AJ Osborne Podcast

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

July 03, 2026

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, man...

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

June 18, 2026

  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...

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

June 04, 2026

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 Holli...