Gregg is a Co-Founder and Managing Partner of Parkway, an experienced investor and a successful entrepreneur and operator. Over his career, Gregg has invested more than $300 million across a variety of venture capital and real estate investments, and achieved outstanding returns.
Gregg is a serial entrepreneur, and active investor, with a business style which is active, forward-thinking and deeply collaborative. Gregg’s constant energy and depth of experience make him an ideal sparring partner for founders who are looking to scale their businesses rapidly.
Prior to co-founding Parkway, Gregg was a founding partner of H&S Capital, an investment business he established with one other partner, primarily to invest for his own account. The most successful of these investments was Frustum, where Gregg was one of the first investors, largest, and as is his hallmark, most active investors.
Gregg is also Co-Founder and CEO of Hill Gray Seven (“HG7”). Gregg started HG7 with an initial investment of approximately $700,000, and since inception in 2000, has developed over 130 medical, self-storage, multi-family and retail properties. HG7 is the preferred developer for numerous Fortune 500 companies, such as Starbucks, DaVita, and Chipotle, and currently operates in 15 states. In addition, HG7 manages over 100 properties, on its own behalf and on behalf of others. Gregg is the Founder of Red Castle Farms, a thoroughbred horse racing corporation located in Pasadena California. Gregg remains CEO, but HG7 now operates independently, on a stand-alone basis and requires limited input from Gregg.
Gregg began his career at the age of 8 years old, when he was identified as an exceptionally gifted athlete, and enrolled in the highly-selective Nick Bollettieri Tennis Academy (now the IMG Academy). Nick Bollettieri nurtured Gregg as a professional tennis player as he did for countless stars, including: André Agassi, Boris Becker, Jim Courier, Tommy Haas, Martina Hingis, Anna Kournikova, Monica Seles, Maria Sharapova, Venus Williams, and Serena Williams (to name a few), and by the age of 18, Gregg was one of the top college tennis recruits in America, doubles partner with Tommy Haas, had competed globally (Wimbledon, etc.) and had been featured on 60-Minutes and countless news outlets. At age of 20, Gregg’s life was abruptly interrupted by a major accident, which effectively finished Gregg’s professional tennis career. However, the drive that made him one of America’s the top college athletes, continues to infuse everything he does.
Gregg studied Economics at University of Southern California on a full athletic scholarship. Gregg has been awarded Orlando Business Journal’s 40 Under 40 (2014) and is a member of The Young Presidents Organization Orlando, and Board Member, and Southeast US Regional Chapter. Gregg is passionate about philanthropy and is deeply involved with is the American Diabetes Association (ADA) and was named the ADA’s “Father of the Year” in 2013. Gregg teamed up with Tommy Haas and launched a new charity called Match Point Impact. Match Point Impact helps raise money to provide the highest level of education and tennis training available to hard working, talented, and financially impacted youth.