Pilot’s Portfolio
Episodes
How to Prepare for Retirement During Turbulent Times
20 Apr 2026
Contributed by Lukas
In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy Pope, breaks down how airline pilots should prepare for retirement dur...
Discipline First, Freedom Later: A Pilot-to-Pilot Money Conversation
06 Apr 2026
Contributed by Lukas
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 ...
When Do Pilots Need More Than Automation? What to Do When Your Financial Life Gets More Complex
23 Mar 2026
Contributed by Lukas
In this episode, our host Timothy Pope looks at automation in financial planning and investing. For many pilots, automation helped build the emergency...
Our listeners have saved nearly $40,000 - What you need to know for real estate transactions this year
09 Mar 2026
Contributed by Lukas
In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP®, Firm Principal and Client Advisor at 360 Aviation Advisors™, is joined by Kevin Walk...
Q&A: Roth, 401a, and DAF Strategy
23 Feb 2026
Contributed by Lukas
In this Q&A episode of Pilot’s Portfolio, Timothy P. Pope, CFP®, Founder and Principal of 360 Aviation Advisors™, answers three listener ques...
Should Southwest Pilots Take Their NEC As Roth?
09 Feb 2026
Contributed by Lukas
In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy P. Pope explains a new option for Southwest pilots, taking their NEC a...
Is Money Ruining Your Relationship?
19 Jan 2026
Contributed by Lukas
In this episode, our host, Certified Financial Planner™ and GA pilot, Tim Pope looks at how money can support or strain relationships, especially fo...
2025 In Review - What To Expect in 2026
05 Jan 2026
Contributed by Lukas
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 exp...
FedEx & UPS Loss of Medical - How do they compare?
08 Dec 2025
Contributed by Lukas
Promoted by pilot questions, our host, Certified Financial Planner™ and GA pilot, Tim Pope compares long-term disability (LTD) coverage for FedEx an...
Opt In or Out? American Airlines Market-Based Cash Balance Plan Explained
24 Nov 2025
Contributed by Lukas
In this time-sensitive episode, Certified Financial Planner and GA pilot Tim Pope unpacks the new Market-Based Cash Balance Plan (MBCBP) for America...
The IRS Wants More: Understanding the 2026 Changes
10 Nov 2025
Contributed by Lukas
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....
Focus on WIN: What's Important Now?
27 Oct 2025
Contributed by Lukas
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 ho...
How Much Should I Be Saving Right Now? Plus - Special Promo! Save Even More on your Next Real Estate Transaction
13 Oct 2025
Contributed by Lukas
In this two-part episode, Tim Pope tackles two critical topics for pilots heading into 2026: real estate strategy and savings goals. First, Jade Barne...
Approaching Year End: What Should I Be Thinking About?
29 Sep 2025
Contributed by Lukas
As the year wraps up, our host Tim Pope highlights key planning reminders for pilots: open enrollment choices, tax strategies, 401(k) adjustments, and...
Real Estate Without the Headaches: DSTs for Pilots
15 Sep 2025
Contributed by Lukas
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'...
Is your 401k a Scam?
18 Aug 2025
Contributed by Lukas
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 p...
How will the New Tax Bill Affect Your Bottom Line?
04 Aug 2025
Contributed by Lukas
In this episode, Timothy P. Pope, CFP®, discusses the newly signed "One Big Beautiful Bill Act" (OBBBA), breaking down the key tax changes ...
What Happens If I Lose My Medical At United Airlines
21 Jul 2025
Contributed by Lukas
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 Uni...
What Happens If I Lose My Medical At Southwest Airlines
07 Jul 2025
Contributed by Lukas
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 ...
What Happens If I Lose My Medical At Delta Air Lines
23 Jun 2025
Contributed by Lukas
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 thei...
Tim Shares Big News + Real Estate Market Trends with Kevin Walker
09 Jun 2025
Contributed by Lukas
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 d...
What Happens If I Lose My Medical At American Airlines
26 May 2025
Contributed by Lukas
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...
Don't Let Market Turbulence Derail Your Financial Goals
28 Apr 2025
Contributed by Lukas
In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP® shares practical strategies for building financial resilience in volatile times. Drawin...
Tax-Savvy Investing for Pilots: A Deep Dive into Oil & Gas
14 Apr 2025
Contributed by Lukas
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 t...
Flying West: Preparing Your Estate as a Pilot
31 Mar 2025
Contributed by Lukas
Join Timothy P. Pope, CFP®, in a profoundly important episode of Pilot's Portfolio, where he tackles the uncomfortable yet crucial topic of esta...
Pilot in Command: Navigating Market Turbulence
17 Mar 2025
Contributed by Lukas
In this insightful solo episode, Timothy P. Pope, CFP®, explores how pilots can maintain command over their personal finances amidst market turbulenc...
Maximizing Real Estate Savings: A Pilot's Guide with Kevin Walker
03 Mar 2025
Contributed by Lukas
Join Timothy P. Pope, CFP®, and Kevin Walker, CEO of Beacon Relocation as they discuss real estate benefits specifically tailored for pilots and air ...
2025 Retirement Update: What Pilots Need to Know
17 Feb 2025
Contributed by Lukas
Join Timothy P. Pope, CFP®, in this informative episode of Pilot's Portfolio as he discusses the latest updates and changes in retirement contri...
Pilot’s Portfolio: What’s Changing in 2025?
03 Feb 2025
Contributed by Lukas
Welcome to "Pilot's Portfolio" formerly known as the Pilot Money Podcast. In our inaugural episode of the new season and under a new b...
Best Of Season 1
23 Dec 2024
Contributed by Lukas
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 co...
