
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

Jun 9, 2020 • 46min
How to Succeed as an Entrepreneur with Dr. Eric Cole
Welcome back to the Cashflow 2 Freedom Podcast!
Our guest for this episode has a unique and totally awesome background who has a wealth of entrepreneurial knowledge and experience. It’s an absolute pleasure to introduce you to Dr. Eric Cole. My introduction here would do little justice, so here it is right from the source - a snippet from his website secure-anchor.com:
“World Renowned Cybersecurity Expert with more than 30 years of network security experience, Dr. Eric Cole is a distinguished cybersecurity expert and keynote speaker who helps organizations curtail the risk of cyber threats. Many of the foundational principles of this course and training in cybersecurity were developed by Dr. Cole. He has worked with a variety of clients ranging from Fortune 50 companies, to top international banks, to the CIA, for which he was a professional hacker.
While he started his career on the offense, he is now fully dedicated to understanding the adversary so he can provide cost effective solutions that actually work. As a pioneer in the area of cybersecurity he has been inducted into the Infosec hall of Fame, awarded the Cyber Wingman Award from the US Air Force, received multiple accommodations from the CIA and was part of the commission on cybersecurity for President Obama. He has been the featured speaker at many security events and also has been interviewed by several chief media outlets such as CNN, CBS News, FOX New and 60 Minutes.”
To say Dr. Cole has an impressive resume would be an understatement. As such, he brings an amazing amount of value to us on this podcast that I’m super excited to share with you guys.
Throughout this episode we talk a lot about Dr. Cole’s entrepreneurial journey and the fundamentals of entrepreneurship that apply to all companies, both large and small. We talk about failing your way to success, how exactly he builds his companies and his teams to run them, and what he likes to target in markets specifically to become an industry leader in that given market.
This such an awesome episode. Enjoy, take notes, and be sure to connect with Dr. Cole on his website at https://www.secure-anchor.com/
You can also keep up and connect with him on social media by simply searching his name Dr. Eric Cole.
Thanks everybody, we’ll see you next time,
AJ

May 29, 2020 • 52min
How to Start Growing an Empire When You’re a Nobody
What is going on everybody!? Welcome back to another episode of the Cashflow 2 Freedom podcast. Today, Roc and I have a special episode for you guys that I’m really excited to roll out. We all want to do great things, but how do we start? How do we get going and how do we get going on the right path to our goal of financial freedom?
Whether you’re starting a business, investing, or working a career, it’s not always a clear cut path from where you’re at to where you want to be.
One of the huge topics of discussion today is perspective and being able to recognize current opportunities. We give several examples of how perspective and knowing when there’s opportunity or not, can either make or break what it is that you want to execute on.
Whether we like to admit it or not, understanding timing of opportunity is critical to our success or our failure.
We also touch base on being able to select the correct wealth vehicles to then be able to attain our visions of success. The path and the vehicle we choose, needs to align with the goal or vision that we’ve set for ourselves. This can be more tricky than it seems a lot of times and something we dissect in the episode as well.
It takes time, work, discipline and execution to get where we want to be. For most of you listening, that means being in control of your life and your finances, it means having financial freedom. It's an amazing process and one we’re excited to share with you.
Thanks for listening everybody,
AJ

May 25, 2020 • 49min
Fundamental Keys to Success in Real Estate Investing with Brian Trippe
Welcome back to the Cashflow 2 Freedom everybody!
On today’s episode I have the pleasure of sitting down with real estate investor Brian Trippe.
We focus in heavily on the concept and critical importance of building your network. Your network is everything - deal flow, financing, investors all come from your network. This solidifies the common theme we’ve talked about several times on the Cashflow 2 Freedom podcast, and that is that success cannot and does not happen on an island. You absolutely have to build and maintain these relationships. Everything is built on people, and we have to be able to attract the right people for your network with common core values?
So how do you do this? What’s the key? It’s a great question and one that we answer in several ways in today’s podcast.
These fundamentals will either make or break you, no matter what direction you choose for your life or your goals. We’ll cover these fundamentals in depth and how you can set yourself and your endeavors up for success.
We also talk about the technical aspects of real estate. Brian shares what he believes will happen in the real estate market and in markets across the world in the near future with the elections coming up. Brian also shares how he is preparing for those potential events.
Brain also shares his advice for those who are just starting or looking to start investing in real estate. Where should you look? What should you look for? Who should you talk to? Brian covers all of these topics and more.
Be sure to check out REI Live, an online community that helps to connect like minded real estate professionals. https://rei.live/
Thanks for listening everybody,
AJ

