Robert Jr. is part of the 7th generation of the Spottswood family to call Key West, home. Attended the University of Florida and graduated with a degree in food and resource economics before studying law at Nova University in South Florida. During his time at Nova, he worked with several environmental groups, including the Everglades Law Clinic, in advocating for responsible development and preservation of vital native habitats for endangered and threatened species.

Robert Jr. joined Baker & Hostetler LLP in 2015 and focused his practice on real estate and the hospitality industry, specifically fractional ownership resorts.

In 2019, Robert Jr. and his wife Stephanie, decided to permanently move to Key West, where they now reside with their children Florence, Eleanor, and Robert III. He is President of Spottswood Companies, Inc., Co-President of Keystar, and is also a Partner at Spottswood, Spottswood, Spottswood, & Sterling, PLLC.

He is also a Board Member of the Fish and Wildlife Foundation of Florida and The Nature Conservancy.