Hey everyone,
Happy Thursday - wishing all the dads out there a wonderful upcoming Father's Day weekend! I'm looking forward to spending some time with my kids, doing a little fly fishing, and having a big family bbq at my dad's house.
Alright, let's get to the resources for this week. Here's what you'll learn:
âś… AI Will Change Real Estate - How to Adapt
✅ The Truth Behind “Passive” Self Storage Investments
âś… Does Dollar Cost Averaging Make You "Automatically Rich"?
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[ AJO Podcast ] This Will Change Real Estate Forever (Adapt or Get Left Behind)
AI has leveled the playing field for new real estate investors, startups, and small businesses. The truth is that most investors still view AI as another productivity tool. But what we’re witnessing is a once-in-a-generation shift in how businesses are built and scaled.
The larger, more established players? Many are still operating the way they always have. All of their systems, processes, and teams were built without AI, and changing course now would require a massive overhaul.
William Hollis, founder of Capital Advisory AI, has seen just how powerful this technology can be in the hands of everyday investors. He and his team have developed a platform that pairs operators with investors, making it easier to raise capital and identify new passive investing opportunities.
But Hollis doesn’t believe every real estate business needs to build its own AI agent or custom tool. He shares exactly how investors can start leveraging existing AI tools to streamline operations, eliminate bottlenecks, and free up time to focus on the work that actually creates wealth.
CLICK HERE TO WATCH THE EPISODE
[ SSI Podcast ] The Truth Behind “Passive” Self Storage Investments (99% Get Wrong)
There’s a massive lie floating around the self storage industry: that it’s passive. It’s not. But it’s so worth it.
And self storage isn’t your average active investment either. It’s a full-fledged business with income, expenses, overhead, marketing, and more. Even self storage facilities that are remotely managed require boots on the ground, fine-tuned systems and processes, and the means to track crucial metrics.
If this is your first self storage facility, you may be wearing multiple hats—at least at first. But the beauty of this asset class is that it’s highly scalable. With the right foundation in place, you could grow a large self storage portfolio that helps you achieve all of your investing goals—all while enjoying the type of lifestyle you want.
From improving your curb appeal and managing move-outs to monitoring your competition, we’re covering everything you need to pay attention to if you want your self storage business to thrive in 2026.
CLICK HERE TO WATCH THE EPISODE
[ Short ] Does Dollar Cost Averaging Make You "Automatically Rich"?
One of the most powerful and successful investing strategies is also one of the simplest*—and because it is so boring, most speculative investors skip right past it. In this video, I break down the exact math behind Dollar Cost Averaging (DCA) and show you how this automated framework forces you into the correct investment behavior without any emotional input.
Hope you enjoy the new resources.
That's it for this week - until next time!
- AJ Osborne