May 22, 2020 • 57min
The Incredible Process of Starting and Running Your Own Business with Trevor Oldham
What’s up everybody!? AJ here with another awesome episode of the Cashflow 2 Freedom podcast.
Today’s guest is Trevor Oldham, founder of Podcasting You.
In college, Trevor had started a social media group that exploded to over 600,000 followers. This inspired Trevor to launch a podcast in addition to their social media presence. Seeing the value of podcasting, Trevor began thinking of ways to leverage the medium.
After years of running his own podcast, it dawned on him, why doesn’t he utilize his experience and advise and assist other content creators with their podcasts. So began Podcasting You.
Podcasting You helps identify and schedule guests for podcasters.
In this episode Trevor shares how he started the company and the struggles he faced throughout the process. We also dive into the importance of knowing who to surround yourself with and who not to surround yourself with, and the experience of living those challenges.
Be sure to check out Podcasting You at https://podcastingyou.com/about
Thanks for listening everybody! Keep crushing it out there!
AJ

May 21, 2020 • 58min
The In’s and Out’s of Syndicating Large Real Estate Deals with Matthew Baltzell
What is going on everybody!? Welcome to another episode of Cashflow 2 Freedom.
Today I had the pleasure of sitting down with Matthew Baltzell. Matthew currently lives in Thailand and works with a company by the name of Boardwalk Wealth. Boardwalk Wealth is a private equity firm that specializes in connecting passive investors with multifamily and other commercial real estate assets.
Matthew has built extensive experience surrounding all aspects of identifying and acquiring large commercial real estate assets. This includes market research, due diligence, investor relations, and property analysis. That said, Matthew brings a ton of value to the table for us today in this episode.
Matthew breaks down how exactly Boardwalk Wealth structures their deals with investors. This includes everything from what preferred return they offer investors, to the structure of the limited partners and general partners. He also shares with us what Boardwalk Wealth has planned for the future and what so many real estate syndicators get wrong.
One of the great topics of discussion today was about relationships with those you choose to work with. It should go without saying, but you should know exactly who you’re going to be working with and who you’ll be associated with in any investment. Whether it's a stock or a real estate asset, knowing your team and those who control the deal, is critical.
You can keep up with Matthew on his website at matthewbaltzell.com and you can also keep up with Boardwalk Wealth on their website boardwalkwealth.com/
Thanks a bunch for listening everybody,
AJ

May 19, 2020 • 49min
Real Estate Investment Strategy to Generate Above Average Returns with Blake Templeton
Welcome everybody to another episode of Cashflow 2 Freedom!
Our guest today is Blake Templeton, CEO of Boron Capital. So who is Blake and just what does Boron Capital specialize in? This clip from Blake’s website boroncap.com will help set the stage:
“Over the past 13 years, Blake has built a private investment firm that specializes in acquiring and developing corporate housing, luxury rentals, and event venue investments in emerging real estate markets, while providing above average returns to his partner investors. Blake has extensive knowledge and expertise in residential and commercial real estate and he has worked with some of the biggest names in the industry. In the last 13 years, his firm has closed over 300+ real estate transactions and most recently has developed a full service corporate housing investment in which Boron Capital owns and manages.”
Apart from that introduction, Boron Capital currently has over $100 Million under management and is poised to keep growing.
That said, today’s episode is packed with value. Blake shares his three dimensional investment strategy and how it has enabled him to consistently generate above average returns. Within his three dimensional strategy, we go into what exact assets to buy and how he identifies these assets.
Also, given the nature of our current economic uncertainty due to Covid-19, Blake shares his insights on the economy and capital markets and what he’s expecting to see over the next few months in this uncharted territory.
Be sure to check out Boron Captial’s website at: https://boroncap.com/meet-the-ceo/
Thanks for tuning in everybody! See you next time.
AJ

