Rose attended Hilton Head Preparatory School until 9th grade when he transfered to Episcopal High School. He spent some time enrolled at the University of Georgia before moving over to Owen Graduate School of Management where he graduated with an MBA in Finance. 
Rose worked in real estate for awhile before the recession pushed him out in 2008. Not long after that he was discovered and selected for a role in the reality TV show, "Southern Charm". Around that time he also opened up his own restaurant called the Palace Hotel. In 2017 Shep landed a spinoff of "Southern Charm" titled "Relationshep", a show that follows Shep as he goes on blind dates around the country. Shep has monetized his social media presence and large following. 
He's also a blogger for the website CharlestonGrit.com where he writes about the absurdities of life under the handle @ShepicFail. 
Shep was born on Hilton Head Island, South Carolina in 1980. His father, William Shepard Rose Jr. was appointed Assistant Attorney General of the United States Department of Justice Tax Division by Ronald Reagan. His mother, Frances Rose, was known for being a patron of the arts. His brother and sister are both practicing attorneys. His brother Whittaker specializes in construction litigation while his sister Kathrin works in bankruptcy and foreclosure law.
The opening season of "Southern Charm" centered around a one-night stand Rose had with co-star Kathryn Dennis. She became pregnant at that time and there was a lot of speculation that the baby might have belonged to Shep, although it was revealed later that he was not the father.