Holly’s career in commercial real estate began in 1990 with Codina Bush Group where he worked as a commercial real estate broker. He worked with Jeb Bush and Armando Codina leasing and selling office building.
1998-2000
Holly moved to Cushman and Wakefield group and worked there in the capacity of an executive director before setting up the Miami office of Insignia/ESG. Over his career of 27 years in the real estate industry, he has represented more than 20 Class A office buildings in the Miami market and also owns the Class A pre-lease office market records for The Coral Gables, Brickell, and Miami Beach submarkets.
2002-2010
Holly founded his own company, Holly Real Estate, a commercial real estate company in 2002, where he was the firm’s chairman and the CEO. Apart from handling development and brokerage, the company had a focus on green development. He developed Miami Green, the first green LEED-certified office building in Miami.
Financial Setbacks
During the 2008 financial crisis, in his stint as a developer, Holly had encountered a financial setback related to his development of approximately $150 million of active commercial real estate projects at that time and sought chapter 7 bankruptcy protection as the guarantor of these projects.
After the Setbacks
2011-2012
After running his own firm for many years, Holly returned to Cushman & Wakefield as an executive managing director. In this role, Holly held one of the most senior titles and positions in the State of Florida.
2012-2014
Holly was named president of Miami-based property management and brokerage firm Pointe Group Advisors which managed more than 3 million sq. ft. of commercial space under management and leasing.
2015–present
He is the founding shareholder of Apollo Bank, Florida Gulf Bank, and Coral Gables Trust. He is also the past president of the Brickell Area Association and the past chairman of the Ransom Everglades Board of Trustees, the past chairman of the Historical Museum of Southern Florida. Holly currently serves as the chairman of the board of Young Presidents Organization Americas Gateway Chapter and the YPO North-eastern Region Board. He is also a board member of JB Green Estate, a local real estate investment firm. Holly is on the board of directors of the German-American Heritage Foundation of the USA, a national non-profit organization based in Washington D.C. that promotes German language, culture, and heritage in the United States and works towards preserving the history of Americans of German ancestry who helped build the United States.
Awards and recognition
2004: Recognized as one of the top ten Hot Commercial Real Estate Brokers in the US by Commercial Property News.
2007: Received the Entrepreneur of the Year Award from the Greater Miami Chamber of Commerce.
2008: Named as one of the top commercial real estate executives nationally.
2008: His company, Holly Real Estate ranked no. 22 on the South Florida Business Journals list of Largest Commercial Real Estate Brokerages.