In this episode of Pilot’s Portfolio , Timothy P. Pope, CFP® continues the Loss of Medical series with a deep dive into what happens if a Southwest Airlines pilot loses their medical. Tim outlines why Southwest’s program may be the most pilot-friendly of all the majors, including generous long-term disability benefits, a built-in COLA, a flexible tax election, and the unique “new hire bridge” benefit for newer pilots. If you fly for Southwest—or are considering it—this episode is packed with pra...
Jul 07, 2025•24 min•Season 2Ep. 11
In this detailed solo episode of Pilot’s Portfolio , Timothy P. Pope, CFP® walks Delta pilots through everything they need to know if they lose their medical and can’t fly. From contractual long-term disability benefits and the Delta Pilots Mutual Aid (DPMA) program to ALPA’s voluntary insurance options, Tim explains how to layer your benefits, understand offsets, and evaluate your real financial protection. This episode is packed with actionable knowledge to help Delta pilots build a smarter, m...
Jun 23, 2025•27 min•Season 2Ep. 10
In this special episode of Pilot's Portfolio , Timothy P. Pope, CFP® sits down once again with Kevin Walker, CEO of Beacon Relocation, to break down current trends in the housing market that every pilot should be paying attention to. From shifting interest rates to buyer leverage, Tim and Kevin discuss what has changed since the last real estate conversation and how pilots can take advantage of current conditions. Plus, Tim shares an exciting update about the future of the financial planning pra...
Jun 09, 2025•34 min•Season 2Ep. 9
In this focused solo episode, Timothy P. Pope, CFP®, breaks down what happens if an American Airlines pilot loses their medical and becomes unable to fly. Tim reviews the employer-provided long-term disability plan, the union-sponsored POD and PMA supplements, and how pilots can combine these for up to 90% of pre-disability income. From elimination periods to taxation choices and income offsets, this episode equips you with the knowledge to protect your financial stability if your career hits un...
May 26, 2025•21 min•Season 2Ep. 8
In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP® shares practical strategies for building financial resilience in volatile times. Drawing parallels between aviation safety and financial planning, Tim explains how pilots can strengthen their financial "redundancy" to absorb unexpected challenges like airline slowdowns, downgrades, or health setbacks. Whether you're buying a home, saving for retirement, or thinking about Roth conversions during market pullbacks, this episode is packed w...
Apr 28, 2025•20 min•Season 2Ep. 7
Join Timothy P. Pope, CFP®, and John Engel, COO of Gulf Coast Western, as they discuss strategic investment opportunities in the oil and gas sector that could help high-earning pilots. This episode offers an insider look into tax benefits and how to leverage investments to offset high W2 incomes and to secure tax advantaged future income. Dive deep into the mechanics of oil investments and learn how to navigate this market with industry insights. What You'll Learn from This Episode: Tax Incentiv...
Apr 14, 2025•54 min•Season 2Ep. 6
Join Timothy P. Pope, CFP®, in a profoundly important episode of Pilot's Portfolio, where he tackles the uncomfortable yet crucial topic of estate and financial planning for pilots. With a recent tragic aviation incident as a backdrop, Tim highlights the necessity of being prepared for unforeseen events. This discussion is not just about planning for growth and success but ensuring stability and security for your loved ones. What You'll Learn from This Episode: Understanding Estate Planning : Th...
Mar 31, 2025•21 min•Season 2Ep. 5
In this insightful solo episode, Timothy P. Pope, CFP®, explores how pilots can maintain command over their personal finances amidst market turbulence and external economic factors. Tim emphasizes the importance of focusing on what pilots can control in their financial planning, from responding to market conditions to proactive financial strategies. Join Tim as he guides you through managing the uncertainties of the financial world with confidence and clarity. What You'll Learn from This Episode...
Mar 17, 2025•20 min•Season 2Ep. 4
Join Timothy P. Pope, CFP®, and Kevin Walker, CEO of Beacon Relocation as they discuss real estate benefits specifically tailored for pilots and air traffic controllers. Recorded shortly after the PSA and army helicopter crash, this episode acknowledges the recent tragedy. This episode focuses on financial savings in real estate transactions for pilots and air traffic controllers. Kevin shares his decades of experience in real estate and how his company has grown from serving Air Traffic Control...
Mar 03, 2025•30 min•Season 2Ep. 3
Join Timothy P. Pope, CFP®, in this informative episode of Pilot's Portfolio as he discusses the latest updates and changes in retirement contributions for pilots. Tim discusses the implications of increased contribution limits and how these adjustments can impact your financial planning. Additionally, he shares an IRS provision that bugs him concerning retirement savings. Tim invites listeners to share their feedback, what do you think about the new IRS savings rules? What You'll learn from thi...
