Best AJ Osborne Podcasts (2025)

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#264: Overcoming Life’s Toughest Challenge with AJ Osborne 1:52:50

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6h ago1:52:50

1:52:50

A man goes into a coma, wakes up totally paralyzed, gets fired from his job in the hospital… and somehow his investments are doing better than before. In this episode, AJ Osborne walks us through the day his body shut down from Guillain-Barré syndrome, what it felt like to wake up trapped in his own head, and the moment he realized his real estate …

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35. The Great Stock Divergence: Why Prices Aren’t Matching Reality 12:33

35m ago12:33

12:33

This looks a lot like the Dot-com bubble. Stock prices are hitting record highs, but their valuations are starting to diverge from reality. Americans are scared they’ll miss out on the rise of AI, so they’re pouring cash into the market in record amounts. Meanwhile, price-to-earnings ratios are inching nearer to Dot-com bubble levels. How close are…

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Why This Husband and Wife Bought Storage Instead of Rentals (No Regrets) 37:19

1h ago37:19

37:19

This husband and wife skipped rental properties and went straight to self storage investing. They kept hearing the regrets from other investors saying “we wish we scaled faster.” So, why wait to scale to bigger properties when you can just buy them from the start? That’s exactly what Matthew Rojas and Jingwen Ni did, and they have zero regrets. It …

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#263: The Real Estate Rundown with Owen and Ted 20:53

1d ago20:53

20:53

This Real Estate Rundown gets personal. Owen and Ted talk through a serious health scare, the nightmare of dealing with the healthcare system, and what happens to your family, your money, and your peace of mind when your body suddenly taps out. Out of that mess came a promise: never again be financially exposed like that. They break down how real e…

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#262: From Burnout to Lifeonaire: Designing a Business That Serves You with Jason Wojo 1:15:49

7h ago1:15:49

1:15:49

Jason “Wojo” spent years doing what entrepreneurs are told to do: grind harder, stack wins, chase the next deal, and assume life will sort itself out later. On paper, it worked. In reality, it cost him his marriage, his health, and his peace. In Episode 262 of REIA Radio, Wojo opens up about what happens when your definition of success quietly burn…

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322. Self Storage Financing for Beginners: How to Fund Your Next Deal (Fast) 54:20

2h ago54:20

54:20

You’ve found a self storage deal, but to get to the closing table, you’re also going to need a lender. For many new investors, self storage financing is the most intimidating part of the process, but in this episode, Conner and George will share everything you need to know to get your first or next self storage facility fully funded. The truth is t…

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#261: The Real Estate Rundown with Owen and Ted 29:01

10h ago29:01

29:01

In this Halloween edition of The Real Estate Rundown, Owen and Ted break down why you shouldn’t sleep on land. They walk through a real-world model where a specialized team handles everything—from finding and entitling the dirt to bringing fully leased, brand-new commercial bays online in about a year. You’ll hear how investors can step into turnke…

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#260 The Self-Made Developer: Building Wealth One Nail at a Time with Jennifer Newby 1:13:52

11h ago1:13:52

1:13:52

In this episode, Ted and Owen sit down with Jennifer Newby, a fearless DIY homebuilder turned developer whose story proves that grit and curiosity can outbuild any limitation. From tearing down her first house with a sledgehammer to constructing luxury homes from scratch, Jennifer turned “learning as you go” into a full-fledged business model. She …

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321. How We (Remote!) Manage Our 19-Facility Self Storage Business 1:07:30

2d ago1:07:30

1:07:30

You can live hundreds of miles away from your self storage facility and still run it successfully. Just hear from Bill DeWaal and Korbin Smoot, founders of Better Self Storage. They’ve got 19 facilities across multiple states and run self storage management to perfection with a team of VAs, a director of operations, and without having to fix, overl…

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#259: The Real Estate Rundown with Owen and Ted 31:12

11d ago31:12

31:12

In this wild Real Estate Rundown, Ted Kaasch and Owen Dashner dive into the unpredictable world of real estate — and life. Between Ted’s Doberman swallowing a metal grill brush (yes, really) and Owen’s six-figure boiler replacement saga, this episode hits every note from chaos to comedy. They share the hidden costs of major repairs, lessons from ma…

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#255: The Real Estate Rundown with Owen and Ted 21:58

6d ago21:58

21:58

In this episode of REIA Radio, hosts Ted Kaasch and Owen Dashner dive into their recent adventures at two major real estate events — the National REIA Owners Conference and BP Con in Las Vegas. Ted shares behind-the-scenes stories from meeting national speaker David Pickron and reveals how REIA groups nationwide are evolving. Owen breaks down his t…

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#254: From the Street Corner to the Boardroom: The Rise of John Uhrich 1:08:28

