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PODCAST

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. Find our video podcast on YouTube: https://www.youtube.com/playlist?list=PLoaCszL7eN9T7EixaJgL49WTLsT-CWLD1

business entrepreneurship

All Episodes

36:27

36. How I Predict the Outcome of (Almost) Every...

AJ Osborne Podcast ·

2025/11/20

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

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12:33

35. The Great Stock Divergence: Why Prices Aren’t...

AJ Osborne Podcast ·

2025/11/06

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

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42:14

34. The Meeting of the Mind: What I Experienced While...

AJ Osborne Podcast ·

2025/10/23

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

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42:34

33. This One Thing Will Make or Break a Commercial...

AJ Osborne Podcast ·

2025/10/09

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

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60:33

32. How to Start Your Own Business (and Replace Your...

AJ Osborne Podcast ·

2025/09/25

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

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39:06

31. The Fed Just Reset the Economic “Cycle”

AJ Osborne Podcast ·

2025/09/22

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

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43:27

30. Why the Masses Miss Every Wealth-Building...

AJ Osborne Podcast ·

2025/09/11

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

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32:14

29. How AI Could Trigger the Next Great Depression

AJ Osborne Podcast ·

2025/08/21

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

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48:28

28. Top 100 Advisor: How to Invest During Market...

AJ Osborne Podcast ·

2025/08/07

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,

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62:49

27. How to Raise Capital for Real Estate (Without...

AJ Osborne Podcast ·

2025/07/24

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

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34:06

26. I Built My Business to “Fail,” Now It’s Worth...

AJ Osborne Podcast ·

2025/07/10

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

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30:42

25. How to Start an AI Vending Machine Business That...

AJ Osborne Podcast ·

2025/06/26

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

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62:05

24. Parenting in a Petri Dish: Raising Independent...

AJ Osborne Podcast ·

2025/06/05

The parenting playbook is changing. Raising independent children has only gotten harder as family units drift apart, grandparents remain out of the picture, schools fail to teach financial literacy for kids, and overprotective helicopter parenting becomes the new norm. But just because society is heading in one direction, doesn’t mean your family has to as well. We’re proof of that, with four independent, high-achieving children raised by us, not society.Who is “we”? Today, I brought my

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52:19

23. Dan Martell: The “Clear” Vision That Creates...

AJ Osborne Podcast ·

2025/05/15

Dan Martell learned how to program at age 17 while in rehab. He traded one addiction for another—starting scalable, successful, profitable software companies. You might know him from his book Buy Back Your Time, where Dan shares the secret to building a business empire that frees you from the chains most solopreneurs and small business owners struggle to break. Today, he’s giving a masterclass on how to do just that.After scaling multiple top-tier teams, Dan has identified the “cancer”

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47:31

22. The Success “Recipe” Top 1% Families Teach Their...

AJ Osborne Podcast ·

2025/05/01

The wealthiest, happiest families in the world use a success “recipe” to raise their children. This leads to happier, healthier, more successful families, while most average Americans struggle to figure out how to teach kids about money. You may be used to fights and tantrums, children refusing to do their chores, and feeling forced to bribe them with allowances, more toys, or screen time. This is the opposite of what America’s wealthiest families do—and today, we’re uncovering their exact

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44:24

21. How I Built My $400,000,000 Business from a...

AJ Osborne Podcast ·

2025/04/24

I grew a $400 million business from scratch, in a wheelchair, and starting around the Great Recession. Almost everything was against me from the beginning. People told me my business would fail and my assets were worthless; banks laughed us out the door when we asked for funding. Then, suddenly, one day, my business needed to run on its own when I became paralyzed, unable to move, talk, or do anything but blink. So, how did I do it?Today, I’m breaking down my $400 million company, how we

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39:56

20. Trauma & Money: Choosing Growth Over Giving Up

AJ Osborne Podcast ·

2025/04/17

Today, we’re talking about the “T-word”… trauma. Before you click away, this is not a downer episode. If you’ve been through trauma, big or small, you know how hard it is to bounce back. For me, without trauma, I wouldn’t have this podcast, my businesses, my wealth, my financial freedom, or much of the gratitude for life I take with me every single day. The worst months of my life used to define me. Now, they’re much of the reason I’ve succeeded.Eight years ago, out of nowhere, I became

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30:09

19. The Billionaire Problem: Why the Rich Thrive...

AJ Osborne Podcast ·

2025/04/03

The billionaire problem: ultra-wealthy business owners and investors aren’t paying into the tax system. The Warren Buffetts of the world are getting wealthier while average Americans struggle to buy necessities like groceries. So, how do the ultra-rich avoid paying taxes? Would a “billionaire tax” work and finally force the ultra-wealthy to fork over their fair share, or will they merely use their legal loopholes to dodge taxes and make the middle class foot the bill?“Tax the rich” is, by

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39:45

18. Fractional General Counsel: How Small Businesses...

AJ Osborne Podcast ·

2025/03/20

What is “fractional general counsel,” and why was not having it one of the biggest business mistakes I ever made? Whether you’re a startup, a self storage operator, or a growing small business, you rarely think about “legal.” You know that big companies will happily pay hundreds of thousands, if not millions, of dollars a year to protect their products and services, but you dismiss it because you’re not “big enough” for that yet.This is a massive mistake, and it potentially cost me

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44:14

17. 2025 Worst Case Scenario: The Downfall of the...

AJ Osborne Podcast ·

2025/03/10

2025 could mark the beginning of the downfall of the United States—and this isn't just clickbait or a catchy intro. The impending economic crisis facing the US economy isn't straightforward; it involves complex factors that could escalate rapidly into a full-blown economic crash with long-lasting implications for you, your money, your business, and the entirety of the United States.This isn’t just about Trump or tariffs. Both political sides will suffer, and both are to blame. In this

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290 results

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