Claim OwnershipPilot’s Portfolio
Subscribed: 8Played: 51
Subscribe
© 2026 Pilot’s Portfolio
Description
Timothy Pope’s Pilot’s Portfolio podcast is provided for general information purposes only and does not constitute accounting, legal, tax or other professional advice. Listeners should not act upon the content or information found here without first seeking appropriate advice from an accountant, financial planner, lawyer or other professional.
Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), a registered investment advisory firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.
55 Episodes
Reverse
In this episode, our host Timothy Pope looks at automation in financial planning and investing. For many pilots, automation helped build the emergency fund, grow the 401(k), and create strong saving habits early in the career. But as income rises, taxes increase, and decisions become more complex, automation by itself usually is not sufficient. Tim explains the shift from simple accumulation to financial coordination. He walks through where automation still shines, where it can quietly create...
In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP®, Firm Principal and Client Advisor at 360 Aviation Advisors™, is joined by Kevin Walker, Co-Founder/CEO, and Jade Barnett, Co-Founder/COO of Beacon Relocation, to discuss how listeners have received nearly $39,000 back through Beacon’s real estate program. They break down how the model works on both the buy and sell side, how credits can come back as a check or closing-cost support, and what buyers need to know about buyer broker agr...
In this Q&A episode of Pilot’s Portfolio, Timothy P. Pope, CFP®, Founder and Principal of 360 Aviation Advisors™, answers three listener questions that surface real-world friction inside airline retirement planning. First, a Southwest pilot asks whether taking NEC as Roth impacts their ability to contribute or convert to a private Roth IRA. Next, a Delta pilot seeks clarity on the difference between 401k, 401a, Roth, and after-tax contributions, and how contribution sequencing affects tax...
In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy P. Pope explains a new option for Southwest pilots, taking their NEC as Roth starting in 2026. He covers what NEC is, how Secure 2.0 made Roth employer contributions possible, and how Southwest is rolling this out. Tim walks through what changes when you elect Roth NEC, including how it shows up on your W-2, what happens with federal income tax and FICA, and why some pilots could be under withheld if they do not pla...
In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy P. Pope looks at how money can support or strain relationships, especially for professional pilots who spend long stretches away from home. He talks about income differences, schedule pressure, and clashing money styles, and how those can quietly build resentment if they are not discussed. Tim shares examples from his planning work and his own marriage, and offers ideas for improving communication, account setup, an...
In the first episode of Season 3, our host, Certified Financial Planner™ and GA pilot, Tim Pope recaps 2025’s market and policy shifts, and he explains why diversification and tax-centered planning made the difference this year, especially for high-income pilots. Tim also highlights key tax law changes, reflects on aviation incidents that underscore the importance of estate planning, and previews what is ahead for the podcast in 2026, including more interviews, peer stories, and strategy focu...
This episode was requested by listener feedback! Our host, Certified Financial Planner™ and GA pilot, Tim Pope compares long-term disability (LTD) coverage for FedEx and UPS pilots, examining how each plan works and how they stack up across the industry. He breaks down union and core benefits, highlighting key differences in benefit duration, tax treatment, monthly caps, waiting periods, and income offsets. The episode also explores how FedEx and UPS compare to passenger airlines, and what ca...
In this time-sensitive episode, Certified Financial Planner™ and GA pilot Tim Pope unpacks the new Market-Based Cash Balance Plan (MBCBP) for American Airlines pilots ahead of the December 15 opt-in deadline. He explains how the plan captures NEC spillover beyond 401(k) limits, who qualifies, and how it differs from other carriers. What You'll Learn from This Episode Plan Basics: How the MBCBP captures NEC spillover when 401(k) limits are hit—by percentage caps or dollar thresholds.Spil...
In this episode of Pilot’s Portfolio, Certified Financial Planner and GA pilot Tim Pope helps pilots close out the year with clarity and confidence. As 2026 approaches, new tax and retirement contribution rules are set to take effect—and Tim explains what they mean for your paycheque, your savings, and your strategy. From 401(k) and IRA limit increases to the controversial new Roth “catch-up” rule, this episode unpacks how to plan ahead and avoid falling into what Tim calls a “2026 tax grab”....
In this episode, we tackle a question many pilots ask themselves: what should I be working on right now? Whether it's debt repayment, buying a home, saving for retirement, or funding your kids' college, it can be hard to figure out which goal takes priority. Our host, Timothy P. Pope, CFP introduces the "WIN" framework: What's Important Now, and walks through how to use your financial plan to identify the highest-impact move based on your stage of life, income level, and risk profile. What Yo...
In this two-part episode, Tim Pope tackles two critical topics for pilots heading into 2026: real estate strategy and savings goals. First, Jade Barnett, USAF Veteran, Chief Operating Officer at Beacon Relocation (sponsor) joins the show to break down current market conditions, what buyers and sellers can expect across various metro areas, and how to navigate PCS or base-related moves. Plus: a new listener-exclusive promo for Pilot's Portfolio listeners - 25% of your agent's commission back w...
As the year wraps up, our host Tim Pope highlights key planning reminders for pilots: open enrollment choices, tax strategies, 401(k) adjustments, and life changes like marriage, divorce, child birth, or buying a new home. He also covers Roth conversions, gain harvesting, FSA timing, and estate document updates. What You'll Learn from This Episode Open Enrollment Considerations: What to review before re-electing benefits, especially if your airline changed providers or you’ve had a majo...
You've probably heard the saying, "The best day of your life is when you sell it": and no, we're not talking about boats. We're talking about self managed rental properties. In this episode, Tim is joined by Trevor Flor, Navy veteran, former Delta pilot, and now a real estate investment advisor specializing in DSTs (Delaware Statutory Trusts) and 1031 exchanges at Aimpoint Investments. Trevor breaks down how 1031 exchanges really work, why DSTs were created, and how this is one potential appr...
In this episode, Tim asks the question many pilots hear in the cockpit: Is your 401(k) a scam? He walks through why 401(k)s exist, how they replaced pensions, and what today’s airline plans actually offer: contribution mechanics, investment menus, legal protections, and employer contributions specific to the majors. Tim also shares a listener email requesting a cargo-carrier disability deep-dive and invites other cargo pilots to weigh in. What You'll Learn from This Episode Pensions vs. 401(k...
In this episode, Timothy P. Pope, CFP®, discusses the newly signed "One Big Beautiful Bill Act" (OBBBA), breaking down the key tax changes and how they'll directly affect your bottom line. Tim explains the impact of maintaining current tax brackets, the increased standard deduction, and significant enhancements to State and Local Tax (SALT) deductions. He covers new provisions for charitable deductions, expanded child tax credits, and special interest deductions on U.S.-assembled vehicles. Ad...
In this final episode of the Loss of Medical series, Timothy P. Pope, CFP® turns the spotlight on United Airlines. Tim offers a full breakdown of United’s disability coverage—from how benefits are calculated to the contractual caps and offsets that impact long-term payouts. He also reviews the ALPA supplement options, including monthly add-ons and a lump sum feature. What You'll Learn from This Episode United’s Disability Formula: Learn how the 1026-hour rule works and what it means f...
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 p...
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,...
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 p...
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...
Comments
Download from Google Play
Download from App Store
United States