Best Pilot Passive Profits Podcasts (2025)

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

24d 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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#108 - Case Study: Real Estate Professional Status That Held Up in Court with Brandon Hall 21:04

3d 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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#107 - Take Control of Your Capital: Infinite Banking Strategy With Brent Kesler 38:43

11d 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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#106 – Time Freedom and Cash Strategies with Brian Herriot 39:31

17d 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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#104 - Active vs. Passive: Storage Strategies from the Flight Deck with Michael Meylor 49:01

1M 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

1M 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

2M 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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#101 - Airbnb for Aircraft: Hangar Investing & Aviation Real Estate with Trenton Ray 41:21

2M 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

2M 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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#99 - Turnkey Real Estate: Passive or Problematic? A Deep Dive with Zach Lemaster 52:24

2M 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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#98 - The Right Coverage: Property Insurance Strategies with Valerie Cusano 49:46

2M 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

3M 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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#96 - Airplane Write-Offs, IRS Audits, and Smart Tax Planning with Ryan DeMoor 49:44

3M 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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#95 - Franchise Investing 101: Insights and Opportunities with Cliff Nonnenmacher 53:31

3M 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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#94 - Fail Fast, Succeed Faster: Wealth-Building and Investment Strategies with Christian Schiller 47:51

3M 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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#93 - Stock Market Insights and Tax Strategies for High-Income Earners with Brian Feroldi 55:19

4M 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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#92 - Opportunity Zones for Passive Income: Unlock Tax Savings and Growth with Nathan Sosa 51:28

4M 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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#91 - Interest Rates, Submarkets, and CRE's Future with Spencer Levy 49:12

4M 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

4M 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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#89 - Air Traffic, Pilot Pay, and Airline Economics with A4A's Chief Economist John Heimlich 41:04

5M 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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#88 - Flight Schools and Passive Income: Insights from Gordon Alvord 46:34

5M 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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#87 - The Mega Backdoor Roth and How Pilots Can Maximize Retirement Contributions with Timothy Pope 50:41

5M ago50:41

50:41

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson welcome back financial expert Timothy Pope to unravel the complexities of retirement strategies for high-income professionals, focusing on the Mega Backdoor Roth. Timothy explains how this powerful tool allows pilots to contribute significantly more to their 401(k) accounts, unlo…

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#86 - Mapping the Skies: The Tech Behind Real-Time Flight Tracking with Ian Petchenik 33:52

5M ago33:52

33:52

Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea and Ryan Gibson step outside financial strategies to explore the world of real-time flight tracking with Ian Petchenik, Director of Communications at FlightRadar24. Ian shares insights into the app that has become essential for aviation enthusiasts and profession…

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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…

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

6M 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…

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

6M 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 1:00:46

6M ago1:00:46

1:00:46

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

6M 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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#80 - Storm-Proofing Your Real Estate Investment with Jules Sneddon and Trevor Moss 51:57

7M 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

7M 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

7M 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

8M 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

8M 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

8M 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…

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

8M 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

9M 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…

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

9M 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

9M 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

9M 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,…

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

9M 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

10M 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

10M 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

10M 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

10M 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.…

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

11M 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…

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

11M 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

11M ago51:33

51:33

By [email protected] (Tait Duryea and Ryan Gibson )

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

11M 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

12M 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…

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

12M 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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