OUR TEAM

Josh Cantwell

Chief Executive Officer

Josh manages over $40M in private money, which is deployed into multifamily real estate and apartments. He has been involved in 1,000+ wholesale, rehab, rental, foreclosure, and apartment transactions, and currently holds a portfolio of over 3,000+ cash-flowing apartments. He is the founder and CEO of a variety of successful businesses including Freeland Ventures and Strategic Real Estate Coach.

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. He also 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 has taught thousands of investors how to replicate his success. Josh has vast knowledge and experience in helping to coach clients and mentor students and borrowers from across the US in finding, structuring, negotiating and closing various types of transactions for a profit.

Josh is also the host of the Accelerated Investor Podcast, which has hosted past guests like Kevin O’Leary, Barbara Corcoran, Donald Trump Jr, Jack Canfield, Rod Khleif, and JV Crum III.

Josh lives in Northeast Ohio outside of Cleveland with his wife Lisa Marie and three children, Giuliana, Alessandra and Dominic (aka the Nooch).

Tyler Brummett

COO/President of Asset Management, Freeland Properties

Tyler is responsible for scaling Freeland’s real estate portfolio and overseeing budgets, expenditures, and property management. He is also responsible for sourcing, reviewing and negotiating all of the real estate opportunities, and is the primary contact for acquisitions and possible joint venture opportunities. He brings 9 years of sales and lending experience in residential, commercial, and private equity, 6+ years running of his own real estate investment companies, and 7+ years being a director for the nation’s largest mortgage lender.

In 2019, Tyler was nominated by Crain’s Cleveland Business “Twenty in their 20’s” as a rising star of top professionals in Cleveland. At Freeland, Tyler is combining his leadership skills with knowledge gained as an entrepreneur renovating and investing in homes throughout the region. He has also refurbished homes for Habitat for Humanity, and currently resides in the Tremont neighborhood in a home he built and designed.

Tyler enjoys traveling and learning new cultures, boating, hiking, and is an avid car collector.

Roberdo Flanders

Chief Financial Officer

Roberdo has served as the Chief Financial Officer of Strategic Real Estate Coach for the past 12 years, and also will hold similar titles in Freeland Fund I, Freeland Accelerated Fund, Freeland Lending and Freeland Servicing. Roberdo also acts as assistant treasurer of the Accelerated Fund. He has an Associate’s degree in Accounting and over 20 years of accounting experience. His responsibilities include overseeing accounts payable & receivable, billing, preparing financial statements and special financial reports, and participating in human resources and payroll initiatives.

He is originally from New York City, and his heart will always remain with the Knicks and Yankees. He and his wife relocated to Cleveland in 2007 to advance their education and careers in the accounting and legal fields respectively, and to give their children a more traditional suburban upbringing.

Jennifer Pennington

Director of Operations

Jennifer started with SREC in November 2014 as a Customer Service Representative/Accountant Assistant. In 2017, she accepted a promotion to work directly with Josh as his Executive Coordinator. This required her moving from the small town in western PA where she had lived her whole life to Cleveland. It was a big change, but one she hasn’t regretted for a second. In 2020, Jen accepted her second promotion utilizing her strong organizational and time management skills, and now serves as Director of Operations.

She has three children: Taylor and Michael, who happily welcomed home baby Sam in the summer of 2019. Her free time is spent enjoying her family.