Wrap Up Your Year: Key Financial Moves Before 2024 Ends
25 Nov 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, as he dives into crucial year-end financial strategies that can significantly impact your financial health. As 2024 draws...
Rates Have Dropped, Should I refi? Mortgage Tips with NMLS 2498573 Bobby Baker
11 Nov 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, as he welcomes NMLS 2498573 Bobby Baker, an experienced aviator and mortgage specialist with Trident Home Loans, to the P...
Optimizing Benefits: Open Enrollment Strategies for Pilots
28 Oct 2024
Contributed by Lukas
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...
Real Talk for Transitioning Veterans with Nik Fialka
14 Oct 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, in a special crossover episode from his appearance on the "Ready 4 Pushback" podcast, hosted by Nik Fialka, rec...
Helping Hurricane Helene Victims | Operation Airdrop
02 Oct 2024
Contributed by Lukas
In this special episode of the Pilot Money Podcast, Timothy P. Pope, CFP®, focuses on the remarkable efforts of pilots providing disaster relief foll...
Take Command of Your Coverage: Aircraft Insurance Tips for Pilots
30 Sep 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, as he sits down with David Hampson, partner at Schrager Hampson Aviation Insurance Group, to explore the critical aspects...
Investing During An Election: Should You Shift Your Strategy?
16 Sep 2024
Contributed by Lukas
In this timely episode of the Pilot Money Podcast, Timothy P. Pope, CFP®, delves into the often-asked question about whether investment strategies sh...
Aircraft Ownership: The Cost Beyond The Purchase
02 Sep 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, as he welcomes Kevin Walker to the Pilot Money Podcast for an enlightening conversation about aircraft ownership. Kevin, ...
Q&A Episode | Should I Buy My House Outright With Cash?
19 Aug 2024
Contributed by Lukas
Join host Timothy P. Pope, CFP®, for this episode of the Pilot Money Podcast as he addresses financial questions from two military aviators. Tim prov...
Aerial Acquisitions: How to Finance Your Dream Aircraft
05 Aug 2024
Contributed by Lukas
In this episode of the Pilot Money Podcast, Timothy P. Pope, CFP® sits down with Preston Holland, Chief Commercial Officer at Firecrown who oversees ...
Can I Retire on My Company's NEC Part II
22 Jul 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, as he continues to unravel the complexities of retirement planning based on airline direct contributions in Part II of th...
From Cockpit to Capital: Real Estate Investing with Tait Duryea
08 Jul 2024
Contributed by Lukas
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 ...
Q&A Episode | How Do I Maximize TSP and Airline 401k?
24 Jun 2024
Contributed by Lukas
In this Q&A episode of the Pilot Money Podcast, host Timothy P. Pope, CFP® tackles retirement planning questions from pilot listeners. This episo...
Mastering Money & Mindset With Jennifer Bower
10 Jun 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, as he explores the intersection of behavioral finance and personal decision-making with Jennifer Bower, a seasoned financ...
I’m Not Contributing to my Airline 401k - Will I Have Enough For Retirement?
27 May 2024
Contributed by Lukas
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 ener...
Charting a Course to Financial Independence: A Pilot's Guide
13 May 2024
Contributed by Lukas
Join Timothy P. Pope, CFP®, a financial planner who specializes in the planning needs of professional pilots, as he welcomes Captain Jason DePew to t...
Holding Short of Impulse Buying
29 Apr 2024
Contributed by Lukas
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 ...
One Pilot-Family’s Financial Planning Journey
15 Apr 2024
Contributed by Lukas
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...
What Does Playing Monopoly Have in Common with Financial Planning?
01 Apr 2024
Contributed by Lukas
In this light but insightful episode, Timothy P. Pope, a CERTIFIED FINANCIAL PLANNER™ who specializes in the planning needs of professional pilots, ...
Tax Planning Tips Using Real Estate
18 Mar 2024
Contributed by Lukas
As tax season is in full swing, now is the perfect time for pilots to begin thinking about the next year. What went well last year and what do you wan...
You Make Too Much To Contribute To a Roth IRA - Now What?
04 Mar 2024
Contributed by Lukas
In this episode, CERTIFIED FINANCIAL PLANNER™ Timothy P. Pope delves into the intricacies of the backdoor Roth IRA strategy. He explains how this me...
How to Navigate an Aviation Down-Turn
19 Feb 2024
Contributed by Lukas
Tim hosts Dylan and Max from the 21. Five Show in this episode. Dylan and Max reflect on their experiences during various aviation downturns, spanning...
My Side Hustle Blew Up! What Can I Do About Taxes?
05 Feb 2024
Contributed by Lukas
In this episode, Tim tackles some burning questions from an enterprising business aviation airman. Due to the airlines sucking a lot of talent from bu...
Flight Plan for Your Paycheck: Unveiling Business Aviation Compensation
22 Jan 2024
Contributed by Lukas
In this episode, Dr. Christopher Broyhill takes us on a journey through the intricacies of business aviation compensation. Buckle up as we explore the...
How To Maximize Your Airline Career + 2024 Contribution Limit Updates
08 Jan 2024
Contributed by Lukas
Join Timothy P. Pope, CFP® as he discusses three key strategies for pilots to maximize their career opportunities. With airline career values easily ...
What's Your Career Worth? Airline Compensation & Trends with Kit Darby
08 Jan 2024
Contributed by Lukas
It's a fantastic time to be a professional pilot. Timothy P. Pope, CFP® and Kit Darby jump into the current trends and drivers of airline compen...
Welcome to the Pilot Money Podcast
08 Jan 2024
Contributed by Lukas
In this episode, Timothy P. Pope, CFP® welcomes you to the Pilot Money Podcast. He shares his background in financial planning and discusses mergin...