Best Pilot Wealth Management Podcasts (2025)

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308. The Silent Tax: How Inflation Erodes Your Retirement 27:31

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10h ago27:31

27:31

In this episode of A Wiser Retirement® Podcast, Casey Smith, and Financial Advisor Michaela Dowdy dive into how retirement planning isn’t just about matching today’s income with today’s expenses. It’s about preparing for the future value of money. Related Podcast Episodes: Ep 245. Strategies for Early Retirement and Long-Term Security Ep 212. Medic…

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#129 - Ego, Taxes, and the Paycheck Trap: Pilot Wealth Myths Exposed 29:42

17h ago29:42

29:42

Why do so many high-earning pilots struggle to build real wealth? Hosts Tait Duryea and Ryan Gibson get candid about the habits, mindset, and blind spots that keep aviators from achieving true financial independence. They reveal the five biggest mistakes pilots make, from lifestyle creep and tax traps to ego-driven investing, and how to replace the…

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#260: Turning a $60 Year Into a $64K Week, Working With the Dallas Mavericks, & Simplifying Your Business w/ Amy Birks 1:22:06

5d ago1:22:06

1:22:06

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307. Unlocking the Power of Trusts: 10 Different Trusts & How to Use Them 45:42

7d ago45:42

45:42

In this episode of the A Wiser Retirement® Podcast, Estate Planning Attorney Arun Gupta joins Shawna Theriault, CFP®, CPA, CDFA® to demystify trusts, what they are, who they’re for, and how 10 common trust types work in real life. Related Podcast Episodes: Ep 295: What Happens If You Die Without a Will? The Legal Nightmare Ep 279: What Should Paren…

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#128 - Inside the Fine Print: PPMs, Trust, and Investor Protection with Seth Bradley 42:46

11d ago42:46

42:46

What do private placement memorandums really mean for you as an investor? Hosts Tait Duryea and Ryan Gibson sit down with attorney and real estate operator Seth Bradley to pull back the curtain on syndication documents, accreditation rules, and what truly protects investors. Seth shares his personal journey from med school to big law to entrepreneu…

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306. Crypto in Your 401(k)? The Future of Retirement Investing 29:00

11d ago29:00

29:00

In this episode of A Wiser Retirement® Podcast, Casey Smith is joined by Robert Swarthout, CEO and Portfolio Manager of Teton Crypto Capital. Together, they dive into the latest crypto news, from the launch of new ETFs to the growing influence of stablecoins in U.S. Treasuries. The conversation explores how these developments could impact retiremen…

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#259: I Dissected An Octopus. Here’s What I Learned… w/ Perry Knoppert 1:22:55

12d ago1:22:55

1:22:55

Today’s episode is… a little strange. As the title suggests, I dissected an octopus. But don’t worry — no nine-brained, three-hearted, blue-blooded sea creatures were harmed in the making of this podcast 🐙. Instead, I brought back a dear friend and Curiosity Island citizen, Perry Knoppert — aka “Dr. Octopus” — the founder of the Octopus Movement, a…

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Black Hawk Helicopter Pilot to Business Ownership | Jason Santiago 1:08:41

13d ago1:08:41

1:08:41

Send us a text From Combat Pilot to Gym Owner: Jason Santiago's Journey of Service and Entrepreneurship Join us in this episode of Pay or Quit as we sit down with Jason Santiago, a former Black Hawk helicopter pilot and military veteran, who has transformed his life from flying high-stakes missions to tackling the challenges of entrepreneurship and…

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305. Just Moved to a New State? Here’s Your Financial To-Do List 31:53

14d ago31:53

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In this episode of A Wiser Retirement® Podcast, Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA® is joined by Financial Advisor William Medcalf, CFP® to discuss the financial implications of moving across state lines, and how a change in location can also mean major changes to your financial life. Related Podcast Episodes: - Ep 77: Tips …

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#127 - LLCs, Trusts, and K-1s: Smarter Asset Protection with Adam Kintigh 52:03