7d ago1:08:28

1:08:28

In this episode of REIA Radio, hosts Ted Kaasch and Owen Dashner sit down with John Uhrich, an entrepreneur whose story goes from selling tickets on a street corner to running a multimillion-dollar online ticket business — and later building a 65-door real estate portfolio… almost by accident. John shares how he built his career from pure hustle, w…

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#258: Navigating Life’s Challenges Through Real Estate: The Journey of Ian Ziegler 1:28:13

22d ago1:28:13

1:28:13

In this powerful episode, Ian Ziegler opens up about his journey through unexpected health battles and how they reshaped his outlook on life and business. From tenant retention and portfolio management to the importance of having multiple exit strategies, Ian dives deep into the realities of real estate investing that most people overlook. He share…

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#256: David Pickron: The Private Investigator’s Guide to Smarter Landlording 1:34:24

16d ago1:34:24

1:34:24

In this episode of REIA Radio, hosts Ted Kaasch and Owen Dashner sit down with David Pickron—real estate investor, licensed private investigator, and CEO of Rent Perfect—to talk about the side of real estate most landlords don’t like to discuss: evictions, screening tenants, and the tough lessons that come with managing rentals. David shares his jo…

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320. How to Make Offers on Self Storage Facilities (LOI vs. PSA) 43:45

14d ago43:45

43:45

You’re about to make an offer on a self storage investment. You’ll need two things: an LOI (letter of intent) and a PSA (purchase and sale agreement). You may need to use one or the other or both, depending on your situation, but not having these two contracts could be stopping you from getting your first or next deal done. Today, AJ and Conner exp…

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#257: The Real Estate Rundown with Owen and Ted 21:50

11d ago21:50

21:50

In this episode of The Real Estate Rundown, Ted and Owen swap war stories about the glamorous (and not-so-glamorous) side of real estate investing and property management — especially when it comes to Airbnb rentals. From last-minute furnace replacements and carbon monoxide scares to guests getting locked out because of rogue brass knobs, this epis…

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34. The Meeting of the Mind: What I Experienced While Paralyzed 42:14

16d ago42:14

42:14

This is about to get weird. I’m opening up about something that has only been shared in very private circles. As some of you know, years ago, I was comatose and paralyzed for months, unable to move or communicate, stuck in a hospital bed, with only my thoughts. Deep into my paralysis, strange things began to happen—breakthroughs I didn’t know were …

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319. Self Storage’s $100 Million Opportunity is Here 38:08

29d ago38:08

38:08

This is the biggest opportunity in self storage since 2008. Last time we were at this stage in the cycle, I was on the cusp of building a $100M+ self storage business. I bought when conditions were almost identical to what we’re seeing today, and now, I’m gearing up to buy even more. But here’s the best part: beginners can get in on this, too. Toda…

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318. The BIG Opportunities Small Investors Have in 2026 That REITs Can’t Touch 1:05:29

23d ago1:05:29

1:05:29

What happens when interest rates spike, self storage demand dips, and REITs start a race to the bottom with rent prices? You’ve got the current state of the self storage industry, with shifting market dynamics that have made things difficult for smaller investors over the last few years. The question now is, where do we go from here? Interest rates…

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#253: The Real Estate Rundown with Owen and Ted 20:20

1M ago20:20

20:20

In this week’s episode of Real Estate Rundown, hosts Ted Kaasch and Owen Dashner sit down for a no-fluff conversation about what’s really happening in today’s real estate world. From Fed rate cuts to mortgage realities, Ted and Owen break down how market headlines often miss the mark — and what investors should actually pay attention to. They dig i…

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33. This One Thing Will Make or Break a Commercial Real Estate Deal w/Kevin Bupp 42:34

1M ago42:34

42:34

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 …

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#252: From Corporate to Real Estate: A Journey of Transformation with Liz Bono 1:17:33

1M ago1:17:33

1:17:33

In this episode of REIA Radio, we sit down with Liz Buonincontri—known to many as Liz Bono—to hear her incredible journey from the corporate world to real estate freedom. Liz shares how she left a Big Four consulting career to build a portfolio of rentals, short-term rentals, and boutique hotels—all while raising a young family. She opens up about …

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317. We Bought 6 Self Storage Facilities While Working Full-Time 47:25

1M ago47:25

47:25

By AJ Osborne

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#251: The Real Estate Rundown with Owen and Ted 24:42

1M ago24:42

24:42

In this episode of the Real Estate Rundown, hosts Owen Dashner and Ted Kaasch dive into the ups and downs of their recent real estate ventures. Owen shares details on his new investment in a small-town car wash, along with the headaches of negotiating offers on his apartment complex. Ted opens up about property management challenges, repair frustra…

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#250: Growing Smart: Systems, Timing, and Avoiding Investor Burnout with Wyatt Simon 1:03:19

