economics with A4A's Chief Economist John Heimlich 41:04

4M ago41:04

41:04

In this episode, Tait Duryea and Ryan Gibson sit down with John Heimlich, Chief Economist for Airlines for America (A4A), to unpack the challenges and wins shaping the airline industry. From air traffic control staffing shortages to the impact of pilot pay increases and aircraft delivery delays, John shares key insights into the state of U.S. airli…

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259. What Pilots (and Others) Should Consider 5 Years Before Mandatory Retirement 51:17

4M ago51:17

51:17

Retirement for pilots comes with its own set of challenges and opportunities, especially with the mandatory retirement age of 65. In this episode of A Wiser Retirement® Podcast, we explore essential financial strategies and lifestyle adjustments to help pilots (and others) navigate a seamless transition into retirement. Other Links: - Click here to…

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#88 - Flight Schools and Passive Income: Insights from Gordon Alvord 46:34

5M ago46:34

46:34

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson talk with Gordon Alvord, Alaska Airlines captain and co-founder of Rainier Flight Service. Gordon shares how a 2008 furlough led to creating Washington State’s largest flight school, with over 70 aircraft and a reputation for innovation. Discover how he and his partner used…

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258. The True Cost of the Holidays: How Much Are We Really Spending? 25:22

5M ago25:22

25:22

Does holiday stress overshadow the joy of the season? Join us on this episode of A Wiser Retirement® Podcast as we dive into the true cost of holiday spending and its impact on both finances and family dynamics. From uncovering hidden expenses like holiday decorations to embracing simple pleasures such as driving through festive neighborhoods, we’l…

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257. The Election Outcome Impact on Crypto, BTC ETFs, and Bitwise Files for Index Product 33:22

5M ago33:22

33:22

Tune in to this episode of A Wiser Retirement® Podcast where we discuss how the post-election landscape is shaping the future of cryptocurrency. Casey Smith and Robert Swarthout from Teton Crypto Capital join us to unravel complex policy shifts and market dynamics. We explore the hurdles and timelines facing U.S. cryptocurrency regulation, drawing …

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#87 - The Mega Backdoor Roth and How Pilots Can Maximize Retirement Contributions with Timothy Pope 50:41

5M ago50:41

50:41

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson welcome back financial expert Timothy Pope to unravel the complexities of retirement strategies for high-income professionals, focusing on the Mega Backdoor Roth. Timothy explains how this powerful tool allows pilots to contribute significantly more to their 401(k) accounts, unlo…

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256. The Best Whiskeys to Gift in 2024 27:32

5M ago27:32

27:32

Tune in to this episode of A Wiser Retirement® Podcast where we explore the best whiskeys to gift in 2024. Discover our top three recommendations for whiskeys in three price ranges: under $50, $50-$100, and over $100. We also share a few thoughtful whiskey-related gift ideas. Whether you're a seasoned connoisseur or just beginning your whiskey jour…

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#86 - Mapping the Skies: The Tech Behind Real-Time Flight Tracking with Ian Petchenik 33:52

5M ago33:52

33:52

Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea and Ryan Gibson step outside financial strategies to explore the world of real-time flight tracking with Ian Petchenik, Director of Communications at FlightRadar24. Ian shares insights into the app that has become essential for aviation enthusiasts and profession…

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255. The Power of Generosity and Its Impact On Your Finances 29:42

5M ago29:42

29:42

In this episode of A Wiser Retirement® Podcast, we're joined by Missie Beach, CFP®, CDFA®, to discuss the power of generosity and its impact on your finances. Together, we delve into strategies for making charitable giving both tax-efficient and meaningful. Discover how to maximize tax benefits through techniques like donating appreciated securitie…

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#85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver 47:59

5M ago47:59

47:59

Welcome back to another episode of Passive Income Pilots! In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson are joined by Erik Oliver, Vice President of Cost Segregation Authority, to dive deep into cost segregation. Erik explains how this tax strategy accelerates real estate depreciation, enabling investors to unlock substantia…

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254. Closing the Year Strong: Key Financial Moves Before Year-End 38:30

5M ago38:30

38:30

Discover how to make your investments work smarter, not harder, with tax-efficient strategies. In this episode of A Wiser Retirement® Podcast, we tackle the big questions, like whether Roth conversions make sense for you, especially if you're in a low tax bracket now but anticipate higher income later. We also explore the potential of direct indexi…

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#84 - Tax-Free Growth & Infinite Loans: Whole Life Insurance Strategies for High-Earners 39:52

6M ago39:52

39:52

Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea hosts Rod Zabriskie and Brenyn McConnell from Money Insights to explore how whole life insurance can be a powerful investment tool. They discuss how pilots and high-income earners can use structured whole life policies to build tax-free growth and take policy loa…

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Pilot Wealth Management Podcasts

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