WBP - Getting In, Cashing Out and Holding On with Josh Cantwell

Josh Cantwell currently manages over $30,000,000 in private money, which is deployed into real estate. He owns 2,208 units of apartments, and manages a real estate private equity fund where he and his team fund hundreds of fix and flips, rentals, small balance commercial deals under $5M and value-add apartments for clients, students and borrowers. 


Josh is a true entrepreneur and prides himself on never having had a boss in his entire adult life. A native of Northeast Ohio, Josh graduated from Baldwin Wallace College in 1998. 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 into closing over 100+ wholesale and short sale deals per year. 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. Josh has vast knowledge and experience in helping coaching clients, mentor students and apprentice partners from across the US in finding, structuring, negotiating and closing various types of transactions for a profit.


He has bought and sold over 700 properties in 25 states, and currently holds a robust portfolio of over 2,200 cash-flowing apartments. He is the founder and CEO 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. 


He speaks with us about value add properties, pancreatic cancer and creating an irresistible offer.



The Rundown

The Timeline


Foreclosure Crisis

Short Sales

Pancreatic Cancer

Flipping Houses

Controlling the Money

Series 6

Top Grading


Distressed Properties

Being Resourceful

Going Outside Your Home Market

Value Add

Quick Refi

Loan to Value

Equity Ownership

Finding Off Market Deals


Raising Capital


Shared Goals

An Irresistible Offer

Project 100

Number Exchange

Proven Sales Process

Prior Relationship

Ask Questions

Single to Multifamily

Doing The Legwork

Habits For Success

Self Care

Book Recommendations

Extreme Ownership

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