AJ Osborne Podcast

AJ Osborne
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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

  1. 39. Once I Figured Out This Formula, I Built 9 Businesses (That Run Themselves) w/Brian Tran

    5H AGO

    39. Once I Figured Out This Formula, I Built 9 Businesses (That Run Themselves) w/Brian Tran

    Could you escape one of America’s toughest neighborhoods to become a self-made millionaire, with the cards stacked against you? Today’s guest is a second-generation American, raised in the streets of Oakland, California—at the time, one of the country’s most dangerous cities. After the traumatic loss of his father, Brian Tran fulfilled his dad’s wish by finishing college, but struggling on a W-2 salary wasn’t in the cards. Fast forward over a decade, Brian owns nine successful businesses and a sizable real estate portfolio, making him a millionaire in the process. This wasn’t supposed to happen—especially not to Brian. But, unlike most people who buy a rental property or two and struggle to reach true financial freedom, Brian did something different. Today, he’s detailing the exact mental map every real estate investor (or business owner) needs to follow before scaling a real estate business. Brian had it put to the test, spending a month in the hospital, all while his businesses paid him out like clockwork. Think you can’t get ahead with today’s interest rates? Think AI will take your job? Feel like your circle is thinking too small? This episode will get you on the path to becoming a self-made millionaire if you follow Brian’s formula.  Insights from today’s episode:  If you can do this for five years, you could be wealthy for the rest of your life The “cheat code” for investing that Brian uses before buying a new business  Why you must run your business (even your rental properties) like a business from the start  Yearly goals? Why Brian says they won’t work and what to try that’s even better  Why you’re so stressed, and the only way you can make it stop affecting your day The #1 actual barrier to success that most Americans are too afraid to hear   — Brian’s Instagram - https://www.instagram.com/mr.briantran/  Brian’s TikTok - https://www.tiktok.com/@mrbriantran?lang=en  Brian’s YouTube - https://www.youtube.com/@Mr.BrianTran

    1h 4m
  2. 38. The Middle Class “Collapse” Is a Lie (Here’s What’s Actually Happening)

    JAN 30

    38. The Middle Class “Collapse” Is a Lie (Here’s What’s Actually Happening)

    The middle class is shrinking, but not for the reason you think. It’s hard to escape the doom-and-gloom narratives: wages are stagnant, the rich are getting richer, and everyday Americans are getting crushed. But when you look at the inflation-adjusted figures, a very different story emerges. For years, we’ve been told that the middle class is collapsing. But it’s not. It’s moving up. Incomes in the U.S. have actually surged over the last 30-40 years. People are getting wealthier, so why doesn’t it feel like it? The reality is that where you live, how you live, and what you owe have a much bigger impact than your tax bracket. Yes, housing has outpaced inflation, but other costs—like college tuition, childcare, and healthcare—have blown past it. A millennial with student debt and less purchasing power feels much poorer than someone in another area of the country—even if they earn the same salary. It’s a tale of two Americas. But there’s an even bigger distinction between millennials who have prospered and those who continue to struggle, and you might have more control over which side you land on after all. Insights from today’s episode:  Why the shrinking middle class actually signals upward income mobility The real reason millennials are divided on lifestyle affordability in the US Why many Americans don’t feel wealthy (despite rising incomes) Why housing affordability isn’t the middle class’s biggest economic challenge Two things you can do today to drastically improve your financial situation — The Wealth System You Were Taught Is a Lie (Here’s the Real One) Sign Up for My Newsletter Here: https://ajosborne.com/newsletter

    38 min
  3. 37. How the Rich Build Wealth with $0 Salaries (You Don’t Need More Income)

    JAN 8

    37. How the Rich Build Wealth with $0 Salaries (You Don’t Need More Income)

    The wealthy hate income and actively avoid it. Most people think income is the key to wealth. The more you grow your income, the higher you climb the corporate ladder, the more money you’ll have to save and spend. This couldn’t be more wrong. Income is a silent wealth-killer because you’re losing money before it ever reaches your pocket. Wealth is ownership—not income, but assets that produce income. We’re all taught to earn money, pay our taxes, and either spend or save the rest. But the rich invert this formula by earning, spending, investing, and then paying taxes. It’s not a tax loophole. It’s how the tax code was designed. The system rewards those who play the long game and keep their money in the system. I didn’t learn this overnight. It took years at an old sales job before I realized just how much money I was leaking with every paycheck. Today, I share exactly how I built my wealth by reinvesting, compounding, and strategically deferring taxable events.  More income just brings more taxes, but ownership brings freedom. Insights from today’s episode:  Why the wealthy “hate” income (and what they do with their money instead) How the rich invert the wealth “formula” to delay taxable events Why debt is a powerful tool (not a liability) for building long-term wealth Why the US tax code benefits those who keep their money “in the system” The exact blueprint I followed to 7X my investing returns — My mission is to help everyday people achieve financial independence by teaching the strategies and principles that the wealthy use—but that most people never learn. If you're tired of working hard but not getting ahead financially, you're in the right place. Sign Up for My Newsletter Here: https://ajosborne.com/newsletter  The Self Storage Bubble Bust… https://www.selfstorageincome.com/blog/the-self-storage-bubble-bust

    25 min
  4. 36. How I Predict the Outcome of (Almost) Every Investment I Buy (4M Framework)

    11/20/2025

    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

    36 min
  5. 35. The Great Stock Divergence: Why Prices Aren’t Matching Reality

    11/06/2025

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

    13 min
  6. 34. The Meeting of the Mind: What I Experienced While Paralyzed

    10/23/2025

    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 happen—breakthroughs 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

    42 min
  7. 33. This One Thing Will Make or Break a Commercial Real Estate Deal w/Kevin Bupp

    10/09/2025

    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

    43 min
  8. 32. How to Start Your Own Business (and Replace Your Salary) with George Mortimer

    09/25/2025

    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

    1h 1m
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4.9
out of 5
148 Ratings

About

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

Information

  • Creator
    AJ Osborne
  • Years Active
    2019 - 2026
  • Episodes
    293
  • Rating
    Clean
  • Copyright
    © 2026 413001
  • Show Website
    AJ Osborne Podcast

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