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 focused episodes pilots can apply.

What You'll Learn from This Episode

• 2025 Market Recap: How the year played out, from early volatility and a 19% drawdown in April to a roughly 17% gain for the S&P500 by year end.
• Why Diversification Mattered: How international stocks, precious metals, and bonds contributed to returns, and how different asset classes responded as the Federal Reserve cut rates.
• New Tax Law Changes: An overview of the extension of the 2017 tax cuts and the increase of the SALT deduction cap to $40K dollars, and why these changes are especially relevant for pilots in higher tax states.
• Planning Through a Tax Lens: How Roth decisions, brokerage account efficiency, charitable strategy, and portfolio rebalancing can be evaluated with taxes in mind.
• Estate Planning Reminder: Why beneficiary designations, guardianship decisions, and core documents such as wills and powers of attorney are important parts of a pilot's financial picture.
• Looking Ahead to 2026: More focused solo episodes, expert guests, and conversations with pilots navigating similar financial decisions.

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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 cargo pilots should keep in mind heading into contract negotiations.

What You'll Learn from This Episode

• UPS Disability Coverage: Core plan pays 66.7% of income for 10 months after a 6-month wait. Union add-ons are tax-free but capped at $7,500/month.
• FedEx Disability Structure: Core pays 60% for 24 months, then 50% coverage via the supplemental policy to age 65, capped by IRS 401(a)(17) limit.
• The lookback advantage: FedEx uses the highest 12 of the last 36 months’ pay, protecting recent high earners.
• Offset Clauses: Fedex reduces benefits for worker’s comp, Social Security and other earned income.
• Tax Treatment Differences: Core plans are taxable; union benefits are tax-free due to after-tax premiums.
• What Could Improve: UPS could extend coverage and reduce wait times; FedEx could drop income caps and continue NECs/ during disability.
• Industry Context: FedEx’s LTD is more in line with major passenger carriers than the UPS plan.
• Planning Note: Union LTD Plus Ups and side income help, but knowing your offset rules and caps is critical.

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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.
• Spill Cash Thresholds: When to expect spill cash based on whether you max your 401(k) (key earnings markers: $264k vs. $360k).
• 3-Year Election Window: Why AA's re-election lock differs from Delta, United, and Southwest—and offers added flexibility.
• Planning Flexibility: When opting out (liquidity, gains, inheritance) or in (avoiding tax drag, timing Roth moves) may make sense.
• Investment Gaps: Why lack of allocation transparency can hinder holistic planning with outside advisors.
• 401(k) vs. MBCBP: Key differences in investment control, Roth conversion flexibility, and contribution mechanics.
• Creditor & Beneficiary Rules: What stays consistent between this plan and your 401(k).
• Roth Strategy Fit: How the MBCBP can indirectly support Roth conversions by freeing up tax room elsewhere.
• Use Case Thinking: This plan isn’t good or bad—it’s a tool that must align with your financial phase.
• Deadline Reminder: Election closes December 15, 2025—locked in (or out) for three years.

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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”.

Tim also encourages reflection on your 2025 financial wins, the goals that didn’t quite land, and what to do differently next year. Whether you’re celebrating a major milestone, planning a move, or eyeing your next savings target, this episode helps you finish the year strong and start 2026 with a smarter plan.

What You'll Learn from This Episode

• How to reflect on 2025’s financial wins and identify what to improve in 2026.
• Which 401(k), IRA, and HSA contribution limits are changing in 2026—and how to plan for them.
• The truth behind the new Roth-only catch-up rule for earners above $145,000.
• How to decide between Roth and pre-tax contributions for tax efficiency.
• The differences between 401(k)s and IRAs—and why each matters for pilots.
• What “super catch-up contributions” mean for those aged 60–63.
• How to use reflection, discipline, and timing to turn frustration into financial advantage.
• Why 2026 may feel like a “tax grab”—and how to stay ahead of it.
  
