
AJ Osborne Podcast
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
Latest episodes

Jan 26, 2021 • 42min
Diversifying Your Investment Strategy Outside of Real Estate with Nick McCullum
Welcome back everybody to the AJ Osborne podcast!
As you know, I’m a huge fan of real estate investing. We’ve had numerous guests on the podcast that have shared their incredible real estate insights and investing strategies. There’s an investment strategy though that we haven’t talked a whole lot about - stock market investing.
That said, I’m super excited to introduce you to Nick McCullum. Nick is the Director or Growth at a Passiv. Passiv is a rebalancing software solution for people who want to invest passively in the stock market.
Nick started looking into and getting interested in the stock market and investing when he was in college. His interest soon lead to a passion and ultimately a change in his degree. After graduating with a math degree, Nick began working for a research firm in the finance world and he hasn’t looked back since.
In today’s podcast we’re going to look at the difference between active and passive investing, the importance of diversification across assets and asset classes, risks you need to analyze, and the big daddy of them all… fees. Fees can absolutely destroy your returns and take tens of thousands or even millions of dollars out of your pocket.
Thanks a ton for listening everybody!
AJ
Keep up with Nick on Twitter at:
@NickJMcCullum - https://twitter.com/NickJMcCullum?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor
Also check out Passiv at:
https://passiv.com/

Jan 19, 2021 • 22min
The Future of Wealth, Capital, the Economy, and Business
Welcome back everybody to the AJ Osborne podcast!
Well everybody, it’s been quite the crazy year for a lot of us. In one way or another we’ve all been affected by these global, national, and local events that have had massive impacts. There’s been a lot of uncertainty and discourse as a result of these events. Rightly so, we all have questions and concerns and a lot of us are looking for direction.
What does all this mean for the long term? How about the short term? Where do we invest? How do we invest? Where do we put our money? What will be the effects of the stimulus being injected into the economy?
These are just a few of the questions I’ve seen coming up over the past several weeks and today’s podcast is going to cover each and every one of these topics.
Something we absolutely need to do is take a long look at where we’ve been and get a really good idea of where we’re going. We need to look at the past to gauge and plan for the future. There are some major social and economic lessons we need to study and learn from our history books. So many of the same or similar events play themselves out over and over again throughout history, we simply need to take note and do what we can to prepare or even totally avoid our social and economic mistakes of the past.
So much of this is exactly why I’ve chosen to invest in real cashflowing assets. I’m going to talk about the importance of cashflowing assets, the perks, understanding risk, and more. At the end of the day, we shouldn’t be asking where to put our money, we should be asking what kind of a strategy can we build where we can control our money and thus, know exactly where to put it and when.
All said and done, I think we have an amazing future ahead, but it’ll take work and smart decision making done with a heavy emphasis on the long term.
Listen in and let me know what you all think. Shoot me your questions and comments on social media (links below), or submit them on our Self Storage Income website (also linked below).
Thanks everybody,
AJ

Jan 12, 2021 • 49min
How Introverts Can Win with Matthew Pollard (His Exact Step by Step Framework)
Welcome back everybody to the podcast, this is your host AJ Osborne!
We have another great guest episode here for you today with the one and only Matthew Pollard. Matthew has built several multi-million dollar companies and has helped other companies build systems that inspire massive and rapid growth. In fact, Matthew is even known as the “Rapid Growth Guy” due to his revolutionary but simplistic approaches to help people and companies move the needle towards greater growth.
Matthew shares with us today the exact steps he took to go from being an uncertain introverted salesman, to the top salesman in a company he was working at. This is a perfect example of how we can take control and live the lifestyles we want to live by making a plan and mastering a skill set.
We dive into the importance of finding not just any mentor, but the best mentor - one that matches your goals and your characteristics. We talk about problems and using them as a way to not find, but to develop solutions, creating systems for yourself to create and experience massive growth, and more.
If you’ve been feeling stagnant, like you’re ready for your next big move, this is an episode you won’t want to miss.
Thanks for listening everybody,
AJ
Be sure to check out Matthew’s website and keep up with all the great info he’s putting out (and don’t forget to check out his new book!):
https://www.matthewpollard.com

