Jay M. Caplin

With a career spanning more than three decades, Jay Caplin is among the industry leaders in real estate investment in the Southeast region known for his reliability, unwavering integrity, creativity, and passion for his profession.

In 2019, Jay co-founded SQUARE2 to create a dynamic investment and operating platform unique to the industry, capable of achieving transformational results.

This vision came to fruition more than a decade after Jay founded and built Steelbridge, a real estate investment firm. During his tenure, he solidified the firm’s national reputation and dramatically expanded its capabilities, portfolio, and capital partners to include prominent institutional private equity firms and lenders such as Apollo Global Real Estate, Blackstone, Square Mile Capital, CommonFund, TFO USA Limited, as well as numerous foreign and domestic high net worth investors and family offices.

Prior to this, Jay spent over two decades at Cushman & Wakefield as an Executive Director. While at Cushman & Wakefield, Jay co-founded the Florida Capital Markets Group and led the expansion and direction of the group’s growth throughout the region. Representing a diverse group of owners, Jay oversaw sales and financing of office, residential, industrial, retail, and hotel properties valued at more than $7 billion.

Jay graduated from Florida State University (FSU) with a double major in Finance and Real Estate. An active alumnus, Jay is a member of the Executive Advisory Board for the FSU Center for Real Estate Education & Research and is Chair of the FSU Real Estate Foundation. Additionally, he is an active member of the Urban Land Institute (ULI) and serves on the Advisory Board for the ULI Southeast/Caribbean region.​​