Best Flight To Financial Freedom Podcasts (2025)

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

4h 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
06.03.25 Ask An Advisor With Wes Moss 43:02

18h ago43:02

43:02

Investing in Gold: Smart Move or Mistake? and Will Entry-Level Jobs Disappear? Should you own gold? How much should you own? Fiduciary financial advisor Wes Moss breaks down the data and shares his take on investing in gold to help you determine if it belongs in your portfolio. Also, the CEO of a major AI company recently said that 50% of all entry…

1
06.02.25 Clark’s Auto Loan Directive / Skimmer Scam Prevention 28:32

1d ago28:32

28:32

June signals upcoming road trips and today, Clark talks about some transportation hazards to avoid. First, when buying a vehicle, know how significant the length of the loan can be to your financial health. Also, skimming scams at gas pumps and beyond - have gotten more sophisticated. Clark shares 2 ways to protect your money. Auto Loan Warning : S…

1
Ask HTM - Early Retirement Target Date Funds, Frugal Personal Hygiene, & Coercive House Painting #991 51:27

2d ago51:27

51:27

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

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

2d 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
05.30.25 Clark Answers His Critics on Clark Stinks / Tech Brakes On Super Speeders 31:52

5d ago31:52

31:52

Help us surprise Clark Howard for his birthday! We're collecting special wishes for Clark (it's a secret!) to celebrate his birthday on June 20th. Use this form to share your wishes for Clark: https://forms.gle/hNtmFTvqkdZc94J49 -- remember it's a secret! ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~Friday - Clark Stinks day! Christa shar…

1
Friday Flight - TACO Trading, Pointless Points, & Millionaire Renters #990 34:17

5d ago34:17

34:17

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

1
#56 - Earth's First Reset (the flood, epic of Gilgamesh, & the teachings of Paul) w/Gary Wayne 2:05:25

6d ago2:05:25

2:05:25

Watch the full video version here: https://youtu.be/e2IRjGH_xXA

1
05.28.25 Best Auto Insurance / Economic Uncertainty: Preparation & Family Communication 37:15

7d ago37:15

37:15

In this episode - As auto insurance rates continue to rise, more people recognize the need to shop around. Clark shares a valuable resource for where to start. Also today - Economic uncertainty necessitates ongoing family conversations about money and the economy, and what can be done to prepare for a possible recession or employment setback. Shop …

1
Pharmacist to Full Time Real Estate Investor w/ Ryan Chaw #989 55:51

7d ago55:51

55:51

Newer listeners may not realize how OBSESSED with investing in real estate we were back in the day. In fact, when we were batting around ideas for a podcast, we initially thought it might be focused only on real estate... Luckily we zoomed out enough to cover personal finance more broadly. And it’s not that we’re not excited about rentals anymore, …

1
Embrace Productivity for a More Impactful Life with Tanya Dalton 38:26

7d ago38:26

38:26

How can we break free from hustle culture? Here’s a hint: The answer is not doing more; it’s being intentional. In this new episode, we sit down with bestselling author and productivity expert Tanya Dalton to discuss: Why traditional productivity advice leaves so many feeling burned out and behind The mindset shift that helps you align your work wi…

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

7d 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…

1
05.27.25 Ask An Advisor With Wes Moss 46:12

8d ago46:12

46:12

10-Step Checklist BEFORE You Retire and How Spending Money in Retirement Actually Works Ready to retire? Fiduciary financial advisor Wes Moss walks you through the essential 10-point checklist you should complete before leaving the workforce. Also, Wes breaks down the often-confusing topic of spending money in retirement. How do you actually access…

1
Ask HTM - Buying a Used Mattress, Best Use of an Inheritance, & Disqualified from a Roth #988 50:36

9d ago50:36

50:36

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
117. Making Smart Transfer Moves: When Speculative Points Transfers are Worth It (And When They’re Not) 27:06

9d ago27:06

27:06

A major points transfer pathway is shutting down—and it's got a lot of people wondering: should I move my Amex points to Alaska Airlines before the door closes? In this episode, I break down the fast-approaching June 30 deadline to transfer Amex points to Hawaiian Airlines (and from there to Alaska), and walk you through my personal decision—includ…

1
05.23.25 Clark Answers His Critics on Clark Stinks / U.S. Air Traffic Control 37:46

