Josh Cantwell

Chief Executive Officer

A native of Northeast Ohio, Josh Cantwell 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. 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 rental portfolio of cash-flowing properties. 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. Josh, along with Glenn Lytle, are the co-founders of Freeland Ventures.

Jason Schlegel

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.

Chris Hofford

General Manager

Chris is the General Manager for Freeland Lending and is responsible for all of the day to day operations.
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.

Jan Cottingham

Loan Closer

Jan Cottingham is a Loan Closer at Freeland Lending. She coordinates closings and track our loans paying off. She grew up in Cleveland Ohio. Lived in California for 17 years. Jan has a lifetime experience of working in the real estate/mortgage industry.

She enjoys family and friends, the metro-parks in the Cleveland area, sporting events, and local restaurants.

Ricardo Caldwell

Project Manager

Ricardo was born and raised in Cleveland, OH and is the devoted husband and father of two. He has been involved in real estate since he graduated from Lakeland Community College in 2002. He is a former high school and college football player and enjoys watching sports, especially the Cleveland teams.

With over 15 years of experience in real estate, he has worked as a loan originator, insurance sales rep, loan processor and in 2005, he began to work as a rehab project manager, providing a vast knowledge involving residential real estate transactions from all sides of the table.

Ricardo has managed over 250 construction rehabs in his young career and continues to grow that number every day working at Freeland.

Brian Pfaffenberger

Service 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.

Carrie Rego


Carrie Rego is the Controller for Freeland Ventures. With her analytic mind and attention to detail, she helps keep any financial details at her disposal in order. Carrie has worked in many different sectors in the accounting field and loves property and financial services accounting the most. Give her a $1 discrepancy and she will find it!

Carrie 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. She lives in Seven Hills with her boyfriend, two dogs & two cats. In her free time, you will probably find her cheering for her Cleveland sports teams (win or lose), working out, playing corn hole, throwing darts, going to live music venues, playing with her dogs, and watching good movies.

Andrew Ziebro

New Business Development & Capital Advisor

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.

Natalie Meyer

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.

Jennifer Pennington

Executive Coordinator to CEO Josh Cantwell

Jennifer started with SREC in November 2014 as a Customer Service Rep/ Accountant Asst. In late 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, OH. It was a big change, but one she hasn’t regretted for a second.

She has two children. Her daughter Taylor is a junior at Baldwin Wallace and her son Michael is a recent high school graduate still figuring things out. Her spare time is spent with family.