AJ Osborne Podcast

People think owning or buying a business is just for the wealthy. For the visionaries with the revolutionary ideas. For the entrepreneurs whose startups beat the odds. But they’re wrong. Over 17 million businesses will change hands in the next several years. As the baby boomer generation ages out , some of these businesses will close their doors. Some will stay within the family. But most of them?...

  The next great depression is closer than you think. For years, Lauren Saidel-Baker , economist at ITR Economics, has predicted an almost unavoidable economic depression , specifically for the United States. We last spoke to her about this in January 2025, and now she’s back—but this time, she’s even more convinced of our path to the 2030s great depression.    Major signals are kee...

AI has leveled the playing field for new real estate investors, startups, and small businesses. The truth is that most investors still view AI as another productivity tool. But what we’re witnessing is a once-in-a-generation shift in how businesses are built and scaled . The larger, more established players? Many are still operating the way they always have. All of their systems, processes, and te...

You’ve just started a business. Now what? If you’re Tanner Herget , you build another…and another…and another. It’s hard enough to grow one business from scratch, but Tanner is the textbook definition of a serial entrepreneur . It’s all he’s known since 22 years old, when he left his full-time job to open his own restaurant. That business failed. Most inexperienced entrepreneurs would’ve walked aw...

We’re living through unprecedented times. Oil shortages , war , disruptive technology , a large wealth gap , and rising inflation . Is history beginning to repeat itself?   There’s one era that looks eerily similar to today’s America: The 1960s-1970s . Civil unrest, rising unemployment, financial strain, and a rapidly changing global landscape. But this time, a few crucial factors are much di...

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 , yo...

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...

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 co...

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 you...

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...

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...

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...

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 busines...

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 t...

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...

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 esta...

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 great...

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.&nb...

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 mas...

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 i...

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 Investo...

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?...

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

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 machi...

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 ind...