May 14, 2020 • 36min
Flips, Wholesalers, and Cashflowing Real Estate with Sean Pan
Welcome back everybody to Cashflow 2 Freedom!
Our awesome guest today is real estate investor Sean Pan.
Sean, who as working as an electrical engineer, decided that financial freedom sounded a lot better than being an employee. He began searching for a solution that would get him on the path to financial freedom and ultimately decided that real estate was the wealth vehicle he was going to drive. It was scalable, one could manage the risks, and there were deals to be had. After studying, going to real estate meet ups, and networking, Sean decided it was time to jump in.
Using his salary from his job, he began purchasing by and hold rental properties in Florida. Living in southern California though, investing out of state was a challenge in and of itself. Sean walks us through how he found deals across the United States in Florida, how he set up a team to be able to get these deals and manage the properties afterwards, and more.
We also talk about the very real importance of diversifying your investments throughout different real estate asset classes and strategies to help limit your exposure to risk.
If you’re looking to get into real estate investing, this is a must listen episode. Sean shares tons of great information that can help you get on the path to achieving your financial freedom.
Sean also has a website, hosts his own podcast, and even organizes meet-ups for real estate professionals. Check all of that out on his website https://everythingrei.com/
Thanks for listening everybody,
AJ

May 11, 2020 • 37min
Getting Started in Real Estate Investing with Lucas Miller
What’s going on everybody!? Welcome back to Cashflow 2 Freedom. Due to the huge amount of interest in the real estate investing episodes we’ve published, we decided to keep the real estate flowing. Which is why I’m excited to bring on our guest today, Lucas Miller.
Lucas initially went to school for and started a bustling career in politics. Finding that the world of politics wasn’t where he wanted to be, like so many of us, he turned to real estate. Also like so many of us real estate investors, Lucas’s first deal was a house hack.
Lucas shares the details of that first deal, where he’s at today, and how he got there through real estate investing. We also touch on a topic that we’re huge on here at Cashflow 2 Freedom - finding and working with a mentor to fast track your way to your goals.
Even with mentors, it’s not always rainbows and sunshine. Lucas shares a particular deal that went bad that lost him and an investor $50,000. He shares why that deal went bad, what he took away from it, and the steps he took to make things right with his investor to maintain a working relationship.
We also talk finding deals, broker relationships, flipping, and the exact criteria he’s using to find and close deals.
Keep up with Lucas - on his podcast Fear Free Passive investing - https://podcasts.apple.com/us/podcast/fear-free-passive-investing/id1456823201
Thanks everybody, we’ll see you next time.
AJ

May 8, 2020 • 45min
How to Build a Multifamily Real Estate Empire with Andrew Campbell
Welcome back everybody to the Cashflow 2 Freedom Podcast.
If you’ve listened to Cashflow 2 Freedom for any period of time, you know that we absolutely love real estate. Today, we have another awesome guest that shares their story of exactly how they went from a career lifestyle, to now having the freedom and flexibility to spend the last eight weeks in Florida, spending time with family.
First having set out to climb the corporate ladder in marketing and advertising, real estate wasn’t always on Andrew’s radar. When he started to want more time, freedom, and flexibility to spend more time with his family.
Andrew shares how exactly he got into real estate - from his first duplex deal to now owning and operating over one thousand units across a vast portfolio of multifamily properties. We talk about raising money, efficiencies of scale, the investment strategies he’s using currently and how you too can build the life you want around real estate investing.
Keep up with Andrew and the awesome work he’s doing on the Wild Horn Capital website at www.wildhorncap.com
Thanks for listening everybody,
AJ

May 5, 2020 • 57min
What Real Freedom Truly Feels Like Through Real Estate Investing with Gary Wilson
Welcome back everybody to another episode of Cashflow 2 Freedom. We have been knocking these guest episodes out of the park for you guys lately and today is no exception.
I’m super excited to introduce you all to the one and only Gary Wilson.
Gary was living the American dream working as a successful job in the corporate banking world. The only problem was… it wasn’t his dream. Gary was sick of the corporate world and was ready to live life on his own terms. He was ready to see what the feeling of true freedom really felt like, and that’s exactly what he did.
Gary has used numerous creative financing strategies, which he shares with us in this podcast, and he also shares with us how he has used lines of credit and various leverage options, to kickstart his real estate investment portfolio.
If you’re just looking at getting started in real estate investing, this is an absolute must listen episode. Gary shares a wealth of knowledge that will help put you years ahead.
Also, be sure to check out https://www.myinvestmentservices.com/ where you can connect with investor realtors (yes, realtors that actually know how to work with and for investors).
Thanks everybody, see you next time.
AJ