  

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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 You'll Learn from This Episode

• WIN Framework: How "What's Important Now" can help pilots reduce overwhelm and focus on the right goal at the right time.
• Debt vs. Retirement Contributions: When high-interest debt should take priority over 401(k) deferrals, and when to grab the match.
• Buy or Rent?: Financial and lifestyle factors to consider when deciding whether to buy a home at a new base or hold off.
• Avoiding the House Poor Trap: How overextending on a mortgage can block other savings goals and limit financial flexibility.
• College vs. Retirement: Why kids can take out loans but you can't borrow for retirement - and when it's okay to help with tuition.
• Time Horizon Planning: How your age, NEC contributions, and market exposure should influence your decision-making.
• Cash Balance Plans: A quick overview of what's changing at American Airlines and how it compares to other carriers.
• Real Talk on Tradeoffs: How to stack and sequence goals using your plan—and when the numbers make the decision clear for you.

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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 when working with Beacon.

In the second half, Tim addresses the question: “How much should I be saving right now?” He walks through how to think about savings rates based on where you are in your career, the impact of the NEC, and how time horizon and compounding influence the outcome, outlining considerations to help you better understand your target savings rate.

What You'll Learn from This Episode

• Real Estate Market Snapshot: Why prices are softening and how buyer leverage is increasing, even with high rates.
• Pilot Relocation Planning: Tips for base transfers, PCS timing, and narrowing down options.
• Buy or Rent?: How to assess your current home and what a CMA (Comparative Market Analysis) can reveal.
• VA Loan Flexibility: How veterans and spouses can reuse or combine benefits strategically.
• Q4 Closing Trends: Why more buyers are closing in December and January.
• Buying with a Strategy: Spreadsheet mindset: compare square footage, districts, and yield.
• Boots on the Ground: Why talking to local agents early gives you an edge.
• Beacon's Year-End Promo: Pilot's Portfolio listeners who contact Beacon in Q4 2025 get 25% of agent commission credited toward closing costs - on both the buy and sell sides - Promo Code: BeaconPilot2025 (valid through all 2026 closings)
• Savings by Career Stage: How targets shift with your time horizon and how NEC contributions help.
• Compounding in Action: How even modest contributions grow with time.
  Early Saver Advantage: Why frontloading builds margin for the future.

Resources:

Visit https://www.beaconrelocation.com/ to learn more.
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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 major life event.
• Life Transitions and Benefits: How marriage, divorce, childbirth, or military retirement can affect your insurance, estate, and legal plan decisions.
• 401(k) Strategy: How to check your contribution progress, set your 2026 target, and re-evaluate Roth vs. traditional deferrals.
• Roth Conversions and Tax Bracket Planning: Why timing and bracket awareness matter when converting pre-tax dollars.
• Tax Gain Harvesting: How a low-income year might open a window to reset capital gains with little to no tax cost.
• Backdoor Roth Contributions: What deadlines actually apply and how to execute this multi-step move.
• FSA and Dependent Care Planning: Ways to prepare for upcoming expenses and reduce taxable income.
• Withholding Checkups: How to avoid surprises (or big refunds) in April by making Q4 adjustments now.
• Balancing Values and Financial Planning: Why it’s okay to spend money when it aligns with what matters to you, and how Tim applied that to a recent family mountain biking expense.

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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 approach to consider.

What You'll Learn from This Episode

• 1031 Exchanges Demystified: How selling investment property can be one potential approach to consider, depending on individual circumstances.
• DSTs as a Solution: Why Delaware Statutory Trusts were created, how they enable fractional ownership, and when they work best.
• Three DST Strategies: Using DSTs as a primary, backup, or complementary approach depending on your goals and exchange value.
• Timeline Rules That Matter: The 45-day identification window and 180-day close deadline - and what happens if you miss them.
• Partial Exchanges and Cash Boot: Can you peel off cash from a sale and still do a 1031? Yes, but at what cost?
• Accredited Investor Requirements: What qualifies you for DST access and what documentation you'll need.
• Types of DST Properties: From multifamily and industrial to storage, hotels, and more - what's available and how it's selected.

Resources:

Trevor Flor’s firm, Aimpoint Investments: www.aimpointinvest.com
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.