Charles Sizemore

Chief Investment Strategist, The Freeport Society

Starting at his grandfather’s knee when he was just 10 years old, Charles Sizemore has pursued a career dedicated to helping people achieve financial freedom through smart investing.

Charles has advised multiple hedge funds globally and managed over $120 million in assets.

He holds a Master’s Degree in Finance and Accounting from the London School of Economics and a Bachelor of Business Administration in Finance with an International Emphasis from Texas Christian University in Fort Worth, where he graduated Magna Cum Laude and as a Phi Beta Kappa scholar.

As a keen market observer, economist, investment analyst, and prolific writer, Charles has been a repeat guest on Fox Business, quoted in Barron’s, and featured in numerous well-reputed publications and financial websites, including MarketWatch, TheStreet, InvestorPlace, MSN Money, Seeking Alpha, Stocks, Futures and Options Magazine, The Daily Reckoning, Benzinga, Minyanville, and Investment International.

While Charles enjoys playing basketball and his grandfather’s old saxophone (which he is also teaching his son), his passion lies in finding investment opportunities that become safe havens for investors navigating this Age of Chaos. He is intolerant of deception, misdirection, and the endless eroding of the ideals that once made America great. He is fiercely determined to help investors regain their lives, their liberty, and their wealth.

Charles’s publications and investment research services include:

Latest from Charles Sizemore

The Freeport Navigator June 13, 2025

The One Investment to Make After Israel Launched Operation Rising Lion

Israel’s attack on Iran overnight has added another risk to the wall or worry investors are trying deal with. Markets reacted strongly in futures trading, but seem to have tempered some throughout the day. So what does this new Middle East war mean for our investment strategy? Today, we explore that.

The Freeport Navigator June 12, 2025

Tariffs Aren’t the Problem. Here’s What Is…

In today’s Navigator, I explain what the recent inflation numbers are pointing to and how that will lead us to one of the biggest investment opportunities of our lifetime: The automation revolution that’s about to reshape the U.S. economy.

The Freeport Navigator June 10, 2025

It’s Harvest Time for Traders

What can we do about the Age of Chaos we’re living in? You could sell everything and sit in cash. Of course, had you done that, you would have missed the most profitable May in 30 years. Or you could take a page out of my friend and master trader Jeff Clark’s book and trade the chaos.

The Freeport Navigator June 9, 2025

Beware Strategy’s Bitcoin “Scam”

There are a few ways to own Bitcoin, but what about speculative plays via the shares of companies converting their cash balances to Bitcoin? Strategy (MSTR) led the way there, followed by GameStop (GME), Trump Media & Technology Group (DJT), and others. To answer that, I’ll pass the baton to James Hickman, my fellow libertarian traveler and co-founder of Schiff Sovereign.

The Freeport Navigator June 6, 2025

Is $34 Billion Enough to Create a Musk TACO Trade?

The very public “divorce” between President Trump and Elon Musk holds several invaluable lessons for investors. It also presents us with some powerful wealth building opportunities.

The Freeport Navigator June 5, 2025

How to Trade This Market Chaos and Come Out Ahead

The typical investor today cut his teeth in the post-2008 world – when it has always paid to buy the dip. But in the chaotic, highly volatile market this approach and the purely buy-and-hold strategy is not going to work. It’s all down to one ominous chart of a “regime change” in the U.S. Treasury market that you need to be aware of.