Best Pilot Financial Freedom Podcasts (2025)

1
287: Five Years Practicing Infinite Banking with Gastil Brothers 47:31

1d ago47:31

47:31

Brothers Garrett and Miles Gastil share their five-year journey practicing the Infinite Banking Concept. From using policies to grow a contracting business to securing family wealth, they reveal lessons on capitalization, control, and building equity. Discover why Infinite Banking is more than numbers, it’s about discipline, freedom, and creating a…

1
The Plot Against Kennedy: The 292nd Evolutionary Lens with Bret Weinstein and Heather Heying 1:36:39

10h ago1:36:39

1:36:39

Today we discuss the dust-up at the CDC, in which RFK Jr. fires the new director, after which other CDC officials resign, and eight former directors of the CDC pen a letter to the New York Times (as does Bernie Sanders) arguing that Kennedy is a hazard to our health. This follows a reveal from months ago that industry was collaborating to get rid o…

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

2d 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
E340: Ryan Graves UAP’s and F18’s 1:10:30

3d ago1:10:30

1:10:30

Ryan Graves, a former F-18 pilot and Executive Director of Americans for Safe Aerospace, joins us to delve into the intriguing and often perplexing world of UAP (Unidentified Aerial Phenomena). We kick off the conversation by exploring Ryan’s journey from aviation novice to military aviator, discussing the intense training and experiences that shap…

1
Zero Click SEO for AI Search, Google Rankings & Agentic AI 40:31

3d ago40:31

40:31

Keywords AI, SEO, zero-click searches, generative engine optimization, agentic AI, LLM, search engine trends, digital marketing Summary In this episode, Dalton Anderson discusses the rapid evolution of AI technologies, particularly in the realm of search engine optimization (SEO). He highlights the shift towards AI-centric workflows and the implica…

1
286: Building Generational Wealth & Legacy Through Infinite Banking with Thomas O’Connell 53:32

6d ago53:32

53:32

What does it mean to retire on your own terms and create a ripple effect of wealth that lasts for generations? What does it mean to retire on your own terms and create generational wealth that lasts? In this episode of Wealth On Main Street, Richard Canfield and Thomas O’Connell explore the Infinite Banking Concept and how it empowers families to b…

1
Freedom, Tyranny, and Childhood Lost: The 291st Evolutionary Lens w/ Bret Weinstein & Heather Heying 1:14:46

8d ago1:14:46

1:14:46

Today we discuss childhood, fitness, and self-defense; the through-line is freedom. First up: Illinois has become the first state in the Union to mandate mental health screening for children in grades 3 – 12, so that conditions from trauma to anxiety can be detected early. How mandatory will these screenings be? How confidential? What is anxiety, a…

1
What AI Will Do to Humanity: Forrest Maready on DarkHorse 1:59:47

8d ago1:59:47

1:59:47

Bret Weinstein speaks with Forrest Maready on the subject of the dual nature of AI, discussing both its potential benefits and risks, particularly in relation to human suffering, dependency, and the evolving concept of truth. Find Forrest Maready on X at http://x.com/forrestmaready and his website http://forrestmaready.com. ***** Sponsors: Everyday…

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

9d 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
E339 Leah Froehlich: From Doubts to Dominating the Skies as a CFI and Aviation Influencer 1:02:00

10d ago1:02:00

1:02:00

In Episode 339 of the Pilot to Pilot Podcast, host Justin Siems chats with Leah Froehlich, a passionate flight instructor and Instagram content creator. Leah shares her unexpected journey into aviation, sparked by a flight with her stepdad after pursuing physical therapy. She opens up about overcoming early confidence struggles, the realities of CF…

1
WHY MADE BY GOOGLE EVENT BOMBED - DESPITE INCREDIBLE PRODUCTS 33:48

10d ago33:48

33:48

Keywords Google, Pixel, AI, technology, presentation, smartphone, innovation, industry trends, product launch, user experience Summary In this episode, Dalton Anderson discusses Google's recent Pixel announcement, highlighting the strong lineup of devices and innovative AI features. He critiques the presentation format, which he finds awkward and u…

