AJ Osborne

AJ Osborne Podcast

Business EN ↓ 302 episodes

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

Author

AJ Osborne

Category

Business

Podcast website

www.ajosborne.com

Latest episode

Jul 3, 2026

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Episodes

Breaking Into Real Estate Through Wholesaling with Chris Craddock 26.07.2021

Welcome back everybody to the AJ Osborne Podcast! I’m your host, AJ Osborne.    Today we’re talking real estate! One of my favorite things to talk about! And it’s not just me that you get to listen to today, it’s the one and only Chris Craddock.    Chris is one heck of a busy guy but he’s taking the time to hang out with us today and share some great insights into the various a...

Growing Wealth Through Business Acquisition with Codie Sanchez 19.07.2021

Welcome back everybody to the AJ Osborne Podcast! I’m your host, AJ Osborne!    It’s my honor and my pleasure to introduce you to the one and only Codie Sanchez. Codie has a background in finance and also worked as a journalist who covered some of the darkest and heaviest subject matter you could as a journalist - human trafficking. It was after this that she chose to pursue a career in...

How to be Successful in Real Estate with Dave Seymour 06.07.2021

Welcome back everybody to the AJ Osborne Podcast! I’m your host, AJ Osborne! Alright, so I feel like I need to prepare you for this incredible guest episode today…. You better be ready for some laughs, some value bombs, and some great company. It’s my absolute pleasure to introduce you to the one and only Dave Seymour, and you better buckle up because this episode was a total hoot! You might recog...

From the North Side of Chicago to Owning 1,000 Doors with Van Sturgeon 29.06.2021

Welcome back everybody to the AJ Osborne Podcast, I’m your host, AJ Osborne! It’s my pleasure to introduce you to Van Sturgeon. Van was born and raised in the Northside of Chicago helping his parents own and operate an apartment building. The economy was bad, vacancies were high, and the family had to perform all the repairs and maintenance on their own to limit cost and to make ends meet. This bu...

How to Build Yourself, Your Relationships, and Your Business with Jay Malloy 25.06.2021

Welcome back everybody to the AJ Osborne Podcast! This is your host, AJ Osborne! I’m super excited today to have the pleasure to introduce you all to the one and only Jay Malloy. Jay is a real estate investor and built his foundations of real estate investing through wholesaling. We touch a bit on what exactly Jay does, but more importantly, we talk about the HOW. So often we talk about strategy (...

The Truth Behind Skyrocketing Lumber Prices with Brian Mullally 22.06.2021

Welcome back everybody to the AJ Osborne Podcast! I’m your host, AJ Osborne! So… if you’ve been online or to your local hardware or lumber store, you might have noticed something - the price of lumber (and materials in general) has skyrocketed. Honestly, saying the cost of lumber has “skyrocketed” even seems like an understatement. This is why I’m having my great friend and our head of acquisition...

How to Go From Single Family to Commercial Real Estate Investing with Brittany Arnason 15.06.2021

Welcome back everybody to the AJ Osborne Podcast! I’m your host, AJ Osborne! I’m extra excited about today’s episode because we get to hang out with one of my favorite real estate friends… the one and only Brittany Arnason! You might know her as investorgirlbritt on social media. She’s become wildly popular on social media with sharing her experiences from BRRR’ing single-family homes. Fun fact -...

How to Align Your Goals, Your Money, and Your Life with Jim Crider 06.06.2021

Welcome back everybody to the AJ Osborne Podcast! I’m your host AJ Osborne! One of the biggest stresses that most of us feel consistently throughout our lives is MONEY. Money problems can crush dreams, marriages, physical and mental health, and our lives as we know them. Money is a big deal to a lot of us, but how do we get to that place where money isn’t a problem, but more so an asset, a lever,...

Our Current Economy & How We Can Succeed 25.05.2021

Welcome back everybody to the Self Storage Income podcast, this is your host AJ Osborne! As you’re probably aware, there’s A LOT of wacky things going on out there currently with the US Dollar, stimulus packages, and interest rates (and a ton of other crap I’m not even going to get into). One huge aspect of today that we have to take into account is this - we’re in totally uncharted economic water...

Taking Control of Your Life and Your Finances with Damari Gold 18.05.2021

Welcome back everybody to the AJ Osborne Podcast, I’m your host, AJ Osborne!   What’s one of the biggest struggles for us Americans? Well, besides loving great food and being almost unable to resist… lol. The answer is MONEY.   The management of our personal finances is often in disarray and maybe even non-existent. It’s super unfortunate but who can blame us right!? Our lives are busy,...

Tech Entrepreneur Turned Angel Investor with Tom Wallace 11.05.2021

Welcome back everybody to the AJ Osborne Podcast, I’m your host, AJ Osborne!   Ever wonder what it’d be like to become an angel investor? Well today, it’s my absolute pleasure to introduce you all to Tom Wallace who has built an investing empire.   Tom began his investment journey in the tech space when personal computers were just beginning to become a reality. Starting a systems integr...

How to Consistently Crush Your Goals and Achieve Massive Results (My Exact Framework) 05.05.2021

Welcome back everybody to the AJ Osborne Podcast, I’m your host AJ Osborne!   We all want results right? We want more money, freedom, opportunity, that six pack for the beach... the list could go on and on. We think all day about how great it would be to have these outcomes in our lives. There’s only one HUGE problem with this… we’re thinking about the end result and NOT the process we need t...

