Best Pilot Financial Freedom Podcasts (2025)

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Think you know your mortgage? Think again. 39:58

1d ago39:58

39:58

Send us a text Think you know your mortgage? Think again. In this episode, we pull back the curtain on the truth about today’s wild housing market — because “hoping it’ll all work out” isn’t a plan. While the market showed a tiny spring stir in May, the year-over-year numbers are still sluggish, and the condo market? Let’s just say it’s having a mo…

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

6d 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…

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Stage It Like You Mean It 41:21

12d ago41:21

41:21

Send us a text Stage It Like You Mean It: Secrets from a Pro Stager with KP Staging & Design “Hey hey, friends! Welcome back ! — to the podcast where we turn big moves into smooth ones, especially for my fellow downsizers, right here in the GTA. Today’s episode? Ooh, it’s a juicy one. If you’ve ever looked around your home and thought: ‘How do I ma…

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

13d 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…

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

20d 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…

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Why Your Credit Score Matters More Than You Think in 2025 23:43

21d ago23:43

23:43

Send us a text Why Your Credit Score Matters More Than You Think in 2025 "Your Credit Score is Judging You—Let’s Talk About It." 📌 In this power-packed episode of Elementary, I start with a BIG announcement—yes, The Globe and Mail featured me in their article on downsizing regrets! 🙌🏽 But here’s what that story really made clear: too many people ma…

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Condo, Bungalow, or Bye-Bye? How to Pick the Right Home Without Losing Your Mind (or Your Wallet) 36:00

26d ago36:00

36:00

Send us a text Condo, Bungalow, or ...? How to Pick the Right Home Without Losing Your Mind (or Your Wallet) Welcome back to Elementary – your real estate reality check with no fluff, just facts (and a sprinkle of sass). 💁🏽‍♀️ This week’s episode is packed tighter than a downtown Toronto condo closet! I’m answering the most common questions I’ve be…

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

27d 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…

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

1M 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…

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

1M 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 …

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Condo Not Selling? 🏘️ Top 5 Reasons ! 28:24

1M ago28:24

28:24

Send us a text Listing Regrets & Condo Crickets: What No One Warns You About! In this episode, I’m keeping it all the way real. If your condo has been sitting on the market collecting dust — this one’s for you. I break down the top five reasons why your GTA condo might not be getting offers, showings, or even looks. From off-the-mark pricing to ter…

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Exhausted but Empowered: Why Right Now Might Be Your Best Move Yet 27:07

2M ago27:07

27:07

Send us a text Exhausted but Empowered: Why Right Now Might Be Your Best Move Yet ☀️ In this episode, I'm answering some of the top real estate questions I've been getting lately. We’re talking about buying power (yes, even in this wild market), selling smart (without second-guessing yourself), and why timelines and conditions could make or break y…

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

2M 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 …

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

2M 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…

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Rents Rising: Why the GTA Rental Market Feels So Wild Right Now 27:10

2M ago27:10

27:10

Send us a text Rents Rising: Why the GTA Rental Market Feels So Wild Right Now Get out and VOTE! Now, let’s dive into today’s topic: rentals. From what’s happening in the Toronto and GTA rental market, to why rent prices feel sky-high lately, we’re breaking it all down in plain language. You might be wondering, “Why is rent so expensive?” Well, it’…

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

2M 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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SHAKING UP SUCCESS: HOW JOHN RONDI TURNED A FAMILY TIKTOK INTO A THRIVING BRAND 1:17:07

2M ago1:17:07

1:17:07

In this week's episode of Cash Flow Corner, we're joined by John Rondi, Co-founder of Johnny Drinks — entrepreneur, content creator, and one half of the viral father-son cocktail duo behind Johnny Drinks. From humble beginnings mixing drinks on TikTok to building a multi-platform brand empire, John shares the authentic journey that led to their une…

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

2M 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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Budgeting and Real Estate Market Update: Expert Tips! 26:48

2M ago26:48

26:48

Send us a text Budgeting and Real Estate Market Update: Expert Tips! Ever feel like you just moved, spent a ton, and now you’re wondering… “How do I enjoy life without overspending?” You’re not alone. Life doesn’t need to feel heavy. You can have joy and peace of mind—even after a big move. Downsizing or starting fresh should feel freeing, not stre…

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

3M 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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#104 - Active vs. Passive: Storage Strategies from the Flight Deck with Michael Meylor 49:01

3M 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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#103 - Multifamily Mastery: Building Cashflow and Legacy with Gino Barbaro 45:35

3M 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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#102 - Creating True Passive Income Through Note Investing with Tom Force 49:39

3M 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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The Shocking Truth About Insurance Hikes 🚗💸 25:45

3M ago25:45

25:45

Send us a text In this episode of Elementary, I'm diving into something that caught me completely off guard — a MASSIVE increase in my auto insurance premium… with absolutely no reason. 🤯 Picture this: same car, same driving history, no accidents, no tickets — nothing has changed. Yet, my insurance shot up from around $2,200 to $3,800 annually with…

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

3M 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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#100 - Getting to Know Tait & Ryan 51:12

4M 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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The Hidden Costs of Holding Onto Your Home Too Long 19:37

