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: 

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Helpful Articles:

🎧 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 

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 business
How to create “asymmetric failure” that your business can weather
The number one reason businesses go under during tough market cycles
Why 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 

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: 

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 

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: 

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 

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: 

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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/ 

The wealthiest, happiest families in the world use a success “recipe” to raise their children. This leads to happier, healthier, more successful families, while most average Americans struggle to figure out how to teach kids about money. You may be used to fights and tantrums, children refusing to do their chores, and feeling forced to bribe them with allowances, more toys, or screen time. This is the opposite of what America’s wealthiest families do—and today, we’re uncovering their exact success “recipe.” 

Scott Donnell has worked with thousands of families, including many of the wealthiest in America. He’s seen households change fast from fragmented parenting and horrible child habits to family-centered success, where everyone, both parents AND children, love to be around each other, learn life skills 99% of Americans are missing, and succeed while remaining deeply connected as a family unit. 

How do you do the same with your children, or if you don’t have kids yet, your future family? Scott describes the exact techniques he uses to change family dynamics for the better, and the three “E’s” that make your children work harder, act more grateful, and help your household run more smoothly. 

Insights from today’s episode: 

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Sign Up for Family Foundations Camp 2025: https://www.foundationsfamilycamp.com/ 

Fig and Eagle: https://figandeagle.com/

Sign Up for My Newsletter Here: https://www.selfstorageincome.com/newsletter?utm_source=youtube&utm_medium=description&utm_campaign=ajopod 

I grew a $400 million business from scratch, in a wheelchair, and starting around the Great Recession. Almost everything was against me from the beginning. People told me my business would fail and my assets were worthless; banks laughed us out the door when we asked for funding. Then, suddenly, one day, my business needed to run on its own when I became paralyzed, unable to move, talk, or do anything but blink. So, how did I do it?

Today, I’m breaking down my $400 million company, how we make money, what we’re invested in, the teams doing the work, and how you can do the same and build a business that gives YOU ultimate financial freedom. We started this business during tough times, when getting money to fund self storage facilities was almost impossible. I’m sharing the creative way we came up with cash by recycling our capital so we never ran out.

Running a multimillion-dollar business is great, but at some point, you will run out of hours in the day. I’ll give you the exact breakdown of how my team runs the businesses for me and why having complete control over your business will stop you from growing, make your life harder, and limit your success. This is a peek behind the curtain of a company most people never get to see—and I’m sharing everything with you in this episode.

Insights from today’s episode:

How I built a $400 million self storage business with ZERO investing experience to start
Why we’re buying (a lot of) real estate right now (and why we always do in recessions)
Getting the funds for your business and my strategy to recycle limited capital
How my company runs without me and why you NEED to make sure yours can do the same
The “smaller” businesses we have that produce over $5 million per year in revenue

—

Growing Wealth in Self-Storage 2.0 (AJ’s Book!) https://www.selfstorageincome.com/book 

🖊️ Enter our survey for a chance to win a signed copy of my Book: https://form.asana.com/?k=da0pR8v74pC8OEgx9dgKRQ&d=1203571084143207 

Sign Up for My Newsletter Here: https://www.selfstorageincome.com/newsletter?utm_source=youtube&utm_medium=description&utm_campaign=ajopod 

Today, we’re talking about the “T-word”… trauma. Before you click away, this is not a downer episode. If you’ve been through trauma, big or small, you know how hard it is to bounce back. For me, without trauma, I wouldn’t have this podcast, my businesses, my wealth, my financial freedom, or much of the gratitude for life I take with me every single day. The worst months of my life used to define me. Now, they’re much of the reason I’ve succeeded.

Eight years ago, out of nowhere, I became paralyzed. My children, who were used to having a strong, stable father, now had a dad who couldn’t move, lying on a hospital bed with tubes running down my throat. I didn’t know if I would ever walk again, hug my children again…or even leave that hospital bed. The pain lasted for months—pain no one should ever have to endure—and still lingers today.

I had two options: give up or give whatever I had left in me. I chose the latter. Now, almost a decade later, I’m financially free, own multiple seven-figure businesses, and see life from a different angle. If your trauma is holding you back, keeping you from achieving great things, please hear me out in this episode. You’re not alone—I’m sharing everything that helped me move forward.

Insights from today’s episode: 

🎙️ Would you be a good guest for the AJ Osborne or Self Storage Income podcasts? You can now apply here! 

https://form.asana.com/?k=TGU88eU0bFTFW1iHcckuTA&d=1203571084143207

Sign Up for My Newsletter Here: https://www.selfstorageincome.com/newsletter?utm_source=youtube&utm_medium=description&utm_campaign=ajopod 

The billionaire problem: ultra-wealthy business owners and investors aren’t paying into the tax system. The Warren Buffetts of the world are getting wealthier while average Americans struggle to buy necessities like groceries. So, how do the ultra-rich avoid paying taxes? Would a “billionaire tax” work and finally force the ultra-wealthy to fork over their fair share, or will they merely use their legal loopholes to dodge taxes and make the middle class foot the bill?

“Tax the rich” is, by most means, a misunderstanding at best and ignorance at worst. I want billionaires to pay more, as they should, but is that possible with the current tax system? What happens if we start taxing billionaires on their unrealized gains? Could this finally solve the government’s tax revenue problem or bankrupt the entire system?

I will explain, in depth, how the rich avoid paying taxes, the consequences of a “billionaire tax,” how much it would benefit the United States, and the EXACT strategies billionaires use to avoid taxes that you can copy.

Insights from today’s episode: 

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The 2025 “Worst Case" Scenario That Could Begin the US Downfall - https://youtu.be/igSJlA0FBJM?si=Dhcx80ocicPK7_J- 

Warren Buffett's Secret Strategy -  https://youtu.be/LS5VApAADPg 

What is “fractional general counsel,” and why was not having it one of the biggest business mistakes I ever made? Whether you’re a startup, a self storage operator, or a growing small business, you rarely think about “legal.” You know that big companies will happily pay hundreds of thousands, if not millions, of dollars a year to protect their products and services, but you dismiss it because you’re not “big enough” for that yet.

This is a massive mistake, and it potentially cost me hundreds of millions of dollars.

Big businesses use their legal counsel to “bury” their competition—it’s all part of their strategy, and until recently, little guys couldn’t access this type of legal network.

That’s why we brought on Jeff Holman, who helps startups and scaling businesses access the right expertise from the right attorney at the right time with his “fractional” legal team. This means even small businesses and new startups can AFFORD to make the same strategic moves as powerful market players for a fraction of the cost of hiring a dozen attorneys. 

This is a game-changer for small businesses and startups, and if you think you’re not ready for it, think again. This episode will show you the dangers of not having legal counsel and the massive opportunities of using a “fractional” team.

Insights from today’s episode:

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Americans vs. Institutions: Why We’ve Had Enough - https://youtu.be/3uOIL6KJbJM?si=KINpdF5nalpPGtL4  

Jeff’s LinkedIn - https://www.linkedin.com/in/holman/ 

Book a Strategy Call with Jeff’s Team - https://www.intellectualstrategies.com/strategy-call/book-a-call