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Estimated from 2 chart positions in 2 markets.
By chart position
- 🇷🇴RO · Entrepreneurship#119500 to 3K
- 🇿🇦ZA · Entrepreneurship#166500 to 3K
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300 to 1.8K🎙 Daily cadence·297 episodes·Last published 1w ago - Monthly Reach
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400 to 2.4K
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On the show
From 13 epsHost
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Recent episodes
47. She Predicted a Depression in 2030. Now She’s Doubling Down. w/Economist Lauren Saidel-Baker
Jun 18, 2026
57m 05s
46. The “Small” Investor’s Edge: How to Use Real Estate AI to Beat the Big Players
Jun 4, 2026
47m 16s
45. From One Failed Restaurant to Over a Dozen Businesses & Millions in Real Estate
May 21, 2026
36m 17s
44. Is History Repeating Itself? Why the 2020s Is Mirroring the 1960s
May 7, 2026
15m 57s
43. Tom Wheelwright: How the Wealthy Avoid Taxes (While W-2 Workers Get Crushed)
Apr 16, 2026
27m 59s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/18/26 | ![]() 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 this colossal event. The Fed is trapped—lowering rates to save our government budget could trigger inflation, again. Social problems are growing—the wealth gap is widening, and those at the bottom can barely afford necessities. And the final linchpin—an aging baby boomer population that will take massive amounts of resources, without giving much in return. We’ve seen problems like this occur in other countries—France and Japan, to name a couple—but nothing on the size of the American economy. So what’s coming next? Are we back to a 2008-style market selloff where asset prices tank? Can AI step in to save us from some of these dangers that a younger workforce can’t solve, and who wins and loses when the shoe drops? Insights from today’s episode: The road to the next great depression: Why 2030 looks like it’s unavoidable The “linchpin” that could set off the domino effect and massively change the economy How to win in the next great depression and what to do to start preparing now The Fed’s “trap” and how they’ll lose control of the economy Why Lauren thinks many people are wrong about AI (and what effect it will really have) __________ ITR Economics: https://hubs.la/Q04h6kdc0 Check out Lauren's previous podcast episode!-https://www.ajosborne.com/podcasts/aj-osborne-podcast/episodes/2148970950 Sign Up for My Newsletter Here: https://ajosborne.com/newsletter | 57m 05s | ||||||
| 6/4/26 | ![]() 46. The “Small” Investor’s Edge: How to Use Real Estate AI to Beat the Big Players✨ | real estateAI technology+3 | William Hollis | Capital Advisory AI | — | real estate AIsmall investors+3 | — | 47m 16s | |
| 5/21/26 | ![]() 45. From One Failed Restaurant to Over a Dozen Businesses & Millions in Real Estate✨ | entrepreneurshipbusiness growth+3 | Tanner Herget | — | — | entrepreneurbusiness strategy+5 | — | 36m 17s | |
| 5/7/26 | ![]() 44. Is History Repeating Itself? Why the 2020s Is Mirroring the 1960s✨ | historical comparisoneconomic analysis+3 | — | AIgovernment | America1960s+1 | historyinflation+6 | — | 15m 57s | |
| 4/16/26 | 43. Tom Wheelwright: How the Wealthy Avoid Taxes (While W-2 Workers Get Crushed)✨ | tax strategieswealth building+4 | Tom Wheelwright | WealthAbilityRich Dad+1 | — | taxeswealthy+6 | — | 27m 59s | |
| 4/7/26 | 42. Housing Won’t Crash, But This Is What WILL Happen Through 2030✨ | housing marketreal estate trends+4 | — | baby boomers | America | housing marketmortgage rates+5 | — | 20m 04s | |
| 3/19/26 | 41. America’s Financial Clock Is Ticking: What Happens When the Dollar Ends? with David Morgan✨ | financial systemeconomic reset+4 | David Morgan | central bankCBDC | United StatesAmerica | financial systemeconomic reset+6 | — | 44m 16s | |
| 3/5/26 | 40. An Economic “Reset” Is Coming: How to Build Real Wealth Before It’s Too Late✨ | economic resetfinancial independence+4 | — | U.S. government | United States | economic resetfinancial independence+5 | — | 28m 42s | |
| 2/19/26 | 39. Once I Figured Out This Formula, I Built 9 Businesses (That Run Themselves) w/Brian Tran✨ | entrepreneurshipreal estate+3 | Brian Tran | — | Oakland, California | self-made millionairereal estate investing+3 | — | 1h 04m 21s | |
