AJ Osborne

AJ Osborne Podcast

Entrepreneurship Self-Improvement Management English

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.

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16 July 2026

49. We Tripled Our Revenue (In Months) by Changing This ONE Thing About Our Business

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...

03 July 2026

48. A “Wave” of Small Businesses Is Changing Hands (They Cost Less Than You Think)

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?...

18 June 2026

47. She Predicted a Depression in 2030. Now She’s Doubling Down. w/Economist Lauren Saidel-Baker

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...

04 June 2026

46. The “Small” Investor’s Edge: How to Use Real Estate AI to Beat the Big Players

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...

21 May 2026

45. From One Failed Restaurant to Over a Dozen Businesses & Millions in Real Estate

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....

07 May 2026

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....

16 April 2026

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...

07 April 2026

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...

19 March 2026

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...

05 March 2026

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...