Ironically, former Special Agent Phillip Sheppard proved to America that he’s not always very good at keeping secrets on last weeks Survivor: Redemption Island, but one thing he is exceptionally good at is roller skating . . . backwards.
The software brokering executive, who also has trouble pronouncing the name “Franscesa” (because of “dry mouth”), was discovered by a Survivor casting scout while skating backwards on his favorite route in Santa Monica, where he’s lived for 10 years.
Sheppard told Santa Monica Patch that he began speed-skating as a young boy in the small town of Dansville, NY, and in adultood began perfecting backward speed-skating. He says he’s only been in one major dust-up:
I was going down Ocean, and a motorcycle was going in the opposite direction. He decided to make a U-turn, with [his] girlfriend on his bike. He stopped, not realizing that I was coming, and I … hit her and knocked her off the bike and wound up sitting on the bike. Turned out we were both OK, and I went on about my skating.
On the first episode of Redemption Island Sheppard didn’t win many friends. His condescending take-charge attitude and bragging about being a Special Agent annoyed even the ladies who grudgingly formed an alliance with him (Kristina, who found an immunity idol, and Fransceca, who got voted out.) The other alliance was led by Survivor veteran “Boston Rob” Moriano, who successfully charmed a group of young women.
At the first tribal council, Sheppard immediately turned on his group, and told everyone what they had discussed about voting Boston Rob out because Kristina had an immunity idol. He then mangled the pronunciation of “Francesca” several million different ways. It wasn’t a stellar start.
In the second episode, Phillip is seen trying to align with Boston Rob, who doesn’t trust the crazy, and rallies his group of hotties to vote out the former Special Again. Rob notes to the camera that government jobs are stressful.
52-year-old Sheppard is the CEO of Enterprise Software Sales Group, which specializes in data management and brokering software.
His Linked In profile says he was a Special Agent for 3 years (1986-9):
The Defense Security Service (DSS) oversees the protection of US and foreign classified information in the hands of industry, administers the National Industrial Security Program for DoD to include issuance of security clearances to industry, supports the Office of Personnel Management (OPM) in the conduct of personnel security investigations for DoD, provides security education and training in core security disciplines to the DoD Community and provides information technology services that support the industrial and personnel security missions of DoD and its partner agencies.
Government Agency; Government Administration industry
1986 – 1989 (3 years)