| 1/30/26 | 38. The Middle Class “Collapse” Is a Lie (Here’s What’s Actually Happening)✨ | middle classincome mobility+4 | — | — | — | middle classincome+6 | — | 37m 45s | |
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| 1/8/26 | 37. How the Rich Build Wealth with $0 Salaries (You Don’t Need More Income)✨ | wealth buildingincome vs assets+4 | — | US tax code | — | wealthincome+5 | — | 24m 57s | |
| 11/20/25 | 36. How I Predict the Outcome of (Almost) Every Investment I Buy (4M Framework)✨ | investment strategiesbusiness success+3 | — | real estatebusinesses+3 | — | investment4M Framework+3 | — | 36m 27s | |
| 11/6/25 | 35. The Great Stock Divergence: Why Prices Aren’t Matching Reality✨ | stock marketAI+4 | — | AI | US | stock pricesvaluations+5 | — | 12m 33s | |
| 10/23/25 | 34. The Meeting of the Mind: What I Experienced While Paralyzed✨ | personal growthself-discovery+3 | — | — | — | paralysiscoma+6 | — | 42m 14s | |
| 10/9/25 | 33. This One Thing Will Make or Break a Commercial Real Estate Deal w/Kevin Bupp | 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 | 42m 34s | ||||||
| 9/25/25 | 32. How to Start Your Own Business (and Replace Your Salary) with George Mortimer | Want to start a business and begin working for yourself? This is how you do it. You don’t need to (and actually should not) invent a product or create a new type of service or technology. You can work for yourself simply by doing what you do right now at your job or what you’re interested in. Becoming your own boss enables you to earn more money, live on your own terms, and build something greater than yourself. This is how to start your own business from scratch, even if you have $0 and are working a full-time job. My guest isn’t wearing a suit, and he’s not driving a Bentley to work. He doesn’t need to, even though he’s COO of Self Storage Income. George Mortimer became my COO through starting his own web design business after not wanting a boss. Now, he’s running teams and a multimillion-dollar business. George and I know what it’s like to do the grunt work, struggle, and finally succeed at being (often) happily self-employed. We’ll walk through how you can do it, too: build your own business, become your own boss, and scale up through the business stages (without burning out). Insights from today’s episode: How to build your own business (or self-employed income stream) from scratch Why creating a “job” for yourself is not a bad thing (but it comes with some struggles) The best “business” for anyone to start who’s currently employed Why big businesses go wrong and how to avoid their massive mistakes Building the “moat” that makes your business stand out from competitors Hey, you! DON’T go and invent a thing! Don’t even think about it! Self Storage Income: https://www.selfstorageincome.com/ Sign Up for My Newsletter Here: https://ajosborne.com/newsletter | 1h 00m 33s | ||||||
| 9/22/25 | 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 — 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 | 39m 06s | ||||||
| 9/11/25 | 30. Why the Masses Miss Every Wealth-Building Opportunity | If you can’t fix this, you’ll never be wealthy. The 99% move like a herd, and the masses scream in fear, duck for cover, and sell in lockstep during every major recession, crash, and recovery. This is why most Americans (or people on Earth, for that matter) will never be wealthy. By letting their fear take over during times of opportunity and their greed override their senses during peaks, the masses buy high, sell low, and remain in the same place. This is avoidable. Anyone can grow wealthy IF they follow the right steps. At some point, I realized that my emotions were controlling too many of my decisions. When I stopped listening to my lizard brain and started operating on a system, everything changed. How did I know to buy so low during the real estate bust in 2008? How did I know my industry was in a bubble before so many others? And why am I back to buying while people are telling me the bottom is yet to come? Keep following the news if you want to remain stuck. Listen to this episode if you want to finally control your financial future. Insights from today’s episode: How to stop your emotions from ruining your wealth-building opportunities The “signal” the wealthy look for that tells them when to buy (and sell) Why allowing yourself to look stupid may be the best decision you ever made My “buy box” formula that controls my investing (not my emotions!) How to capitalize on market confusion and buy when everyone else is too scared to act — AJ Osborne YouTube Channel - https://www.youtube.com/@AJOsborneOfficial Sign Up for My Newsletter Here: https://ajosborne.com/newsletter | 43m 27s | ||||||