16d ago52:03

52:03

How protected is your wealth if something goes wrong? In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with asset protection expert Adam Kintigh to share practical strategies every pilot and high-income professional should know. From real estate privacy trusts that cut transfer taxes to Wyoming LLCs that safeguard synd…

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#258: From Wendy’s Value Meals to Managing $33 Billion & How You Can DESIGN True Wealth w/ Anthony Englert 1:30:14

19d ago1:30:14

1:30:14

At 19, Anthony Englert thought he’d cracked the wealth code. He was living in a million-dollar mansion, cashing checks from a hedge fund with 12% monthly returns, and feeling on top of the world… …until his business partners accused him of not being willing to take enough risk, kicked him out of the company, and he lost everything — including his e…

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304. Under the Radar: Wealth Strategies for the Quietly Rich 41:02

21d ago41:02

41:02

In this episode of A Wiser Retirement® Podcast, Casey Smith and William Medcalf, CFP® dive into what it really means to be “quietly rich” and how smart habits, not flashy spending lay the foundation for financial independence. Related Podcast Episodes: - Ep 73: Leave a Legacy of Generosity - Ep 260: 10 Financial Habits That Lead to Long Term Succes…

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#126 - Early Real Estate Mistakes and Lessons Learned 33:11

23d ago33:11

33:11

What separates pilots who want to invest from those who actually succeed? In this episode, Tait Duryea and Ryan Gibson share the real stories behind their first deals, the mistakes they made, and the lessons that still guide them today. From disastrous single-family rentals to managing multifamily properties, they explain why failure is often the b…

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#257: BTS Of The Relationship Powering A Podcast With 175 MILLION Downloads… w/ Kate Dumas of EO Fire 1:01:20

26d ago1:01:20

1:01:20

I’ll never forget my sophomore year of college, wandering the cobblestone streets of Sevilla, Spain, earbuds in… listening to something brand new to me at the time: Podcasts. One show in particular stood out: Entrepreneurs on Fire. Hearing real entrepreneurs talk about building businesses that made an impact felt revolutionary compared to the dry, …

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Is outbound sales right for you? | Ben Smith 59:15

27d ago59:15

59:15

Send us a text Mastering Outbound Sales with Ben Smith In this episode, Shawn interviews Ben Smith, the founder of Bright Reach Sales, who has over seven years of experience in driving revenue through effective sales strategies. Ben shares his journey from insurance sales to founding Bright Reach, emphasizing the importance of outbound sales for bu…

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303. Pilot’s Guide to Financial Turbulence: Planning for Medical Disabilities 34:45

28d ago34:45

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In this episode of A Wiser Retirement® Podcast, we discuss the importance of commercial airline pilot medical disability planning and why it’s often overlooked compared to life insurance. We explain how airline disability benefits work, the differences between short-term and long-term coverage, and why “own occupation” policies are essential. The c…

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#256: My Framework For Experience Design: Have Your MOM Make A WAFFLE (w/ Special Guest Interviewer, Meredith Grundei) 52:35

1M ago52:35

52:35

Back in March, I hosted the first ever LIVE event for my community, Curiosity Island. We hired my friend and Curiosity Island “Castaway” Bob Regnerus to produce the video footage for our event: Click right here to watch the video Why am I sharing this with you? * Incoming humble brag * If you listen to that video, there was definitely a theme in wh…

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The Yoga Of Work - Andrew Taggart 1:37:38

1M ago1:37:38

1:37:38

Click here to watch a video of this episode. Mentioned in the episode Andrew Taggart’s website Pathways to the Dao (Andrew’s Substack) Leisure: The Basis of Culture by Josef Pieper Secular Monks (article by Andrew Taggart) Why Buddhism is True by Robert Wright Pierre Hadot (Philosophy as a Way of Life) The Pathless Path by Paul Millerd (00:00) - In…

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302. What should I do five years before I retire? 34:50

1M ago34:50

34:50

Retirement isn’t just a finish line, it’s a brand new chapter. In this episode of A Wiser Retirement® Podcast, Casey Smith and Financial Advisor Michaela Dowdy outline eight key things you should focus on starting five years before retirement. While more time is always better, the 3–5 year mark is when many people get serious. Here's how to make th…

