AJ Osborne Podcast

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 have any heirs at all. What happens when Generation X or millennials are given mom and dad’s house while struggling to pay off their student loans, car debt, and keep their own family afloat? Simple: they sell. What happens when mom and dad try to hand down the family business, but every family member refuses to take it over? It either gets sold or stops functioning. 

So who will be there to buy the assets? There are more sellers than buyers, meaning you have the opportunity to pick up businesses, real estate, and other assets at a fraction of what they’d cost just a decade or so ago. Do you take the chance and claim your own version of the great wealth transfer, or do you ignore the opportunity and wish that you did a decade from now?

Insights from today’s episode: 

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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 financing structure that could help you buy a high-quality small business with very little money out of pocket.

But the opportunity goes far beyond financing. These are great assets with enormous upside because they’re already profitable, and yet, they can be improved for even more revenue.

The key to owning one of these assets isn’t being an expert in that industry or having access to a ton of capital. It’s simply knowing how to structure one of these deals, and that’s exactly what I’m going to show you how to do.

Insights from today’s episode: 

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BizBuySell Insight Report - https://www.bizbuysell.com/insight-report/ 

M&A Seller Financing: A Complete Guide - https://morganandwestfield.com/knowledge/ma-seller-financing-a-complete-guide/ 

Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep52 

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 are being formed that were impossible just a couple of years ago, and it’s not an “if” AI impacts your life and work, but a “when” type of question. 

Millennials are scared. They don’t want their jobs to be displaced or terminated entirely, and just like the baby boomers during the age of the internet, there’s a lot of fear for the future. But what comes next? Can we learn from the boomers' mistakes so we can take full advantage of an inevitable change, instead of clinging to a structure that has been broken by new technology?

This is your last chance, or you'll face the same fate as many of the boomers. 

Insights from today’s episode: 

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Microsoft 2026 Work Trend Index Annual Report - https://news.microsoft.com/annual-work-trend-index-2026/ 

Sign Up for my Newsletter! I share news and advice weekly about: business, entrepreneurship, economics, finance, commercial real estate and more! https://ajosborne.com/newsletter?el=pc-ajo-ep51 

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 for it. 

Everyone thinks the Baby Boomers are only leaving behind a massive inheritance to their children, spending it on medical care, or splurging on travel and leisure—not quite. 60% of boomer businesses—boring businesses like HVAC, plumbing, drywall, and electrical businesses—have zero succession plan. Their kids aren’t inheriting them—they will merely stop functioning. What if you could buy that business (for cheaper than you think) and use it to produce income for decades to come?

I’m buying these businesses right now. And today, I’m showing you how to, too.

Insights from today’s episode: 

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How to Invest with Just $10 (Fractional Investing Explained) - https://youtu.be/eTDCbHXfwmI?si=_SxeA5lMo5DnAIwO 

✍️ Sign Up for my Newsletter! I share news and advice weekly about: business, entrepreneurship, economics, finance, commercial real estate and more! - https://ajosborne.com/newsletter?el=pc-ajo-ep50 

▶️ I am hosting a FREE 3-part webinar series where I will be diving into how to identify if a business is even worth buying, how to structure the deal, and how to build systems that let you run a profitable business. Date and time will be announced soon! Save your seat here: www.ajosborne.com/webinar 

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 thousands of dollars in revenue, simply by optimizing their marketing strategy.

We’re sharing real case studies of businesses we’ve been able to turn around in a matter of months. More importantly, we’ll show you how to replicate these results—not by overhauling your product or reinventing your business model—but by simply building a marketing “machine” that actually works.

Whether you’re buying your first business or scaling your tenth, these fundamental marketing principles are often the difference between a struggling business that’s scraping by and one that turns a massive profit year after year.

Insights from today’s episode: 

Join us for a free webinar where we break it all down step by step. Save your seat here: www.ajosborne.com/buildingthemachine See you there!

Sign up for my weekly newsletter here: https://ajosborne.com/newsletter?el=pc-ajo-ep49

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:

Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep48  

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?el=pc-ajo-ep47 

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?el=pc-ajo-ep46 

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:

Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep44