

AJ Osborne Podcast
AJ Osborne
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
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
Episodes
Mentioned books

Sep 25, 2025 • 1h 1min
32. How to Start Your Own Business (and Replace Your Salary)
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.

Sep 22, 2025 • 39min
31. The Fed Just Reset the Economic “Cycle”
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
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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

17 snips
Sep 11, 2025 • 43min
30. Why the Masses Miss Every Wealth-Building Opportunity
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.

Aug 21, 2025 • 32min
29. How AI Could Trigger the Next Great Depression
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.

4 snips
Aug 7, 2025 • 48min
28. Top 100 Advisor: How to Invest During Market Chaos w/Adam Koós
This discussion features Adam Koós, one of Investopedia’s Top-100 Most Influential Financial Advisors, known for his expertise in technical analysis and trend following. He dives into strategies for investing during chaotic market conditions, providing insights on how to capitalize on any market cycle. Adam shares his unique investment methods and a five-year economic forecast that challenges common views on inflation. With a focus on emotional stability and systematic decision-making, he emphasizes the importance of building a resilient portfolio.

Jul 24, 2025 • 1h 3min
27. How to Raise Capital for Real Estate (Without Going to Prison) w/Mauricio Rauld
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
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Helpful Articles:
https://www.selfstorageincome.com/blog/the-truth-about-real-estate-investing
https://www.selfstorageincome.com/blog/the-secret-investments-of-the-wealthy-1
🎧 Listen to Drunk Real Estate: https://www.drunkrealestateshow.com/
🔗 Mauricio’s LinkedIn: https://www.linkedin.com/in/mauriciorauld/
📚 Mauricio’s Coaching: https://coachingwithmauricio.com
🎙️ Have a story worth sharing? Apply to be a guest on the Self Storage Income or AJ Osborne podcasts: https://form.asana.com/?k=TGU88eU0bFTFW1iHcckuTA&d=1203571084143207
📚 Want the full blueprint? Get my latest book on how to build and scale a successful self storage business: https://a.co/d/aRSKcSq
📉 Ready to invest alongside us? Take advantage of today’s market conditions and grow with our team at Cedar: https://cedar.cc/invest

14 snips
Jul 10, 2025 • 34min
26. I Built My Business to “Fail,” Now It’s Worth Hundreds of Millions
Discover why the most successful businesses are those built with failure in mind. Learn how entrepreneurs often fail due to an overly optimistic approach. Embrace failure as a necessary part of growth and resilience. Explore how to navigate turbulent economic waters while managing investments wisely. Understand the unique challenges millennials face in this landscape and why a growth mindset can turn setbacks into opportunities. It's all about building systems that can weather any storm!

Jun 26, 2025 • 31min
25. How to Start an AI Vending Machine Business That Makes Thousands Per Month w/Michael Hoffmann
This investor makes tens of thousands a month from his “AI vending machine” business. A business so simple a teenager could run it—and make more than most Americans do at their day job. We’re not talking about those old vending machines in the back of bowling alleys selling Cokes for $1.50. We’re talking about an AI vending machine business plan that generates $1,200 to $2,000 per month per machine.
Michael Hoffmann—better known as ‘Mr. Passive’—has been running his vending machine side hustle for over five years. But he’s made a serious business out of it, leveraging his Silicon Valley tech background to perfect the purchasing experience.
A customer simply walks up to your machine, taps their card, grabs what they need, and leaves. You make a massive markup, and the customer gets what they want—fast. Want to know how to repeat it? Michael is sharing exactly how much he makes, how much a machine costs, the profit margins, and a step-by-step plan so you or even your kid can start a vending machine business.
Insights from today’s episode:
How much vending machines make AND how much a vending machine costs
The new “AI vending machines” with bigger purchases and better margins
A step-by-step business plan for starting your own vending machine business
How to scale your vending machine side hustle into a full-time business
The best way to teach your kids entrepreneurship? Why AJ is bullish on vending machines for HIS kids
Join the Waitlist for VendHub! - https://www.vendhub.ai/
Learn how to do this yourself and subscribe to Michael’s YouTube Channel! - https://www.youtube.com/@UCCr13sXOZgWCqpPv8WPKhwQ
🎙️ Do you have a great story or advice to share on the AJ Osborne podcast? Apply here! https://form.asana.com/?k=TGU88eU0bFTFW1iHcckuTA&d=1203571084143207
📖 Get AJ's book that teaches you everything he knows about self-storage https://a.co/d/aRSKcSq
📉 Take advantage of today’s market conditions and invest with our company, Cedar Creek Capital: https://cedar.cc/invest

17 snips
Jun 5, 2025 • 1h 2min
24. Parenting in a Petri Dish: Raising Independent Kids When the System Falls Short w/My Wife Tessa Osborne
In this insightful conversation, Tessa Osborne, Board of Directors member at Innovate Academy and founder of Family Foundations Camp, shares her unique approach to parenting. She emphasizes the importance of raising self-sufficient and financially literate kids amid societal challenges. Tessa discusses the need for hands-on life skills and the value of sibling interactions in fostering resilience. They also touch on the significance of intergenerational connections and the vital role of storytelling in developing identity, proving that intentional parenting can lead to independent, happy children.

May 15, 2025 • 52min
23. Dan Martell: The “Clear” Vision That Creates Successful Companies
In this engaging discussion, Dan Martell, an entrepreneur and author of "Buy Back Your Time," shares his inspiring journey from rehab to building successful software companies. He dives into strategies for hiring and promoting team members while addressing toxic influences that can sabotage growth. Martell emphasizes the importance of a clear team vision and effective executive compensation to foster commitment. Learn how to empower a self-sustaining business that thrives even in your absence, along with insightful reflections on resilience and adapting through adversity.