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AMA Episode 200 - I answer questions on parenting, courage, being a prophet, taking risks, and money 29:55

1M ago29:55

29:55

I took questions from people for episode 200. Enjoy! Click here to watch a video of this episode. (00:00) - Introduction and Podcast Background (03:08) - Future of Education and Teaching (05:29) - Thoughts on Being a Prophet (06:09) - Current Pulling Forces and Changes (08:30) - Special Hardcover Edition Plans (10:05) - Managing Financial Anxiety (…

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301. Crypto Update: Clarity Act, GENIUS Act, and Stablecoins 26:34

1M ago26:34

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In this episode of the A Wiser Retirement® Podcast, Casey Smith sits down with Robert Swarthout, founder and CEO of Teton Crypto Capital, to discuss how fast cryptocurrency is evolving and how banks are getting involved. - Ep 296: Crypto Update: Big Beautiful Bill, GENIUS Act, & Crypto Company IPOs - Ep 286: How can I evaluate crypto as a potential…

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#125 - Oil & Gas Investing for High-Income Pilots with Mark Fleming 52:18

1M ago52:18

52:18

Can oil and gas really be a smart play for high-income professionals? In this episode, Tait Duryea and Ryan Gibson sit down with Mark Fleming, petroleum engineer and Turbine Capital’s oil & gas advisor, to break it down. From the basics of how drilling works to the tax advantages that can offset W2 income, you’ll learn the realities of this often-m…

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#255: How To Use “Choice Mapping” To Make Choices With Confidence And Clarity w/ Kim DeYoung 1:16:36

1M ago1:16:36

1:16:36

Imagine this: You’re driving to a high-end coaching workshop—an event you’ve just spent a big chunk of money to attend. You’re hopeful, nervous, not totally sure if you even should be going… And then, mid-drive, you get into one final painful conversation with your mother—and decide, in that moment, to end the relationship. This was a pivotal momen…

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300. Built to Last: The History and Future of Wiser Wealth Management 51:39

1M ago51:39

51:39

In this episode of A Wiser Retirement® Podcast, we celebrate hitting a major milestone, 300 episodes! In this special episode, President Casey Smith and Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®, reflect on the history of Wiser Wealth Management, the growth of the podcast, and the firm’s mission to provide real, relationship-drive…

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#124 - $44 Trillion and the Future of Retirement Investing with Mat Sorensen 50:52

2M ago50:52

50:52

Tait Duryea and Ryan Gibson welcome Mat Sorensen, CEO of Directed IRA, for a powerful discussion on how pilots and high-income professionals can unlock private investment opportunities through retirement accounts. From self-directed IRAs to Solo Ks, Mat explains the mechanics of rolling over old 401(k)s, navigating recent regulatory changes, and ta…

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#254: BC Time Machine: Conscious Storytelling w/ Michael Hauge, Jude Charles, & Britt Lefkoe 38:38

2M ago38:38

38:38

One of my core values is something I call conscious storytelling. I believe the stories we tell — both internally to ourselves and externally to the world — create our reality. Change your story, and you can change your reality. That’s why in this Beyond Curious Time Machine episode, I wanted to hit both sides of storytelling: How do we tell more m…

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How To Retire Well: Dennis Owen on Moving Abroad, Building Community, Volunteering, Adapting to New Cultures, Creating Routine, Consulting After Retirement, Managing Money Mindset Shifts, Staying Current ... 1:02:39

2M ago1:02:39

1:02:39

In this episode, I talk with Dennis Owen about his journey from a long career in the airline industry to building a purposeful and active retirement in Chiang Mai, Thailand. Dennis shares how he intentionally “retired to” a new life filled with volunteering, consulting, and community involvement, rather than just leaving work behind. We discuss the…

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299. Financial Conversations Every Couple Should Have Before Saying 'I Do' 44:24

2M ago44:24

44:24

In this episode of A Wiser Retirement® Podcast, Shawna Theriault, CFP®, CPA, CDFA® and Financial Advisor Michaela Dowdy dive into the essential financial conversations couples should have before saying “I do.” From discussing mindsets and money habits to navigating joint goals and future planning, they offer guidance on how to build a healthy finan…

