Best Finance Flight Path Podcasts (2025)

1
#135 - The Truth About Oil and Gas Investing with Tim Pawul 52:50

Play Pause

3d ago52:50

52:50

Are you unknowingly passing up five-figure tax savings available right now? Tait Duryea and Ryan Gibson sit down with oil and gas expert Tim Pawul to reveal why minerals, royalties, and non-operated working interests have become one of the most powerful tools for cash flow and tax strategy. Get ready to understand the real reason hydrocarbons aren’…

1
143. Your Holiday Points Prep Checklist: 5 Steps to Maximize Seasonal Spending 11:58

6d ago11:58

11:58

This week marks the biggest points-earning opportunity of the entire year—especially if you're planning to shop online. While everyone else is focused on Thanksgiving prep, points and miles travelers know this is the week to turn everyday purchases into tens of thousands (or more) of bonus points. In this short and focused episode, I'm sharing my 5…

1
#134 - Fatigue, Flight Deck Safety, and the Science of Sleep with Dr. Adam Shapiro 49:53

11d ago49:53

49:53

Sleep becomes exciting, especially when it’s with Dr. Adam Shapiro. Tait Duryea and Ryan Gibson sit down with this board-certified sleep specialist and ATP pilot to uncover what every aviator needs to know to protect their health and their medical. Get ready for practical guidance on staying sharp, staying healthy, and staying in the cockpit longer…

1
142. How Points Become a Tool for Freedom, Joy & the Life You Want to Live with Dielle Charon 48:03

13d ago48:03

48:03

Travel is never just about the destination — it's about what the journey makes possible. In today's episode, we explore how learning to earn and use credit card points isn't just a smart financial decision. It's a pathway to freedom, abundance, and experiences that reflect the life you actually want to live. From upgraded flights to dream hotels, p…

1
#133 - Year-End Tax Moves Pilots Can’t Miss with Toby Mathis 52:37

17d ago52:37

52:37

Taxes become more exciting, especially when it’s with Toby Mathis. Tait Duryea and Ryan Gibson welcome back tax strategist and investor Toby Mathis for another powerhouse session on how to keep more of your money before year-end. From bonus depreciation and the short-term rental loophole to smarter charitable giving and donor-advised funds, Toby re…

1
141. Listener Q&A: Canceling Cards, Transfer Partner Confusion & Shopping Portals vs. Welcome Bonuses 1:05:39

20d ago1:05:39

1:05:39

This episode is all about your questions—and real answers. I'm back with another listener Q&A, tackling the points and miles decisions you're actually making right now. From whether it's possible to move points between airline partners to deciding if that old United card still deserves a spot in your wallet, we're covering it all. We'll walk throug…

1
#132 - How to Buy an Airport with Robert DeLaurentis 55:43

24d ago55:43

55:43

What happens when a real estate investor decides to buy an airport? In this episode, host Tait and Ryan sit down with Robert DeLaurentis, the “Peace Pilot,” to unpack how he transformed a rundown airport into a thriving hub of aviation and community life. Robert shares how his decades in multifamily real estate funded his passion for flying, why le…

1
140. Points Path: The Tool That Shows You the Best Value for Every Flight 49:23

27d ago49:23

49:23

Ever look at Google Flights and wonder, "Should I use points for this or just pay cash?" If you've ever felt unsure about which option gives you the best value, this episode is for you. In the final episode of our Streamline, Stack, and Save mini-series, I'm joined by Julian Kheel, former editorial director at The Points Guy and senior editor at CN…

1
#131 - Reading the Economy: Insights from the Bowtie Economist, Dr. Elliot Eisenberg 40:38

1M ago40:38

40:38

Where should you put your money right now? Ryan Gibson and Tait Duryea sit down with economist Dr. Elliot Eisenberg to decode the markets, interest rates, and the economic forces shaping your portfolio. From AI layoffs to multifamily real estate, they break down how high-income earners, especially pilots, can build wealth intelligently amid uncerta…

1
139. Stack Shopping Portals and Card Offers for Bigger Rewards with Savewise 56:10

1M ago56:10

56:10

Do you ever find yourself opening multiple tabs, comparing shopping portal payouts, and trying to figure out which site is going to give you the most rewards for your online shopping — only to give up before you actually earn the points? If that sounds familiar, today's episode is for you. In this Streamline, Stack, and Save mini-series episode, I'…

