AJ Osborne Podcast
AJ Osborne Podcast

AJ Osborne Podcast

AJ Osborne

Overview
Episodes

Details

Welcome to the AJ Osborne Podcast. Twice a month, I’ll sit down with guests or fly solo to share incredible stories, give my take on today’s economy, and show you how to build wealth the right way. We bring high-value guests - solely for the purpose of long-form, high-impact discussions. By working together, we can build a better future for ourselves and our families. Find our video podcast on YouTube: https://www.youtube.com/playlist?list=PLoaCszL7eN9T7EixaJgL49WTLsT-CWLD1

Recent Episodes

36. How I Predict the Outcome of (Almost) Every Investment I Buy (4M Framework)
NOV 20, 2025
36. How I Predict the Outcome of (Almost) Every Investment I Buy (4M Framework)

I have a framework that tells me which investments (and businesses) have the highest odds of succeeding. I’ve used this framework to build multiple $10M+ businesses and own a $100M+ real estate portfolio. I didn’t do this all by luck, and it isn’t because I’m a genius. It’s all because of this simple framework that anyone can use, with any budget, at any stage in their life.

 

Most businesses fail. Restaurants open, then close a month later. Stocks get sold off and drop to zero. Companies lay off their staff and shut their doors. This is all while other industries, companies, and investments see record profits. They all had a dream, but only some of them succeeded. What’s the secret to knowing which ones will make it? 

 

The 4M Framework.

 

The 4M Framework has personally helped me invest (and divest) in industries at the exact right times, making the most money possible and growing my wealth to $10M+. I’m finally sharing it, after testing it for over 20 years and seeing incredible results. You can use it, too, no matter how much money you have. I’m breaking down all four stages so you can multiply your money faster and stop getting burned. 

 

Insights from today’s episode: 

 

  • The 4M Framework: the ultimate way to predict the odds of any investment or business 
  • How I knew exactly when to sell one of my largest investments at precisely the right time 
  • The “shortcut” through the four stages of wealth and what will make you richer faster 
  • How to know whether a business has a “moat” or will get taken down by competitors quickly 
  • Signs that a business or investment is underpriced and has the potential to take off 
  • The one thing that will sink a business, even if it’s poised to succeed 

See My 4M Breakdowns on Instagram - https://www.instagram.com/ajosborne 

Sign Up for My Newsletter Here: https://ajosborne.com/newsletter 

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36 MIN
35. The Great Stock Divergence: Why Prices Aren’t Matching Reality
NOV 6, 2025
35. The Great Stock Divergence: Why Prices Aren’t Matching Reality

This looks a lot like the Dot-com bubble. Stock prices are hitting record highs, but their valuations are starting to diverge from reality. Americans are scared they’ll miss out on the rise of AI, so they’re pouring cash into the market in record amounts. Meanwhile, price-to-earnings ratios are inching nearer to Dot-com bubble levels. 

 

How close are we to the AI bubble bursting? Is this just another mania, or will AI deliver such strong production and profit increases that this type of stock market becomes the new reality? 90% of investors think the stock market is overpriced…so why is everyone still buying?

 

I’m sharing my thoughts in today’s episode as we compare the Dot-com bubble in 2000 to the 2025 stock market, which is seeing unprecedented price growth thanks to AI. I’ll admit this isn't the same economic environment as the Dot-com bubble, but the similarities are getting hard to ignore. 

 

Stocks could pull back, as they often do after a massive run-up. The question is: will the AI bubble burst, or is this the new reality?

 

Insights from today’s episode: 

 

  • The stock market’s “divergence” from reality and why valuations are growing much faster than profits 
  • The 2000 Dot-com bubble vs. the AI craze of 2024 and 2025 
  • Bubble indicators that are flashing major warning signs, but nobody is paying attention 
  • The almost unbelievable size of US stock valuations, dwarfing other major countries
  • Can this really last if AI provides the performance gains investors are looking for?

