Hey everyone,
Hope you had a fantastic long weekend celebrating the Fourth of July and America's 250th anniversary. The family and I headed up to one of my favorite vacation spots, Coeur D'Alene, and enjoyed some golf and the lake.
Alright, let's get to the resources for this week. Here's what you'll learn:
âś… Buying cash-flowing small businesses in 2026
âś… How AI is changing the way self storage does business
âś… The 5 stages of business ownership
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[ AJO Podcast ] How to Buy a Cash-Flowing Small Business with Only 5% Down
People think owning or buying a business is for the wealthy. For the visionaries with the revolutionary ideas. For the entrepreneurs whose startups beat the odds. But they’re wrong.
Over 17 million businesses will change hands in the next several years. As the baby boomer generation ages out, some of these businesses will close their doors. Some will stay in the family and get passed down. But most of them? They’ll be sold. To whom? Maybe you.
You don’t need millions of dollars to buy them. In fact, many of these small businesses cost less than the median price of a single-family home. Serial business-buyer Tim Delaney found this out when he stumbled on a local wine and liquor store 13 years ago. He bought it with just $35,000 down, and that investment gave him a reliable cash flow stream, provided for his family, and made the next venture that much easier.
And buying an established business isn’t nearly as risky as you probably think. Tim shares the green and red flags to look for when analyzing a small business, the different levers you can pull to fund one, and the value-add playbook that can turn any mom-and-pop operation into a staple of your community.
CLICK HERE TO WATCH THE EPISODE
[ SSI Podcast ] AI Is About to Change Self Storage Forever
AI has changed everything about self storage investing. Not just for the REITs, but for the “small” self storage investor, too—the operator who owns just one or two self storage facilities.
It’s so revolutionary that investors who dismiss it as the latest “tech trend” are at serious risk of becoming obsolete.
My self storage business saved $1,000,000 in the last year alone by deploying AI throughout our company. It helped us cut over 250 man hours per month and has prevented us from hiring any extra staff, despite scaling our portfolio by 30%. Today, I’m showing you how to do it, too.
Travis Morrow, CEO and Chairman of Storelocal, is seeing a very similar impact, and he’s only been working with these tools for a week. In this episode, we’re breaking down the specific ways we’re integrating AI within our self storage businesses—from automating self storage tasks and generating detailed reports to optimizing marketing strategies and eliminating organizational bottlenecks.
AI is no longer the “future” of self storage. It’s arrived. And operators have two options: adapt or get left behind. Which one will you choose?
CLICK HERE TO WATCH THE EPISODE
[ Short ] Self-Employed vs. Business Owner: The 5 Stages of Ownership
Many people mistake being self-employed for being a true business owner, but the reality is they require completely opposite functions, mindsets, and leadership skills. In this video, I break down the 5 Stages of Ownership that every entrepreneur must navigate to transition from trading active hours for cash to building true, generational wealth.
Hope you enjoy the new resources.
That's it for this week - until next time!
- AJ Osborne
