Best Sky High Finance Podcasts (2024)

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#85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver 47:59

5m ago47:59

47:59

Welcome back to another episode of Passive Income Pilots! In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson are joined by Erik Oliver, Vice President of Cost Segregation Authority, to dive deep into cost segregation. Erik explains how this tax strategy accelerates real estate depreciation, enabling investors to unlock substantia…

1
Under Gray Skies on a Shipwrecked Coast 13:25

1d ago13:25

13:25

My wife and I stood at the edge of the world—or at least what felt like it—squinting through the murk and sea spray to snap photos of a decommissioned lighthouse. Less like some beacon of hope, its white tower loomed like a ghost, haunting the craggy cliffs of coastal Victoria and my vacation prospects. We’d arrived at the sleepy Victorian coastal …

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#84 - Tax-Free Growth & Infinite Loans: Whole Life Insurance Strategies for High-Earners 39:52

1d ago39:52

39:52

Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea hosts Rod Zabriskie and Brenyn McConnell from Money Insights to explore how whole life insurance can be a powerful investment tool. They discuss how pilots and high-income earners can use structured whole life policies to build tax-free growth and take policy loa…

1
#83 - Market-Based Cash Balance Plans with Jesse Reed 53:55

8d ago53:55

53:55

In this episode, hosts Tait Duryea and Ryan Gibson welcome back financial planning expert and pilot Jesse Reed to dive deep into market-based cash balance plans—a retirement vehicle being implemented by airlines specifically for high-earning pilots facing 401(k) spillover limits. Jesse unpacks how pilots can strategically manage these plans to maxi…

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#82 - From LLCs and HSAs to Roth IRAs: Mastering Wealth Protection with Mark Kohler 1:01:03

16d ago1:01:03

1:01:03

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson welcome tax attorney Mark Kohler to answer popular questions on tax strategies for high-income professionals. With two decades of experience, Mark breaks down essentials from self-directed IRAs to maximizing HSAs, Roth IRAs, and other tax-advantaged accounts, plus strategie…

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#81 - The Power of AI and Passive Income Strategies for Pilots with Jim Higgins 45:51

23d ago45:51

45:51

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson sit down with Jim Higgins, a former airline pilot turned co-founder and COO of a successful tech startup, Thread. Jim shares his unique journey, from negotiating contracts for American Eagle during 9/11 to leading a company that uses drones and AI for utility inspections. T…

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The Flat White Chronicles 13:18

1M ago13:18

13:18

Australians, it seems, are utterly smitten with coffee. The beverage of choice appears to be the flat white, a silky yet buttoned-down cousin to the latte or cappuccino. We landed in Sydney at dawn, dragging two hefty bags from baggage claim. Our first order of business was to snag a flat white before leaving the terminal. Ever the minimalist, I se…

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#80 - Storm-Proofing Your Real Estate Investment with Jules Sneddon and Trevor Moss 51:57

29d ago51:57

51:57

Welcome back to another exciting episode of Passive Income Pilots! This week, Tait and Ryan talk with Jules Sneddon and Trevor Moss from the National Real Estate Insurance Group to explore everything you need to know about insuring your real estate investments. From protecting against storm damage to navigating the rising insurance costs in high-ri…

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#79 - From Cockpit to Space: On Grit, Leadership, and Space Travel with Col. Eileen Collins 1:01:32

1M ago1:01:32

1:01:32

Welcome back to another inspiring episode of Passive Income Pilots! In this episode, Tait and Ryan sit with Colonel Eileen Collins, the first woman to command a NASA space shuttle. Colonel Collins shares her incredible journey, from becoming a pilot to breaking barriers in space exploration. She dives into leadership lessons, risk management, and t…

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#78 - Lifestyle Investments: Leveraging Seaside Property for Passive Income with Casey Roloff 51:50

2M ago51:50

51:50

In this episode of Passive Income Pilots, Tait and Ryan sit down with Casey Roloff, the visionary behind Seabrook, a seaside town in Washington. They explore how pilots and high-income professionals can strategically invest in real estate within Opportunity Zones while leveraging short-term rental tax loopholes and self-directed IRAs for significan…

