Dear Reader,
Happy Monday. Happy September.
This weekend a friend asked me a curious question:
“What’s the longest bear market in history?”
At first I thought of the Great Depression. That was a long, brutal bear market, compounded by policy mistakes—tight monetary policy and trade tariffs that only made things worse.
But the more I thought about it, the answer was clear.
The longest bear market in American history isn’t in stocks. It isn’t in bonds.
It’s in the U.S. dollar.
Over the last 100 years, the dollar has lost 95% of its purchasing power.
Since the year 2000 alone, it’s lost more than 40%.
According to data from the Bureau of Labor Statistics and the St. Louis Fed, $100 in 2000 now buys just $58.80 worth of goods.
Think about that.
When I was growing up, $20 felt like $100. A $100 bill could buy dinner, movies, maybe even a night out with friends.
Today? That same $100 is worth less than $60.
So yes, the longest bear market in history is the slow decline of the U.S. dollar.
Should we be worried?
Of course—it’s a valid question. But the real issue isn’t whether the dollar loses value (it always does). The question is whether it ever gets replaced as the world’s reserve currency.
Here’s the other side of the story:
Despite the dollar’s decline, American living standards have skyrocketed.
GDP, wages, and asset values have grown faster than inflation.
● U.S. household net worth is the highest in the world.
● U.S. real GDP is the highest in the world.
● Median U.S. real income ranks fifth globally.
● The median U.S. worker is in the top 1% of global earners.
● And U.S. stocks have massively outperformed inflation.
So what does that really tell us?
It tells us that holding cash is the surest way to lose wealth over time.
You need to be invested to preserve and grow your capital.
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So let’s run the numbers.
If you had $100,000 in 2000 and stuffed it under a mattress, today that money only buys $58,000 worth of goods.
That’s the penalty for hoarding cash.
Or as Keynes put it: “In the long run, we are all dead.”
And so are all fiat currencies.
Every currency in history has eventually died. The dollar will be no exception.
Our responsibility is to delay that fate as long as possible—to make sure it doesn’t happen under our watch, and that our children inherit a stronger system than we did.
Because if it doesn’t, the consequences are ugly.
Think Weimar Germany. Think hyperinflation. Think stories of families pushing wheelbarrows full of cash to buy a single loaf of bread.
That’s not the world I want my kids—or yours—to grow up in.
And yet the Fed openly admits that its goal is for the dollar to lose value every year.
Their inflation target is 2%. Which means they want the dollar to decline 2% annually—forever.
Of course, in practice, inflation has been much higher.
From Trump’s first term through Biden’s COVID stimulus, Washington printed trillions. From 2016 to 2024, the national debt ballooned by $15 trillion.
The result: the dollar has weakened, prices have surged, and asset values—stocks and real estate—have jumped.
Good for those of us who own assets. Terrible for those who don’t.
That’s why the gap feels so wide.
If you’ve owned stocks or real estate, you’ve kept pace—or even profited—from inflation.
But if you’ve just saved in cash or wages, you’ve fallen behind.
And that’s one of the biggest drivers of today’s populist anger—on both the left and the right.
Because here’s what’s next.
There’s an entire generation of 20- and 30-somethings making $100,000 or $200,000 a year… who can’t afford a house.
They’re hoarding dollars that lose value every year.
They’re locked out of assets that keep rising.
That frustration is fuel for more populism—and likely, more radical political change.
What started as a fun conversation with a friend about bear markets led to this:
The dollar’s century-long decline is the most important bear market of all.
It’s why we invest.
It’s why we own assets.
And it’s why cash, in the long run, is the most dangerous position you can hold.
So please, make sure you check out our special Labor Day Wealth package here>>>
You have 24 hours to make what could be the most important financial decision of your lifetime.
Happy Monday. Enjoy September.
I’ll speak to you tomorrow.
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