12d ago37:46

37:46

Friday - Clark Stinks day! Christa shares Clark Stinks posts with Clark. Submit yours at Clark.com/ClarkStinks. Also today, Clark discusses how the shortage of air traffic controllers and lack of current tech will impact air travel this summer, looks to Canada’s successful model, and shares his playbook for navigating air travel Clark Stinks: Segme…

1
Friday Flight - Credit Crunch, MAGA Money, & Gas Gouging #987 36:13

12d ago36:13

36:13

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

1
#111 - Five Investing Strategies for High-Earning Pilots 44:56

12d ago44:56

44:56

Get ready to fast-track your financial freedom. In this power-packed solo episode, Tait Duryea and Ryan Gibson share the top strategies from over 110 episodes of Passive Income Pilots. From unlocking hidden cash in your 401(k) and home equity to leveraging life insurance and short-term rentals for major tax breaks, they distill years of pilot-speci…

1
#55 - The Altar of Anxiety (counterfeit wisdom, self-reliance, & rewiring fear) 1:57:55

13d ago1:57:55

1:57:55

Watch the full video version here: https://youtu.be/ASnMgsS5MMM

1
05.21.25 The Airline Recession / Student Loan Repayment 37:07

14d ago37:07

37:07

Travel demand has slowed and airlines are cutting service. Today Clark discusses the airline recession taking place, and the hazard & opportunity this presents for travelers. Also, Clark addresses some of the confusion surrounding student loan repayment. What you need to know if you or a family member has student loan debt. Air Travel Guidance: Seg…

1
Impoverished Upbringing to Money Monster w/ Listener Nick Gangwer #986 53:10

14d ago53:10

53:10

We’re trying something completely new for our episode today: we’re hearing from a listener. Not in the form of a question submitted via voice memo, but we’re actually sitting down and having a ‘real money’ conversation, with Nick Gangwer. We met Nick at a listener hang about a year ago and his personal story and the proactive steps that he had take…

1
05.20.25 Ask An Advisor With Wes Moss 39:48

15d ago39:48

39:48

Are We in a Passive Investing Bubble? and Lump Sum Investing vs. Dollar Cost Averaging Is passive investing creating a stock market bubble? Fiduciary financial advisor Wes Moss dives into the rise of index funds, why they became so popular, and the potential concerns. Also, Wes covers a classic investing strategy: Dollar Cost Averaging (DCA). He ex…

1
05.19.25 The True Costs Of 401(k) Loans / Checked Bags - Lost & Found 29:47

16d ago29:47

29:47

The 401(k) is a great retirement instrument because saving is automatic and investments grow over time. So is it ever OK to ⁠borrow from a 401(k)⁠? Know the “opportunity costs” involved. Also - good news if you like to ⁠check bags⁠ on flights. 401(k) Loans: Segment 1 Ask Clark: Segment 2 No More Lost Luggage!: Segment 3 Ask Clark: Segment 4 Mention…

1
Ask HTM - Special Roth Accounts, Investing During A Sabbatical, & Reverse Mortgages #985 51:28

16d ago51:28

51:28

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
116. The Award Travel Trick Hiding in Plain Sight: Fifth Freedom Flights 25:26

16d ago25:26

25:26

If you’ve ever struggled to find award space—especially in business class—this is the episode you’ve been waiting for. In this episode, I’m diving into a unique but often overlooked type of airline route called a fifth freedom flight. These flights are legal exceptions in commercial aviation that allow an airline to fly between two foreign countrie…

1
05.16.25 Clark Answers His Critics on Clark Stinks / Bumpy Ride For Car Buyers 33:29

19d ago33:29

33:29

Friday - Clark Stinks day! Christa shares Clark Stinks posts with Clark. Submit yours at Clark.com/ClarkStinks. Also, potential car buyers face a lot of questions right now - should you buy new or used? If buying used, is Certified Pre-Owned (CPO) the way to go? Clark shares advice to help you navigate decision making. Clark Stinks: Segments 1 & 2 …

1
Friday Flight - Streaming Sports, Trade-In Tradeoffs & AI Lies #984 36:53

19d ago36:53

36:53

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

1
#54 - The Cult of Mind Control (dissociation, Luciferian bloodlines, & the Gospel) w/Nathan Reynolds 2:27:54

