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    Business

    AJ Osborne Podcast

    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.

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-description

    Advertise

    Copyright: © Copyright 2019 All rights reserved.

    • Apple Podcasts
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    • Spotify

    Latest Episodes:
    34. The Meeting of the Mind: What I Experienced While Paralyzed Oct 23, 2025
    Show notes

    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?el=pc-ajo-ep34


    33. This One Thing Will Make or Break a Commercial Real Estate Deal w/Kevin Bupp Oct 09, 2025
    Show notes

    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?el=pc-ajo-ep33


    32. How to Start Your Own Business (and Replace Your Salary) with George Mortimer Sep 25, 2025
    Show notes

    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


    31. The Fed Just Reset the Economic “Cycle” Sep 22, 2025
    Show notes

    The long-awaited Fed announcement is here. After the recent Fed meeting, where we got more clarity on rate cuts, the economic “cycle” seems to have been just reset. This will have significant consequences for the economy and prime specific industries for a resurgence. If you own any of these assets or work in any of these sectors, you could be riding a new “wave” of wealth for years to come.

    After years of economic tightening and high interest rates, stubborn inflation, and American purchasing power shrinking dramatically, the Fed has finally reversed course, heading towards an “easing” cycle. But something more interesting than rate cut news came out of recent Fed meetings—it’s what the Fed didn’t say.

    Jerome Powell has switched from familiar verbiage to some new phrasing, priming us that we could be in a much different position than we’ve been in before. This has enormous implications for the next moves the Fed makes, and whether we’ll see interest rates fall even more as a result. Was the Fed too late with this move, with unemployment already rising and job revisions pushing us into an even deeper hole? I’m explaining who will win and who will get left behind in this next cycle.

    Insights from today’s episode:

    • The Fed announcement on rate cuts and what it means for the economy
    • Who will win in this next economic cycle (industries and investments)
    • A big pivot? Why the Fed backed off its 2% inflation goal
    • Was the Fed too late? Can employment bounce back?
    • What a tightening vs. easing “cycle” means for the average American

    —

    Why U.S. Debt is Everyone’s Problem (Including Yours) - https://youtu.be/DFDZwj64EeQ?si=t6jH1zLvRBn0Wmas

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep31


    30. Why the Masses Miss Every Wealth-Building Opportunity Sep 11, 2025
    Show notes

    If you can’t fix this, you’ll never be wealthy. The 99% move like a herd, and the masses scream in fear, duck for cover, and sell in lockstep during every major recession, crash, and recovery. This is why most Americans (or people on Earth, for that matter) will never be wealthy. By letting their fear take over during times of opportunity and their greed override their senses during peaks, the masses buy high, sell low, and remain in the same place.

    This is avoidable. Anyone can grow wealthy IF they follow the right steps.

    At some point, I realized that my emotions were controlling too many of my decisions. When I stopped listening to my lizard brain and started operating on a system, everything changed. How did I know to buy so low during the real estate bust in 2008? How did I know my industry was in a bubble before so many others? And why am I back to buying while people are telling me the bottom is yet to come?

    Keep following the news if you want to remain stuck. Listen to this episode if you want to finally control your financial future.

    Insights from today’s episode:

    • How to stop your emotions from ruining your wealth-building opportunities
    • The “signal” the wealthy look for that tells them when to buy (and sell)
    • Why allowing yourself to look stupid may be the best decision you ever made
    • My “buy box” formula that controls my investing (not my emotions!)
    • How to capitalize on market confusion and buy when everyone else is too scared to act

    —

    AJ Osborne YouTube Channel - https://www.youtube.com/@AJOsborneOfficial

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep31


    29. How AI Could Trigger the Next Great Depression Aug 21, 2025
    Show notes

    AI could trigger a new economic crisis—the next great depression—and most people are ignoring it. I’m not just talking about job loss or automation replacing salaries. There’s a much deeper problem—one that could erode the last remnants of stability in the US economy and government. Is AI taking jobs? Yes. But that’s just one of our worries.

    “Second-order consequences” are coming fast. Nobody is talking about them. The government, the economy, and everyday US citizens are not prepared. And this isn’t just a US problem. Many developed nations are dealing with a generational shift, massive national debt, and a shrinking workforce. Will AI solve this problem or make it even worse?

    I’m sharing my theory on how AI will shift the US economy and you individually, the effects that most people are completely overlooking, and a growing concern that is going to hit the US government head-on. AI could be the solution to many of our problems—it could also be our downfall. Which road will we take?

    Insights from today’s episode:

    • The shrinking labor force problem that AI can only superficially solve
    • How the US government’s debt crisis will ramp up once AI replaces jobs
    • The growing wealth gap that could further widen thanks to AI
    • How to protect your personal wealth when AI is taking high-paying jobs
    • Could taxing the rich fix any of this—or just make it worse?

    Why U.S. Debt is Everyone’s Problem (Including Yours) - https://www.youtube.com/watch?v=DFDZwj64EeQ&pp=0gcJCcwJAYcqIYzv

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep29


    28. Top 100 Advisor: How to Invest During Market Chaos w/Adam Koós Aug 07, 2025
    Show notes

    The stock market crashed in March, but now it’s back to all-time highs. You might have sat frozen, waiting for a recovery or a better buying opportunity. Chances are, you didn’t make any moves that made you richer. Was that a mistake? During “trendless” markets like these—where price swings feel random and directionless—most Americans sit on the sidelines. Others, like Adam Koós, one of Investopedia’s Top-100 Most Influential Financial Advisors in the U.S., made money in the peaks, valleys, and in between.

    So, how do you invest in chaotic markets where the “trend” seems nonexistent? What’s the investment strategy beginners can use to protect from the crashes and buy on the way back up? If you’re wondering where to invest now, Adam has the answer.

