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The Jason and Pili Project

Oct 28, 2019

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Josh Cantwell is Chief Executive Officer of Strategic Real Estate Coach and Freeland Ventures. A native of Northeast Ohio, Josh graduated from Baldwin Wallace College in 1998 with a Major in Business Administration and a Minor in Communications. Although a full-time student and college athlete, Josh was already driven to succeed in his career. After graduation, he obtained his Series 6, 63, 66 and life and health insurance licenses, and worked as a Financial Advisor from 1997-2004. In 2004, Josh took his knowledge of raising capital and the financial markets and started investing in real estate full time.

He was able to combine his knowledge of Financial Investing with real estate to create a very successful business, which quickly grew. In turn he began training and teaching apprentice partners and students. He founded Strategic Real Estate Coach in 2007, and since then has been involved in 700+ wholesale, rehab, rental, foreclosure, pre-foreclosure and short sale transactions, and taught thousands of investors how to replicate his success. He is the founder of a variety of successful businesses including Freeland Ventures, Strategic Real Estate Coach, and several others. Josh lives in Northeast, Ohio with his wife, Lisa Marie, and three children.

Some topics covered:

-When was the moment Josh decided to go into real estate and why?

-How Josh’s fathered played a role in why he made a change to real estate?

-How did Josh push through the first couple of months when starting out in real estate and how coaching helped him get over the hurdles?

-What’s Josh’s elevator speech when asked what he does?

-Key steps Josh took when he first started and what steps you should take?

-How and when Josh filled roles so he could get his time back?

-How do you break bad habits?

-What does the future look like for Josh’s business, what is he working towards?

-What makes a great operator?

-Is it the market or opportunity or something else that Josh looks at when looking to invest?

-What is Josh’s morning routine?

-Words Josh lives by

-Actionable step a new investor can take today?

-Best way to find out more about Josh and his company:  or



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