Chief Executive Officer
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 attended Baldwin Wallace College and graduated in 1998. He worked as a Financial Advisor from 1997-2004, and obtained his Series 6, 63, 66 and life and health insurance licenses.
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 to coach 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.
Chief Operating Officer
Over the course of Jason’s career – first as a restaurant GM and now as Chief Operating Officer – he has optimized business systems that drive breakthrough performance. Operational excellence has also enabled him to support new business launches, company turnarounds, and cultural transformations.
One of the keys to excellence is to thoughtfully build strategies and plans before executing ideas. He has instilled this discipline in his employees, and it has led to business-enhancing automations, seamless corporate relocations, and exceptional client experiences. While he certainly has a bias for action, he agrees with Abe Lincoln when he said, “give me six hours to chop down a tree and I will spend the first four sharpening the axe.”
In the end, operational excellence cannot be attained without a capable and engaged workforce. At every stop in Jason’s career, he has emphasized learning cultures, mentorship at all organizational levels, and development through stretch assignments. When professionals feel like they are growing and moving forward, it maximizes effort – which benefits his employees, company, and customers.
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.
Vice President of Lending
Chris was born in Cleveland, Ohio but has lived all over the southern United States. Chris met his wife in Fort Lauderdale, FL and shortly after they got married they moved to Phoenix where they lived for 20 years before moving back to Cleveland to be near family. Chris is a big sports fans and loves all Cleveland sports teams, going to concerts, trying new restaurants and just getting out and discovering new places in our great state to visit.
Chris has over 15 years in the real estate and lending industries and he has performed virtually all of the functions necessary to buy or lend on a piece of real estate. In this business, we only interact with our clients for a short period of time, but we can really make a difference in their lives and that’s the part that keeps him going.
Vice President of Business Development
Tyler is responsible for scaling up Freeland’s small business lending activities. He brings 9 years of sales experience, plus 3+ years running his own real estate investment company, which makes financing easier for low-income families seeking safe and affordable housing. His company now manages a multimillion-dollar investment portfolio across various Cleveland neighborhoods. Tyler is also currently nominated for the Crain’s Cleveland 2019 Twenty in their 20s as a rising top professional.
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.
Carrie J. Rego
Director of Finance
Carrie is part of the senior executive team, and is responsible for the company’s financial health. She oversees all of the organization’s financial activities such as investments, budgets and expenditures, creates financial policies and goals, reduces expenses and develops financial strategies. Carrie also handles the onboarding of new investors and is the point of contact for all investors. Carrie’s most significant, and rewarding, investor task is the calculation and handling of the quarterly investor returns.
Carrie has been in Finance and Accounting for over twenty years, where she has experienced many different sectors of the field. Carrie joined Freeland Ventures after having held the position of Senior Property Accountant at a local management & development real estate company, where she handled over 72 properties and the company’s government AIA construction draws. She spearheaded the financial reviews of the countless draws for their largest VA Hospital construction project.
Carrie is self-motivated, detail oriented and enjoys being part of the ever-growing Freeland team. She was born and raised in Northeast Ohio and loves all things Cleveland sports. She also loves trying new restaurants (and old favorites) and loves to travel.
Director of Client Services
Sheila and her husband of 25 years have been Clevelanders their whole lives. She has a son, Patrick, and a dog named Oreo. Sheila started her career with Strategic Real Estate Coach as a negotiator, and worked her way up to Customer Service Director before her promotion to Director of Client Services for both Freeland Ventures and SREC. She has always been in customer-focused positions, and is committed to helping others reach their real estate goals.
Director of Marketing
Natalie originally moved from Buffalo, NY to Cleveland, where she graduated from John Carroll University with a B.S.B.A. in Business Management. While at JCU, she also studied abroad at Bond University in Gold Coast, Australia. She has 14 years of experience ranging from marketing to advertising, project management and business operations. Natalie enjoys interior decorating, running (including completing two half-marathons), and spending time with her family.
Director of Content & Media
Remy is responsible for the production of digital media and A/V needs for company-wide marketing initiatives, live events, and the Accelerated Investor Podcast. He attended Full Sail University in Winter Park, Florida and has over 12 years of experience in film, television, and video production. Remy enjoys traveling with his wife, playing music in dive bars around Cleveland, and watching TV with his two dachshunds.
