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Content Roundup - Week of October 5, 2026

Oct 08, 2026
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Hey everyone,

This week, we’re looking at some big shifts happening across the economy—and, more importantly, where the opportunities are hiding within them.

We’re digging into why Americans have lost so much trust in the institutions they once relied on, how one self storage investor turned his first facility into a million-dollar wealth-building opportunity, and why the massive wave of assets Baby Boomers will need to sell could create one of the biggest buying opportunities of our lifetime.

There’s a lot changing right now. The key is understanding those changes early enough to position yourself on the right side of them. 
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[ AJO Podcast ] Why Americans Have Completely Lost Faith in Institutions

Americans haven't just lost trust in their foundational institutions—they are actively turning on them. From public education and healthcare to the news media and federal government, the critical systems that built the nation over the last 200 years have shifted away from serving citizens to protecting themselves.   

When an institution prioritizes its own expansion, survival, and protectionism over the individual, output collapses while costs explode. Most people feel the daily weight of this systemic decay through higher taxes, unpayable medical bills, declining educational standards, and skyrocketing housing costs, but few realize how deeply interconnected these failures actually are.   

In this video, I walk through hard economic and demographic data over the last century to uncover why Americans are fed up, how administrative bloat crushed our systems, and why the collapse in institutional trust created a massive populist revolt.

While it’s impossible to cover every single reason Americans are fed up in a 20-minute video, this breakdown hits the core economic and historical data driving systemic decay. Although I originally put this together a while back, the trends have only accelerated, making this breakdown more relevant today than ever.

What foundational systems frustrate you the most right now, and what concrete steps do you think we can take to fix them? Drop your thoughts in the comments below!

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] ONE Self Storage Facility Made Me a Millionaire

Alex Quezada’s first self storage facility made him over a million dollars. That has to be just luck, right? Over the next six years, he bought 18 more self storage investments, selling several for a $1M+ payday and keeping the others that would cash-flow him to financial freedom. And get this—he did it in Florida, the state with some of the wildest insurance costs and taxes. 

How did Alex scale so quickly and build a portfolio that takes even the experts decades to do?

Back in 2020, Alex was a tired single-family rental landlord. Whether it was holidays, weekends, or birthdays, it didn’t matter—tenants were blowing up his phone. Toilet problems, AC issues —the usual. This wasn’t sustainable; the money wasn't worth it, and he needed a way to build truly scalable wealth. The answer was self storage.

Since that first deal, Alex has bought 18 more facilities, sold four, and held on to 15. He’s done seller financing to fund many of them, direct mail campaigns to get off-market owners to the table, and runs call centers with AI for zero downtime and fast customer service, so no tenant is ever locked out of a unit or a gate. Alex is a master in this game, and we got him to share everything, from structuring seller financing to his exact cadence of direct mail for the most lead flow.

A $1,000,000 check could change any investor's life. This is how Alex does it routinely. 

CLICK HERE TO WATCH THE EPISODE

 


[ Short ] Boomers Are About to Sell EVERYTHING

A generational wealth transfer is unfolding now — but it’s not what you think. Baby boomers aren’t simply handing away all their wealth or spending it on assisted living, medical care, or vacations. Instead, for a savvy few, the $90 trillion baby boomer wealth transfer will be unlocked, even if you don’t have wealthy parents. Because here’s the truth — the baby boomers have to sell everything. 

So who will be there to buy the assets? There are more sellers than buyers, meaning you have the opportunity to pick up businesses, real estate, and other assets at a fraction of what they’d cost just a decade or so ago. Do you take the chance and claim your own version of the great wealth transfer, or do you ignore the opportunity and wish that you did a decade from now?

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 October 5, 2026
  Hey everyone, This week, we’re looking at some big shifts happening across the economy—and, more importantly, where the opportunities are hiding within them. We’re digging into why Americans have lost so much trust in the institutions they once relied on, how one self storage investor turned his first facility into a million-dollar wealth-building opportunity, and why the massive wave of asse...
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  Hey everyone, For years, we’ve had a problem in self storage that almost nobody talks about. We have a lot of industry data. We have quarterly earnings reports. Occupancy numbers. Street-rate reports. Cap-rate surveys. Construction forecasts. Transaction data. But there’s a catch: Most of the numbers we call “self storage industry data” have never actually measured the entire storage industry...
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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...

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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