AJ Osborne Podcast 29. How AI Could Trigger the Next Great Depression 

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12 MIN
34. The Meeting of the Mind: What I Experienced While Paralyzed
OCT 23, 2025
34. The Meeting of the Mind: What I Experienced While Paralyzed

This is about to get weird. I’m opening up about something that has only been shared in very private circles. As some of you know, years ago, I was comatose and paralyzed for months, unable to move or communicate, stuck in a hospital bed, with only my thoughts. Deep into my paralysis, strange things began to happenbreakthroughs I didn’t know were possible. Personalities became unlocked, and a part of me I thought had died began to escape. 

 

This led me to what I now call the “meeting of the mind,” a major shift in my life that has not only led me to more success, but greater happiness, a deeper understanding of myself, and the ability to unlock my mind’s full potential. This is something very few people have ever experienced, but today I’m giving you the tools to try this experiment on your own.

 

This will allow you to unlock all your different personalities, including the one who gives you crystal clear clarity to see things as they truly are. If you were expecting an episode on business building or economic changes, sorry, this isn’t it. But knowing how to have your own “meeting of the mind” will amplify any area of life you want to succeed in. 

 

Insights from today’s episode: 

  • What I saw (and realized) while I was in a coma and paralyzed 
  • How to practice the “meeting of the mind” for yourself and see your true personalities (yes, multiple)
  • “The observer” who creates clarity no matter the situation you’re in 
  • How allowing my personalities to interact made me much more successful 
  • My mental rebirth and the part of AJ who died the day I was paralyzed 

 

Sign Up for My Newsletter Here: https://ajosborne.com/newsletter  

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42 MIN
33. This One Thing Will Make or Break a Commercial Real Estate Deal w/Kevin Bupp
OCT 9, 2025
33. This One Thing Will Make or Break a Commercial Real Estate Deal w/Kevin Bupp

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.  

Insights from today’s episode: 

  • The most crucial factor of a “good” real estate investment that so many got wrong in 2020 - 2022
  • The best loan to use for commercial real estate investing that can save your deal during bad times 
  • What sets the successful real estate investors apart from the rest (99% of people can’t handle this)
  • How Kevin built his portfolio, lost it all, and rebuilt it better and stronger than before 
  • How to filter out the BS when getting started in real estate investing 

Sunrise Capital Investors: https://sunrisecapitalinvestors.com/fund-4/

Kevin’s Website: https://kevinbupp.com/

Kevin’s LinkedIn: https://www.linkedin.com/in/kevinbupp/  

Sign Up for My Newsletter Here: https://ajosborne.com/newsletter 

 

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42 MIN
32. How to Start Your Own Business (and Replace Your Salary) with George Mortimer
SEP 25, 2025
32. How to Start Your Own Business (and Replace Your Salary) with George Mortimer

Want to start a business and begin working for yourself? This is how you do it. You don’t need to (and actually should not) invent a product or create a new type of service or technology. You can work for yourself simply by doing what you do right now at your job or what you’re interested in. Becoming your own boss enables you to earn more money, live on your own terms, and build something greater than yourself.

 

This is how to start your own business from scratch, even if you have $0 and are working a full-time job.

 

My guest isn’t wearing a suit, and he’s not driving a Bentley to work. He doesn’t need to, even though he’s COO of Self Storage Income. George Mortimer became my COO through starting his own web design business after not wanting a boss. Now, he’s running teams and a multimillion-dollar business. George and I know what it’s like to do the grunt work, struggle, and finally succeed at being (often) happily self-employed.

 

We’ll walk through how you can do it, too: build your own business, become your own boss, and scale up through the business stages (without burning out).

 

Insights from today’s episode: 

  • How to build your own business (or self-employed income stream) from scratch 
  • Why creating a “job” for yourself is not a bad thing (but it comes with some struggles)
  • The best “business” for anyone to start who’s currently employed 
  • Why big businesses go wrong and how to avoid their massive mistakes 
  • Building the “moat” that makes your business stand out from competitors 
  • Hey, you! DON’T go and invent a thing! Don’t even think about it!  

 

Self Storage Income: https://www.selfstorageincome.com/    

Sign Up for My Newsletter Here: https://ajosborne.com/newsletter 

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60 MIN