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#77 - The Pilot's Flight Plan to Passive Income: Aircraft Leasing and Tax Benefits with Luke Lysen 44:35

2M ago44:35

44:35

Welcome back to another exciting episode of the Passive Income Pilots! Today, Tait and Ryan dive into the world of aircraft ownership, tax advantages, and leaseback strategies with guest Luke Lysen from The Flight Academy and Aerista. They explore how pilots and high-income earners can purchase an aircraft, rent it out to a flight school, and lever…

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#76 - MOST POPULAR EPISODE: Reduce Taxes & Maximize Returns Using PROVEN Strategies with Toby Mathis 1:10:31

2M ago1:10:31

1:10:31

In this episode of Passive Income Pilots, Tait Duryea takes you back to one of the most downloaded episodes in the show's history with Toby Mathis from Anderson Advisors. Discover how tax laws can work for you through real estate investments, cost segregation, and bonus depreciation strategies. Toby breaks down the game-changing legal strategies hi…

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#75 - Unlocking Real Estate Professional Status (REPS) with Brandon Hall 51:23

2M ago51:23

51:23

Welcome back to Passive Income Pilots! This week, Tait and Ryan are joined by Brandon Hall, a top CPA and founder of Hall CPA, PLLC, to dive into one of the most powerful tax strategies for high-income professionals: real estate professional status. With over 800 clients and a specialization in real estate tax strategies, Brandon breaks down the be…

1
Yonder Goes Little Maggie 28:34

3M ago28:34

28:34

They say that grief comes on like a tsunami, a wave of incredible power and uncontrollable force that washes over us. The metaphors are many—trains and dump trucks, roller coasters and rivers—and they all check out. Grief comes on hard and renders us powerless in its wake. But I’ve been consumed less by a powerful force and more by the emptiness of…

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#74 - The Inside Track: Mastering Real Estate Syndications for Long-Term Success 54:10

3M ago54:10

54:10

Welcome to another episode of Passive Income Pilots! This week, Tait and Ryan dive deep into the world of real estate syndications—a game-changing investment strategy for busy professionals, especially pilots. They break down what syndications are, how they work, and the pros and cons of this passive income stream. From navigating the complexities …

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#73 - From Market Cycles to REITs: What Every Pilot Investor Should Know with Glenn R. Mueller, PhD 47:29

3M ago47:29

47:29

Welcome to another insightful episode of Passive Income Pilots! This week, Tait and Ryan are joined by Dr. Glenn Mueller, a seasoned economist and real estate professor with over 40 years of experience. Dr. Mueller explores the current economic landscape, the real estate market, and the fascinating REIT world. Whether you're curious about market cy…

1
David Champion: The Psychological Challenge Of Early Retirement 1:35:02

3M ago1:35:02

1:35:02

Retirement is often an ideal detached from reality. When overwhelmed by daily routines, it’s easy to imagine retirement as a stress-free life with a blank calendar and complete freedom. However, retirement often brings unexpected psychological challenges, including a lack of purpose, boredom, relationship strain, and a troubling sense of isolation.…

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#72 - Cleared for Takeoff: Updated FAA Mental Health Regulations with Joe LoRusso 24:09

3M ago24:09

24:09

In this week's episode of Passive Income Pilots, Tait and Ryan are thrilled to have Joe LoRusso back on the show for an essential update on the evolving landscape of pilot mental health regulations. Since his last appearance, significant changes have been implemented by the FAA, including new guidelines for mental health treatments and expanded med…

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#71 - 5 Creative Ways To Find Investment Cash 26:39

3M ago26:39

26:39

Welcome back to another episode of Passive Income Pilots! Today, Tait and Ryan dive into five unconventional ways to unlock cash for your next investment. Whether leveraging home equity, rolling over an old 401k, or borrowing against your stock portfolio, this episode is packed with actionable strategies to help you soar to new financial heights. T…

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#70 - Leveraging Life Insurance for Passive Income with Rod Zabriskie and Blake Brogan 44:42

4M ago44:42

44:42

Welcome to another enlightening episode of Passive Income Pilots! Today, Tait and Ryan welcome Rod and Blake from Money Insights. Previously featured in episode 47, Rod and Blake are experts in leveraging life insurance for wealth-building. In this deep dive, we uncover how to use a specialized life insurance strategy to enhance investment returns,…

