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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:  The baby boomer wealth transfer that will force them to sell trillions in assets  Why cash-flowing baby boomer businesses are far cheaper to buy than you think What happens when tens of millions of boomers pass away over the next decade?  How the real estate market could be “flooded” with inventory as heirs opt to sell  Why millennials are way off on the “inheritance” they think they’re owed — 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-ep53

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:  How much it actually costs to buy an existing small business Why the down payment needed for a small business is usually less than you think The three-layer structure for financing a small business Why over six million small businesses will change hands by 2035 Value-add opportunities that could add thousands to your business’s bottom line — 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:  Why millennials are becoming the new baby boomers unless they start adapting ASAP Microsoft’s new Work Trend Report that shows how work structures are dramatically changing  The boom of new small businesses and how AI is enabling Americans to do what they could never before  Your job may not be around in a few years (but here’s how to get a better one) The new “system” and how work will be done in the AI age (protected roles) — 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:  The wealth-building opportunity of a generation (and why we only have so much time left) Baby Boomer businesses for sale that cost less than a house but generate high income Proof that “smart money” is putting billions of dollars into “boring businesses” many overlook  How to buy a business for cheap, improve it, and make it worth multiples more  Moving yourself from “income” to “owner” class in the American economy  — 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:  The number one issue that plagues most struggling businesses today Real case studies where we were able to increase revenue (in months) How to optimize each stage of your business’s sales funnel The two main reasons potential customers drop out of your funnel When to use direct and indirect marketing within your business 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: Why 17 million businesses are changing hands right now (and how to buy one) How Tim bought his first small business with just $35,000 Why buying an existing business isn’t nearly as risky as you think Three ways to fund a business acquisition with low money down The biggest red (and green) flags to watch for when analyzing a business 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:  The road to the next great depression: Why 2030 looks like it’s unavoidable  The “linchpin” that could set off the domino effect and massively change the economy  How to win in the next great depression and what to do to start preparing now The Fed’s “trap” and how they’ll lose control of the economy  Why Lauren thinks many people are wrong about AI (and what effect it will really have) __________ 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: How Hollis is using AI to bridge the gap between operators and investors Why AI gives startups and small businesses more leverage over the big players The best ways to integrate AI within your own real estate business The two biggest barriers operators face after getting a property under contract Three steps to using AI effectively in your real estate business 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:  Tanner’s journey from failed restaurant owner to serial entrepreneur The “three-legged stool” that allows entrepreneurs to build massive wealth How to optimize an existing business through vertical integration Two things that directly impact the success of any new business How to balance productive businesses and passion projects The biggest risks to keep in mind when forming a business partnership  Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep45

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: Is history repeating itself? 1960s America vs. 2020s America  America’s “major transformation” that could create a defining era  Why things seem worse today than in the past (is that really true?) Economic crises then vs. now, and why it could get worse for us Why you must make moves when everyone else freezes in fear   Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep44

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:  The seven investments the U.S. government will pay you to make What most Americans don’t understand about the United States tax code Why investments, not income, shelter more of your money from taxes The short-term rental “loophole” and other real estate tax deductions explained Questions your tax advisor should be asking you (not the other way around) — Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep43 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:  Why the housing market won’t “crash” like most people think it will  What happens to home prices and mortgage rates over the next five years The “silent killers” that are putting homeowners in a tough spot  Why home sales are still dropping even as mortgage rates fall further  Markets with the most risk as baby boomers pass away and sell or transfer their homes    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep42

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:  The economic “reset” that is brewing after many years of increased financialization Why the shift from paper assets to hard assets is accelerating in the United States The “slow” deterioration of the U.S. dollar (and the rise of a new currency) What comes after America’s “fourth turning” in the current economic cycle Why a central bank digital currency (CBDC) could threaten our basic freedoms — Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep41  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:  How to build and preserve wealth as the U.S. economy “resets” Why hard assets, not income, are the key to achieving financial independence How the U.S. government plans to “solve” its $38 trillion spending problem Why the financialization of the U.S. has brought a “return to fundamentals” The areas where artificial intelligence will help (and hurt) the American workforce Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep40

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:  If you can do this for five years, you could be wealthy for the rest of your life The “cheat code” for investing that Brian uses before buying a new business  Why you must run your business (even your rental properties) like a business from the start  Yearly goals? Why Brian says they won’t work and what to try that’s even better  Why you’re so stressed, and the only way you can make it stop affecting your day The #1 actual barrier to success that most Americans are too afraid to hear   —  Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep39   Brian’s Instagram - https://www.instagram.com/mr.briantran/  Brian’s TikTok - https://www.tiktok.com/@mrbriantran?lang=en  Brian’s YouTube - https://www.youtube.com/@Mr.BrianTran