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Content Roundup - Week of August 31st, 2026

Sep 03, 2026
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Hey everyone,

We’re in the middle of some pretty massive shifts right now—from AI changing the way we work, to a changing self storage market, to economic forces reshaping how wealth is built and protected.

And while change can create a lot of uncertainty, it also creates opportunity. This week’s resources are all about understanding what’s changing, spotting the opportunities most people are missing, and positioning yourself to take advantage of what comes next.

Here's what you'll learn: 

 âś… The "Boomer Trap" Millenials are now falling for

âś… Finding the storage deals that most investors overlook

âś… The $34 trillion shift that will change America
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[ AJO Podcast ] Millennials Are Falling for the Same Trap as the Boomers

Millennials are quickly becoming the new baby boomers. They’re falling for a trap that caught the boomer generation at the turn of the century, but most Millennials have no idea. Unless they change their ways now, many Millennials may end up jobless, economically helpless, and angry at a future they themselves are actively creating.

Before you get upset with me, let me explain.

A new report from Microsoft is showing that AI is overhauling the system as we know it. Structures are changing from the bottom up, new businesses and ideas are being formed that were impossible just a couple of years ago, and it’s not an “if” AI impacts your life and work, but a “when” type of question. 

Millennials are scared. They don’t want their jobs to be displaced or terminated entirely, and just like the baby boomers during the age of the internet, there’s a lot of fear for the future. But what comes next? Can we learn from the boomers' mistakes so we can take full advantage of an inevitable change, instead of clinging to a structure that has been broken by new technology?

This is your last chance, or you'll face the same fate as many of the boomers. 

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] How to Find Self Storage Facilities That 99% of Investors Overlook

For months, we’ve been saying the same thing: The self storage industry has finally turned a corner. We’re now in a buyer’s market, and we’re seeing some of the best self storage deals in years.

But if that’s the case, where are these deals?

We’re answering this exact question on today’s episode. Of course, you can find self storage facilities the “normal” way—by building your buy box and giving it to your broker to pull properties already listed for sale. But some of the deepest discounts and greatest wealth creation opportunities come from buying off-market, mom-and-pop facilities with high value-add potential.

And today, we’re providing a three-part strategy anyone can use to find them, even if you’re brand new to self storage investing. We’ll even share a few case studies of real self storage investors who have been able to create several hundred thousand dollars in value by using these exact tactics.

Whether you’re on the hunt for your first self storage facility or looking to grow your portfolio, these time-tested strategies will help you do just that!

CLICK HERE TO WATCH THE EPISODE

 


[ Short ] The $34 Trillion Shift That Will Change America Forever

Wealth inequality today has reached astronomical levels. In 2017, the world 

There is a single economic term that is going to reshape the investing landscape over the next ten years, yet almost nobody understands it: *Fiscal Dominance*. 

For decades since leaving the gold standard, the Federal Reserve acted as the ultimate economic force—raising rates to tame inflation and cutting them to stimulate growth. But that model is mathematically breaking down. When federal debt explodes, monetary policy loses its independence, trapping the Fed in a zero-win scenario where standard economic tools no longer work.

In this video, I break down why Fiscal Dominance is a structural reality (not a cyclical forecast) and reveal the exact shift you must make to protect and grow your wealth over the next decade.

WATCH THE SHORT HERE

 


Hope you enjoy the new resources.

That's it for this week - until next time!

 

- AJ Osborne

Content Roundup - Week of August 31st, 2026
  Hey everyone, We’re in the middle of some pretty massive shifts right now—from AI changing the way we work, to a changing self storage market, to economic forces reshaping how wealth is built and protected. And while change can create a lot of uncertainty, it also creates opportunity. This week’s resources are all about understanding what’s changing, spotting the opportunities most people are...
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Hey everyone, I can't believe we're already into August. It feels like summer just got started, and before we know it, vacations will be winding down and routines will start picking up again. I hope you're finding some time to enjoy the season. We've got a great mix of content for you this week, covering everything from major economic shifts to practical strategies you can put to work in your b...

AJ Osborne Playbook

Welcome to the AJ Osborne Playbook! I'm AJ, and I provide insights into financial independence, entrepreneurship, business, and life. With over 20 years of experience and a portfolio that's transacted over $400M, I have found financial freedom. Now, I want to help others achieve the same.
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