1
#69 - Sky-High Returns: Discover Off-Market Real Estate Gems with Sean O'Toole 40:39

4M ago40:39

40:39

Welcome aboard another episode of Passive Income Pilots! This week, Tait and Ryan are joined by Sean O'Toole, PropertyRadar.com founder, to discuss how pilots can find and invest in off-market rental properties. Sean shares his insights on leveraging public records, innovative strategies for contacting property owners, and the benefits of seller fi…

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#68 - Cruising to Success: Optimizing Your Short-Term Rentals with Airbnb Insider Daniel Rusteen 55:18

4M ago55:18

55:18

Welcome to another exciting episode of Passive Income Pilots! This week, Tait and Ryan are joined by Daniel Rusteen, a former Airbnb employee turned short-term rental expert. Daniel shares his insider knowledge on optimizing Airbnb listings to maximize revenue. From selecting the perfect market to managing properties remotely, Daniel’s unique persp…

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#67 - Protecting Your Wings: What Pilots Need to Know with Dr. Dan Monlux 44:16

4M ago44:16

44:16

Welcome back to Passive Income Pilots! In this special "Friday for Flyers" episode, we're diving into a critical topic for every pilot – medical certifications and aeromedical issues. Today, we have the honor of hosting Dr. Dan Monlux, an experienced AME, former F-18 pilot, and founder of Wingman Med. Dr. Monlux brings a wealth of knowledge and exp…

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#65 - Cashing In on Convenience: The Secret Economy of Vending Machines 50:49

4M ago50:49

50:49

Welcome to another exciting episode of Passive Income Pilots! We're diving into a fascinating and often overlooked passive income stream: vending machines. Our guest, Mike Hoffmann, also known as "Mr. Passive," shares his journey of creating a vending machine empire and how this low-barrier investment can yield significant returns. Whether you're a…

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#66 - Frequent Flyer Health Hacks from Special Forces Coach Alex Racey 35:50

5M ago35:50

35:50

In this episode we welcome special guest Alex Racey, a renowned personal performance coach with an extensive background in the military. The discussion focuses on the importance of maintaining physical and mental health, particularly for aviators, frequent flyers, and professionals who sit for long periods. Alex Racey, who served 25 years in the U.…

1
Cory Richards: The Color of Everything 2:03:12

5M ago2:03:12

2:03:12

Perhaps no one has quit their job like my guest today, Cory Richards. Richards, still a world-renowned photographer, abruptly ended his career as an elite mountaineer in April 2021 at the foot of the world’s seventh-highest peak. Over several days, Richards experienced what he later described as a mixed bipolar episode. With one hundred thousand do…

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#64 - Shark Tank Pilot Episode: Nick Friedman's College Hunks Hauling Junk 39:39

5M ago39:39

39:39

Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea and Ryan Gibson sit down with Nick Friedman, co-founder of College Hunks Hauling Junk, who appeared on the pilot episode of Shark Tank. Nick shares his journey from starting a small moving and junk removal business in college to building a multi-million dollar fr…

1
Life Without Money Scarcity Might Just Make You Lazy 25:06

6M ago25:06

25:06

Recently, I’ve been increasingly conflicted by several dueling experiences and sensations: Reduced Stress: Since departing from the Standard Corporate Office Environment (SCOE), I’ve enjoyed decreased stress and anxiety levels. While stress has its upsides, reducing chronic stress is foundational to living a good life. Mounting pressure to be part …

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#63 - Keith Rosenkranz: The Delta Captain Who Chartered His Own Retirement Flight 54:11

5M ago54:11

54:11

In this special episode, we have the honor of flying with Keith Rosenkranz, the legendary Delta Captain who chartered his own retirement flight. Keith's incredible story has captivated the aviation community, and today, he shares the details of his epic farewell flight, his career journey, and his strategies for building a financially secure retire…

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#62 - Pilot Math: Wealth Strategies for Aviators with Jason Depew 51:33

5M ago51:33

51:33

By producer@passiveincomepilots.com (Tait Duryea and Ryan Gibson )

