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Content Roundup - Week of November 2, 2026

Nov 05, 2026
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Hey everyone,

There's a growing divide in America between those who are building wealth and those who are struggling to keep up. And while the headlines might tell one story, the reality is a lot more complicated.

This week, we're digging into why some Millennials are wealthier than previous generations while others are falling further behind, and what owning cash-flowing assets has to do with it. We're also breaking down the fundamentals of self storage investing for anyone looking to get started, plus why today's falling facility prices could be creating one of the best buying opportunities we've seen in years.

Whether you're just getting started or already growing your portfolio, there's plenty to take away from this week's resources.

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[ AJO Podcast ] Why Half of Millennials Are Rich (And the Other Half Are Broke)

Last year a Wall Street Journal report made headlines by claiming that Millennials, when adjusted for inflation, hold roughly 25% more wealth than Gen Xers and Baby Boomers did at a similar age. To most Millennials dealing with soaring home prices, high interest rates, and stubborn inflation, that statement feels completely disconnected from reality.   

*While the raw data is technically accurate, the headline ignores the economic divide between the haves and the have-nots*. Generational wealth isn't a monolith—it is shaped by geography, Federal Reserve policy, timing, and whether or not you own cash-flowing assets.   

In this video, I break down the economic realities separating Millennials from Baby Boomers, the impact of historical interest rates, and why a specific subset of Millennials pulled ahead while millions of others were left behind.   

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] New to Self Storage Investing? Watch This (Beginner’s Guide)

Are you brand-new to self storage investing?

It’s easy to become overwhelmed by all of the different terminology, processes, and strategies. But at its core, self storage is a straightforward business. You buy a large metal building, rent units out to customers, and (ideally) make a profit.

You don’t need to know every last term, but you do need to build a solid foundation. Today, we’re going to help you fill in the necessary knowledge gaps so you have a better idea of what goes into buying and running a self storage business.

We’ll break down some of the lingo you may have heard before, like cap rates, cash flow, net operating income (NOI), and debt service coverage ratio (DSCR). We’ll also compare the roles of general and limited partners and explain why you need a letter of intent before a purchase and sale agreement.

Most importantly, we’ll walk you through the three things every self storage investor needs to get started: deal flow, capital, and people. Master these building blocks, and you’ll be well-positioned to buy your first or next self storage facility with confidence!

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] AI Is Holding the Fed Hostage

Did we just hit the bottom for self storage prices? 

There’s a lot of distress in the self storage industry right now. High interest rates are expanding cap rates, which means prices are going down—fast. Buyers have been taking advantage, but most of the industry is still on the sidelines, waiting for the “opportunity” right in front of them. This sounds a lot like what happened in 2008.

Facilities are selling for far less than people think, and if you’re only looking at the list price a broker gives you, you could miss deals that may not come around for a decade. I’ve been screaming this from the rooftops, but nobody seems to listen, even as I buy self storage facilities for a fraction of what they cost a few years ago.

Are you going to miss the opportunity so many begged for?

WATCH THE VIDEO HERE

 


Hope you enjoy the new resources.

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

 

- AJ Osborne

Content Roundup - Week of November 2, 2026
  Hey everyone, There's a growing divide in America between those who are building wealth and those who are struggling to keep up. And while the headlines might tell one story, the reality is a lot more complicated. This week, we're digging into why some Millennials are wealthier than previous generations while others are falling further behind, and what owning cash-flowing assets has to do wit...
Content Roundup - Week of October 26, 2026
  Hey everyone, There's a lot happening in the economy right now, and while some investors are sitting on the sidelines waiting for things to settle down, others are finding opportunities in places most people are overlooking. This week, I'm pulling back the curtain on a struggling business I purchased and grew from $250K to over $930K in revenue in just one year, including the mistakes, challe...
Content Roundup - Week of October 12, 2026
  Hey everyone, There's a massive generational shift happening in America right now, and it's creating opportunities that most people aren't even paying attention to. This week, we're digging into where the trillions of dollars in Baby Boomer wealth are actually going, why everyday investors may have a bigger opportunity than Wall Street, and how one investor went from owning zero self storage ...

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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