Jeffrey was born in Kansas City, Mo., to Duane Holsman and Catherine Tiehen Holsman, his paternal grandmother, Helen, belonged to the Daughters of the American Revolution . He graduated from Ruskin High School, where he was Cross Country Man of the Year his senior year. Jeffrey joined the United States Marine Corps, and served with ElMaCo, 1st Maint. Bn, 1st FSR., Camp Pendleton, CA.. After his Honorable Discharge as Sergeant, he returned to Kansas City and worked with the NBA Kansas City Kings as an Account Executive. When the team relocated to Sacramento, Jeffrey moved to New York City, and worked as a bartender at Formerly Joe's in Greenwich Village alongside Chris Cousins & Michael Chiklis. Jeffrey studied with Oscar nominated William Hickey, Tony nominated Earle Hyman, and Amy Wright at HB Studio. He performed off Broadway in Tennessee Williams' 'Talk to Me Like the Rain', Edwin Klein's 'Smile and Say Hello', and his first film lead was in Keir Pearson's Squam Lake. Jeffrey moved to Los Angeles in 1998, and studied with Rick Edelstein, and the incomparable W. Morgan Sheppard, who also directed Jeffrey in Sam Shepard's 'Angel City'. He appeared in national commercials, print campaigns, and Coup D'Grace (2007). Jeffrey moved to Puerto Rico in 2009 following the Writers Guild of America strike. He can been seen in the Puerto Rico Lo Hace Mejor tourism campaign (2011), Stranded in Paradise (2014), Curse of the Fuentes Women (2015), The Preppie Connection (2015), Attraction (2017), 5 Headed Shark Attack (2017), and Replicas (2017).