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Content Roundup - Week of October 27, 2025

Oct 30, 2025
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Hey there,

Happy Halloween! I hope your having a fantastic week, and looking to indulge your sweet tooth a bit in tomorrow's festivities. I'm excited to share a few new resources this week, here's what you'll learn: 

âś… How to spot GOOD commercial real estate deals

âś… Why now is the time to invest in self storage

âś… The 5 EASIEST beginner investments

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[ AJO Podcast ] How to Spot a “Good” Commercial Real Estate Deal (From CRE Expert)

 

 

There’s one thing that separates a “good” commercial real estate deal from the rest—and you have complete control over it. Get it right, and your returns are much closer to being locked in. Get it wrong, and you could have a cash-draining property on your hands. 

Kevin Bupp, 20+ year investing veteran and mobile home park and parking lot expert, is here to help. He built a massive real estate portfolio from nothing, starting at the young age of 20, lost it all in the 2008 crash, and rebuilt it bigger, better, and (much) safer than before. He’s learned the lessons the hard way, so you don’t have to.

In this episode, we’re talking about commercial real estate underwriting, how to separate the “good” deals from the BS, and the most crucial factor that makes or breaks a real estate investment. Kevin is buying multimillion-dollar deals, meaning his margin for error can only be tiny. This is the way he decides whether to buy or move on to the next opportunity. 

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] Last Time This Happened, Self Storage Investors Made Millions

 

 

This is the biggest opportunity in self storage since 2008. Last time we were at this stage in the cycle, I was on the cusp of building a $100M+ self storage business. I bought when conditions were almost identical to what we’re seeing today, and now, I’m gearing up to buy even more. But here’s the best part: beginners can get in on this, too. Today, I’m showing you how. This could be your $100M opportunity if you know what’s coming down the pipeline.

CLICK HERE TO WATCH THE EPISODE 

 


[ Youtube Short ] Easiest Beginner Investments (I've Done All 5)

 

 

Here are 5 semi-active to active investment strategies you can build while keeping your day job. Some require less than an hour a week - maybe not even an hour a month. These aren't theoretical - I'm currently doing ALL of these, including: House hacking, Cash-flowing websites, Simple services (Intrapreneurship), Niche down + digital products, Micro storage facilities, BONUS: AI vending machines. Check out the video to learn more!

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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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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