    Adam has the technical trading knowledge that 99.9% of investors (and even advisors) lack. His full-time job is identifying trends, capitalizing on them, and moving more money into his all-star roster of investments. He’s sharing his actual investment strategy today (piece-by-piece!)—so you can apply the same principles to your own portfolio. Plus, he even provides his five-year forecast and an optimistic view on interest rates.

    Insights from today’s episode:

    • How to invest even during market chaos, tariffs, wars, and more
    • Adam’s exact investing strategy to take advantage of any market cycle
    • A five-year economic forecast and a contrarian take on future inflation
    • How to build a stock portfolio of “playoff teams” that will take YOU to the financial Super Bowl
    • Beginner investments you can make now that protect you during crashes and build wealth during bull runs

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep28

    Libertas Wealth: https://www.libertaswealth.com/

    Elevate and Exit: http://elevateandexit.com/

    Connect with Adam on LinkedIn: https://www.linkedin.com/in/adamkoos/

    Alphatrends: https://alphatrends.net/


    27. How to Raise Capital for Real Estate (Without Going to Prison) w/Mauricio Rauld Jul 24, 2025
    Show notes

    For over a decade, as I built my portfolio, I didn’t raise capital from outside investors. Why? I didn’t want to take the risk. Raising capital for real estate is something you cannot afford to get wrong. No one wants to end up in prison because they funded a deal the wrong way. Good news? I’ve got SEC attorney and good friend Mauricio Rauld here to tell you how to do it right. Even better news? AI is about to make it cheaper (and easier) for all of us.

    Seriously, why pay a lawyer tens of thousands of dollars to come up with your documents when AI can compile everything for a fraction of the cost? Most lawyers don’t want to hear this, but Mauricio is fully on board. The change is coming, and it’s about to bring huge cost savings to all of us who run businesses or invest in real estate. Plus, accredited investor rules could change soon, making it even easier for average Americans to invest in bigger deals. Will the move actually go through?

    If you’re even thinking about raising money, listen to this episode. You could be paying thousands of dollars for what Mauricio is about to tell you. We’re also sharing the best career advice you’ll ever receive, our thoughts on AI’s new lawyer-replacing features, and why the middle class is stuck, getting squeezed while the rich get richer.

    Insights from today’s episode:

    • How to raise capital for real estate (the rules you MUST follow before you do)
    • New AI lawyers that can draft your legal docs for a fraction of the cost
    • Why you have way more control than you think when raising capital for real estate
    • Crucial career advice if you feel like you don’t know what your “passion” is
    • Changes to accredited investor rules? Why this could be good for average Americans

    —

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep27

    🎧 Listen to Drunk Real Estate: https://www.drunkrealestateshow.com/

    🔗 Mauricio’s LinkedIn: https://www.linkedin.com/in/mauriciorauld/

    📚 Mauricio’s Coaching: https://coachingwithmauricio.com


    26. I Built My Business to “Fail,” Now It’s Worth Hundreds of Millions Jul 10, 2025
    Show notes

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep26

    Markets are volatile. Whispers of a recession are getting louder. Some industries—like commercial real estate—are already in recession. This has been one of the most difficult market cycles for business owners and self storage investors to navigate. Want to know how to start a business that thrives in any economic environment? I break it down in today’s episode!
    We’re coming off arguably the greatest bull market in history. The problem? People start businesses expecting success, which is exactly why they fail. Their systems, models, and contracts aren’t designed for the worst-case scenario. The truth is, if you want to succeed long-term, you can’t build to succeed. You must build to fail. It sounds backwards, but it’s the only way to survive the storms.
    Make no mistake—you will fail. But how you fail makes all the difference. You don’t need to be fearless, just aware of the risks and prepared for the valleys. In this episode, I show you how to fail the right way—small, fast, and forward!


    Insights from today’s episode:
    Why “building to succeed” is a fatal flaw in this economy (and what to do instead)
    The biggest mistake entrepreneurs make when starting a new business
    How to create “asymmetric failure” that your business can weather
    The number one reason businesses go under during tough market cycles
    Why you must treat every new investment opportunity like a business.


    25. How to Start an AI Vending Machine Business That Makes Thousands Per Month w/Michael Hoffmann Jun 26, 2025
    Show notes

    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep25

    This investor makes tens of thousands a month from his “AI vending machine” business. A business so simple a teenager could run it—and make more than most Americans do at their day job. We’re not talking about those old vending machines in the back of bowling alleys selling Cokes for $1.50. We’re talking about an AI vending machine business plan that generates $1,200 to $2,000 per month per machine.

    Michael Hoffmann—better known as ‘Mr. Passive’—has been running his vending machine side hustle for over five years. But he’s made a serious business out of it, leveraging his Silicon Valley tech background to perfect the purchasing experience.

    A customer simply walks up to your machine, taps their card, grabs what they need, and leaves. You make a massive markup, and the customer gets what they want—fast. Want to know how to repeat it? Michael is sharing exactly how much he makes, how much a machine costs, the profit margins, and a step-by-step plan so you or even your kid can start a vending machine business.

    Insights from today’s episode:

    • How much vending machines make AND how much a vending machine costs
    • The new “AI vending machines” with bigger purchases and better margins
    • A step-by-step business plan for starting your own vending machine business
    • How to scale your vending machine side hustle into a full-time business
    • The best way to teach your kids entrepreneurship? Why AJ is bullish on vending machines for HIS kids

    Join the Waitlist for VendHub! - https://www.vendhub.ai/

    Learn how to do this yourself and subscribe to Michael’s YouTube Channel! - https://www.youtube.com/@UCCr13sXOZgWCqpPv8WPKhwQ


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