Pilot’s Portfolio

66 Episodes

Reverse

2026 Tax Deadlines for Pilots: What You Need to Review Before Year-End

2026-11-0315:31

The end of 2026 is approaching, and for airline pilots, some of the most important financial decisions of the year cannot wait until tax season. In this episode of Pilot's Portfolio, Timothy P. Pope, CFP®, principal at 360 Aviation Advisors, walks through the year-end deadlines pilots and their families should review before opportunities expire. From airline open enrollment and disability coverage elections to 401(k) contributions, Roth conversions, charitable giving, and tax-loss harvesting,...

Pilot Life Insurance: Building a Plan for Your Family, with Brianna Fanning

2026-10-0537:21

Your airline may provide life insurance, but how well does that coverage fit your family, your income, and the flying you do outside work? In this episode, I’m joined by Brianna Fanning, Director of Outside Sales at The Pilot Insurance Center and a licensed pilot, to explore the questions that can uncover gaps in a pilot’s life insurance plan. We discuss aviation exclusions, the limits of relying on employer benefits, and how existing assets, family responsibilities, and a spouse’s contributi...

How Should Pilots Use Their Accounts? HRAs, Deferred Comp, Cash Balance Plans, and ESPPs

2026-09-2117:17

Professional pilots can accumulate more than just 401(k)s, IRAs, Roth accounts, and brokerage accounts over the course of a career. Airline benefits can also include Health Reimbursement Arrangements, Retiree Health Reimbursement Arrangements, deferred compensation plans, market-based cash balance plans, Employee Stock Purchase Plans, and other employer-linked accounts that work differently from the accounts pilots manage directly. In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP® b...

How Should Pilots Use Their Accounts? 401(k)s, Roths, HSAs, and Brokerage Accounts

2026-09-0716:58

As pilots move through their careers, financial accounts can start to build up across different stages of life. A current 401(k) or TSP. Old employer plans. Rollover IRAs. Roth accounts. Backdoor Roth opportunities. An HSA. A taxable brokerage account. Spouse accounts. Each one may have been opened for a good reason, but over time the full picture can start to feel scattered. In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP® begins a practical account-by-account conversation for pro...

How Can Pilots Pay Less in Taxes? Part 2: Think Beyond One Year

2026-08-2416:54

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...

#box-pro-ellipsis-179439660957144{-webkit-line-clamp:2;}Pilot’s Portfolio