2M ago1:03:19

1:03:19

In this episode of REIA Radio, Wyatt Simon dives deep into his real estate journey, from starting in 2018 with nothing to building multi-million-dollar businesses and portfolios. He shares how building systems is the key to scaling—covering everything from property management to leveraging tech, labor, capital, and media. Wyatt explains his “Perfec…

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316. How to Analyze a Self Storage Facility from Scratch (6 Steps) 1:03:05

2M ago1:03:05

1:03:05

How do you know your first or next self storage investment is worth the money? This is how you do self storage analysis in six steps, even if you’ve never invested in storage before. With the most basic of numbers, you can analyze a self storage facility to see if it’s a worthwhile deal. And you don’t need any experience in commercial real estate o…

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#249: The Real Estate Rundown with Owen and Ted 46:28

2M ago46:28

46:28

In this episode, the hosts dive deep with Wyatt Simon into the realities of building and scaling a real estate business. The conversation covers everything from near-death experiences and personal growth to content creation, mentorship, and the sometimes misunderstood world of legal wholesaling. Wyatt shares his journey into coaching, the launch of…

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32. How to Start Your Own Business (and Replace Your Salary) with George Mortimer 1:00:33

2M ago1:00:33

1:00:33

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, l…

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#248: Networking Your Way Into Deals, Markets, and Momentum with Collin Schwartz 54:15

2M ago54:15

54:15

In this powerful episode of REIA Radio, we bring you Collin Schwartz’s keynote from our REIA Mastery Live Event. Collin shares his journey from humble beginnings to building a portfolio of over $330M in assets and more than 3,300 units. He breaks down the truth about risk, sacrifice, and why speed over perfection separates real estate dreamers from…

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315. Self Storage Could Be the Biggest Winner of Lower Interest Rates 25:35

2M ago25:35

25:35

This is the biggest thing to happen to the self storage industry in years. Last week, the Fed made their much-anticipated decision to cut rates. In the weeks leading up to the decision, interest rates fell sharply, reigniting the homebuying process for hundreds of thousands of Americans sitting on the sidelines. Rate cuts and mortgage rate declines…

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31. The Fed Just Reset the Economic “Cycle” 39:06

2M ago39:06

39:06

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 ridi…

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#247: The Real Estate Rundown with Owen and Ted 52:46

2M ago52:46

52:46

In this episode, Owen and Ted unpack a heavy week filled with tragic headlines and personal reflections. They shift gears into lessons learned from event planning, share insights from historical biographies like Titan on John D. Rockefeller, and explore how the past shapes today’s business world. The conversation also dives into an ongoing redevelo…

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#246: Creative Deal Structures, Legal Strategies & Raising Capital Like a Pro with Chris Pomerleau 1:11:43

2M ago1:11:43

1:11:43

In this REIA Mastery Series live event episode of REIA Radio, we bring you Chris Palmley—an Army vet, former attorney, and now co-founder of Leavenwealth Capital and Liquid Lending Solutions, with over $330M in assets under management. Chris shares his no-BS approach to creative financing, deal structuring, and negotiation that helped him go from f…

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314. Buying Your First Self Storage Facility While Working Full-Time w/Braedon Haertling 54:30

2M ago54:30

54:30

This one small-town storage facility has made today’s guest over $500,000. And if you’re interested in buying your first storage facility, there’s no better inspiration than this. With one self storage investment, Braedon Haertling has added another 9-5-sized income stream and increased value by close to $1,000,000, all while working a full-time jo…

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#245: The Real Estate Rundown with Owen and Ted 48:16

2M ago48:16

48:16

In this Real Estate Rundown episode, Chris Pomerleau returns for a deep dive into the systems, structure, and strategies that have helped him scale his real estate empire. Fresh off his crowd-favorite talk at the REIA Mastery Series, Chris joins Ted and Owen to unpack the business side of investing—from managing thousands of units to navigating cap…

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30. Why the Masses Miss Every Wealth-Building Opportunity 43:27

2M ago43:27

43:27

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…

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#244: Professional Property Management Systems for 5–25 Unit Success with Andy Kouri 59:02

2M ago59:02

59:02

In this powerhouse REIA Mastery Series live session, Andy Kouri breaks down what it really takes to grow a property management company that doesn’t just survive—it scales. Andy shares the full story of how his family’s business, Corey Management, went from 379 units to managing over 2,700 doors across Omaha and Des Moines. From stepping in after hi…

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313. 12 Red Flags of a Risky Self Storage Investment (& How to Avoid Them) 1:02:16

2M ago1:02:16

1:02:16

Buying a storage facility? Make sure you spot any of these 12 self storage investing red flags. If you’re able to avoid them successfully, you could be buying a killer next investment, with high occupancy, high rates, and steady cash flow. After investing in dozens of self storage facilities, with millions of rentable square feet, we’ve nailed down…