Dec 31, 2020 • 26min
The Best Real Estate Investment Tool You’ve Never Heard of with Yonah Weiss
Welcome back everybody to the Self Storage Income podcast (or the AJ Osborne podcast – whichever one you’re listening to right now). I’m your host AJ Osborne and this episode was so great, we wanted to be sure to release it on BOTH of our podcasts – Self Storage Income and the AJ Osborne podcast (formerly Cashflow 2 Freedom).
Are you a current real estate investor? Looking to become a real estate investor? Then today’s episode is definitely for you. Whether it’s storage, multi-family, single family, homes, manufactured homes, or pretty much any other real estate asset, the strategy and concept we’re going to cover today can apply to you all.
That said, I’m extra excited about today’s episode because we get to dive into this subject that could save you thousands and even millions of dollars in taxes. The subject?
Cost segregation. Not only do we get to learn about this amazing tax strategy and tool, we get to learn about if from the expert himself - Yonah Weiss.
Yonah shares with us his story of how he went from being a teacher, to commercial real estate, to making taxes interesting by becoming a cost segregation expert. Yes… we used the words “taxes” and “interesting” in the same sentence… don’t worry! You’ll totally understand after listening to this episode. Saving thousands or millions of dollars in taxes is certainly an exciting idea.
You might even be wondering at this point - what even is cost segregation? Don’t worry you’re not alone. As a teacher, Yonah discovered that a large number of real estate investors needed to be educated about cost segregation and the power it can hold.
Yonah goes into what exactly cost segregation is, when you can use it, how to use it, and the amazing benefits it has to offer real estate investors.
This is absolutely one of those episodes you’ll want to take notes on. It’s also a subject that you’ll want to learn more about. That said, talk to Yonah himself by reaching out to him at:
https://www.yonahweiss.com/
and…
https://madisonspecs.com/
Thanks for listening as always everybody and we’ll see you next time!
AJ

Dec 29, 2020 • 35min
Manufactured Home Investing - The In’s and Out’s with Jonathan Tuttle
Welcome back everybody to the AJ Osborne Podcast!
Today we have another special guest in the house… and not just any house…
Today we’re talking everything manufactured home investing with the one and only Jonathan Tuttle.
We’re going to kick everything off by diving into how Jonathan got started investing in manufactured homes. Just a few spoilers if you didn’t already know - the economics of manufactured home investing are extremely good. The market is still fragmented (even more than the self storage market). They are not capital intensive like some asset classes. The demand for affordable housing only continues to skyrocket, all the while, supply is shrinking.
We go more in depth on these great economic drivers of manufactured home investing and how you can leverage these aspects to yield great returns.
This may not even be an asset class you’ve considered investing in, but there’s no two ways about it, the real estate trends and investment opportunities are changing dramatically. Are you ready to adapt? Tune in and listen in on how Jonathan got started, where he’s at today, what his plans are for the future, and how you too can realize huge returns from manufactured home investing.
Thanks for listening everybody,
AJ
Be sure to keep up with Jonathan at: www.midwestparkcapital.com

Dec 22, 2020 • 26min
How Not to Fail - What You Need to do to Build Great Investments
Welcome back everybody to the AJ Osborne Podcast!
That’s right, we’re moving to totally re-brand the Cashflow 2 Freedom podcast to simply be the AJ Osborne podcast. There are a lot of reasons for this re-brand and I actually dive into some of the reasons why in the beginning of today’s podcast.
After we cover that, we’re going to get right to it - we’re going to get into entrepreneurial archetypes, the dangers, and what you need to know as a growing entrepreneur. So much of this has to do with the bigger picture of what it actually means to build a thriving company. It doesn’t have so much to do with what people think and feel.
Here are some of the topics we’re going to get into today that will help you shift your focus from where it is, to where it really matters:
What really makes a business successful? What really makes businesses fail? How do you plan for or limit the risk of failure?
I’m also going to share with you guys my very own driving investment principles, what I learned from the 2008 downturn, and how I’ve structured my investments to build both consistent cashflow and stability over time.
I don’t know about you guys, but when it comes to my financial future, my investments, and so forth, I don’t gamble. You shouldn’t either.
Thanks for listening everybody,
AJ

Dec 17, 2020 • 37min
Are You Hustling or Building a Business? The Dangers of the “Hustler” Mindset
Welcome back to the AJ Osborne show, this is your host AJ Osborne.
Man do we have an incredible episode lined up for you today. We have Roc back in the house for you all and I’m super excited to dive into this topic because it’s something that every entrepreneur needs to know and understand.
On today’s episode, we’re talking about what so many people like to call “hustling”, and building business. We hear it seriously ALL the time from people that we should “hustle”, that they’re their “hustlers”, and so on and so forth. Working hard is great and it’s absolutely necessary to truly build something big.
There’s a major problem with being a hustler though…
I know, I know, you’re saying, “AJ… you just told me that working hard was good!?” Let me explain - there is a vast difference between “hustling” and building a business and being a businessman/women.
This difference is what we’re going to dive into on today’s episode. You need to identify whether or not you’re building a business, or if you’re merely hustling to get by. I’m happy to break it to you - hustling is not a system and you’ll never reach your businesses true potential by hustling.
If you’re hustling, you need to start planning and building systems in your business that will allow you to start working ON and not IN the business. As business owners we need scalable, repeatable systems to grow for the decades to come. We need a long term plan, not a “I’m going to hustle harder this week and get back to where I was a couple weeks ago… again…”.
I don’t know, maybe there are people out there who want to stay in “hustle” mode forever. If you do, great. But if you really want to build an empire, then listen in and learn what you need to start doing to get to the next level. We break all of this down in a step by step format here on the podcast so get ready to take notes and start implementing.
Thanks for listening everybody,
AJ