| 8/21/25 | 29. How AI Could Trigger the Next Great Depression | 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 | 32m 14s | ||||||
| 8/7/25 | 28. Top 100 Advisor: How to Invest During Market Chaos w/Adam Koós | The stock market crashed in March, but now it’s back to all-time highs. You might have sat frozen, waiting for a recovery or a better buying opportunity. Chances are, you didn’t make any moves that made you richer. Was that a mistake? During “trendless” markets like these—where price swings feel random and directionless—most Americans sit on the sidelines. Others, like Adam Koós, one of Investopedia’s Top-100 Most Influential Financial Advisors in the U.S., made money in the peaks, valleys, and in between. So, how do you invest in chaotic markets where the “trend” seems nonexistent? What’s the investment strategy beginners can use to protect from the crashes and buy on the way back up? If you’re wondering where to invest now, Adam has the answer. Adam has the technical trading knowledge that 99.9% of investors (and even advisors) lack. His full-time job is identifying trends, capitalizing on them, and moving more money into his all-star roster of investments. He’s sharing his actual investment strategy today (piece-by-piece!)—so you can apply the same principles to your own portfolio. Plus, he even provides his five-year forecast and an optimistic view on interest rates. Insights from today’s episode: How to invest even during market chaos, tariffs, wars, and more Adam’s exact investing strategy to take advantage of any market cycle A five-year economic forecast and a contrarian take on future inflation How to build a stock portfolio of “playoff teams” that will take YOU to the financial Super Bowl Beginner investments you can make now that protect you during crashes and build wealth during bull runs Libertas Wealth: https://www.libertaswealth.com/ Elevate and Exit: http://elevateandexit.com/ Connect with Adam on LinkedIn: https://www.linkedin.com/in/adamkoos/ Alphatrends: https://alphatrends.net/ 🎙️ 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 | 48m 28s | ||||||
| 7/24/25 | 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 — 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 | 1h 02m 49s | ||||||
| 7/10/25 | 26. I Built My Business to “Fail,” Now It’s Worth Hundreds of Millions | Sign Up for My Newsletter Here: https://ajosborne.com/newsletter Markets are volatile. Whispers of a recession are getting louder. Some industries—like commercial real estate—are already in recession. This has been one of the most difficult market cycles for business owners and self storage investors to navigate. Want to know how to start a business that thrives in any economic environment? I break it down in today’s episode! We’re coming off arguably the greatest bull market in history. The problem? People start businesses expecting success, which is exactly why they fail. Their systems, models, and contracts aren’t designed for the worst-case scenario. The truth is, if you want to succeed long-term, you can’t build to succeed. You must build to fail. It sounds backwards, but it’s the only way to survive the storms. Make no mistake—you will fail. But how you fail makes all the difference. You don’t need to be fearless, just aware of the risks and prepared for the valleys. In this episode, I show you how to fail the right way—small, fast, and forward! Insights from today’s episode: Why “building to succeed” is a fatal flaw in this economy (and what to do instead)The biggest mistake entrepreneurs make when starting a new businessHow to create “asymmetric failure” that your business can weatherThe number one reason businesses go under during tough market cyclesWhy you must treat every new investment opportunity like a business. 🎙️ Do you have a great story to share on the SSI or AJ Osborne podcasts? You can now apply here! https://form.asana.com/?k=TGU88eU0bFTFW1iHcckuTA&d=1203571084143207 📉 Take advantage of today’s market conditions and invest with us: https://cedar.cc/invest | 34m 06s | ||||||
