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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

27:59

43. Tom Wheelwright: How the Wealthy Avoid Taxes...

AJ Osborne Podcast ·

2026/04/16

It’s no secret that the wealthy pay very little in taxes. But how do they get away with it? It’s not because they’re cheating the system or finding a clever workaround.It’s by design. The tax code was written in a way that incentivizes building businesses, creating jobs, and investing in real estate. If you’re a consumer—even a high-earning one—you’re heavily taxed. But if you’re producing, you’re rewarded. In fact, there are seven investments the government will actually pay you to make

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20:04

42. Housing Won’t Crash, But This Is What WILL Happen...

AJ Osborne Podcast ·

2026/04/07

The housing market isn’t crashing—and it’s not going to. Something more gradual, and for many, painful, will be drawn out over the next five years, as a “slow motion reset” takes place on a scale many of us have never experienced. You can already see it around you. Houses are sitting on the market longer, even as mortgage rates fall. People want to buy a home, but who can take the risk in this job market? Pending sales are down, but more Americans are trying to get a mortgage. This is a

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44:16

41. America’s Financial Clock Is Ticking: What...

AJ Osborne Podcast ·

2026/03/19

America’s financial system is a ticking time bomb.For years, the United States has become increasingly financialized, and we’ve finally reached a boiling point. History shows us that there are cycles, and we’re in the “fourth turning” of one now. What comes next? A complete reset. At this point, it’s the only option left after the politically wealthy and banking system elites have backed the country into a corner. We can’t pay off the national debt, and getting out of debt was never the

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28:42

40. An Economic “Reset” Is Coming: How to Build Real...

AJ Osborne Podcast ·

2026/03/05

The United States economy is about to reset.Government systems are largely self-serving. Trust in the country’s institutions has eroded. We’ve reached the point of no return. But empires don’t crumble overnight. This “transformation” will be slow, difficult, and likely painful. But on an individual level, there’s still a clear path to safety—to achieving financial independence and protecting your wealth, even amid a complete reshaping of the U.S. economy as we know it. It’s no secret that

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64:21

39. Once I Figured Out This Formula, I Built 9...

AJ Osborne Podcast ·

2026/02/19

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

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37:45

38. The Middle Class “Collapse” Is a Lie (Here’s...

AJ Osborne Podcast ·

2026/01/30

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

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24:57

37. How the Rich Build Wealth with $0 Salaries (You...

AJ Osborne Podcast ·

2026/01/08

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

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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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