Pilot’s Portfolio

Is now a good time for pilots to buy a home, or does it make more sense to wait? In this episode of The Pilot’s Portfolio, Timothy P. Pope, CFP® welcomes back Kevin Walker, and Jade Barnett, respectively CEO and COO of Beacon Relocation, for a mid-year housing market check-in. Tim, Kevin, and Jade revisit earlier real estate forecasts and discuss how today’s market is actually playing out, from hi...

In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy Pope, speaks directly to Spirit Airlines pilots and families navigating an unexpected and deeply challenging career disruption. Tim focuses on the practical financial side of the situation, including emergency funds, household burn rate, retirement-account decisions, lower-income-year tax opportunities, and the unique co...

In this updated re-issue of one of Pilot’s Portfolio’s early conversations, Timothy P. Pope, CFP®, revisits a timely question with compensation expert Kit Darby: what is a pilot career really worth? Tim adds 2026 reflections throughout, connecting Kit’s insights to today’s planning reality: income should become flexibility, resilience, and long-term options. When this episode first aired, pilot pa...

In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy Pope, breaks down how airline pilots should prepare for retirement during periods of market turbulence, particularly within the final five years before leaving the workforce. He explains the shift from accumulation to retirement readiness, and why volatile markets don’t require a new philosophy, but a more disciplined an...

In this Peer-to-Peer episode of Pilot’s Portfolio, our host, Certified Financial Planner™ and GA pilot, Timothy Pope sits down with First Officer André for a grounded conversation about discipline, freedom, and how financial habits shape long-term confidence. André shares his path from flight instructing and corporate flying to Envoy, furlough, and eventually American, along with the financial les...

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 fi...

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...

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 b...

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...

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 pl...

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...

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 incom...

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 MBC...

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” rul...

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 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...

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 revi...

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...

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 a...

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 c...

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 T...

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” bene...

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...

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...

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, t...