1
#130 - From Wall Street to Real Wealth: Lessons from Ted Greene 28:56

1M ago28:56

28:56

What does true diversification look like when you’re building wealth as a pilot? In this episode, Ryan Gibson sits down with his longtime colleague and friend, Ted Greene, to unpack how to define success with your spouse, avoid emotional investing, and create a portfolio that brings peace of mind. From surviving Wall Street lawsuits to building las…

1
138. How to Track, Manage, and Maximize Your Credit Cards with Travel Freely 1:02:05

1M ago1:02:05

1:02:05

Have you ever opened a new credit card for the welcome bonus, only to forget how much you've spent or when the deadline hits? Or maybe you're juggling multiple cards and can't remember which one to use next. In this next episode of our Streamline, Stack, and Save mini-series, I'm joined by Zac Hood, founder of Travel Freely, an app that helps you t…

1
137. Stop Guessing, Start Earning: How CardPointers Does the Work for You with Emmanuel Crouvisier 42:20

2M ago42:20

42:20

Do you ever forget which credit card to use for a purchase — or worry you're missing out on bonus points and statement credits? It's easy to lose track when every card has different categories, offers, and perks. This episode is part of our Streamline, Stack, and Save mini-series, where we're exploring tools and strategies that simplify how you ear…

1
#129 - Ego, Taxes, and the Paycheck Trap: Pilot Wealth Myths Exposed 29:42

2M 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…

1
136. Mini Retirements: Redefining How You Work, Rest, and Live with Jillian Johnsrud 59:17

2M ago59:17

59:17

Do you think you have to wait until your sixties before you can retire? Maybe not. At least not the way we've been taught. In this episode, I'm joined by Jillian Johnsrud — author, podcast host, and coach — who challenges the idea of a traditional retirement in favor of taking mini retirements throughout your life and career. Jillian never expected…

1
#128 - Inside the Fine Print: PPMs, Trust, and Investor Protection with Seth Bradley 42:46

2M 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…

1
135. Amex Platinum Cards Refresh: What's New, What's Missing, and What We Really Think 1:00:44

2M ago1:00:44

1:00:44

Back in June, Chase refreshed its personal Sapphire Reserve card and introduced the Chase Sapphire Reserve Business card, complete with highest ever annual fees for rewards cards. Not to be outdone, American Express quickly followed with its own updates to the personal and business Platinum Cards. Now that the details are here, it's time to look at…

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

2M 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…

1
134. The New Era of Award Travel: What's Changing and How to Adapt 29:00

2M ago29:00

29:00

If you've been in the points game for years, you've probably noticed how much has changed recently. And if you're newer, you might be wondering if you're already too late. In this episode, I share why I don't believe we're in the "golden age" of award travel right now — but also why points are still incredibly valuable if you know how to adapt. Ove…

1
#126 - Early Real Estate Mistakes and Lessons Learned 33:11

2M 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…

1
133. 7 Keys to Better Award Flight Bookings 48:51

3M ago48:51

48:51

You've built up a stash of transferable credit card points. Maybe you've been working hard to optimize your cards, your categories, and your spending. But when it comes time to actually book the flights you've been dreaming about, you hit a wall. You're not alone. For most points travelers, the hardest part isn't earning points — it's redeeming the…

1
132. From Frustration to $150K in Points Redemptions 1:03:57

3M ago1:03:57

1:03:57

What does it really look like to transform your travel with credit card points? In this special episode, you'll hear directly from Dr. Faryal Michaud, a past Points Made Easy student who went from feeling confused and frustrated by points to booking over $150,000 worth of award travel. From Qsuites to the Maldives, South Africa, Tahiti, and beyond,…

1
#125 - Oil & Gas Investing for High-Income Pilots with Mark Fleming 52:18

3M 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…

1
131. Unpopular Opinion: Top 5 Reasons You Should Book Travel Through a Credit Card Travel Portal 41:07

3M ago41:07

41:07

Think booking through your credit card travel portal is always a mistake? Not so fast. Last week, I shared five reasons why you'll want to avoid making travel bookings through your credit card portal. But that's not the whole story. There are also situations where using your card's travel portal can be the smarter move. In this episode, I'm breakin…

1
#124 - $44 Trillion and the Future of Retirement Investing with Mat Sorensen 50:52

3M 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…

1
130. Top 5 Reasons to Avoid Booking Travel Through Credit Card Travel Portals 39:06