1
🕵️ Before you sign on that shiny new condo, here are the red flags hiding in plain sight. 26:55

13d ago26:55

26:55

Send us a text The Truth About Condos in Toronto & the GTA Let’s be real—condos in Toronto spark strong opinions. Some people swear by them. Others avoid them like the plague. But here’s the truth: condos can be your ticket to smart homeownership—or your biggest headache. It all depends on how much you know before you buy. In this episode, I take y…

1
EP 46: Private Credit & Pilot Training: Investing Beyond Wall Street | Brandon Marini & Madhavi Jain 57:16

14d ago57:16

57:16

In this episode of Think Outside the Stocks, host Madhavi Jain sits down with Brandon Marini, 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 pil…

1
Where has all the science gone? The 290th Evolutionary Lens with Bret Weinstein and Heather Heying 2:09:08

14d ago2:09:08

2:09:08

Today we are all over the map. First: Elon, AI, and humanoid robots, with discussion of sex, the industrial revolution, specialization, the Pleistocene, feminism, men’s work, porn, clankers, and vaping. Obviously. Then: are there differences between moral panics and social contagions, and is the current focus on pedophilia one or both? Finally: how…

1
285: Breaking Free Financially Through Infinite Banking with Riccardo Manazza 1:01:17

15d ago1:01:17

1:01:17

Wealth On Main Street 285: Breaking Free Financially Through Infinite Banking with Riccardo Manazza Picture having complete control over your money and the freedom to decide exactly how it works for you. In a recent episode of Wealth On Main Street, Richard Canfield welcomed Riccardo Manazza to share an uplifting and empowering story of how the Inf…

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

16d 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
E338 - No Regrets: Why You Should Take the Leap into Aviation 1:04:42

17d ago1:04:42

1:04:42

Flying High with Charlie Gasmire: Lessons from the Cockpit and Beyond Join us as we soar into the world of aviation with Charlie Gasmire, the brain behind Airplane Academy. With a family legacy of aviators, Charlie’s journey from a young boy inspired by his grandfather and father to a successful pilot and entrepreneur is nothing short of inspiring.…

1
My Takeaways from Extreme Ownership by Jocko Willink & Leif Babin 48:24

18d ago48:24

48:24

Keywords Extreme Ownership, Leadership, Accountability, Teamwork, Jocko Willink, Leif Babin, Business Strategies, Communication, Military Leadership, Personal Development Takeaways Extreme ownership means taking responsibility for everything. Accountability leads to better team performance. Good leaders create good teams; bad leaders create bad tea…

1
Confused about whether to buy, sell, or just sit tight? You’re not alone—and in today’s GTA market, confusion is the most expensive mistake you can make. 17:57

18d ago17:57

17:57

Send us a text On this episode of Elementary, I dive into one of the biggest questions I keep hearing lately: “I’m so confused… should I buy, should I sell, or should I wait?” Downsizers, move-up buyers, and anyone feeling stuck in the current Toronto/GTA market—this one’s for you. I unpack the messy middle of decision-making and share how to start…

1
Real Estate Wholesaling: From $60K Loss to $700M Empire with David Choi 58:03

21d ago58:03

58:03

David Choi, CEO of Leverage Companies, reveals how he transformed a $60,000 first-year loss into a $700 million annual DSCR lending operation. Learn the exact systems, hiring practices, and mindset shifts that built his real estate empire. What You'll Learn: How to scale real estate wholesaling operations Call center systems for property acquisitio…

1
284: Taking Financial Control: Being the Pilot of Your Finances with John T. Urbik IBCP 50:53

22d ago50:53

50:53

Wealth On Main Street 284: Taking Control: Being the Pilot of Your Finances with John T. Urbik IBCP You are the pilot of your own financial aircraft. If you don’t take the controls, someone else will, often without your best interests in mind. Thousands of hours logged in the cockpit. Countless missions flying B-52 bombers through war zones. In thi…

