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 businesses cost less than the median price of a single-family home. Serial business-buyer Tim Delaney found this out when he stumbled on a local wine and liquor store 13 years ago. He bought it with just $35,000 down, and that investment gave him a reliable cash flow stream, provided for his family, and made the next venture that much easier.

And buying an established business isn’t nearly as risky as you probably think. Tim shares the green and red flags to look for when analyzing a small business, the different levers you can pull to fund one, and the value-add playbook that can turn any mom-and-pop operation into a staple of your community.

Insights from today’s episode:

Connect with Tim on Instagram: https://www.instagram.com/timtdelaney/

Are You Ready to Buy a Business? (Take the Quiz): https://www.powerofbiz.com/ajo

The Business Buying for Financial Independence Podcast: https://podcasts.apple.com/us/podcast/business-buying-for-financial-independence/id1823816760

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 the bottom can barely afford necessities. And the final linchpin—an aging baby boomer population that will take massive amounts of resources, without giving much in return.

We’ve seen problems like this occur in other countries—France and Japan, to name a couple—but nothing on the size of the American economy. So what’s coming next? Are we back to a 2008-style market selloff where asset prices tank? Can AI step in to save us from some of these dangers that a younger workforce can’t solve, and who wins and loses when the shoe drops?

Insights from today’s episode: 

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ITR Economics:  https://hubs.la/Q04h6kdc0 

Check out Lauren's previous podcast episode!-https://www.ajosborne.com/podcasts/aj-osborne-podcast/episodes/2148970950 

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

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 in the hands of everyday investors. He and his team have developed a platform that pairs operators with investors, making it easier to raise capital and identify new passive investing opportunities.

But Hollis doesn’t believe every real estate business needs to build its own AI agent or custom tool. He shares exactly how investors can start leveraging existing AI tools to streamline operations, eliminate bottlenecks, and free up time to focus on the work that actually creates wealth.

Insights from today’s episode:

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

Connect with Hollis on LinkedIn: https://www.linkedin.com/in/rei-hollis

Capital Advisory AI: https://capitaladvisory.ai/

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 gave him the confidence to tackle his next venture.

Over the next 20 years, Tanner started more than a dozen businesses, many of which he still owns and operates today—from cash-flowing, brick-and-mortar establishments to long-term equity plays.

Today, we discuss what makes a business “work,” the hidden risks of partnerships, and the three-pronged approach to building wealth through entrepreneurship. Whether you’re launching your first startup or actively scaling, Tanner shares the strategy, mindset, and grit it takes to keep going when others would quit.

Insights from today’s episode: 

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 can we use to make better decisions today, even when it feels like the world is ending. 

In this episode, I’m going piece by piece through these two pivotal eras, describing what’s different, what’s the same, and what new risks and opportunities present themselves to today’s Americans. Everyone is stuck in fear as the news and social media bombard them with information 24 hours a day. 

While everyone is frozen, are you going to make a move?

Insights from today’s episode:

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 Dad Advisor, CPA for Robert Kiyosaki, and founder of WealthAbility, breaks down some of these investments and the different ways to build wealth without sharing half of it with Uncle Sam.

With tax increases likely on the horizon, high earners face a critical decision: stay trapped in earned income or move into the asset economy. Whether you’re filing your 2025 return or tax planning for 2026, we cover strategies and approaches to building wealth that could save you thousands of dollars.

Insights from today’s episode: 

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

Tax-Free Wealth - https://www.amazon.com/Tax-Free-Wealth-Permanently-Lowering-Advisors/dp/1937832058 

TFW Advisors - https://tfwadvisors.us/ 

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 that will last until 2030, but what does that mean for the average American?

Some markets will fare better than others. Some are already seeing delinquencies and foreclosure rates rise, leaving sellers in a bind. A “silent killer” is coming after these homeowners, and “soft” pricing could be on the table for years to come.

Which markets are the most (and least) at risk? Will the housing market crash? Where will Americans move to when job prospects dwindle, and what’s the one big outlier that could change everything?

The reset has already begun. Are you prepared for what’s coming?

Insights from today’s episode: 

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

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 broken.

The dollar’s days are numbered, but what will replace it? David Morgan, an expert on macroeconomics, precious metals, and the storm that’s currently brewing, believes it’s only a matter of time before a central bank digital currency (CBDC) is ushered in.

Everything will change—how our money is saved, spent, and even traced.

The real question isn’t just how to protect your wealth in uncertain times, but how society can come together, help each other, and return to the principles our country was founded on: hard work, productivity, and the things that matter far more than money.

Insights from today’s episode: 

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David’s Website - https://www.themorganreport.com/ 

Silver Sunrise - https://silversunrise.tv/ 

Resource Wars - https://www.amazon.com/Resource-Wars-Landscape-Conflict-Introduction/dp/0805055762 

The Fourth Turning - https://www.amazon.com/Fourth-Turning-American-Prophecy-Rendezvous/dp/0767900464 

How a $30 Billion Welfare Program Became a ‘Slush Fund’ for States - https://www.wsj.com/politics/policy/how-a-30-billion-welfare-program-became-a-slush-fund-for-states-c39b8311 

ISO 20022 - https://www.iso20022.org/ 

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 even tell the whole story. The government’s game plan? “Inflate” it away, devalue the dollar, but don’t actually solve the issue.

We should have seen this coming because we’ve seen it many times before. In 2008, in response to the growing financialization of the U.S. economy, I built businesses around physical, cash-flowing assets. It wasn’t new, trendy, or sexy, but it made me millions.

Now, it’s time to return to fundamentals once again:

Knowledge. Skills. Productivity. Real value. Tangible, income-producing assets.

This “winning” playbook is the only way to weather a storm that most Americans are simply unprepared for.

Insights from today’s episode: 

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

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 supposed to happen—especially not to Brian. But, unlike most people who buy a rental property or two and struggle to reach true financial freedom, Brian did something different.

Today, he’s detailing the exact mental map every real estate investor (or business owner) needs to follow before scaling a real estate business. Brian had it put to the test, spending a month in the hospital, all while his businesses paid him out like clockwork. Think you can’t get ahead with today’s interest rates? Think AI will take your job? Feel like your circle is thinking too small?

This episode will get you on the path to becoming a self-made millionaire if you follow Brian’s formula. 

Insights from today’s episode: 

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