If you're a pilot, there's a good chance your retirement savings are sitting in a target date fund you selected years ago and haven't thought about since. The problem is that the fund doesn't know anything about your pension, your spouse's income, your retirement timeline, or the unique challenges pilots face. In this episode, Ryan explores a little-known feature inside many 401(k) plans and shares research that may change the way you think about retirement planning.

Here’s what we cover in this episode:

📉 DIY Penalty: The cost of going alone

🧠 Behavior Gap: Emotions hurt investor returns

💧 Cost Leaks: Small expenses compound over time

✈️ SDBAs Explained: More options inside your 401(k)

📋 Case Study: Personalized planning in action

🚀 Pilot Advantage: Retirement planning beyond average

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Many pilots assume that as retirement gets closer, they should automatically become more conservative with their investments. But according to Ryan, that's not always the right move. He explains why risk management has less to do with your age and more to do with your time horizon, income sources, and retirement goals. If you're trying to strike the right balance between growth, protection, and income planning, Ryan shares a valuable framework for thinking about risk.

Here’s what we cover in this episode:

✈️ Risk Management: Matching risk to your situation

📅 Time Horizon: Why age isn't the deciding factor

⚖️ Asset Allocation: Finding the right balance

🚨 Common Mistakes: When being too conservative backfires

💰 Income Planning: Building retirement paychecks

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Risk is unavoidable. The real question is whether the risk you're taking makes sense for where you are in life.

In this episode, Ryan explores three common financial personalities among people in their 30s and 40s, and the steady contributor quietly building wealth over time. If you're trying to figure out whether you're taking too much risk—or not enough—Ryan offers a practical framework for evaluating where you stand and where you want to go.

Here’s what we cover in this episode:

🚀 Aggressive Investing: Why speculation isn't a strategy

💵 Playing It Too Safe: The hidden risk of cash

📈 Power of Compounding: Time is your greatest asset

⚖️ Finding Balance: Taking risk with a purpose

✈️ Pilot Perspective: Why discipline beats prediction

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

It's summer and nothing says summer quite like Tom Cruise as Maverick soaring across the sky in Top Gun. This year marks the 40th anniversary of the original film, and with Tom Cruise's birthday on July 3rd, Ryan figured it was the perfect excuse to revisit some of the most iconic quotes from the franchise and see what they have to say about your financial life. Because Maverick didn't become the best by flying blind and hoping for the best. He had a plan, a co-pilot, and enough self-awareness to know when the risk was worth it.

Here’s what we cover in this episode:

🚀 Need for Speed: Avoiding get-rich-quick investing

😎 Ego & Mistakes: Keeping emotions in check

⚠️ Danger Zone: Understanding risk and volatility

📜 Future Planning: Preparing for life's uncertainties

🤝 Find a Co-Pilot: Why guidance matters in retirement

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

In this episode, Ryan is joined once again by CPA Zach Smith to unpack the FedEx TA 26 retirement choices, this time from a tax and long‑term planning angle. Instead of just chasing the biggest paycheck, they explore how pensions, 401(k)s, and new cash-balance options can create either freedom or a “ticking tax time bomb” in retirement. If you’re a FedEx pilot facing this decision, this conversation will challenge how you think about taxes, flexibility, and your family’s legacy.

Here’s what we cover in this episode:

💰 Three Choices: Each leads to very different outcomes

🧨 Tax Pressure: Income stacking creates future problems

🛡️ Guaranteed Income: Stability comes with tradeoffs

🧾 Limited Control: Some plans restrict your flexibility

🚀 More Flexibility: After-tax dollars give you options

💡 Smarter Mix: Roth + brokerage create long-term advantages

FedEx TA26 Retirement Option Tool:

https://retirepilots.com/fedex-ta26-tool/

FedEx TA 2026: 3 Retirement Options That Could Change Everything

https://pilotsadvisor.podbean.com/e/fedex-ta-2026-3-retirement-options-that-could-change-everything/

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

USE THIS: FedEx TA26 Retirement Option Tool. Check out our educational modeler - https://retirepilots.com/fedex-ta26-tool/

FedEx pilots are facing a major decision with three very different retirement options, each with long-term implications for income, flexibility, and legacy in the 2026 tentative agreement. While the details are still evolving, the choice between a pension-style income, a hybrid approach, or a more flexible contribution-based plan could shape your financial future for decades. In this episode, Ryan breaks down each option in simple terms, highlighting the pros, cons, and key factors to consider.

Here’s what we cover in this episode:

✈️ Three options offer very different retirement outcomes

💰 Taxes play a major role in long-term results

📊 Control vs. guarantees is a key tradeoff

⏳ Longevity impacts which option makes sense

🧠 Personal goals matter as much as the math

Get the Summary of Proposed FedEx Retirement Changes: https://retirepilots.com/wp-content/uploads/2026/04/FedEx_TA_2026_Retirement_Plan_Options-PDF-Recap-for-Show-Notes.pdf

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

AI isn’t just a buzzword, it’s quickly becoming one of the biggest unknowns in retirement planning. Pilots in their 50s and 60s are actively searching for answers about how this technology could impact their future. Ryan tackles the most common AI-related questions pilots are Googling right now, and where human judgment still plays a critical role.

Here’s what we cover in this episode:

📊 Portfolio Exposure: Many investors don’t realize how much AI exposure they already have

⚖️ Risk vs Opportunity: AI could drive growth, but also increased volatility

⏳ Early Retirement Thinking: Fear shouldn’t be the reason you retire early

🧠 AI Planning Tools: Helpful for information, but not a replacement for strategy

🚧 Human Element: Emotion, context, and experience still matter in decision-making

See the Morgan Stanley prediction: https://finance.yahoo.com/news/morgan-stanley-predicts-ai-won-073000488.html?guccounter=1

Invesco’s Winter 2026 DC Participant Pulse Survey: https://401kspecialistmag.com/dc-participants-open-to-private-markets-and-ai-with-guardrails-invesco-survey/

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

AI is changing everything right now, and aviation isn’t going to be immune to that. The question is… what does it actually mean for you as a pilot? Ryan breaks down what AI is really going to do to the cockpit, what parts of the job might change, and why he doesn’t see pilots going anywhere anytime soon. But there are some shifts coming, and they’re worth paying attention to. We also zoom out and talk about how AI is impacting the broader economy, what that could mean for your portfolio.

Here’s what we cover in this episode:

🛫 AI in aviation: Enhancing systems, not replacing pilots anytime soon

👨‍✈️ Pilot demand: Shortage continues to drive pay and workload changes

🤖 AI in society: Creating winners and losers across industries

📈 Investing impact: Diversification matters more in uncertain environments

🧠 Human element: Judgment and experience still critical in flying and planning

Retire Pilots - https://retirepilots.com

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

Pilot Tax - https://pilot-tax.com/

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2