3M ago39:06

39:06

If there's one thing nearly every points traveler has done at least once, it's book a flight, hotel, or car rental directly through their credit card's online travel portal. With promises of 5x, 8x, even 12x bonus points, it can feel like the obvious choice. But as I share in today's episode, those tempting multipliers often come at a serious cost—…

1
#123 - Market Cycles, Debt, and Real Estate Opportunities with Hunter Thompson 49:22

3M 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…

1
129. Fan Favorite: The Psychology of Learning & Mastering Points Travel 29:49

3M ago29:49

29:49

In this week's episode, we're re-airing a fan favorite that so many listeners have loved and revisited. If you missed it the first time, or just need a refresher, this is one you don't want to skip. I love discussing discrete award travel topics like individual rewards credit cards and how best to leverage them, or the specific airlines and hotels …

1
#122 - How Pilots Use Whole Life Insurance to Fund Investments with Rod Zabriskie 49:50

4M 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 …

1
128. The New Citi Strata Elite: Game Changer or Missed Opportunity? 35:58

4M ago35:58

35:58

If a $595 annual fee premium credit card hits the market, should it automatically earn a place in your wallet? In this episode, I take a detailed look at Citi's newest addition to the transferable points landscape: the Citi Strata Elite Card. From its standard 80,000-point welcome bonus to the elevated 100,000-point offer available through certain …

1
#121 - Short-Term Rentals, Long-Term Wealth with Pilot Couple Brad Hilton and Aubrey Carlson 54:12

4M 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…

1
127. Lounge Access Update: Credit Card Changes, Perks & Picks with Traci Siegel 48:27

4M ago48:27

48:27

If you've ever been confused about airport lounge access—what counts, what's changed, and what's still worth it—you're not alone. In this episode, I welcome back guest Traci Siegel for an updated look at lounge access using rewards credit cards in 2025. We unpack the biggest changes to credit card lounge access this year, including new restrictions…

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

4M 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,…

1
126. How Much Is a Point Really Worth? A Deep Dive with Frequent Miler's Greg Davis-Kean 54:43

4M ago54:43

54:43

If you've ever hesitated before transferring points—or wondered if a redemption was "good enough"—this is the episode you've been waiting for. In this conversation with Greg Davis-Kean (a.k.a. Frequent Miler), we unpack how to think more strategically about the value of your points. Whether you're sitting on a big stash or navigating your first tra…

1
125. Maximizing the Citi Ecosystem with Dr. Suzy Spadafora 59:22

4M ago59:22

59:22

Ever feel like Citi cards get overlooked in points conversations? If you've written off Citi's ecosystem—or just haven't known how to make it work for your travel goals—this episode is full of smart, real-life strategy. Dr. Suzy Spadafora returns to discuss the strengths (and limitations) of the Citi points ecosystem. From the points earning cards …

1
#119 - LLCs, Trusts, and Bulletproof Asset Protection with Adam Kintigh 53:43

5M 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…

1
124. Mid-Year Points Update: What I Burned, Booked & Learned 42:03

5M ago42:03

42:03

Ever wonder what's actually possible with points? In this episode, I'm taking you behind the scenes of how I've already booked and taken 5 international trips in 2025—spending 2.9 million points on award flights and hotels, and saving over $150,000 in travel costs. From a spring break family trip to Paris to a spontaneous 2-day Tokyo adventure, I'm…

1
#118 - The Big Beautiful Tax Bill with Nathan Sosa 48:38

5M 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…

1
123. Using Real Estate Spending to Maximize Credit Card Points with Jaina Pallasigui 33:02

5M ago33:02

33:02

Have you ever wondered how real estate investments could help you travel more—without spending more? In this episode, I'm joined by Jaina Pallasigui, a public health professional, real estate investor, and points enthusiast who turned her real estate expenses into business class flights and luxury hotel stays around the world. From managing short-t…

1
#117 - How to Evaluate and Join Real Estate Syndications 43:12

5M ago43:12

43:12

Ever wonder what happens when you invest in a syndication? In this episode, hosts Tait Duryea and Ryan Gibson break down how real estate syndications work, from deal sourcing and underwriting to legal docs, fees, and investor returns. Learn how passive investors get access to large-scale deals, what to look for in a sponsor, and what happens after …