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EP 46: Private Credit & Pilot Training: Investing Beyond Wall Street | Brandon Martini & Madhavi Jain 57:16

2M ago57:16

57:16

In this episode of Think Outside the Stocks, host Madhavi Jain sits down with Brandon Martini, co-founder and COO of Stratus Financial, to explore an alternative investment class that helps aspiring pilots finance their training while delivering strong, risk-adjusted returns for investors. Brandon shares his journey from Navy veteran and airline pi…

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#123 - Market Cycles, Debt, and Real Estate Opportunities with Hunter Thompson 49:22

2M ago49:22

49:22

Is now the right time to buy real estate or to hold cash? In this episode, Tait Duryea and Ryan Gibson sit down with Hunter Thompson, founder of Asym Capital and host of Cash Flow Connections, to unpack today’s real estate market. They cover cycles, debt structures, the COVID impact, rising interest rates, and why current distress is more about fin…

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#253: From Gang Life to Serving Global Influencers… and How to Create Your Greatest Influence, Impact, and Income Through Your Fullest Expression w/ Dmitriy Kozlov 1:20:12

2M ago1:20:12

1:20:12

As a 13-year-old immigrant struggling to fit in, Dmitriy Kozlov found rap music. In some ways it saved him — it gave him an outlet and a path to self-expression. But in other ways it nearly killed him. Dmitriy ended up getting involved with gang activity — and eventually, the very gang he ran with turned on him and nearly killed him… more than once…

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298. America's Balance Sheet: A Financial Advisor's Deep Dive into National Debt 40:28

2M ago40:28

40:28

In this episode of A Wiser Retirement® Podcast, Casey Smith, Andrew Pratt, CFA, CBDA, and Shawna Theriault, CFP®, CPA, CDFA®, dive deep into the state of America’s national debt, what it is, how it got this large, and what it could mean for the country and for everyday investors. While it’s common to compare government debt to household finances, n…

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#122 - How Pilots Use Whole Life Insurance to Fund Investments with Rod Zabriskie 49:50

2M ago49:50

49:50

What if your life insurance could help you invest without selling a single asset? Tait Duryea and Ryan Gibson welcome back Rod Zabriskie of Money Insights to demystify how whole life insurance can be used as a wealth-building tool. They break down the differences between term and whole life, how cash value grows, and why this strategy avoids risks …

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#252: GPT Biking: Exactly How I Get My Highest Quality Work Done While Training For A 100 Mile Bike Ride 31:39

2M ago31:39

31:39

Last year I committed to a new endurance challenge: A 100 mile bike ride. Somewhere along the way, a wild idea hit me… What if I could work while riding? Not just answering emails — I’m talking deep, creative, transformational work. Fast forward to today, and I’m getting more done on my bike than I do at my desk. I call it GPT Biking. In this episo…

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297. The Stay-at-Home Equation: Financial Aspects of Leaving the Workforce 26:12

2M ago26:12

26:12

In this episode of the A Wiser Retirement® Podcast, we explore the financial and emotional realities of stepping away from the workforce to become a stay-at-home parent. Whether you're considering staying home temporarily or long-term, it's a decision that deserves careful financial planning. From budgeting for a single income and understanding the…

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EP:45 Think Outside the Stocks: Unveiling the $230B Life Settlement Market with Matthew Paine (Part 2) 1:01:39

2M ago1:01:39

1:01:39

What if your life insurance policy could do more than just offer peace of mind—it could become a powerful wealth-building asset? In Part 2 of this eye-opening series, Madhavi Jain continues her conversation with Matthew Paine, a seasoned expert in the life settlement market, to uncover one of the most overlooked yet powerful investment opportunitie…

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296. Crypto Update: Big Beautiful Bill, GENIUS Act, & Crypto Company IPOs 27:59

2M ago27:59

27:59

In this episode of A Wiser Retirement® Podcast, Casey Smith sits down with Robert Swarthout, founder and CEO of Teton Crypto Capital, to unpack how recent legislation is reshaping the crypto landscape in the U.S. From tax changes to new opportunities for investors, here’s what you need to know. Related Podcast Episodes: - Ep 281: Crypto Update: Tar…

