Best Pilot Financial Freedom Podcasts (2025)

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Scam-Proofing Seniors 18:16

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3h ago18:16

18:16

Send us a text The digital age has brought unprecedented convenience to our lives, but for seniors, it's also created a landscape fraught with sophisticated scams that even the tech-savvy might fall for. Jacqueline Watson, a Toronto realtor specializing in working with downsizers and seniors, pulls back the curtain on the alarming evolution of seni…

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My Wife Reveals What It's REALLY Like Being Married to an Entrepreneur 34:07

10h ago34:07

34:07

In this deeply personal episode, Spencer sits down with his wife Beth Pascal for an unfiltered conversation about what it really takes to build a successful relationship when one partner is living the high-performance entrepreneur lifestyle. From late-night business calls to constant travel, this episode pulls back the curtain on how they've naviga…

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Episode 37: Selling Digital Art on Auto-Pilot: How to Turn Art into Ongoing Income 9:51

22h ago9:51

9:51

Do you have a creative ability? 🎨 In this episode of Make Money While You Sleep, Angelina & Michael dive into how artists and designers can turn digital art into a passive income powerhouse. Learn how to sell your art online without handling inventory, shipping, or customer service—just create once and earn forever! 🎨 Whether you're into wall art, …

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Episode 36: Crypto for Creators: Is It a Smart Passive Play or Hype? 12:48

3d ago12:48

12:48

Crypto for Creators: Is It a Smart Passive Play or Just Hype? Can creators really earn passive income through crypto—or is it just buzz? In this episode of Make Money While You Sleep, Angelina & Michael break down the exciting (and sometimes confusing) world of crypto for content creators, artists, and digital entrepreneurs. From NFTs and creator c…

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

3d 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…

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Tesla's Robotaxi Pilot: The $4.20 Ride: 25:25

2d ago25:25

25:25

Keywords Tesla, Robo Taxi, Autonomous Driving, EV, Waymo, Pilot Program, Cyber Cab, Competition, Technology, Transportation Summary In this episode of the Bench Step Podcast, Dalton Anderson discusses the recent rollout of Tesla's Robo Taxi pilot program in Austin, Texas. He reflects on the evolution of Tesla's autonomous driving technology, the li…

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Episode 35: Rental vs. REITs — Which Real Estate Path is Right for You? 12:39

6d ago12:39

12:39

Ready to dive into real estate but not sure where to start? In this episode of Make Money While You Sleep, Angelina & Michael compare the two most popular passive income strategies in the real estate world: rental properties vs. REITs (real estate investment trusts). Whether you're dreaming of becoming a landlord or want completely hands-off invest…

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

6d 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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Episode 34: Passive Income with ETFs: Hands-Off Investing for Beginners 14:47

9d ago14:47

14:47

Curious about investing but overwhelmed by the options? In this episode of Make Money While You Sleep, Angelina & Michael unpack how ETFs (exchange-traded funds) can be your ticket to passive income—even if you're a complete beginner. Learn how to get started, minimize risk, and let your money grow while you sleep. No stress, no spreadsheets, just …

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

10d 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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Episode 33: From Hobby to Empire: Turning Small Ideas into Scalable Systems 13:27

11d ago13:27

13:27

Do you have a hobby that you love? What if that passion project could be the seed of your passive income empire? 💰 In this episode, Angelina & Michael dive into how to transform small ideas into systems that scale—without burning out. Whether you’re into crafting, writing, designing, or something uniquely you, this is your blueprint to turning fun …

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Toolchains vs. Monoliths: Apple's Illusion of Thinking 31:05

11d ago31:05

31:05

Keywords Apple, AI, Large Reasoning Models, Innovation, Technology, Cost Efficiency, Modular AI, Market Positioning, User Experience, Competitive Landscape Summary In this episode of the VentureStep podcast, host Dalton Anderson discusses Apple's recent AI paper titled 'The Illusion of Thinking' and critiques the company's current position in the A…

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Episode 32: Your First Virtual Assistant: What to Outsource for Maximum Passive Impact 13:21

13d ago13:21

13:21

Ready to stop doing it all yourself and start building a business that runs without you? In this episode of Make Money While You Sleep, Angelina & Michael dive into how hiring your first virtual assistant can unlock real passive income potential. Learn what tasks to delegate first, where to find the right VA, and how to free up your time while grow…

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Episode 31: Clone Yourself with Automation: Tools to Free Up Time & Make More 11:53

15d ago11:53

11:53

Want to free up your time, scale your income, and finally stop doing everything yourself? In this episode of Make Money While You Sleep, Angelina & Michael explore how to "clone" yourself using smart automation tools that work around the clock. From email marketing to evergreen funnels and AI-powered systems, you’ll learn how to set up a business t…

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Stage It Like You Mean It 41:21

16d 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

18d 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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Episode 30: Turn Your Hobby Blog into a Profit Engine 13:20

18d ago13:20

13:20

Are you ready to turn your passion into profit? In this episode of Make Money While You Sleep, Angelina & Michael explore how you can transform your hobby blog into a money-making machine—without losing the fun! From affiliate marketing to digital products, discover smart strategies to monetize your blog and create income streams that work while yo…

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The Hard Thing About Hard Things: If You’re Gonna Eat Sh*t, Don’t Nibble 50:47

18d ago50:47

50:47

Keywords Ben Horowitz, leadership, entrepreneurship, wartime CEO, peacetime CEO, hard decisions, company culture, management, startups, business strategy Summary In this episode of the VentureStep podcast, Dalton Anderson discusses Ben Horowitz's book, 'The Hard Thing About Hard Things.' The conversation explores the challenges of leadership, the d…

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Episode 29: Evergreen Sales Funnels: Your 24/7 Salesperson That Never Sleeps 14:29