| 6/26/25 | 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 | 30m 42s | ||||||
| 6/5/25 | 24. Parenting in a Petri Dish: Raising Independent Kids When the System Falls Short w/My Wife Tessa Osborne | The parenting playbook is changing. Raising independent children has only gotten harder as family units drift apart, grandparents remain out of the picture, schools fail to teach financial literacy for kids, and overprotective helicopter parenting becomes the new norm. But just because society is heading in one direction, doesn’t mean your family has to as well. We’re proof of that, with four independent, high-achieving children raised by us, not society. Who is “we”? Today, I brought my better half, Tessa, to the show. Tessa is on the Board of Directors at Innovate Academy, founded the Family Foundations Camp, and is author of the upcoming (hold her to that!) book Parenting in a Petri Dish. Tessa spends all day, every day, thinking about how we can create better futures with our children, not just for them. This “petri dish” parenting is the playbook we use to raise our children to be self-sufficient, financially savvy, and compassionate, caring individuals. Has the system failed us as parents? You probably already know the answer. So how do we take control of our kids’ cultivation? Simple: practice life skills at home! But how? Today, Tessa and I share what we do to raise children we’re proud of, why daughters and sons need different challenges, and why focusing only on outcomes will fail your child in the long run. Insights from today’s episode: The “petri dish” style of parenting that leads to successful (and happy) kids Call your grandparents! Why older generations MUST be included in your kids’ lives Male vs. female learning patterns and why you should treat your daughters and sons differently How to “manufacture” challenges in the home that build your kid’s character Why focusing on outcomes (not skills and habits) is a huge mistake Family Foundations Camp: https://www.foundationsfamilycamp.com/ Innovate Academy: https://innovatehigh.com/ The Comfort Crisis: https://www.amazon.com/Comfort-Crisis-Embrace-Discomfort-Reclaim/dp/0593138767 | 1h 02m 05s | ||||||
| 5/15/25 | 23. Dan Martell: The “Clear” Vision That Creates Successful Companies | Dan Martell learned how to program at age 17 while in rehab. He traded one addiction for another—starting scalable, successful, profitable software companies. You might know him from his book Buy Back Your Time, where Dan shares the secret to building a business empire that frees you from the chains most solopreneurs and small business owners struggle to break. Today, he’s giving a masterclass on how to do just that. After scaling multiple top-tier teams, Dan has identified the “cancer” behind a business environment that can erode your company and everything you’ve worked hard for. He gets into his exact strategy for hiring, firing, and promoting people on his team for the best results, and how to compensate others so they deliver their best work and grow your company—while you focus on your highest-value actions. Maybe you’ve already got a team. How do you keep them on the same page and rowing in the same direction? Dan’s got a simple framework for that—something so clear, your team can move forward even if you’re not around. Dan is an expert in business-building, team management, and hiring. This is crucial advice if you own a business or want to one day. Insights from today’s episode: How to build your team for your small (or large) business that can run the ship without you Who you should hire, fire, and promote IMMEDIATELY in your organization How to hire executives that will multiply your business faster than you ever could Why you MUST ensure your employees are there for the long haul (and how to reward them to stay) NEVER do profit sharing for an employee…here’s why — Buy Back Your Time https://www.amazon.com/Buy-Back-Your-Time-Unstuck/dp/059342297X Dan’s Instagram https://www.instagram.com/danmartell/?hl=en Dan’s YouTube https://www.youtube.com/@danmartell/ | 52m 19s | ||||||
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