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Content Roundup - Week of July 21, 2025

Jul 24, 2025
Connect!

 

Hey there,

We are gearing up for Self Storage Income LIVE 2025 in Sunriver, Oregon, and are pleased to announce the schedule for the event is taking shape! Check out our current list of educational sessions designed to help you land your first deal, or expand your storage portfolio, by clicking here.

If you are thinking about registering, NOW is the time to act. Our hotel block is quickly filling up, and space is limited. Click here to learn more and register now.

Alright, moving onto the resources for this week. Here's what you'll learn: 

âś… Building a busines to fail (and how it made me millions)

âś… Self storage development 101

âś… Why real estate is cracking from the inside

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[ AJO Podcast ] I Built My Businesses to Fail (and It Made Me Millions)

 

 

Markets are volatile. Whispers of a recession are getting louder. Some industries—like commercial real estate—are already in recession. This has been one of the most difficult market cycles for business owners and self storage investors to navigate. Want to know how to start a business that thrives in any economic environment? I break it down in today’s episode!
 
We’re coming off arguably the greatest bull market in history. The problem? People start businesses expecting success, which is exactly why they fail. Their systems, models, and contracts aren’t designed for the worst-case scenario. The truth is, if you want to succeed long-term, you can’t build to succeed. You must build to fail. It sounds backwards, but it’s the only way to survive the storms.
 
Make no mistake—you will fail. But how you fail makes all the difference. You don’t need to be fearless, just aware of the risks and prepared for the valleys. In this episode, I show you how to fail the right way—small, fast, and forward!

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] $350K/Year by BUILDING, Not Buying Self Storage (Development 101)

 

 

What goes into a self storage development deal? You’re about to find out! Today, we’re breaking down the first self storage facility we ever built—everything from the property’s financials and the construction timeline to how we ultimately turned a $4.3-million project into a $13-million self storage business that generates over $350,000 in annual cash flow!

In this episode, AJ and George will show you how to take an initial concept and turn it into a fully stabilized self storage facility, step by step. The truth is that many developers approach self storage from the wrong angle, so we’ll show you what to focus on before getting started—like narrowing down your target customer and building with them in mind to the dangers of cutting corners on quality and focusing more on upfront costs than revenue potential. Whether you’re curious about the development side of the self storage industry or seriously considering your own development project, you don’t want to miss this one!

CLICK HERE TO WATCH THE EPISODE 

 


[ Youtube Short ] Why Real Estate Is Cracking From the Inside

 

 

Commercial real estate is in freefall—but most people don’t see it yet. I’ve been investing through every major downturn since 2008, and I’ve never seen the setup we’re facing now. In this video, I’m breaking down why this recession is different—and what’s really causing the pain in today’s market.

CLICK HERE TO WATCH THE SHORT 

 


Hope you enjoy the new content.

 

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

 

- AJ Osborne

 

The Self Storage Default Myth: What the Data Actually Shows - and Where the Real Opportunity Is
  Hey there, Today I want to dive into one of the most repeated statistics in this industry - and explain what it actually means. After 20+ years operating self-storage and building Cedar Creek Capital from the ground up through multiple market cycles, I’ve learned that the most expensive mistakes investors make don’t come from bad assets. They come from misunderstood risk. Let’s look at the da...
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  Hey there, Have you heard? I'm retiring this year. Yep, throwing in the towel...traveling the world...no more work.  April fools. It would take a mountain to move me out of my career. You all know how much I love what I do! Alright, let's get to the resources for this week. Here's what you'll learn:   ✅ The wealth gap from the Roman Empire to today, explained ✅ The "tiered" pricing model that...
Content Roundup - Week of March 16th, 2026
  Hey there, Hope you had a great St. Patrick's Day. I'm currently enjoying some family time in Hawaii - though the weather hasn't exactly cooperated with us. Either way, it's nice to get out of the office and spend some time with loved ones. Alright, let's get to the resources for this week. Here's what you'll learn:   ✅ The middle class is shrinking - but not how you think ✅ How to start inve...

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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