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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 financial coordination. He walks through where automation still shines, where it can quietly create blind spots, and how to recognize when your financial life needs more strategy, judgment, and oversight than financial autopilot can provide.
What You'll Learn from This Episode
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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, 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 come back as a check or closing-cost support, and what buyers need to know about buyer broker agreements and negotiable fees. The episode also explores this year’s housing market, including tight inventory below $500,000, more options at higher price points, and practical strategies for buyers and sellers.
What You'll Learn from This Episode
Resources:
Visit https://www.beaconrelocation.com/
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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 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 between 401k, 401a, Roth, and after-tax contributions, and how contribution sequencing affects tax strategy and long-term flexibility.
Finally, Tim walks through donor-advised funds, including how they work, how they can reduce taxable income, and the 2026 tax law changes pilots should understand before making charitable contributions.
What You'll Learn from This Episode
• How donor-advised funds can reduce taxable income in high-income years
• Why appreciated stock donations may be more efficient than cash
• Whether NEC as Roth affects Roth IRA contributions
• The difference between Roth and after-tax inside airline retirement plans
• How 402g and 415(c) limits work together
• Why contribution order matters for high earners
• How to avoid accidentally crowding out tax-advantaged space
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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, 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 with federal income tax and FICA, and why some pilots could be under withheld if they do not plan ahead. He also shares simple examples to frame the decision, how tax bracket and time horizon matter, and how pilots at other airlines can use in plan Roth conversions even if they do not have a Roth NEC election.
What You'll Learn from This Episode
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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, 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 planning work and his own marriage, and offers ideas for improving communication, account setup, and trust so couples feel more aligned with both their relationship and their financial plan.
What You'll Learn from This Episode
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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 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
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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
Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: [email protected]
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.
From the publisher's feed
Timothy Pope’s Pilot’s Portfolio podcast is provided for general information purposes only and does not constitute accounting, legal, tax or other professional advice. Listeners should not act…
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.

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