Pilot’s Portfolio
by Timothy P. Pope, CFP®
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On the show
From 13 epsHosts
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Recent episodes
How Can Pilots Pay Less in Taxes? Part 2: Think Beyond One Year
Aug 24, 2026
16m 54s
How Can Pilots Pay Less in Taxes? Part 1: Start With the Right Number
Aug 10, 2026
15m 48s
Should Pilots Buy Now or Wait? Rates, Prices, and the Housing Market, with Beacon Relocation
Jun 15, 2026
31m 13s
Spirit Airlines Shutdown: What Pilots Should Do Next
May 18, 2026
27m 04s
What's Your Career Worth? 2026 Updates - Airline Compensation & Trends with Kit Darby
May 4, 2026
40m 41s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 8/24/26 | How Can Pilots Pay Less in Taxes? Part 2: Think Beyond One Year | In Part 1 of this conversation, Timothy P. Pope, CFP, started with the first step in tax planning: understanding what the tax number actually means. If you missed that episode, stream it here: In this following part, Tim continues the tax conversation by moving from deductions to longer-term planning, exploring taxable brokerage accounts, investment tax efficiency, tax-loss harvesting, embedded capital gains, and why pilots may benefit from looking beyond a single tax return. He also discusse... | 16m 54s | ||||||
| 8/10/26 | How Can Pilots Pay Less in Taxes? Part 1: Start With the Right Number | After a short summer break, Pilot’s Portfolio is back with a refreshed format and a new Season (4)! This next run of episodes is built around real questions Timothy P. Pope, CFP® receives from professional pilots and their families in planning conversations. This is a two-part deep-dive on one of the biggest questions professional pilots bring to the planning table: “How can we pay less in taxes?” Whether the number is six figures or simply higher than expected, the starting point is understa... | 15m 48s | ||||||
| 6/15/26 | housing marketreal estate forecasts+3 | Kevin WalkerJade Barnett | Beacon Relocation | — | pilotshousing market+4 | — | 31m 13s | ||
| 5/18/26 | financial planningcareer disruption+4 | — | Spirit Airlines | — | Spirit Airlinesfinancial planning+5 | — | 27m 04s | ||
| 5/4/26 | airline compensationpilot career value+3 | Kit Darby | Pilot’s Portfolio | — | pilot compensationcareer worth+3 | — | 40m 41s | ||
| 4/20/26 | retirement planningmarket turbulence+3 | — | Certified Financial Planner™ | airline | retirementmarket volatility+3 | — | 23m 55s | ||
| 4/6/26 | financial habitsbudgeting+4 | André | EnvoyAmerican | — | financial planningpilot finances+3 | — | 50m 44s | ||
| 3/23/26 | financial planningautomation+4 | — | — | — | automationfinancial planning+6 | — | 23m 49s | ||
| 3/9/26 | real estate transactionssavings+4 | Kevin WalkerJade Barnett | 360 Aviation AdvisorsBeacon Relocation | — | real estatesavings+5 | — | 30m 17s | ||
| 2/23/26 | Roth IRA401a+4 | — | 360 Aviation Advisors™Southwest+1 | — | Roth IRA401a+5 | — | 25m 24s | ||
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| 2/9/26 | Southwest pilotsRoth contributions+4 | — | SouthwestSecure 2.0 | — | Southwest pilotsNEC+6 | — | 17m 07s | ||
| 1/19/26 | money and relationshipsfinancial planning+4 | — | — | — | moneyrelationships+5 | — | 31m 36s | ||
| 1/5/26 | market shiftstax planning+4 | — | — | 20252026 | market recaptax law changes+4 | — | 20m 31s | ||
| 12/8/25 | long-term disabilitypilot benefits+3 | — | FedExUPS+1 | — | long-term disabilityFedEx pilots+5 | — | 17m 21s | ||
| 11/24/25 | Market-Based Cash Balance PlanAmerican Airlines pilots+3 | — | American Airlines401(k) | — | Market-Based Cash Balance PlanAmerican Airlines+3 | — | 22m 07s | ||
| 11/10/25 | The IRS Wants More: Understanding the 2026 Changes | 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”.... | 24m 05s | ||||||
| 10/27/25 | Focus on WIN: What's Important Now? | 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... | 20m 50s | ||||||
| 10/13/25 | How Much Should I Be Saving Right Now? Plus - Special Promo! Save Even More on your Next Real Estate Transaction | 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... | 42m 37s | ||||||
| 9/29/25 | Approaching Year End: What Should I Be Thinking About? | 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... | 27m 26s | ||||||
| 9/15/25 | Real Estate Without the Headaches: DSTs for Pilots | 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... | 52m 44s | ||||||
| 8/18/25 | Is your 401k a Scam? | 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... | 22m 13s | ||||||
| 8/4/25 | How will the New Tax Bill Affect Your Bottom Line? | 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... | 20m 10s | ||||||
| 7/21/25 | What Happens If I Lose My Medical At United Airlines | 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... | 20m 24s | ||||||
| 7/7/25 | What Happens If I Lose My Medical At Southwest Airlines | 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... | 23m 33s | ||||||
| 6/23/25 | What Happens If I Lose My Medical At Delta Air Lines | 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,... | 27m 03s | ||||||
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