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by AJ Osborne
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- 1 weeks ago15 min
44. Is History Repeating Itself? Why the 2020s Is Mirroring the 1960s
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
- Apr 16, 202627 min
43. Tom Wheelwright: How the Wealthy Avoid Taxes (While W-2 Workers Get Crushed)
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 Tax-Free Wealth - https://www.amazon.com/Tax-Free-Wealth-Permanently-Lowering-Advisors/dp/1937832058 TFW Advisors - https://tfwadvisors.us/
- Apr 7, 202620 min
42. Housing Won’t Crash, But This Is What WILL Happen Through 2030
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
- Mar 19, 202644 min
41. America’s Financial Clock Is Ticking: What Happens When the Dollar Ends? with David Morgan
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 — 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/
- Mar 5, 202628 min
40. An Economic “Reset” Is Coming: How to Build Real Wealth Before It’s Too Late
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
- Feb 19, 20261h 4m
39. Once I Figured Out This Formula, I Built 9 Businesses (That Run Themselves) w/Brian Tran
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 — 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
- Jan 30, 202637 min
38. The Middle Class “Collapse” Is a Lie (Here’s What’s Actually Happening)
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 reality is that where you live, how you live, and what you owe have a much bigger impact than your tax bracket. Yes, housing has outpaced inflation, but other costs—like college tuition, childcare, and healthcare—have blown past it. A millennial with student debt and less purchasing power feels much poorer than someone in another area of the country—even if they earn the same salary. It’s a tale of two Americas. But there’s an even bigger distinction between millennials who have prospered and those who continue to struggle, and you might have more control over which side you land on after all. Insights from today’s episode: Why the shrinking middle class actually signals upward income mobility The real reason millennials are divided on lifestyle affordability in the US Why many Americans don’t feel wealthy (despite rising incomes) Why housing affordability isn’t the middle class’s biggest economic challenge Two things you can do today to drastically improve your financial situation — The Wealth System You Were Taught Is a Lie (Here’s the Real One) Sign Up for My Newsletter Here: https://ajosborne.com/newsletter
- Jan 8, 202624 min
37. How the Rich Build Wealth with $0 Salaries (You Don’t Need More Income)
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 invert this formula by earning, spending, investing, and then paying taxes. It’s not a tax loophole. It’s how the tax code was designed. The system rewards those who play the long game and keep their money in the system. I didn’t learn this overnight. It took years at an old sales job before I realized just how much money I was leaking with every paycheck. Today, I share exactly how I built my wealth by reinvesting, compounding, and strategically deferring taxable events. More income just brings more taxes, but ownership brings freedom. Insights from today’s episode: Why the wealthy “hate” income (and what they do with their money instead) How the rich invert the wealth “formula” to delay taxable events Why debt is a powerful tool (not a liability) for building long-term wealth Why the US tax code benefits those who keep their money “in the system” The exact blueprint I followed to 7X my investing returns — My mission is to help everyday people achieve financial independence by teaching the strategies and principles that the wealthy use—but that most people never learn. If you're tired of working hard but not getting ahead financially, you're in the right place. Sign Up for My Newsletter Here: https://ajosborne.com/newsletter The Self Storage Bubble Bust… https://www.selfstorageincome.com/blog/the-self-storage-bubble-bust
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About AJ Osborne Podcast
Welcome to the AJ Osborne Podcast. Twice a month, I’ll sit down with guests or fly solo to share incredible stories, give my take on today’s economy, and show you how to build wealth the right way. We bring high-value guests - solely for the purpose of long-form, high-impact discussions. By working together, we can build a better future for ourselves and our families. Find our video podcast on YouTube: https://www.youtube.com/playlist?list=PLoaCszL7eN9T7EixaJgL49WTLsT-CWLD1
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