AJ Osborne Podcast

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 

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 

Discover the powerful 4M Framework that helps predict investment success. Learn the critical stages of wealth building and how to transition from public to private markets. Find out why analyzing market trends, focusing on margins, and understanding your business's moat are key. Gain insights on strategic selling and how to use other people's money to accelerate your wealth. This framework, tested over 20 years, is your guide to making smarter financial decisions and scaling your investments effectively.

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 is overpriced…so why is everyone still buying?   I’m sharing my thoughts in today’s episode as we compare the Dot-com bubble in 2000 to the 2025 stock market, which is seeing unprecedented price growth thanks to AI. I’ll admit this isn't the same economic environment as the Dot-com bubble, but the similarities are getting hard to ignore.    Stocks could pull back, as they often do after a massive run-up. The question is: will the AI bubble burst, or is this the new reality?   Insights from today’s episode:    The stock market’s “divergence” from reality and why valuations are growing much faster than profits  The 2000 Dot-com bubble vs. the AI craze of 2024 and 2025  Bubble indicators that are flashing major warning signs, but nobody is paying attention  The almost unbelievable size of US stock valuations, dwarfing other major countries Can this really last if AI provides the performance gains investors are looking for? — AJ Osborne Podcast 29. How AI Could Trigger the Next Great Depression   Sign Up for My Newsletter Here: https://ajosborne.com/newsletter 

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 life that has not only led me to more success, but greater happiness, a deeper understanding of myself, and the ability to unlock my mind’s full potential. This is something very few people have ever experienced, but today I’m giving you the tools to try this experiment on your own.   This will allow you to unlock all your different personalities, including the one who gives you crystal clear clarity to see things as they truly are. If you were expecting an episode on business building or economic changes, sorry, this isn’t it. But knowing how to have your own “meeting of the mind” will amplify any area of life you want to succeed in.    Insights from today’s episode:  What I saw (and realized) while I was in a coma and paralyzed  How to practice the “meeting of the mind” for yourself and see your true personalities (yes, multiple) “The observer” who creates clarity no matter the situation you’re in  How allowing my personalities to interact made me much more successful  My mental rebirth and the part of AJ who died the day I was paralyzed    Sign Up for My Newsletter Here: https://ajosborne.com/newsletter  

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 the lessons the hard way, so you don’t have to. In this episode, we’re talking about commercial real estate underwriting, how to separate the “good” deals from the BS, and the most crucial factor that makes or breaks a real estate investment. Kevin is buying multimillion-dollar deals, meaning his margin for error can only be tiny. This is the way he decides whether to buy or move on to the next opportunity.   Insights from today’s episode:  The most crucial factor of a “good” real estate investment that so many got wrong in 2020 - 2022 The best loan to use for commercial real estate investing that can save your deal during bad times  What sets the successful real estate investors apart from the rest (99% of people can’t handle this) How Kevin built his portfolio, lost it all, and rebuilt it better and stronger than before  How to filter out the BS when getting started in real estate investing  — Sunrise Capital Investors: https://sunrisecapitalinvestors.com/fund-4/ Kevin’s Website: https://kevinbupp.com/ Kevin’s LinkedIn: https://www.linkedin.com/in/kevinbupp/   Sign Up for My Newsletter Here: https://ajosborne.com/newsletter   

George Mortimer, COO of Self Storage Income and former web designer, shares his journey from employee to entrepreneur. He reveals how to start a business using your current skills, emphasizing that you don't need to invent anything new. The conversation covers valuable strategies for testing market fit and highlights the importance of maintaining your job while building. They discuss the stages of business growth—service, business, and enterprise—while detailing how to create a unique value proposition that stands out in today's competitive landscape.

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” cycle. But something more interesting than rate cut news came out of recent Fed meetings—it’s what the Fed didn’t say.   Jerome Powell has switched from familiar verbiage to some new phrasing, priming us that we could be in a much different position than we’ve been in before. This has enormous implications for the next moves the Fed makes, and whether we’ll see interest rates fall even more as a result. Was the Fed too late with this move, with unemployment already rising and job revisions pushing us into an even deeper hole? I’m explaining who will win and who will get left behind in this next cycle.    Insights from today’s episode:  The Fed announcement on rate cuts and what it means for the economy Who will win in this next economic cycle (industries and investments) A big pivot? Why the Fed backed off its 2% inflation goal  Was the Fed too late? Can employment bounce back? What a tightening vs. easing “cycle” means for the average American   — Why U.S. Debt is Everyone’s Problem (Including Yours) - https://youtu.be/DFDZwj64EeQ?si=t6jH1zLvRBn0Wmas  Sign Up for My Newsletter Here: https://ajosborne.com/newsletter 

Fear and herd mentality can doom wealth-building efforts. The key to success lies in managing emotions and understanding market dynamics. Discover how to seize opportunities when others panic. Insights include identifying intrinsic value versus noise and applying a strategic 'buy box' formula. Learn to embrace risk and stay focused on long-term gains, especially during market chaos. It’s about making smart, calculated decisions rather than reacting with fear or greed.

Could AI be the catalyst for the next great depression? This discussion dives into the intricate relationship between AI, job displacement, and a shrinking workforce. It emphasizes the alarming second-order consequences that many are overlooking. The conversation also tackles the growing wealth gap and the U.S. government's escalating debt crisis. With questions about taxing the rich and protecting personal wealth, it's a thought-provoking examination of whether AI will be our salvation or downfall.