Header Logo
Community Services Success Book Podcast Invest
Log In

Content Roundup - Week of October 27, 2025

Oct 30, 2025
Connect!

 

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

-- -- --

[ 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

Why Most Businesses Fail (And How I Designed Mine To Survive)
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 ...
Content Roundup - Week of December 1, 2025
  Hey there, I wanted to start out by offering a warm welcome to any newbies to the newsletter. And even if you've been here for a while - we are super thankful to have you! Something a little different: This week, I'm including a bonus resource that I talked about in the SSI podcast last week - our complete Self Storage Income Investor Checklist (click here to download). This is literally an A...

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.
Terms & Conditions Privacy Policy Disclaimer
© 2026 Self Storage Income

Why Join My Newsletter?

It’s packed with valuable insights to help you navigate the ever-changing world around us. Whether you’re thinking about starting a business, curious about the economic outlook, or want to understand how politics shape our finances, I’ve got you covered. Of course, I’ll be diving into the world of storage, too!

And if there’s something specific you’d like to hear more about, just let me know! I want to provide the content that matters most to you.

Let’s explore these topics together and find ways to thrive!