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#243: The Real Estate Rundown with Owen and Ted 48:10

2M ago48:10

48:10

In this episode of the Real Estate Rundown, Owen, Ted, and guest Andy Corey pull back the curtain on what it’s really like to speak at a big real estate event for the first time—and why saying yes to uncomfortable opportunities can blow your business wide open. Andy shares the chaos leading up to his REIA Mastery Series keynote, the panic, the prep…

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#242: REIA Mastery Series Special Episode: Ancillary Income & CEO Mindset – with Jeri Schlickbernd 58:35

3M ago58:35

58:35

In this replay of her keynote from the REIA Mastery Series Day, Jeri Schlickbernd delivers a powerhouse session on how to think like a true real estate CEO. With 20+ years in the game and 300+ flips under her belt, Jeri breaks down how she and her husband built a full ecosystem of income-generating businesses around their real estate portfolio—from…

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312. The Final “Wave” of Self Storage Investing Is Here 24:25

3M ago24:25

24:25

The final wave of wealth creation in self storage is here. After this, smaller investors will have a very tough time breaking into the industry. I already missed out on the first wave, but successfully rode the second. Now, the self storage swell is starting again, but this time, small, medium, and large self storage investors will all benefit. Are…

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#241: The Real Estate Rundown with Owen and Ted 23:00

3M ago23:00

23:00

In this Real Estate Rundown episode, Owen Dashner and Ted Kaasch recap the packed REIA Mastery Series event—The Mid-Size Multifamily Playbook—and share some behind-the-scenes chaos, lessons learned, and major takeaways from the day. With over 110 attendees, including 55 licensed agents, the event wasn’t just a success—it was a clear sign that the O…

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#240: Beyond the Grind – Byron Thompson on Beating Burnout in Real Estate 48:59

3M ago48:59

48:59

In this powerful live episode from an Omaha REIA event, Byron Thompson, co-owner of Meraki Realty Group, pulls back the curtain on the real estate hustle and shares how to build a seven-figure business without burning yourself to the ground. Byron walks through his personal journey—from sleeping on the floor with -$17 in his bank account to running…

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311. First Investment? Why You Should Buy a Self Storage Facility 47:56

3M ago47:56

47:56

With so many investment options—single-family homes, duplexes, the stock market—it’s easy to overlook self storage. But the truth is that a self storage facility is one of the best first investments, and you’re about to find out why. Whether you’re just starting your investing journey or looking to diversify your portfolio, storage could be a super…

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#239: The Real Estate Rundown with Owen and Ted 28:55

3M ago28:55

28:55

Ted and Owen are back with a raw episode after losing one of their best interviews to tech issues. They regroup with a real-time look at what’s happening in the market—expired listings, nervous investors, and why cash flow feels harder than ever. Owen breaks down how interest rate cuts don’t directly impact mortgage rates and shares the numbers on …

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29. How AI Could Trigger the Next Great Depression 32:14

3M ago32:14

32:14

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. “Secon…

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#238: From Rentals to Reform: Alex Feria’s Leap into Lending and Local Politics 1:10:22

3M ago1:10:22

1:10:22

In this episode, Alex Feria shares his journey from Cuba to Louisville, Kentucky, where he has built a successful career in mortgage lending and hard money investing. He talks about the growth of Louisville’s Cuban community, the challenges of launching and scaling a brokerage, and the values that have helped him build trust and reputation—like doi…

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310. Complete Walkthrough of Our Newest Self Storage Purchase (Financials) 53:32

3M ago53:32

53:32

Today we’re giving a complete financial walkthrough of our newest self storage investment. From purchase price to rental income, return numbers, and how we’re funding it, this is a complete breakdown of a facility that could very well be bringing in $1,000,000/year in the near future. This was not only a deal but a steal, and proves that there are …

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#237: The Real Estate Rundown with Owen and Ted 24:18

3M ago24:18

24:18

In this chaos-filled episode of the Real Estate Rundown, hosts Owen Dashner and Ted Kosh let it rip on the all-too-real challenges of property management—from $70K boilers and $50K sewer line descaling quotes to tenants leaving behind disaster zones and thousand-dollar make-ready bills. Sound familiar? They don’t just vent. They offer up smart, scr…

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#236: Flipping, Failing, and Figuring It Out: The Real Investor Life of Jackson Udy 1:07:18

3M ago1:07:18

1:07:18

In Episode 236 of REIA Radio, we dive into the investing journey of Jackson Udy, a full-time chemical engineer who’s been quietly building a real estate portfolio across state lines. Jackson shares how he got started by buying a duplex in Omaha while living in California, the ups and downs of managing from afar, and why partnering with family—espec…