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#61 - NFL Defensive Legend Cliff Avril: Crushing Real Estate After Crushing QBs 43:15

6M ago43:15

43:15

Welcome back to Passive Income Pilots, where we dive into the intersection of aviation, finance, and personal success. Today, we have a special treat for both football enthusiasts and aspiring investors. Our guest is none other than Seattle Seahawk NFL Defensive Legend and Super Bowl Champion, Cliff Avril. Known for his ferocious defense and countl…

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#60 - Cleared for Takeover: Collin Hathaway on the Boomer Business Buyout Boom 53:06

6M ago53:06

53:06

Welcome to another episode of Passive Income Pilots! This week, your hosts Tait Duryea and Ryan Gibson are thrilled to bring you an insightful conversation with private equity mogul Collin Hathaway of Skylight Capital, a seasoned entrepreneur specializing in business acquisitions. In this episode Collin shares his journey from buying his first plum…

1
The Illusion of Skill and How to Make Better Predictions 26:56

6M ago26:56

26:56

Imagine being faced with the daunting task of predicting the future with nothing but incomplete information and a handful of hunches. Perhaps you're considering new experiences, like travel or moving to a different town. When I imagined quitting my job, I envisioned a happier world, free from the perceived burden of corporate work. In the following…

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#59 - The Silver Tsunami: Dwayne Clark on the Future of Senior Living Investments 39:52

6M ago39:52

39:52

Welcome to another episode of Passive Income Pilots, where we delve into the burgeoning world of assisted living investments. Join hosts Tate Duryea and Ryan Gibson as they discuss the impact of the demographic shift known as the "Silver Tsunami" with Dwayne Clark, founder of Aegis Living. Dwayne shares his extensive experience in building a premie…

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#58 - Tax Tactics: The TOP 5 Ways You Can Save with Toby Mathis 53:34

6M ago53:34

53:34

Welcome back to Passive Income Pilots! In this episode we delve into essential tax strategies tailored specifically for pilots. With the expertise of Toby Mathis from Anderson Advisors, we explore five key ways you can reduce your tax liability effectively. Toby brings his depth of tax knowledge directly to our pilot audience, discussing everything…

1
What Two Writers Taught Me About How to Think 24:34

7M ago24:34

24:34

In 1949, a college junior named Barbara Beattie wrote a letter for a school journalism assignment. We can only speculate on Beattie’s youthful expectations: Was she so naive to expect a response, or were these different times? She’d written playwright Arthur Miller at a time when the Broadway run of his most famous work, The Death of a Salesman, wa…

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#57 - From Handshakes to High Stakes: The Best Ever Blueprint for Building Wealth Through Connections with Joe Fairless 46:28

7M ago46:28

46:28

Welcome to another thrilling episode of Passive Income Pilots, where we navigate the high-flying world of passive income opportunities. Today, we're joined by Joe Fairless, a titan in real estate investment and co-founder of Ashcroft Capital. Joe is renowned for his groundbreaking "Best Ever" conference, which is exactly where our hosts first cross…

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#56 - Black Box Wealth: Earning Passive Income On The Blockchain with PIVX DAO Advisor Hans Koning 43:31

7M ago43:31

43:31

In this thought-provoking episode of Passive Income Pilots, we sit down with blockchain expert Hans Koning to navigate the complexities and opportunities within the blockchain landscape, especially in light of recent global events like the Bitcoin halving and rising geopolitical tensions. Hans shares his profound insights into how these factors inf…

1
Is My Rent Too High? 30:29

7M ago30:29

30:29

In normal times, rent prices, like most everything else, slowly yet surely increase at about 2-3% per year. This is inflation. But in terms of the housing market, these aren’t normal times. In the pandemic era, as demand surged in supply-restricted markets, both sale and rent prices soared, with year-over-year inflation rates at 30% or more in some…

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#55 - First Class Intro to Angel Investing with OfferUp Founder Nick Huzar 54:06

7M ago54:06

54:06

Ever wonder how to turn your entrepreneurial dreams into reality? Tune into our latest episode of Passive Income Pilots as we soar into the world of angel investing and marketplace innovation with Nick Huzar, the CEO and founder of OfferUp! Discover how Nick's room full of unwanted items sparked the vision for a multi-billion-dollar company that re…