20d ago2:27:54

2:27:54

Watch the full video version here: https://youtu.be/bEFtrokEfAI?si=dS91yHneeb3gVv49

1
05.14.25 Saving Strategy: Series I Savings Bonds / The U.S.-China Tariff Reprieve 31:44

21d ago31:44

31:44

Today, learn more about I-Bonds. Are they still worth buying? Clark explains how I-Bonds work and why they can be a solid part of your saving strategy. Also, the tariff news keeps coming, with a temporary reprieve on goods from China now in effect. Clark discusses what this will mean for consumers and merchants moving forward. Series I Savings Bond…

1
Practical AND Beautiful Investing Advice w/ Callie Cox #983 56:40

21d ago56:40

56:40

What it means to have a practical and beautiful portfolio. How recent policy decisions have roiled the stock market. Right-sizing your risk tolerance… These are just a few of the topics we discuss with our guest Callie Cox who is a part of the Ritholtz Wealth Management team. She is also the author of OptimistiCallie, her newsletter where she seeks…

1
Master the Mindset of Transformation With Courtland Warren 49:00

21d ago49:00

49:00

What does real transformation actually take? Courtland Warren, thought leader, master facilitator, and SUCCESS® Leadership Lab facilitator, shares why transformation is permanent—and how to lead yourself and others through true change. Learn how to shift from fear to purposeful action, release limiting beliefs, and live with discipline and self-mas…

1
#110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury 54:06

21d ago54:06

54:06

In this episode, hosts Tait Duryea and Ryan Gibson welcome Ramez Fakhoury from IRA Club. This episode dives into how pilots can unlock old 401(k)s, TSPs, and HSAs for real estate and other alternative investments. Hear a detailed story of a Southwest pilot transitioning to American Airlines and learn what decisions made the biggest impact. Whether …

1
05.13.25 Ask An Advisor With Wes Moss 43:08

22d ago43:08

43:08

Breaking Down ETFs/Index Funds/Mutual Funds and Retirement vs. Brokerage Accounts Confused about ETFs, index funds, and mutual funds? Fiduciary financial advisor Wes Moss breaks down these "cousins" of investing – including when to use them. Also, retirement accounts vs. brokerage accounts – what’s the difference and what’s the best option for you?…

1
05.12.25 Income Inequality / Privacy Alert! Alexa Can Hear You 29:06

23d ago29:06

29:06

The Congressional Budget Office update found the top 10% of earners in the U.S. have 70% of the nation’s wealth, possibly the greatest disparity in our history. Today, Clark discusses the severity of income inequality and its effects on our society. Also - if you have a smart device in your home, you might not realize some of the privacy concerns, …

1
115. Rhythms, Routines, and REM: Expert Tips to Manage Jet Lag & Sleep Disruption While Crossing Time Zones 43:38

23d ago43:38

43:38

No matter how dreamy your destination is, there’s one thing that can make or break your trip: sleep. In this episode, I’m joined by sleep therapists Leah Corkum and Marlee Boyle, co-founders of Sleep-Works, a Canadian-based virtual sleep education company helping individuals and families improve their sleep health. With certifications in CBT for in…

1
Ask HTM - Unnecessary Credit Cards, Creatively Funding Grad School, & Dropping Car Insurance To Save #982 52:42

23d ago52:42

52:42

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
05.09.25 Clark Answers His Critics on Clark Stinks / How Restaurants Survive 35:51

26d ago35:51

35:51

Friday - Clark Stinks day! Christa shares Clark Stinks posts with Clark. Submit yours at Clark.com/ClarkStinks. Also - Restaurants of all types are having to adapt to difficult market conditions. Many have failed in the last two years due to high food, labor and leasing costs. Those that succeed offer lessons in adaptation for all businesses. Clark…

1
Friday Flight - Paper Wealth, Target Date Trends, & Bye Bye Buffett #981 36:01

26d ago36:01

36:01

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

1
05.07.25 Protect Your Home Title / What Job Seekers Should Know 33:48

28d ago33:48

33:48

In today’s episode - you may have heard ads for services that allegedly lock your home’s title. Are they worth it? Clark talks about how best to guard your greatest asset - your home. Also, as the economy goes into lower gear with layoffs more frequent, Clark has important new info for today’s job seekers. Home Title Protection: Segment 1 Ask Clark…