20d ago14:29

14:29

Hey dreamers and doers! 👋 Ever wish you had a tireless salesperson working for you around the clock? In this week's episode of Make Money While You Sleep, Angelina & Michael dive into the magic of Evergreen Sales Funnels—your automated 24/7 revenue generator that never takes a coffee break or needs sleep! Learn how to set up these powerful systems …

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Episode 28: Print-On-Demand Profits: How to Sell Designs Without Inventory? 15:02

24d ago15:02

15:02

Want to turn your creative designs into cash—without the hassle of holding inventory💰 In this episode of Make Money While You Sleep, Angelina & Michael dive into the world of print-on-demand profits! Discover how to sell your designs on products like t-shirts, mugs, and more, with zero upfront costs. We walk you through the best platforms, tips for…

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

25d 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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Veo 3’s Visual Uprising: AI’s Video Magic and the Shift Back to Text 39:15

25d ago39:15

39:15

Keywords AI, VO3, content creation, storytelling, media, authenticity, social media, technology, entrepreneurship, trends Summary In this episode of the VentureStep podcast, host Dalton Anderson discusses the advancements in AI technology, particularly focusing on the VO3 model developed by Google. He explores the rapid evolution from VO2 to VO3, h…

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

25d 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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Episode 27: Digital Goldmines: Create & Sell Ebooks, Templates, and Printables That Sell Themselves 8:22

27d ago8:22

8:22

Ever dreamed of making money while you sleep with products that sell themselves?💰 In this episode of Make Money While You Sleep, Angelina & Michael unlock the secrets of digital goldmines! Learn how to create and sell ebooks, templates, and printables that generate passive income around the clock. Whether you’re a designer, writer, or creative hust…

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

1M 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

1M 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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Scaling Venture Step: Guest Goals, Production Glow-Up, and Paul Graham Vibes 45:48

1M ago45:48

45:48

Keywords podcast, entrepreneurship, scaling, production value, New York, Paul Graham, essays, guest requests, feedback, milestones Summary In this episode of the VentureStep podcast, host Dalton Anderson reflects on the journey of the podcast, celebrating milestones such as reaching over a thousand downloads and nearly 40,000 views on YouTube. He d…

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Episode 26: The Sleep Test: Is Your Business Really Making Money Without You 10:07

1M ago10:07

10:07

Are you really making money while you sleep, or is your business secretly tied to your time and energy? In this episode of Make Money While You Sleep, Angelina & Michael dive into the ultimate test of passive income—the "Sleep Test"! Find out how to measure your business’s true autonomy, where the hidden pitfalls lie, and actionable steps to make s…

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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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Isaac GR00T N1: The First Open Humanoid Robot Foundation Model 47:08

1M ago47:08

47:08

Keywords Robotics, AI, NVIDIA, Open Source, Automation, Technology, Innovation, Industry Trends, Future of Work, Robotics Applications Summary In this episode, Dalton Anderson explores the latest advancements in robotics and AI, focusing on NVIDIA's innovations, the importance of open-source models, and real-world applications of robotics. He discu…

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Episode 25: Set It and Forget It: 10 Passive Income Streams You Can Launch in a Weekend 13:02

1M ago13:02

13:02

Are you ready to kickstart your passive income journey without the long wait? In this exciting episode, Angelina & Michael share 10 smart, realistic ways you can create new income streams in just one weekend! This is perfect for busy dreamers who want to set it and forget it. Hit play, pick an idea, and start building your future today! 🌟 Follow, r…

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

2M 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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TAKE IT DOWN Act: Fighting Digital Abuse Against Non-consensual Imaging 50:48

2M ago50:48

50:48

Keywords Deep Fakes, Take It Down Act, Non-Consensual Imaging, AI Technology, Social Media, Legislation, Revenge Porn, Digital Privacy, Advocacy, High-Profile Cases Summary In this episode, Dalton Anderson discusses the alarming rise of deep fakes and the implications of the newly passed Take It Down Act. He explores the technology behind deep fake…

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

2M 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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Episode 24: From Zero to Passive Hero: Starting Your First Income Stream the Smart Way 10:39

2M ago10:39

10:39

Feeling overwhelmed about where to start with passive income? 💰 In this motivating episode, Angelina & Michael walk you through smart, beginner-friendly strategies to launch your very first income stream. No experience needed—just a dream and a plan! Hit play and start your journey from zero to hero today! Don't forget to like, follow, rate, and sh…

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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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The B&W Prospective: Finding a Colorful World Through Tech and Color Minimalism 34:19

2M ago34:19

34:19

Keywords technology, smartphone, black and white, digital detox, Lite Phone 3, screen time, notifications, productivity, mental health, minimalism Takeaways Reevaluating your relationship with technology can lead to better focus. The Lite Phone 3 promotes a simplified phone experience. Turning off notifications can reduce distractions significantly…

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Episode 23: Future Trends in Passive Income: What’s next in the world of earning money while you sleep 12:57

2M ago12:57

12:57

Ready to future-proof your income? 💰✨ In this exciting episode of Make Money While You Sleep, Angelina & Michael explore emerging trends and futuristic ideas shaping the world of passive income. From AI-powered investments and digital assets to Web3 and subscription-based everything—get ahead of the curve and learn how to tap into tomorrow’s income…

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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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Google Cloud Next 25: Building and Managing AI Agents A2A Protocol 37:38

2M ago37:38

37:38

Keywords Google Cloud Next, Agent to Agent Protocol, AI technology, Anthropic, Vertex AI, customer service automation, agent communication, AI advancements, technology integration, hyperscalers Summary In this episode of the Midget Step Podcast, host Dalton Anderson discusses the key takeaways from the Google Cloud Next 2025 conference, focusing on…