Servicing & Compliance Manager
Brian was born and raised in Cleveland, OH and graduated from Cleveland State University in 1999 with a B.B.A., Finance Major. Brian has over 15 years of diversified experience in sales and loan servicing within mortgage banking operations. Brian lives in Northeast, Ohio with his wife and daughter. In his free time, he enjoys spending time with his family and friends.
Project & Asset Manager
Tim is responsible for underwriting the rehab portion of loans and assessing possible future acquisitions for Freeland, while analyzing potential properties that can be dispositioned in variety of ways from wholesaling to fix/flip and holds. During Tim’s tenure as the Owner Operator of his solely owned company, he managed multiple remodel project simultaneously, including several Freeland Ventures properties. Prior to this role, Tim served as the Maintenance Supervisor over a 444-unit, 37 building, 22-acre apartment complex with three other technicians reporting to him.
Tim’s construction career began with his completion of the Construction Trades program from Polaris Career Center. He then earned his Associate’s Degree in Applied Science of Building Maintenance from Vatterott College. He was also certified from the Institute of Inspection Cleaning Restoration Certification as a Water Remediation Technician, Advanced Structure Drying Technician and Applied Microbial Remediation Technician.
Many of Tim’s strong leadership skills were developed from his four-year service in the US Army as an Infantryman. During his time in the service, he received the following commendations: Army Service Ribbon, Global War on Terrorism, Expert Marksmanship Badge, Army Commendation Medal (Fourth Award), Army Achievement Medal (Third Award), Overseas Service Ribbon, Iraq Campaign Medal with Campaign Star, Expert Infantryman Badge and Combat Infantryman Badge.
Business Operations Manager
Julie was born and raised in Cincinnati, Ohio. She originally moved to Northeast Ohio to attend The University of Akron on a swimming scholarship. She graduated in 2012 with B.S.B.A. in Sales Management and E-Marketing. Julie brings over 7 years of mortgage lending experience.
At Freeland, Julie is responsible for identifying and analyzing loans to help push them to close as quickly and efficiently as possible. She is also helping to develop new processes to increase productivity from origination to closing. She works in tandem with the origination staff to effectively and efficiently move a file directly to the closing team.
Julie currently lives in Lakewood with her fiancé in a home they built and designed. She also enjoys being involved in the community. She was a member of Champion’s Club at the 2018 Walk to End Alzheimer’s based on her fundraising efforts. She has also worked with Habitat for Humanity to rehab homes in the lower income neighborhoods of Cleveland. She enjoys hiking, yoga, traveling and spending time with her family.
Business Development Manager
Andrew is focused on new business development, borrower and passive investor relations and acquisitions. He is a lifelong Clevelander who has also spent time living abroad in Europe and South America, where he met his wife in Ecuador. They have two young children together and run a successful Airbnb nightly rental portfolio on the west side of Cleveland.
After working 25 years in the restaurant industry Andrew is now a wine sommelier. He’s a wine expert. He’s educated in wines and grapes from around the world.
In his first two years of investing he completed over 40 deals ranging from flips, turnkey rentals, wholesales, tax certificates, foreclosures, defaulted notes and more. He is focused on bringing that broad range of skills to Freeland and growing their private lending, passive investing and managing client relationships.
Business Development Manager
Scott is responsible for new business development, while building borrower and investor relationships. He brings years of real estate investing experience, and bought his first rental property at the age of 22. Prior to joining Freeland, Scott was a retirement planning specialist. A Strongsville native, he graduated from Cleveland State University with a B.B.A. in Finance. Scott enjoys the analytical process of finding a good deal, and is passionate about helping others grow their own finances.
Senior Loan Closer
Jan diligently coordinates loan closings and meticulously tracks loan payoffs. She grew up in Cleveland, Ohio, and also lived in California for 17 years. Jan has a lifetime of experience of working in the real estate/mortgage industry.
She enjoys her time with family and friends, the Cleveland Metroparks, in the Cleveland area, sporting events, and local restaurants.
Loan Support Specialist
Vanessa provides a number of essential elite client services to our national borrowers. She has been involved in the real estate business most of her life, and understands the challenges and opportunities that are presented to our borrowers. She was born in sunny California and grew up in Cleveland, Ohio where she graduated from Baldwin Wallace College with a B.B.A., majoring in Marketing with a minor in Public Relations. When she isn’t working, she enjoys spending time with her family and friends and loves to travel.
Executive Coordinator to the CEO
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.
She has two children. Her daughter Taylor attends Baldwin Wallace, and her son Michael is a recent high school graduate. Her free time is spent with family.
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