Pilot’s Portfolio

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Pilot’s Portfolio

Timothy P. Pope, CFP®

50 episodes

1 day ago

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...

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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...

Show more...

Episodes (20/50)

Pilot’s Portfolio

2025 In Review - What To Expect in 2026

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...

1 day ago

20 minutes

Pilot’s Portfolio

FedEx & UPS Loss of Medical - How do they compare?

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...

4 weeks ago

17 minutes

Pilot’s Portfolio

Opt In or Out? American Airlines Market-Based Cash Balance Plan Explained

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...

1 month ago

22 minutes

Pilot’s Portfolio

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”....

1 month ago

24 minutes

Pilot’s Portfolio

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...

2 months ago

20 minutes

Pilot’s Portfolio

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...

2 months ago

42 minutes

Pilot’s Portfolio

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...

3 months ago

27 minutes

Pilot’s Portfolio

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...

3 months ago

52 minutes

Pilot’s Portfolio

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...

4 months ago

22 minutes

Pilot’s Portfolio

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...

5 months ago

21 minutes

Pilot’s Portfolio

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. Description: What You'll Learn from This Episode United’s Disability Formula: Learn how the 1026-hour rule works and wh...

5 months ago

20 minutes

Pilot’s Portfolio

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...

6 months ago

23 minutes

Pilot’s Portfolio

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,...

6 months ago

27 minutes

Pilot’s Portfolio

Tim Shares Big News + Real Estate Market Trends with Kevin Walker

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...

7 months ago

34 minutes

Pilot’s Portfolio

What Happens If I Lose My Medical At American Airlines

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...

7 months ago

20 minutes

Pilot’s Portfolio

Don't Let Market Turbulence Derail Your Financial Goals

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 packe...

8 months ago

19 minutes

Pilot’s Portfolio

Tax-Savvy Investing for Pilots: A Deep Dive into Oil & Gas

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 Incen...

8 months ago

54 minutes

Pilot’s Portfolio

Flying West: Preparing Your Estate as a Pilot

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: ...

9 months ago

21 minutes

Pilot’s Portfolio

Pilot in Command: Navigating Market Turbulence

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 Epis...

9 months ago

20 minutes

Pilot’s Portfolio

Maximizing Real Estate Savings: A Pilot's Guide with Kevin Walker

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 Cont...

10 months ago

30 minutes