1
Escaping Your Lane: The 289th Evolutionary Lens with Bret Weinstein and Heather Heying 1:34:36

22d ago1:34:36

1:34:36

Today we discuss the reasons not to stay in your lane, wildlife in the Pacific Northwest, and whether Americans want a handout, or to be left alone. First: Bret responds to critique from Geert Vanden Bossche on his characterization of intramuscular vaccines and their capacity to produce mucosal immunity. Then: how science discovers reality, the ris…

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

23d 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
E337 - Exploring Contract Flying with Evan Luft 1:15:58

24d ago1:15:58

1:15:58

Evan Luft joins us on the podcast today, and he's here to share his unique journey through the world of aviation as a contract pilot. One of the standout points we discuss is that you don't have to follow the traditional path of becoming an airline pilot to enjoy a fulfilling and lucrative career in aviation. Evan's experiences flying over the stun…

1
THE WINDSURF STORY: FROM BILLION-DOLLAR DREAMS TO FOUNDER BACKLASH 35:55

24d ago35:55

35:55

Keywords Windsurf, OpenAI, acquisition, Microsoft, Google, startup culture, leadership, employee loyalty, market pressures, business decisions Summary This episode discusses the tumultuous acquisition saga of Windsurf, a startup that faced significant market pressures and ultimately saw its acquisition deal with OpenAI fall through. The fallout fro…

1
No Klan Do: Daryl Davis on DarkHorse 2:21:37

24d ago2:21:37

2:21:37

Bret Weinstein speaks with Daryl Davis on his experience engaging with members of the KKK, emphasizing the importance of dialogue, empathy, and understanding in breaking down barriers. Find Dary Davis at https://daryldavisspeaking.com and on X at https://www.x.com/realdaryldavis ***** This episode is sponsored by Timeline. Timeline accelerate the c…

1
EP:45 Think Outside the Stocks: Unveiling the $230B Life Settlement Market with Matthew Paine (Part 2) 1:01:39

27d 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…

1
283: Double Your Financial Freedom: Bitcoin and Infinite Banking Together with Shaun Somers 46:43

29d ago46:43

46:43

Wealth On Main Street 283: Double Your Financial Freedom: Bitcoin and Infinite Banking Together with Shaun Somers Imagine having a financial system where your savings are safe from government overreach and bank restrictions, while your child’s first major purchase is financed through your family’s own private banking system. In a recent episode of …

1
Kennedy, Pharma, and the Battle over mRNA: The 288th Evolutionary Lens with Bret Weinstein and Heather Heying 1:44:45

29d ago1:44:45

1:44:45

Today we discuss the cancellation of mRNA vaccine contracts by Secretary Kennedy. What are the risks, are they as limited as he suggests, and what can we look forward to from this technology in the future? Conversation includes Covid and the Covid shots, repurposed drugs, and the nature of science and knowledge. What does it mean for a claim to be …

1
Couple Goals: How Erin and Paul Built Their Dream Plane 1:07:43

1M ago1:07:43

1:07:43

Erin and Paul, the dynamic husband-wife pilot duo, have taken their passion for aviation to new heights by building their very own Bearhawk 5. In this episode, they share the incredible journey of finding the perfect aircraft, navigating the world of airplane kits, and the challenges of construction, all while balancing their personal and professio…

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

1M 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
CAN AI AND DATA CENTERS BE SUSTAINABLE? THE TENSION BETWEEN TECH AND COMMUNITIES 39:50

1M ago39:50

39:50

Keywords data centers, legislation, environmental impact, community resistance, technology solutions, water usage, energy consumption, regulatory changes, economic impact, zoning laws Summary This episode discusses the challenges posed by data centers, including their significant water and energy consumption, and explores various legislative and co…

1
"You Can't Learn to Save Money Unless You Have It to Save" 13:20

1M ago13:20

13:20

For Episode 5, Kyla reconnects with Vernell—the original host of the Rooted podcast and one of the first students in the $50 Study. They talk candidly about how receiving $50 a week shaped their views on independence, responsibility, and financial literacy. From side hustles like candle-making and T-shirts to real talk about how cash transfers buil…