1
#54 - The Inner Game of Real Estate with Leka Devatha 45:11

7M ago45:11

45:11

Join us in this insightful episode of Passive Income Pilots as we explore the multifaceted world of real estate with Leka Devatha. From her early beginnings to overcoming the inherent challenges of the industry, Leka shares her journey of resilience, intuition, and strategic diversification. Discover actionable insights and inspiration whether you’…

1
An Emerging Revolution in the Treatment of Chronic Pain 1:04:06

8M ago1:04:06

1:04:06

According to the Centers for Disease Control and Prevention, chronic pain—pain lasting at or beyond three months—affected over 20% of U.S. adults, or 51.6 million people, in 2021. Symptoms were severe enough to substantially restrict daily activity for 6.9% of Americans that same year. And with chronic pain comes soaring medical costs, pharmaceutic…

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#53 - Eyes On The Horizon: Real Estate Insights from Kathy Fettke 51:03

8M ago51:03

51:03

In today's episode hosts Tait Duryea and Ryan Gibson navigate through the vast skies of real estate investing with the guidance of real estate titan, Kathy Fettke. As a renowned expert and a beacon of knowledge in real estate and economics, Kathy brings invaluable insights into the current real estate market, investment strategies, and the future o…

1
A Therapist on Satisfaction in Sport, Life, and Love 1:34:48

8M ago1:34:48

1:34:48

If you haven’t noticed, the concept of achievement and even competitiveness has weighed heavily on my mind as of late. A gift of the nontraditional life is the opportunity to step back and see the world around us with a degree of unusual clarity, far from the treadmill. For years I valued athletic and professional progress in ways that weren’t maki…

1
#52 - Economic Tailwinds: How 1031 Exchanges Propel Real Estate Portfolios With Kyle Williams 44:20

8M ago44:20

44:20

Unlock the potential of 1031 exchanges with Kyle Williams, Senior VP at Velocity 1031, on this enlightening episode of Passive Income Pilots. Designed for aviators aiming to navigate the complex skies of real estate investment, this discussion sheds light on tax deferral strategies that can significantly impact your financial trajectory. Whether yo…

1
All Work and No Play Makes You…Normal 16:53

8M ago16:53

16:53

The concept of play conjures the image of my three-year-old (and blonder) self, plastic shovel in hand, amorphous stains down the front of my pants. And certainly slobber. Lots of slobber. That three-year-old was certainly not concerned with social hierarchy or status, lacking a whiff of ambition to put the best version of himself forward. He playe…

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#51 - Navigating Turbulence: Mental Health & Legal Safeguards for Pilots with Joe LoRusso 49:00

8M ago49:00

49:00

Join hosts Tait Duryea and Ryan Gibson on Passive Income Pilots as they engage in a profound conversation with Joe LoRusso, aviation law expert and Director of Aviation at Ramos Law. This episode takes an earnest look into pilot mental health and legal challenges, spotlighting the systemic issues and proposing a transformative approach to aviation …

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Four Years of Financial Independence: The Slow Growth 15:10

9M ago15:10

15:10

For four years I’ve watched something slowly bloom. In my old life, the “before time” you might call it, I moved from task to task. If I wasn’t working, I unknowingly made a practice of turning recreational or hobbyist pursuits into something that, from an outsider’s perspective, looked an awful lot like work. Goals and accolades were everything, a…

1
#50 - Real Estate Investing: Building Resilient Wealth and Financial Independence with David Phelps 54:08

9M ago54:08

54:08

On this episode of Passive Income Pilots, Tait and Ryan interview David Phelps. Dr. David Phelps, founder of Freedom Founders, spent 27 years as a former general dentist and business owner. His life took a significant turn when his daughter Jenna faced leukemia. This personal crisis prompted Dr. Phelps to reassess his priorities and shift his focus…

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The Psychology Behind Poor Investments and Other Important Decisions 22:38

10M ago22:38

22:38

When we make important decisions, we are often not as rational or objective as we’d like to believe. The base rate fallacy is the tendency to misjudge the probability of a situation by not accounting for all relevant information. This cognitive bias affects everything from first impressions to voting preferences to broad market behavior. Support th…

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