Best Pilot Wealth Management Podcasts (2025)

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

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5h 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

3d 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

3d 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

9d 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

8d 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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303. Pilot’s Guide to Financial Turbulence: Planning for Medical Disabilities 34:45

10d ago34:45

34:45

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

18d 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

16d 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

16d 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

23d 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

21d ago26:34

26:34

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

25d 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

23d 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

23d 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

1M 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

29d 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

2M 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

2M 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

2M 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…

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294. What Flying a Plane Teaches Us About Financial Risk 45:21

2M ago45:21

45:21

In this episode of the A Wiser Retirement® Podcast, we cover how principles from aviation, like threat and error management, proactive and reactive planning, and strong team communication, can be applied to personal financial planning. Casey Smith is joined by airline Captain Evan Bogan to explore how pilots handle unexpected challenges and how fam…

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#249: What “Death Mindfulness” Has To Do With Selling 2 Million Books, Being Blessed By Madonna, & Designing Your To-Die-For Life w/ Karen Salmansohn 54:10

2M ago54:10

54:10

Imagine you’re at your favorite restaurant when — out of the corner of your eye — you spot Madonna. Most people would whisper about it to their friends and watch from afar. Not Karen Salmansohn. Karen — a best-selling author of 20+ books with over 2 million copies sold — didn’t just say hi. She walked right up to Madonna’s table, dropped her hilari…

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How much money do you need to quit? I debate with Nick Maggiulli (and rabbit holes: wealth > income, why COAST FIRE rocks, and more...) 1:19:11

2M ago1:19:11

1:19:11

In this episode, I'm pumped to welcome back Nick Maggiulli to the podcast (https://youtu.be/deMXbaI-Ir4). We dive into various topics about money and financial independence, with a focus on Nick's endorsement of the 'COAST Fire' strategy, something I accidentally embraced after quitting my job. Nick shares his personal stories of financial challeng…

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293. Retirement for Business Owners: Selling Your Business or Passing It On 35:57

2M ago35:57

35:57

Whether you're planning to retire, sell your business, or pass it on to the next generation, having a clear succession plan is essential. Unfortunately, many business owners delay this process, putting the value of their life's work at risk. In this episode of the A Wiser Retirement® Podcast, we cover the key steps every business owner should take …

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#119 - LLCs, Trusts, and Bulletproof Asset Protection with Adam Kintigh 53:43

2M ago53:43

53:43

What if your rental property is a lawsuit away from costing you everything? Tait Duryea connects with asset protection expert Adam Kintigh of Nevada Corporate Headquarters to break down what every investor should know about shielding wealth. From piercing the corporate veil to choosing between LLCs and real estate privacy trusts, this episode cover…

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#248: Interview With My Grandpa Fong: Immigrating From a War-Torn Country at Age 8 → How He Turned $5/Week Into a Community Pillar 1:07:11

2M ago1:07:11

1:07:11

Twelve days after his 87th birthday, my grandpa passed away. After we said our goodbyes at the funeral and shared a meal together, my family gathered back at his house. That’s when many of them found out something they hadn’t known: Several years before his passing, I sat down with my grandpa for six hours of interviews — just asking him questions …

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EP 44: Why EVERY Millionaire Has Trauma Around Money (Wealth Manager Exposes The Truth) 57:04

2M ago57:04

57:04

What if wealth management wasn’t just about numbers, but about transforming who you become? In this profound episode, host Madhavi Jain sits down with Tim “Jai” Baker, a wealth manager who has spent over four decades revolutionizing how we think about money, values, and life purpose. After losing his daughter in 2005, Tim’s journey to India led to …

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292. Is an MBA Worth the Investment? 37:30

2M ago37:30

37:30

In this episode of the A Wiser Retirement® Podcast, we explore whether pursuing an MBA is truly worth the investment. We’re joined by Nancy Mercer, Assistant Dean and Director of MBA Marketing and Admissions, and Dr. Lauren Heller, Dean of the Campbell School of Business at Berry College, for an inside look at how MBA programs have evolved and what…

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#118 - The Big Beautiful Tax Bill with Nathan Sosa 48:38

2M ago48:38

48:38

Get ready to demystify the 2025 Tax Bill. Hosts Tait Duryea and Ryan Gibson sit down with Nathan Sosa, tax strategist at Hall CPA, to uncover what this sweeping legislation really means for pilots and high-income earners. From the return of 100% bonus depreciation to new deductions for auto loans and overtime, Nathan breaks down exactly who benefit…