The Keys to Progress | How to Move Forward with Certainty in Uncertain Times 27.04.2021

Welcome back everybody to the AJ Osborne podcast! I’m your host, AJ Osborne! If you’ve listened to this podcast or my Self Storage Income podcast, you might have heard me talk about my three pillars that drive everything I do - Impact, Freedom, and Progress. Each one of these pillars have their own unique challenges. However, Progress is one of those things that so many of us have such a hard time...

The Current State of the US Economy & What We Need to Understand 22.04.2021

Welcome back everybody to the AJ Osborne podcast! I’m your host AJ Osborne.   If you follow me on social media you may have noticed these past couple weeks, I’ve been posting quite a bit on the current economic events happening here in our country. What we’re seeing is honestly unprecedented and in our country’s history we haven’t seen or experienced quite what we are today. That said, I’ve b...

How to Structure & Put Together Great Real Estate Deals with Lance Pederson 13.04.2021

Welcome back everybody to the AJ Osborne podcast! I’m excited you’re here and even more excited about the great guest I have on the podcast for you today. It’s my pleasure to introduce you to the one and only Lance Pederson. Lance helps investors navigate what so many believe to be the complexities of the investment world. I say, “what so many believe to be the complexities” because as we discuss...

The Key to Tapping into the Millionaire Mindset with Cydney O’Sullivan 30.03.2021

Welcome back everybody to the AJ Osborne Podcast, I’m your host, AJ Osborne!   I have an amazing guest for you all today who has done everything from working the corporate job, to owning and operating business, writing books, organizing events, and teaching others to do the same… she’s done it all.   It’s a pleasure to welcome and introduce Cydney O’Sullivan.   Cydney has lived a li...

Exposing Financial Truths to Get You on the Path of Building Wealth with Jonathan DeYoe 23.03.2021

Welcome back everybody to the AJ Osborne Podcast, I’m your host, AJ Osborne! Today we have an awesome guest lined up for you. We’re talking everything wealth and finance with the one and only Jonathan DeYoe. It’s an unfortunate truth and one we can see almost everywhere we look - when it comes to wealth and finance a large majority of the population is drastically under educated and under prepared...

Wealth Creation - The Keys to Building and Attaining Real Wealth 16.03.2021

Welcome back everybody to the AJ Osborne Podcast, I’m your host AJ Osborne!   The goal for so many of us is to become wealthy and live the lives that we’ve always wanted to live. To build real, true financial freedom. To separate your income from your time and to be able to spend your time however you please. Building wealth is a beautiful thing.   There’s only one problem…   How do...

The Wealth Building Strategy You’ve Never Heard of with Tom Laune 09.03.2021

Welcome back everybody to the AJ Osborne Podcast!   We have an incredible guest lined up for you guys today that is going to share some amazing looks behind the curtain of wealth building. It’s my pleasure to welcome and introduce Tom Laune.   Tom wasn’t always in the financial industry. He actually worked an exciting job in the music industry for 29 incredible years as a producer and mi...

Passive Real Estate Cashflow Using Multifamily Syndication with Lane Kawaoka 02.03.2021

Welcome back everybody to the AJ Osborne Podcast! I’m your host, AJ Osborne. I have another amazing guest lined up for you all today - the man himself Lane Kawaoka. Lane began like most of us do - he had a secure job working as a railroad engineer, he had a house, he was building his life. Being gone so much for work though, Lane decided to start renting out his house. One thing after another happ...

The Official Launch of the New AJ Osborne Podcast 23.02.2021

Welcome back everybody to the AJ Osborne Podcast, this is your host AJ Osborne! That’s right, Cashflow 2 Freedom is no more! But don’t worry, this podcast isn’t going anywhere. As you might know, we’ve been re-branding the Cashflow 2 Freedom podcast into this new AJ Osborne Podcast. I’ve talked about it a couple times to give you a heads up, but as of an episode or so ago, it’s official. The podca...

Multi-Family Real Estate Investing | An Insider’s Look with Ashley Wilson aka BadAshInvestor 16.02.2021

Welcome back everybody to the AJ Osborne podcast! I have an incredible guest lined up for you all today that I know you’re going to enjoy and take a lot away from. Our guest today is the one and only Bad Ash Investor herself Ashley Wilson. As you know, I’m quite the fan of real estate and the amazing advantages it provides for offsetting taxes, cashflow, diversifying income, and much more. Ashley...

Making the Leap from Career to Full Time Investor with Justin Hannah 09.02.2021

Welcome back everybody to the AJ Osborne podcast! I’m excited to bring you yet another incredible guest for this episode todaywho shares a wealth of knowledge with us about real estate investing, family, and the process of building the life you’ve always dreamed of. It’s my pleasure to introduce you to full time real estate investor Justin Hannah. We all dream about our perfect or ideal life - the...

Wealth Preservation & Estate Planning with Steve Goodman 03.02.2021

Welcome back everybody to the AJ Osborne Podcast! I’m super excited about today’s episode because we have another amazing guest lined up for you today. Our guest today is the one and only Steve Goodman. For over 30 years Steve has helped clients navigate the challenges of business succession, the preservation of wealth, charitable planning, and has helped address the various wealth planning needs...

Diversifying Your Investment Strategy Outside of Real Estate with Nick McCullum 26.01.2021

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...

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