AJ Osborne Podcast

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   

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?el=pc-ajo-ep33   

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?el=pc-ajo-ep31 

AI could trigger a new economic crisis—the next great depression—and most people are ignoring it. I’m not just talking about job loss or automation replacing salaries. There’s a much deeper problem—one that could erode the last remnants of stability in the US economy and government. Is AI taking jobs? Yes. But that’s just one of our worries. “Second-order consequences” are coming fast. Nobody is talking about them. The government, the economy, and everyday US citizens are not prepared. And this isn’t just a US problem. Many developed nations are dealing with a generational shift, massive national debt, and a shrinking workforce. Will AI solve this problem or make it even worse?  I’m sharing my theory on how AI will shift the US economy and you individually, the effects that most people are completely overlooking, and a growing concern that is going to hit the US government head-on. AI could be the solution to many of our problems—it could also be our downfall. Which road will we take? Insights from today’s episode:  The shrinking labor force problem that AI can only superficially solve  How the US government’s debt crisis will ramp up once AI replaces jobs The growing wealth gap that could further widen thanks to AI How to protect your personal wealth when AI is taking high-paying jobs  Could taxing the rich fix any of this—or just make it worse? Why U.S. Debt is Everyone’s Problem (Including Yours) - https://www.youtube.com/watch?v=DFDZwj64EeQ&pp=0gcJCcwJAYcqIYzv  Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep29 

For over a decade, as I built my portfolio, I didn’t raise capital from outside investors. Why? I didn’t want to take the risk. Raising capital for real estate is something you cannot afford to get wrong. No one wants to end up in prison because they funded a deal the wrong way. Good news? I’ve got SEC attorney and good friend Mauricio Rauld here to tell you how to do it right. Even better news? AI is about to make it cheaper (and easier) for all of us.    Seriously, why pay a lawyer tens of thousands of dollars to come up with your documents when AI can compile everything for a fraction of the cost? Most lawyers don’t want to hear this, but Mauricio is fully on board. The change is coming, and it’s about to bring huge cost savings to all of us who run businesses or invest in real estate. Plus, accredited investor rules could change soon, making it even easier for average Americans to invest in bigger deals. Will the move actually go through?   If you’re even thinking about raising money, listen to this episode. You could be paying thousands of dollars for what Mauricio is about to tell you. We’re also sharing the best career advice you’ll ever receive, our thoughts on AI’s new lawyer-replacing features, and why the middle class is stuck, getting squeezed while the rich get richer.    Insights from today’s episode:  How to raise capital for real estate (the rules you MUST follow before you do) New AI lawyers that can draft your legal docs for a fraction of the cost  Why you have way more control than you think when raising capital for real estate  Crucial career advice if you feel like you don’t know what your “passion” is Changes to accredited investor rules? Why this could be good for average Americans   — Sign Up for My Newsletter Here: https://ajosborne.com/newsletter?el=pc-ajo-ep27 🎧 Listen to Drunk Real Estate: https://www.drunkrealestateshow.com/ 🔗 Mauricio’s LinkedIn: https://www.linkedin.com/in/mauriciorauld/ 📚 Mauricio’s Coaching: https://coachingwithmauricio.com