Dec 15, 2020 • 47min
How to Build Wealth BETTER with the Engineer of Finance Ken Greene
Welcome back everybody to the AJ Osborne podcast, this is your host AJ Osborne.
Today we have another incredible guest for you - the one and only Ken Greene, or as others like to call him - The Engineer of Finance.
Ken started his journey as an engineer but discovered that his path had to change. He decided that insurance or finance was going to be his future and he ultimately came to rest on the world of finance. But it was everything but rest when he dove into the financial industry.
Everywhere Ken looked, there were financial gurus striking huge success. There was only one issue… where was their client’s success?
Come to find out, Ken discovered that the majority of the finance world was built around making the financial industry money… not making the clients of the financial industry money (YOU). Unfortunately the financial industry has created a number of tools and systems that help build their own wealth and success, usually leaving clients with sub par returns and little solutions that actually serve people’s best interests.
Ken set out to tackle this issue and flip the script. He wanted to put the power back into your hands as an investor and that’s exactly what he’s doing for his clients today.
In today’s episode we talk about various aspects of the financial industry that EVERYONE should know and understand. We talk about the importance of liquidity, the velocity of money, breaking the financial mould, how to get in the path of money, and how to get out of the game you’re being convinced to play, a game you can never win.
Gear up and get ready to take notes. This isn’t an episode you’ll want to just put on and listen to once. Listen again and again. Soak up all this great info and put the power back into your hands and the dollars back into your pocket.
Thanks everybody,
AJ
Be sure to keep up with Ken on his website at: www.engineeroffinance.com

Dec 5, 2020 • 32min
Why Saving Money Makes You Poor and Makes Others Rich
Welcome back everybody to the podcast! This is your host, AJ Osborne.
That’s right, you read that title correctly. But wait, how in the world could saving money make you poor? You save money and that means you have more of it right? In a perfect world, that may be true. But here in real life with the economic forces that be, if you’re saving money, you’re losing money.
Unfortunately, most people don’t even know or realize it. What’s even worse is that even more people don’t know that all that money they’re saving in the bank is actually being used against them. How?
You see, you’re either a producer or a consumer and being solely a consumer (and a saver) is a major major pitfall. In today’s episode I’m going to share with you all exactly why simply saving money is not a good wealth building strategy. In fact, I can tell you right now, simply saving money will never make you financially free or wealthy.
I’m first going to cover some basic economics of currency, inflation, interest rates and how they’re used to control the economy and so forth. Then we’re going to jump into the nitty gritty of it all and I’ll show you exactly how you’re actually losing money by saving money. I’ll also show you how you’re not only losing money, but how your own money is being leveraged against you as a consumer.
As always everybody, buckle up and get ready to take some notes, listen to this epsiode a couple times if you need to, whatever it takes to absorb the value here today. These principles, ideas, and understandings that we go over here today are foundational when it comes to building wealth.
Thanks for tuning, we’ll see you next time everybody,
AJ

Nov 28, 2020 • 30min
The Perfect Time to Invest | How to Succeed in Any Market with a Timeless Investment Strategy
Welcome back to the podcast everybody! This is your host AJ Osborne.
It goes without saying that there’s been a lot of uncertainty this past year. From politics to markets, to industry, people are concerned and curious. Not only that, they have a lot of questions.
People want to know whether or not the real estate market is going to continue upwards, or if there is going to be another correction. People want to know if now is the right time to invest in certain industries and asset classes. People want to time their investments and resources as best they can.
So is it a good time to take the plunge and jump in? Or should you wait for a better opportunity at a later date?
The answer… is yes. Yes to both of those questions. But there’s more to answering these questions and being able to effectively recognize when it’s go time, or when you need to take a step back. This is exactly what we’re going to dive into and dissect today.
We’re going to look at the things that you need to be thinking about and paying attention to in order to answer these questions. We’re going to talk about the importance of having a timeless investing strategy that you understand. We’re also going to talk about risk, letting your money make decisions for you, and much much more.
Our goal here today is to give you the tools and to help prepare you for success no matter the market conditions.
Thanks for listening as always everybody, and we’ll see you next time.
AJ