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#121 - Short-Term Rentals, Long-Term Wealth with Pilot Couple Brad Hilton and Aubrey Carlson 54:12

2M ago54:12

54:12

What if your first home turned into your first big win? Tait Duryea and Ryan Gibson welcome Brad Hilton and Aubrey Carlson, a powerhouse pilot couple who turned a VA loan into a cash-flowing real estate business. From renovating a dated beach house to designing destination-worthy cabins in Julian, CA, Brad and Aubrey break down how they scaled a sh…

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#251: Spiritual Branding, Becoming a Category of One, & Why Your Brand Should Be Gay (Even If You’re Not) w/ Re Perez 1:00:20

2M ago1:00:20

1:00:20

Today’s guest has one of the boldest book titles I’ve ever come across… It’s called: “Your Brand Should Be Gay (Even If You’re Not): The Art and Science of Creating an Authentic Brand.” And what I love so much about that title is that Re Perez lives it. In today’s episode, you’ll hear how Re went from growing up in an all-boys Catholic Jesuit schoo…

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Worldschooling 2.0: Rekha Magon on Location-Independent Schooling, co-founding Boundless Life, Lessons during bed rest, rethinking family in a digital age, travel, freedom, and raising global citizens 1:05:54

2M ago1:05:54

1:05:54

In this video, I talk with Rekha about Boundless Life and the idea of location-independent education. We cover her background, what led her to start Boundless Life, and how the program works for families who want a different approach to learning and community. For more: Boundless Life Boundless Education Rekha on LinkedIn Rekha on Instagram (00:00)…

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295. What Happens If You Die Without a Will? The Legal Nightmare 31:39

2M ago31:39

31:39

In this episode of the A Wiser Retirement® Podcast, Estate Planning Attorney Arun Gupta joins Senior Financial Advisor Shawna Theriault to discuss how taking the simplest step in estate planning, creating a will, can make a profound difference. While many assume estate planning is only for the ultra-wealthy, a will helps ensure your assets are dist…

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EP 45: Banks, Billionaires, and Life Insurance: What They’re Not Telling You (Part 1) 54:01

2M ago54:01

54:01

🔍 Join host Madhavi Jain on Think Outside the Stocks as she sits down with Matthew Paine, Managing Director at LifeCap and a 24-year veteran who's revolutionizing how we think about life insurance as an investment vehicle. This conversation challenges the widespread "buy term and invest the difference" philosophy, revealing why it could be sabotagi…

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#120 - How to Evaluate Markets, Properties, and Risks in Real Estate with Derrick Harris 1:00:00

3M ago1:00:00

1:00:00

What separates a solid real estate deal from a costly mistake? In this episode, hosts Tait Duryea and Ryan Gibson welcome Derrick Harris, SVP at Spartan Investment Group, to walk us through the real-world process of evaluating markets, properties, and operational risks. With a portfolio that spans millions of square feet, Derrick shares what works,…

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#250: The Steve Sims Trilogy: A Tribute to the Guest Who Deeply Impacted My Life — and Left a Legacy of Living Boldly, Passionately, and Without Limits 2:56:09

3M ago2:56:09

2:56:09

Episode 250 of the Beyond Curious Podcast marks a huge milestone… and also carries a heavy heart. This episode is dedicated to a podcast guest who profoundly impacted my life — and who left us far too soon. His name was Steve Sims. You may have heard me talk about Steve before. He’s the “Real Life Wizard of Oz” who helped his clients do things like…

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The Inner Game of Work: Pranab Sachi on Codependent Origination, Rob Burbea, Quake Books, Attentional Co-Piloting, Michael Taft, and "Non-Success" 1:21:31

3M ago1:21:31

1:21:31

In this episode, I interview my friend Pranab Saachi, and we get specific about the ideas and influences that have shaped his thinking. We talk about codependent origination from Buddhist philosophy, the concept of “quake books” that have shifted his worldview, and his own approach to “attentional co-piloting” as a practical alternative to traditio…