4M ago19:37

19:37

Send us a text The Hidden Costs of Holding Onto Your Home Too Long In this episode, we’re diving into a tough but important topic: the real cost of holding onto a home longer than you should. Many homeowners—especially downsizers and seniors—struggle with the decision to move because of memories, fear of change, or simply not knowing where to start…

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

4M 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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How to Become an Airline Pilot After 30: A Finance Professional's Journey | EP 2 54:47

4M ago54:47

54:47

Ever found yourself staring out your office window, wondering if there's more to life than the 9-to-5 grind? Meet Anthony, who turned his childhood fascination with aviation into a 25-year career commanding the skies. If you've ever thought about a complete career change but worried it might be too late, this episode will show you how one decisive …

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

4M 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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#97 - Creative Deal Structuring: Smart Real Estate Strategies with Chris Prefontaine 53:27

4M 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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Nailed It or Failed It? 🏗️🔨 The Real Costs of Pre-Construction You Didn’t See Coming 24:16

4M ago24:16

24:16

Send us a text Nailed It or Failed It? 🏗️🔨 The Real Costs of Pre-Construction You Didn’t See Coming Pulling back the curtain on the true financial realities of buying pre-construction properties in Toronto and the GTA. While glossy brochures and model suites make these projects look like a dream come true, the hidden costs and risks often tell a di…

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

5M 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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✨ Energy is all around us — but how often do we pause long enough to feel it? 36:40

5M ago36:40

36:40

Send us a text ✨ Energy is all around us — but how often do we pause long enough to feel it? I’m so excited you’re here today. I recently had the privilege of hosting a beautiful live Reiki session with the incredible Veronica (@vsreikimaster36), and let me tell you, it was absolutely magical. Energy is all around us, even when we can’t see or touc…

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

5M 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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Clear the Clutter, Ditch the Debt, and Conquer the Market 28:24

5M ago28:24

28:24

Send us a text Clear the Clutter, Ditch the Debt, and Conquer the Market In this episode, we're diving into three game-changing topics to help you simplify your life, take control of your finances, and easily navigate the real estate market. Here's what's in store: Breaking Up with Clutter Is your home overflowing with "stuff" you don't need? We'll…

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💡 Tipping Talk: When Did Takeout Become a Tip Trap? 🍟💸 7:53

5M ago7:53

7:53

Send us a text 💡 Tipping Talk: When Did Takeout Become a Tip Trap? 🍟💸 We're diving into the changing world of tipping. Is discretionary still discretionary, or is tipping for takeout the new norm? Let's discuss it! This episode of Tipping the Hot Topic explores the shifting expectations surrounding tipping culture. Gone are the days when tipping wa…

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

5M 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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Master Your Budget & Beat the Winter Blues No 27:00

5M ago27:00

27:00

Send us a text Welcome to Elementary! Today, I’m diving into two topics that hit close to home for so many of us. First, we’ll talk about managing your budget because times are changing, and knowing how to save and spend wisely is essential. What better time to get started than right now, at the beginning of the year? Then, we’ll shift gears and ta…

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

5M 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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From Vending Machines to Commercial Real Estate Guru: Roy Pascal's Journey 50:25

5M ago50:25

50:25

Welcome to the pilot episode of Cash Flow Corner Podcast, hosted by Spencer Pascal, Real Estate Investor and CEO of Commerce Park Investor. In this episode, Spencer sits down with his father Roy Pascal, a veteran in the real estate industry with over 40 years of experience and known as the Commercial Real Estate Guru. The episode offers a unique bl…

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

6M 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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New Year New YOU With Bailey Macnamara 31:35

6M ago31:35

31:35

Send us a text NEW YEAR, NEW YOU! In this episode, I kick off 2025 with an exciting guest, @baileymacnamara, a fitness coach known for her empowering and welcoming approach to health and wellness. We dive into her philosophy of making fitness accessible to everyone and the importance of creating a supportive space for all. Bailey also shares some e…

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

6M 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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#90 - Balancing Flying, Business Ownership, and Financial Growth with Carl Valeri 49:22

6M 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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Welcome to Cash Flow Corner Podcast 2:03

6M ago2:03

2:03

Feeling stuck in your career? Dreaming of turning your multiple passions into profit but don't know where to start? Tune in to Cash Flow Corner with Spencer Pascal, Real Estate Investor and CEO of Commerce Park Investor, where we unlock the secrets of financial freedom through real, unfiltered conversations. Each episode, we bring you diverse indus…

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

6M 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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Unlock the Secret: Should You Add a Co-Borrower to Your Canadian Mortgage? 22:35

6M ago22:35

22:35

Send us a text Unlock the Secret: Should You Add a Co-Borrower to Your Canadian Mortgage? Are you thinking about adding someone to your mortgage? This episode discusses the benefits, potential risks, and legal implications of making this decision in Canada. We also discuss the impact on liability, credit, and ownership, what happens if the other pe…

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

7M 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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📢 Big Changes Are Coming! 🚨 New Mortgage Rules Dec 15 44:09

7M ago44:09

44:09

Send us a text We’re diving into everything you need to know about the upcoming mortgage rules with the expert @mortgagemani! 🏡✨ These changes could impact how you buy your next home, refinance, or plan your future investments. Whether you're a first-time buyer or a seasoned investor, staying informed is key! 🎙️ Tap the link to listen now and get a…

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Pilot Financial Freedom Podcasts

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