1
122. Listener Q&A: Adding a Third Points Currency, Booking Emirates First, and Points Regret 1:09:45

5M ago1:09:45

1:09:45

This episode is all about your questions—and real answers. I'm back with another listener Q&A, tackling the exact points and miles decisions you're working through right now. Ever feel like you're making credit card decisions in a vacuum? From wondering if it's time to add Capital One or Mesa to your rewards card portfolio, to recovering from redem…

1
#116 - Medical Checkride: Medical Myths, Truths, and Tips with Dan Monlux 55:19

5M ago55:19

55:19

What could cost you your flying career? Not being prepared for your medical. Hosts Tait Duryea and Ryan Gibson welcome back Dan Monlux of Wingman Med to discuss how pilots can protect their FAA medical certificates. Dan breaks down what happens during a medical exam, the importance of primary care, and why early detection matters. This is a must-li…

1
121. Chase's New Business Card Just Dropped & The CSR Gets An Update—Here's Why We're Not Impressed 56:05

5M ago56:05

56:05

Chase just launched a new business credit card and rolled out changes to the Chase Sapphire Reserve—but are these updates actually worth getting excited about? In this episode, I'm joined once again by Kelly from The Points and Miles Doc for a candid review of what's new in the Chase ecosystem. From rising annual fees to underwhelming credits and a…

1
#115 - Inside Self-Storage: A Hidden Powerhouse for Investors 50:47

6M ago50:47

50:47

Get ready to uncover the secrets of one of commercial real estate’s most resilient and misunderstood asset classes: self-storage. In this in-depth episode, Tait Duryea and Ryan Gibson explore why self-storage continues to outperform in uncertain times, how millennials are transforming storage use, and what makes it such a powerful wealth vehicle fo…

1
120. The biggest surprises (and letdowns) of 2025 so far 1:20:15

6M ago1:20:15

1:20:15

Have you been wondering what's really happening in the world of credit card points and award travel this year? In this episode, I'm joined by Kelly, The Points and Miles Doc to break down the biggest shifts in 2025 so far. From major devaluations to standout sweet spots, we're giving you an honest look at what's working now—and what's not. We also …

1
#114 - Trusts, Taxes & Transfers: What Every Investor Should Know with Amanda Wynalda 59:50

6M ago59:50

59:50

In this episode, hosts Tait Duryea and Ryan Gibson sit down with attorney Amanda Wynalda from Anderson Advisors to unpack everything pilots and high-income earners need to know about trusts, wills, and asset protection. From revocable vs. irrevocable trusts to layering LLCs and avoiding the due-on-sale clause, this episode is a blueprint for protec…

1
119. Alaska Airlines Sweet Spots: Amazing Ways to Use Alaska Miles (That You Might Be Missing) 28:41

6M ago28:41

28:41

Have Alaska miles—or thinking of transferring your Amex points before the June 30 deadline? In this episode, I'm breaking down some of the most valuable ways to redeem Alaska Airlines miles right now. From low-cost domestic redemptions to hard-to-find international business class flights, this guide walks you through the sweet spots that make Alask…

1
#113 - The Fed, The Treasury, and Your Portfolio with Dr. Peter Linneman 53:42

6M ago53:42

53:42

In this episode, hosts Tait Duryea and Ryan Gibson talk with chief economist Dr. Peter Linneman to demystify interest rates, the national deficit, and how it all affects pilots, real estate investors, and entrepreneurs. Discover why U.S. debt may not be the threat it’s made out to be, how capital flows drive values, and what most people get wrong a…

1
118. Jet-Set with JAL: Bilt's Boldest Transfer Partner Yet 38:25

6M ago38:25

38:25

Have you ever dreamed of flying to Japan in business class—without paying out of pocket? Bilt just made that a lot easier. In this episode, I'm joined by award travel strategist Ben Komenkul to talk about the newest (and most exciting) Bilt Rewards transfer partner: Japan Airlines. This partnership opens the door to premium flights across Asia and …

1
#112 - The Tax Strategies Every Pilot Should Know in 2025 with Thomas Castelli 47:15

6M ago47:15

47:15

In this episode, Tait Duryea and Ryan Gibson welcome CPA Thomas Castelli of Hall CPA to break down the latest tax developments affecting high-income earners. From the potential return of 100% bonus depreciation to how the real estate professional status works in practice, Tom shares key strategies to help you keep more of what you earn. Whether you…