1
EP 45: Banks, Billionaires, and Life Insurance: What They’re Not Telling You (Part 1) 54:01

1M 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…

1
282: How Millennials Are Rewriting the Money Rules with Infinite Banking 39:07

1M ago39:07

39:07

Wealth On Main Street 282: How Millennials Are Rewriting the Money Rules with Infinite Banking If you’ve ever wondered why the old money advice doesn’t quite sit right with you, you’re not alone. Millennials have lived through economic upheaval, student debt crises, housing bubbles, and a digital revolution. In this episode of the Wealth On Main St…

1
Dangers of the mental multiverse: The 287th Evolutionary Lens with Bret Weinstein and Heather Heying 1:43:23

1M ago1:43:23

1:43:23

Today we discuss “gender affirming surgeries”, AI and the future of cognition, and wild foxes. Kaiser Permanente is pausing surgery on trans-presenting children—we discuss sex and gender, meaning and identity, delusion and madness. Then: unlike the physical multiverse, mental multiverses are common, and becoming more so, as AI makes it ever more di…

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

1M 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
HOW AI DATA CENTERS ARE DRAINING POWER, WATER, AND PATIENCE: THE HIDDEN COSTS OF THE CLOUD 49:05

1M ago49:05

49:05

Keywords AI data centers, energy consumption, water usage, environmental impact, local communities, health concerns, technology, politics, sustainability, future trends Summary This podcast episode delves into the rapid growth of AI data centers, their significant energy consumption, and the environmental and social implications they bring to local…

1
💰 Unlock Home Equity: Smart Moves in Today's Market! 🏡 18:06

1M ago18:06

18:06

Send us a text 💰 Unlock Home Equity: Smart Moves in Today's Market! 🏡 Feeling stuck with a house full of equity but no clue what to do with it? You’re not alone. You’ve got a house that’s worth a fortune — but you’re stuck. You’re not sure if you should sell, borrow, or stay put… and all the advice out there? Confusing, generic, and not designed fo…

1
281: Taking Charge of Your Wealth That Lasts Generations with Justin Maxwell 40:15

1M ago40:15

40:15

Wealth On Main Street 281: Taking Charge of Your Wealth That Lasts Generations with Justin Maxwell You’ve worked tirelessly to build a thriving business, but there’s a quiet question you carry: Am I just earning a high income, or am I truly building wealth that will last beyond me? It’s a question that goes beyond bank accounts or investment portfo…

1
THE SICKNESS: 30-POUND FEVER DREAM 28:44

1M ago28:44

28:44

Keywords entrepreneurship, health, illness, recovery, mindset, travel, vertigo, life lessons, podcast, personal growth Summary In this episode, Dalton Anderson shares his personal journey of overcoming a severe illness that left him bedridden for weeks. He reflects on the lessons learned from his experience, including the importance of maintaining …

1
Can we have your liver? The 286th Evolutionary Lens with Bret Weinstein and Heather Heying 1:57:51

2M ago1:57:51

1:57:51

Today we discuss organ donation, and parenting in the animal world. Organ donation: how can we modify incentives so that people who need organs have a good chance of getting them, but people with healthy organs are never sent to an early death because their organs are valuable? Then: a natural history primer on parental care and feeding ecology of …

1
The Truth About Nazi Doctors: A Conversation with Dr. Jonathan Hudson and Dr. Michael S. Bryant 2:58:47

2M ago2:58:47

2:58:47

Bret Weinstein speaks with Dr. Jonny Hudson and Dr. Michael S. Bryant on the subject of Nazi doctors. Dr. Jonny Hudson has a PhD in Holocaust and Genocide Studies and Dr. Michael S. Bryant has a PhD in Modern European History and is a Professor of History and Legal Studies at Bryant University. He is also the author of “Confronting the ‘Good Death’…

1
#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…

1
280: How Legacy Planning Protects Your Family’s Generational Wealth with Shane Stirling 42:26

2M ago42:26

42:26

Wealth On Main Street 280: How Legacy Planning Protects Your Family’s Generational Wealth with Shane Stirling If you're building something meaningful, a business, a legacy, a future for your kids, then you've likely asked yourself: How do I ensure this wealth doesn't vanish in a generation or two? Honestly, it’s a question more families should be a…

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