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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

 

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This time of year has a way of stripping away noise. The inbox gets a little quieter, and you’re left thinking about the bigger picture: what you’re building, how resilient it really is, and whether it can survive the next cycle (not just the last one). With that, I wanted to share some of my personal reflections with you. If you’ve ever wondered how real businesses cross nine figures without ...
Content Roundup - Week of December 8, 2025
  Hey there, As we enter the holiday season, things tend to cool down for most people - but that's when I double down. Me and my team are working hard to finish the year strong so we can carry that momentum into 2026. Having said that, it's also a priority for me to spend as much time with family and loved ones as possible (so basically, my days are jam-packed). That's why we're doing all this ...

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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