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Content Roundup - Week of September 1, 2025

Sep 04, 2025
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Hey there,

It's almost here - Self Storage Income LIVE 2025 is happening in 2 weeks! Would love to see you there Click here to learn more and register now. 

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

âś… 5 Things I WISH I had known for my first investment

âś… Why self storage is a great first investment asset class

âś… How to join the "ownership" class without being rich

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[ AJO Podcast ] 5 Things To Know For Your First Investment

 

If you’re trying to figure out how to make your first investment, this video is for you. When I started, I didn’t have much—I was working full-time, raising kids, and trying to save every dollar I could. Today I manage hundreds of millions in assets.

This isn’t theory—I share the strategies I used to grow from small $100k properties to a multi-million-dollar portfolio, and how you can apply the same principles starting today.

In this video, I’ll walk you through the 5 things you must look for in your first investment:
âś… Protecting your downside so you stay in the game
âś… Focusing on cash flow over speculation
✅ Understanding what you can control vs. what you can’t
âś… Making asymmetrical bets with limited risk and big upside
âś… Keeping it simple and clear

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] Why Self Storage Is the Best FIRST Investment (Less Risk, High ROI)

 

 

With so many investment options—single-family homes, duplexes, the stock market—it’s easy to overlook self storage. But the truth is that a self storage facility is one of the best first investments, and you’re about to find out why. Whether you’re just starting your investing journey or looking to diversify your portfolio, storage could be a supercharger for your wealth. 
 
Self storage is one of the lowest-defaulting assets in the US, meaning it’s much more profitable and less risky than you probably think. We get into the advantages these facilities have over residential real estate, as well as how direct investments compare to public markets (like stocks). We’ll also discuss the massive value-add opportunities that institutional investors are leaving to you, the small investor!

CLICK HERE TO WATCH THE EPISODE 

 


[ Youtube Short ] How to Join the Ownership Class Without Being Rich

 

 

No money? No problem. You don’t need to be born wealthy to join the ownership class. In this video, I break down exactly how everyday people build real wealth without starting capital—and how I did it myself. From leveraging skills and time to using OPM (other people’s money), buying underperforming businesses, and structuring creative real estate deals, I show you the real path to ownership.

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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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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