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

15 Minute Friday: Diversification Through Scale 20.09.2019

On this edition of 15 Minute Friday AJ discusses why his company has invested in many different assets and why he's diversified his investments. How he uses scale to not only grow his business but to diversify. How to scale your business right. Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Est...

How to Budget 16.09.2019

Budgeting is important. Whether it's for your business or personal life, having a balanced budget is key to achieving financial freedom. In this episode, AJ and Roc discuss some basic principles about budgeting.  Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Stora...

15 Minute Friday: Goin' To Vegas 13.09.2019

On this edition of 15 Minute Friday, AJ recaps their time in Vegas and what they learned about the different markets. Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments Links:   https://cashflow2freedom.co...

All About Debt 09.09.2019

AJ Osborne and Roc Pilon discuss the good, the bad and the ugly as it relates to debt. The "do's" the "don'ts" and how leverage it smartly. This episode, is all about debt. Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflo...

To Buy or Not to Buy 03.09.2019

The market fluctuate and so does the economy. AJ and Roc discuss how to manage your business so you won't be crushed by the market.   Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments Links:   https:...

15 Minute Friday: Project Based Income 31.08.2019

What is project based income? AJ explains on this segment of 15 Minute Friday.   Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments Links:   https://cashflow2freedom.com  

How to Underwrite Self Storage with Sam Whitaker 27.08.2019

One of Bitterroot's partners, Sam, joins the podcast to discuss the importance of underwriting. *Note: We had some audio issues towards the end, but the information shared is still very important. The more you know, the less risk there is. This is the idea behind today's episode. Sam works as an underwriter with AJ and they have learned what to look for in getting involved with deals. Not only do...

15 Minute Friday: Asset Types 23.08.2019

On this edition of 15 Minute Friday, AJ discusses the different types of assets and highlights another one of his projects. Topics of Discussion include: Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments Links:   https://cashflow2freedom.com...

Real Estate Investor Michael Blank 19.08.2019

Real Estate Investor Michael Blank joins the podcast to discuss investing in multi-family units. He also recommends four books for everybody to read including "Rich Dad Poor Dad" by Robert T. Kiyosaki . Michael focuses on helping educate people to broadening their horizons away from just single-family homes or stock market investments. Instead, he suggests you go straight for the multi-family hous...

15 Minute Friday: The Firm 16.08.2019

On this edition of 15 Minute Friday, AJ takes us to one his insurance firms to discuss how sales opened a lot of doors for him.  Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments Links:   https://cas...

Luck and College...They Matter 12.08.2019

Is college worth it? How do you create luck? AJ and Roc Pilon tackle both questions in this episode. Starting out, AJ and Roc talk about "Chase Chance and Creativity" by James H. Austin  and the four different types of "luck" or chance.  If you were to have engineered the modern computer, would you be as rich as Bill Gates? Or does luck come into play, and if so, which kind? Most luck is...

15 Minute Friday: Office Space 09.08.2019

On this edition of 15 Minute Friday, AJ takes us on a tour of a great work in progress....their new office space. Did you know office hacking is a thing? AJ explains. Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow...

Larry Goins- Original Virtual Investor 05.08.2019

Larry Goins joins this episode of Cashflow2Freedom.  https://larrygoins.com Living in South Carolina, Larry has worked with close to 1,000 deals. Closing about 7 to 10 a month currently. He's a firm believer in "going where the deals are", and it's obviously working. Larry is an innovator in the world of digital real estate investing. You can check out his book, here:   Getting Star...

15 Minute Friday: The Reno Project 02.08.2019

For this edition of 15 Minute Friday, AJ takes us to one of his biggest assets, a self storage facility in Reno.  Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments Links:   https://cashflow2freedom.c...

Brittany Arnason 29.07.2019

AJ Chats with Brittany Arnason, a DYI real estate investor with a unique approach to home buying. Learn how Brittany has achieved financial freedom and check her out on Instagram to see how she develops her property. From a young age Brittany knew she wanted to work with real estate investing. She grew up watching her mom buy and sell rental properties and helped work on fixing them up in order to...

15 Minute Friday: Part One 26.07.2019

This is the first installment of 15 minute Friday. AJ updates the listeners on all of the great things he's doing with his company and of course, shares some insights so the audience can start their journey to financial freedom. Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in...

The Value of Opportunity 22.07.2019

In this episode AJ and Roc discuss the value of opportunities. Opportunity is all around us, and if we recognize it and are prepared, it can lead to financial freedom. Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Inv...

How to Start and Grow a Profitable Business 15.07.2019

In this Episode, AJ and Roc continue their series of discussions about entrepreneurship. They share their experiences and discuss how to go about starting a business. Topics of discussions include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Inv...

Paul Moore 04.07.2019

Paul Moore of Wellings Capital joins AJ for this episode. Paul shares his expertise and discusses the power of commercial real estate. To learn more about Paul and Wellings Capital visit his website linked below.   https://www.wellingscapital.com/our-story   Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Inco...

The Basics of Entrepreneurship Part 2 01.07.2019

AJ and Roc continue their discussion about how to start a business. "Capital is King" as AJ says. Topics of discussion include:   Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments

The Basics of Entrepreneurship Part 1 24.06.2019

AJ and Roc discuss how to take your idea and turn it into a profitable venture and the value in finding a good mentor. Topics of discussion include:    Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments

Self Storage 101: AJ's Background & Everything You Need To Know To Get Started 24.05.2019

AJ and Roc discuss the ins and outs of the Self Storage Business. Topics of discussion include: Financial Freedom Creating Cash Flow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments

AJ's Four Pillars Of Wealth: Create Systems To Build Sustainable Wealth 09.05.2019

AJ and Roc share their Four Pillars to financial freedom and discuss "fuel" for wealth vehicles. Topics of discussion include: Financial Freedom Creating Cashflow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments  

24 Year Old Entrepreneur, Roc on Building a Million Dollar E-Commerce Brand & Investing the Profits 08.05.2019

A young entrepreneur named Roc joins the podcast to discuss his real estate investments, e-commerce business and more. Topics of discussion include: Financial Freedom Creating Cashflow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments

Wealth Vehicles: Building The Avenue That's Right For You 08.05.2019

 AJ discusses 'wealth vehicles' and provides insight in creating an avenue to financial wealth. Topics of discussion include: Financial Freedom Creating Cashflow Real Estate Self Storage Buying Self Storage Passive Income Investing in Real Estate Investing in Self Storage Financial Freedom with Real Estate Cashflow Investments

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