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Content Roundup - Week of May 25th, 2026

May 28, 2026
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Hey there,

Hope you had a fantastic long weekend, a great Memorial Day, and enjoyed some time off. Shoutout to our servicemen and veterans - thank you for your service, we so appreciate you!

Alright, let's get to the resources for this week. Here's what you'll learn: 

 âś… Finding success through failure

âś… Creative ways to acquire self storage

âś… Return On Investment, explained

-- -- --

[ AJO Podcast ] His First Company Failed: Now Every Business He Touches Turns to Gold

It’s hard enough to grow one business from scratch, but Tanner is the textbook definition of a serial entrepreneur. It’s all he’s known since 22 years old, when he left his full-time job to open his own restaurant.

That business failed.

Most inexperienced entrepreneurs would’ve walked away. For Tanner, giving up wasn’t an option. He quickly pivoted, transforming his struggling restaurant into a popular nightclub. It kept the lights on, but it also gave him the confidence to tackle his next venture.

Over the next 20 years, Tanner started more than a dozen businesses, many of which he still owns and operates today—from cash-flowing, brick-and-mortar establishments to long-term equity plays.

Today, we discuss what makes a business “work,” the hidden risks of partnerships, and the three-pronged approach to building wealth through entrepreneurship. Whether you’re launching your first startup or actively scaling, Tanner shares the strategy, mindset, and grit it takes to keep going when others would quit.

CLICK HERE TO WATCH THE EPISODE

 


[ SSI Podcast ] Creative ways to acquire self storage

People think you need millions to get started in self storage. You don’t.

You’re about to hear about someone who just bought a self storage facility for less than a single-family home. Now, rather than dealing with tenants and toilets, they’re getting a 42-unit self storage business that provides immediate cash flow and offers serious value-add potential.

Today, we’re highlighting wins just like these, from “small” investors just like you. We’ll get into how smart investors are building out their capital “stacks,” structuring partnerships, and identifying the best markets to invest in.

We’re also addressing the most common pain points and questions investors have when running a self storage business. What are the best ways to leverage AI? Should you have cell towers installed on your property to increase revenue? Is it a good idea to do away with security deposits? How do you get insurance costs under control? We answer all of these and more!

CLICK HERE TO WATCH THE EPISODE 

 


[ Short ] Return On Investment Explained In 3 Minutes (What Investors Actually Look At)

Return on Investment (ROI) is more than a simple formula—it's the decision-making tool that separates successful investors from everyone else. But most people get it completely wrong.

The Basic Formula: Invest $100K, make $10K back = 10% ROI. Make $5K = 5% ROI. Simple, right? Wrong. That's only half the story.

What Everyone Misses - Risk: Higher returns almost always mean higher risk. A 20% ROI opportunity isn't automatically better than a 10% one if the first has a 50% chance of total loss. This is why sophisticated investors focus on risk-adjusted returns, not just raw percentages.

The Hidden Variables - Control: Can you influence the outcome? Tax benefits: Real estate investors often accept "lower" ROI because depreciation and other tax advantages make their actual returns far higher than stocks with bigger headline numbers.

WATCH THE SHORT HERE

 


Hope you enjoy the new resources.

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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