AJ Osborne Podcast

Entrepreneurship isn’t what most people think.

It’s not all passive income, Porsches, and private jets. Early on, it’s often the exact opposite. You don’t pay yourself. You work around the clock. And you learn to get comfortable with failure.

The truth is, entrepreneurship is hard. Really hard.

Today, I’m sharing the harsh realities of business ownership—the stuff most people never see. There are five things about business that all entrepreneurs learn firsthand, and if you dream of starting your own business, you need to be prepared for them, too.<...

Interest rates keep climbing higher. But the real culprit isn’t the Federal Reserve, the White House, the Iran War, or anything else that probably comes to mind.

It’s AI.

The truth is that the recent AI boom has impacted the economy in more ways than one. Because the government is now competing with hyperscaling AI companies for the same pool of bond investors, it’s forced to increase yields. Meanwhile, AI is driving massive stock market gains. The problem is, those gains are highly concentrated, so most people aren’t feeling the positive effects...

A generational wealth transfer is unfolding now—but it’s not what you think. Baby boomers aren’t simply handing away all their wealth or spending it on assisted living, medical care, or vacations. Instead, for a savvy few, the $90 trillion baby boomer wealth transfer will be unlocked, even if you don’t have wealthy parents. Because here’s the truth—the baby boomers have to sell everything. 

Over the next ten years, tens of millions of baby boomers will pass away. Many of them own businesses, real estate, or assets their heirs do not want, or don’t...

How much money do you really need to buy a business? Far less than you probably think.

Over six million small businesses will change hands by 2035, as baby boomers look to part with their mom-and-pop operations. This is your opportunity. 

These businesses aren’t trading for tens of millions, or even millions of dollars. In fact, most of them cost less than the median price of a single-family home, and the amount you have to put down to acquire them is often a small fraction of the purchase price. Today, I’m sharing the three-layer finan...

Millennials are quickly becoming the new baby boomers. They’re falling for a trap that caught the boomer generation at the turn of the century, but most Millennials have no idea. Unless they change their ways now, many Millennials may end up jobless, economically helpless, and angry at a future they themselves are actively creating.

Before you get upset with me, let me explain. 

A new report from Microsoft is showing that AI is overhauling the system as we know it. Structures are changing from the bottom up, new businesses and ideas...

The wealth-building opportunity of a generation ends in 2035. Smart money (Wall Street and private equity firms) is already taking advantage. Most Americans either don’t know about it or think they can’t share in the profits. This couldn’t be more wrong.

If you hesitate over the next decade and don’t take advantage of the unparalleled opportunity to come, you, like many Americans, may stand to regret it. I took advantage of opportunities like this in 2008 when everyone thought I was crazy. Fast forward nearly two decades, and we have $400M in assets to show f...

Every business is trying to solve the same equation:

Find leads. Make them customers. Repeat.

Yet many businesses, if not most, get it all wrong. It’s not because they have a product problem, personnel problem, or even a lead problem. Most of the time, it’s a conversion problem. They crank up their ad spend and chase more traffic without patching the leaks in their funnel. The result? Shrinking margins.

The good news is that this is fixable.

AJ and George have scaled businesses across multiple industries, adding hundreds of thou...

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? They’ll be sold. To whom?

Maybe you.

You don’t need millions of dollars to buy them. In fact, many of these small busine...

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 keeping us from swerving this colossal event. The Fed is trapped—lowering rates to save our government budget could trigger inflation, again. Social problems are growing—the wealth gap is widening, and those at...

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 teams were built without AI, and changing course now would require a massive overhaul.

William Hollis, founder of Capital Advisory AI, has seen just how powerful this technology can be...

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 away. For Tanner, giving up wasn’t an option. He quickly pivoted, transforming his struggling restaurant into a popular nightclub. It kept the lights on, but it also ga...

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 different. We’ve got trillions in government debt, AI advances that are making the average American worry about the future of their job, and massively increased investment opportunities. 

What lessons of the past ca...

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. Tom Wheelwright, Rich Da...

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 stalemate t...

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 game plan.

The system is...

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 America has a spending problem, and the $38 trillion national debt doesn’t eve...

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 suppo...

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 real...

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 inver...

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 th...

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...

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...

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 t...

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 w...

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...

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 s...

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 generationa...

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 w...

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...

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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...

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 f...

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 better half, Tessa, to the show. Tessa is on the Board of Directors at Innovate Academy, founded th...

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” behind a business environment that can erode your company and everything you’ve worked hard for. H...

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 success “recipe.” 

Scott Donnell has worked with thousands of families, including many of the wealthiest in America. He’...

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 make money, what we’re invested in, the teams doin...

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 paralyzed. My children, who we...

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 most means, a misunderstanding at best and ignorance at worst. I want billionaires to pay more, a...

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 hundreds of millions of dollars.

Big businesses use...

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 episode, I’m going in-depth on the complicated economic conditions developing for 2025, exploring how government actions and unpr...

What if everything you thought about money and making money was wrong? For centuries, most people have been fed a series of money lies, preventing them from building wealth or escaping poverty. When recessions and economic depressions happen, those believing these lies get wiped out, forcing them to restart while the rich take advantage. To break free from this, I’m sharing three crucial money “truths” the rich know but the poor don’t.

Once I describe these truths, I will show you exactly how to take advantage of the value-creating assets that can make you massively wealthy...