The Pilot Money Guys

Publicly listed emails

info@leadingedgeplanning.com

charlie@leadingedgeplanning.com

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Flight #139: Should You Change Your Investments When Markets Feel Overvalued?

October 02, 2026

When headlines are shouting about AI, market highs, and economic uncertainty, how do you know what deserves your attention and what is simply noise? In this episode, we unpack listener questions that many investors are quietly asking. Listen in as we explore whether AI is creating a bubble, why all-time market highs aren't necessarily a warning sign, what history tells us about downturns, and more. You can find show notes, resources and more at: https://tinyurl.com/5dfatzax 

Flight #138: Hope, Courage and a Different Perspective on Life with Mike Penn

September 18, 2026

What can eight months in a North Vietnamese prison camp teach you about hope, courage and putting the rest of life into perspective? Former Navy pilot and Vietnam POW Mike Penn shares the extraordinary story behind his book, Hope and Courage, from the mission that led to his capture and his time in the Hanoi Hilton to the experiences that shaped his life long after he returned home.  Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resour...

Flight #137: Indexing 101 with DFA Rob Harvey

August 28, 2026

What if the index fund you thought was simple was actually shaped by a complex set of rules, decisions, and trade-offs? In this episode, we sit down with Rob Harvey, Co-Head of Product Specialists and Vice President at Dimensional Fund Advisors, to unpack what indexing really means. You'll learn how indexes are constructed, who actually makes the rules, how index funds are managed, and why "passive" investing may not be as passive—or straightforward—as it sounds. Take The Pilot Wealth Index...

A Little Bit Richer · Medium booking difficulty · 1,000 - 10,000 listeners