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