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Passive Income Pilots

Tait Duryea and Ryan Gibson

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Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success. Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life. Whether you're ...
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Pilot Money Podcast

Timothy P. Pope, CFP®

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The podcast about financial planning for professional pilots! Get answers to your most pressing personal finance questions. Timothy Pope is a Certified Financial Planner™ offering securities and insurance products offered through Cetera Investment Services LLC, member FINRA, SIPC. Advisory services are offered through Cetera Investment Advisers LLC. Tim’s Branch Office is located at 5200 77 Center Drive, Suite 330, Charlotte, NC 28217. Branch phone number 704-717-8900. The views depicted in ...
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This is THE premier podcast for passive real estate investing. Learn the inside secrets on how to be a successful passive real estate investor. Matt Jones interviews passive investors about their experiences and insight, as well as active investors on how they help passive investors. This podcast is brought to you by Hawkwing Capital, which connects passive investors with solid real estate investments run by proven operators. Find out more at www.HawkwingCapital.com The music is Overcome by ...
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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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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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Join Timothy P. Pope, CFP®, as he explores what to expect during open enrollment, a key time for pilots to reassess and select their benefits for the upcoming year. As we approach the end of 2024, it's essential to make informed decisions that align with both your immediate needs and long-term financial goals. This episode provides a thorough break…
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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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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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Join Timothy P. Pope, CFP®, in a special crossover episode from his appearance on the "Ready 4 Pushback" podcast, hosted by Nik Fialka, recorded on March 18, 2024. In this episode, Tim shares financial advice for pilots, particularly focusing on veterans transitioning to civilian aviation careers. Tim delves into the nuances of managing finances in…
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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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In this special episode of the Pilot Money Podcast, Timothy P. Pope, CFP®, focuses on the remarkable efforts of pilots providing disaster relief following Hurricane Helene. As the storm wreaked havoc from Florida to Virginia, causing unprecedented damage and displacement, the pilot community, led by Operation Airdrop, rallied to deliver essential a…
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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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Join Timothy P. Pope, CFP®, as he sits down with David Hampson, partner at Schrager Hampson Aviation Insurance Group, to explore the critical aspects of aviation insurance. This episode helps pilot owners understand the nuances of insuring aircraft. From pleasure use to business use corporate jets, and the importance of having the right coverage ca…
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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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In this timely episode of the Pilot Money Podcast, Timothy P. Pope, CFP®, delves into the often-asked question about whether investment strategies should change during an election year. With the U.S. presidential election looming, Tim explores the potential impacts of election outcomes on the financial markets and what investors—particularly pilots…
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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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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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Join Timothy P. Pope, CFP®, as he welcomes Kevin Walker to the Pilot Money Podcast for an enlightening conversation about aircraft ownership. Kevin, with his extensive experience as an air traffic controller and a general aviation pilot, shares his perspective on owning various types of aircraft over the years. In this episode, Kevin describes his …
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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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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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Join host Timothy P. Pope, CFP®, for this episode of the Pilot Money Podcast as he addresses financial questions from two military aviators. Tim provides detailed, actionable insights tailored to the financial questions these pilots have, from optimizing tax free retirement income to timing decisions of major purchases. This Q&A session features qu…
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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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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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In this episode of the Pilot Money Podcast, Timothy P. Pope, CFP® sits down with Preston Holland, Chief Commercial Officer at Firecrown who oversees the Aviation Finance Division. Preston shares the influence aviation had in his early life and how he’s become a key player in the aviation media and finance. The discussion highlights the nuts and bol…
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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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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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Join Timothy P. Pope, CFP®, as he continues to unravel the complexities of retirement planning based on airline direct contributions in Part II of this pivotal series. Building on the insights from Episode 13, this episode dives deeper into whether pilots can and should rely only on their company’s contributions to secure a comfortable retirement. …
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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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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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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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Join Timothy P. Pope on this episode of the Pilot Money Podcast as he delves into the intriguing world of real estate investment with Tait Duryea, an airline pilot and real estate entrepreneur. Tait shares his career journey, starting as a passionate aviator influenced by a family legacy at Hawaiian Airlines, to becoming a savvy real estate investo…
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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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In this Q&A episode of the Pilot Money Podcast, host Timothy P. Pope, CFP® tackles retirement planning questions from pilot listeners. This episode is a Q&A session where Tim addresses questions about optimizing retirement contributions across multiple employer plans and how to best handle bonuses. Join Tim as he explores the intricacies of managin…
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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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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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Join Timothy P. Pope, CFP®, as he explores the intersection of behavioral finance and personal decision-making with Jennifer Bower, a seasoned financial coach with roots in the aviation community. With her unique blend of intelligence background and financial acumen, Jennifer offers a fresh perspective on tackling financial challenges and behaviora…
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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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Join Timothy P. Pope, CFP®, as he delves into an intriguing financial analysis in this solo episode of the Pilot Money Podcast. Drawing from the energetic discussions with Jason DePew on achieving early financial independence, Tim pivots to a scenario that many pilots might ponder: Can relying solely on company contributions suffice for a comfortab…
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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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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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Join Timothy P. Pope, CFP®, a financial planner who specializes in the planning needs of professional pilots, as he welcomes Captain Jason DePew to the Pilot Money Podcast. Jason DePew, a captain at a major airline and personal finance enthusiast, shares his journey towards financial independence. This discussion is not just about numbers; it's a d…
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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…
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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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Join Timothy P. Pope, CFP® in this relatable solo episode of the Pilot Money Podcast. Tim shares a personal story about his recent close-call with impulse buying. Tim explores the triggers and tactics he used to maintain financial discipline. This episode also touches on Tim’s passion for aviation and his recent flights with his family. Listen as T…
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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…
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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…
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In this eye-opening episode of the Pilot Money Podcast, Timothy P. Pope, CFP® sits down with Nik and Anna Fialka for a deeply personal and insightful conversation about the financial challenges and triumphs of a pilot's family. Nik, the host of "Ready for Pushback," and Anna, the unsung hero managing the behind-the-scenes dynamics of the Fialka hou…
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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’…
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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…
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In this light but insightful episode, Timothy P. Pope, a CERTIFIED FINANCIAL PLANNER™ who specializes in the planning needs of professional pilots, draws parallels between the game of Monopoly and real-world financial planning. After delving into technical topics in previous episodes, Tim decides to share a more relaxed conversation about five cruc…
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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…
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As tax season is in full swing, now is the perfect time for pilots to begin thinking about the next year. What went well last year and what do you want to change for next year’s tax season? In this episode we explore real estate investment opportunities with an emphasis on proactive tax planning strategies. Whether actively managing properties or i…
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