Feb 17, 2025•19 min•Season 2Ep. 2
Welcome to " Pilot's Portfolio " formerly known as the Pilot Money Podcast . In our inaugural episode of the new season and under a new banner, Timothy P. Pope, CFP®, reintroduces the show with fresh insights and a renewed focus. As we begin a new year of financial planning for professional pilots, Tim discusses the recent market results, the implications for your investments, and strategies to ensure you're not "falling asleep at the yoke." What You'll learn from this episode: A New Season for ...
Feb 03, 2025•18 min•Season 2Ep. 1
Join Timothy P. Pope, CFP®, as we soar through the most impactful moments of our inaugural season on the Pilot Money Podcast. This special episode compiles the best insights, advice, and discussions from the past year, featuring key financial strategies, listener favorites, and expert tips tailored for pilots. From navigating investments to planning for retirement and beyond, relive the highlights that have equipped our community to tackle their financial challenges with confidence . Listen to y...
Dec 23, 2024•11 min
Join Timothy P. Pope, CFP®, as he dives into crucial year-end financial strategies that can significantly impact your financial health. As 2024 draws to a close, Tim emphasizes the importance of making timely decisions that utilize year-end financial opportunities like Roth conversions, tax loss harvesting, and charitable giving. Each of these strategies has specific deadlines and benefits, making them essential considerations for effective tax planning and long-term financial stability. What Yo...
Nov 25, 2024•19 min•Season 1Ep. 26
Join Timothy P. Pope, CFP®, as he welcomes NMLS 2498573 Bobby Baker, an experienced aviator and mortgage specialist with Trident Home Loans, to the Pilot Money Podcast. In this episode Bobby shares his dual expertise in aviation and home financing, offering tailored mortgage solutions for pilots. Drawing from his unique background in both the military and commercial aviation, Bobby discusses how pilots can navigate the often-complex landscape of home loans, emphasizing options like VA loans and ...
Nov 11, 2024•45 min•Season 1Ep. 25
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 breakdown of the various benefits available—from health insurance to legal benefits—and how to choose well based on your personal circumstances. What You'l...
Oct 28, 2024•19 min•Season 1Ep. 24
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 such transitions, emphasizing the importance of understanding and maximizing military benefits for a secure financial future. What You'll learn from ...
Oct 14, 2024•40 min•Season 1Ep. 23
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 aid to those hardest hit, particularly in Western North Carolina. Timothy discusses the urgent logistical challenges faced by affected areas, where roa...
Oct 02, 2024•19 min
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 cannot be overstated. David shares his journey from a young aviation enthusiast to a key figure in aviation insurance, merging his passion with professi...
Sep 30, 2024•58 min•Season 1Ep. 22
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—should consider. Tim addresses common concerns about market uncertainty in election seasons and provides a well-rounded view on why maintaining a ste...
Sep 16, 2024•19 min•Season 1Ep. 21
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 personal journey in aviation, from the early influence of his father to his multiple aircraft ownership experiences. He discusses the practical aspect...
Sep 02, 2024•41 min•Season 1Ep. 20
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 questions from an active-duty Navy aviator planning his transition to civilian aviation and contemplating a major real estate purchase, and another ...
Aug 19, 2024•22 min•Season 1Ep. 19
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 bolts of aircraft financing and explores how Preston's team, armed with industry knowledge, make the purchasing process easy for pilots. Preston outlines...
Aug 05, 2024•56 min•Season 1Ep. 18
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. Timothy breaks down different scenarios based on career length. Using Delta’s 2026 pay rates and projections, Timothy discusses the practicality of ex...
Jul 22, 2024•18 min•Season 1Ep. 17
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 investor and the CEO of Turbine Capital. In this conversation, Tait explains his initial foray into real estate several years after the Great Recession, his ...
Jul 08, 2024•1 hr 10 min•Season 1Ep. 16
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 managing 401(k) contributions and TSP accounts simultaneously, illustrating how pilots can effectively strategize their retirement savings to maximiz...
Jun 24, 2024•18 min•Season 1Ep. 15
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 behavioral patterns that impact financial health. In this episode, Jennifer shares her transformative insights from a fraud investigator to a financial coach, ...
Jun 10, 2024•47 min•Season 1Ep. 14
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 comfortable retirement? This episode unpacks the realities of pilot contracts, company contributions, and the lifestyle choices that affect financial planning ...
May 27, 2024•29 min•Season 1Ep. 13
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 deep dive into the disciplined financial strategies and mindset that have shaped Jason’s approach, reflecting on the parallels between piloting and fin...
May 13, 2024•44 min•Season 1Ep. 12
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 Tim recounts back-to-back moments of resisting the temptation to clean out the shelves at a local hardware store and avoiding making a fun but untimely...
Apr 29, 2024•18 min•Season 1Ep. 11
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 household, share their unique perspectives on navigating the unpredictable financial landscape of the aviation industry. From enduring years of income un...
Apr 15, 2024•52 min•Season 1Ep. 10