1
Creating a Post-Layoff Action Plan w/ Marlo Lyons #980 54:54

28d ago54:54

54:54

Gone are the days of constantly job hopping in order to rapidly boost your salary! Remember when perusing new job listings during your lunch break while WFH led to a 10-30% pay bump?! Now, with the uncertainty we’re experiencing in the overall market, it’s not just the new hires who are a bit nervous about hanging onto their jobs. Even government w…

1
#109 - The Flight Plan for Syndications: Risk, Returns, and Real Wealth 39:19

28d ago39:19

39:19

In this episode, hosts Tait Duryea and Ryan Gibson deliver an in-depth, pilot-friendly primer on syndications and passive real estate investing. They break down the risk spectrum from core to opportunistic deals, while sharing real-world analogies and experiences from their own projects, like the Canyon City land entitlement. Learn how to properly …

1
05.06.25 Ask An Advisor With Wes Moss 44:28

29d ago44:28

44:28

Is Owning a Home Still a Good Investment? and 5 Areas To Cover With a Financial Advisor Ever wonder if buying a home is still a smart move in today's market? Fiduciary financial advisor Wes Moss reveals why housing can be a powerful "forced savings plan" and a hedge against inflation, especially for happy retirees. He examines historical trends, th…

1
05.05.25 Burglars Go High Tech / Avoid This Hotel Booking Mistake 34:08

30d ago34:08

34:08

Today, Clark has 2 key warnings. First - you won’t believe how burglars are casing your home now using hidden high tech - what to look out for. And - how to avoid getting burned when booking a hotel. Plus, Clark answers your questions - post at Clark.com/ask. Burglar Surveillance: Segment 1 Ask Clark: Segment 2 Hotel Booking Warning: Segment 3 Ask …

1
114. Finally! Turning Your Mortgage into Points: How Mesa is Flipping the Script on Rewards 30:56

30d ago30:56

30:56

There’s finally a card that rewards you for the one expense that’s been completely ignored in the points world: your mortgage. In this episode, I’m talking with Kelley Halpin, CEO of Mesa, about the first credit card that lets you earn points for mortgage payments—plus other major homeowner expenses like daycare, utilities, and home improvement. Ke…

1
Ask HTM - Pro Help to Break the Paycheck to Paycheck Cycle, Down Payment Money Market Accounts, and Viable Student Loan Forgiveness Plans #979 45:33

30d ago45:33

45:33

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
05.02.25 Clark Answers His Critics on Clark Stinks / Tariff Adaptation 33:43

1M ago33:43

33:43

Friday - Clark Stinks day! Christa shares Clark Stinks posts with Clark. Submit yours at Clark.com/ClarkStinks. Also today, Clark talks about innovation in the face of tariffs. A new tool has been created to help some businesses navigate prices, and it’s a great example of American ingenuity. Clark Stinks: Segments 1 & 2A Tariff Tool: Segment 3 Ask…

1
Friday Flight - Thrifty Trucks, Pricey Parking, & Soaring Secondary Costs #978 34:36

1M ago34:36

34:36

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

1
#53 - The Cost of Being Chosen (movements, obscurity, & submission) 2:12:48

1M ago2:12:48

2:12:48

Watch the full video version here: https://youtu.be/pzK9FfuQocw

1
#108 - Case Study: Real Estate Professional Status That Held Up in Court with Brandon Hall 21:04

1M ago21:04

21:04

In this episode, Tait Duryea flies solo to spotlight a powerful tax strategy many high-income earners overlook: real estate professional status. Featuring Brandon Hall from Hall CPA, this episode breaks down a real tax court victory by a harbor pilot who leveraged a flexible W-2 job schedule to claim REP status and unlock massive tax savings. Disco…

1
04.30.25 Tariff Proof Your Wallet / SAVE on Home Energy 28:39

1M ago28:39

28:39

Today, Clark talks about where you can find deals that aren’t subject to tariffs. Also, now is the time to consider ways to lower home energy costs and Clark shares some money saving ideas. Buy Secondhand First: Segment 1 Ask Clark: Segment 2 Home Energy: Segment 3 Ask Clark: Segment 4 Mentioned on the show: 9 Things You Should Always Buy Used Auto…

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