Shortly after his participation on the series, he released the EP Pretend, which reached the top ten on Billboard's Heatseekers chart.

[5][6] When he was 13, his mother remarried and moved to another city in Florida, and Woolf and his older sister Emily remained in North Port with their father.

"[7] Woolf later became interested in music as a career, took singing lessons from an opera teacher, Bob Lischetti, and performed locally in Bradenton.

[2] He also was mentored at the Del Couch Music Education Foundation and went to Interlochen Arts Camp in Michigan for four weeks the summer after his second year of high school.

In the summer of 2013, Woolf completed a five-week program at the Berklee College of Music and was selected as one of the top four songwriters for their singer showcase, where he performed an original song, "The Same.

[8][9] Woolf performed nationally in the American Idol season 13 tour,[10] then held a 'Welcome Home' concert in Bradenton, Florida at IMG Academy Stadium on September 27, 2014.

[11] He opened a similar homecoming concert for his fellow American Idol season 13 finalist, Alex Preston, at the Capitol Center For the Arts in Concord, New Hampshire on November 8, 2014,[12] and on February 28, 2015, he performed in Lakewood Ranch, Florida's Winterfest, along with The Doobie Brothers, War, Jefferson Starship, Matt Walden and performers from the Del Couch Music Education Foundation.

[48][49] He has also performed at Dream Fest in Tampa, the Warwick Summer Concert Series in New York, the Boston Arts Festival, and the Riverwalk Regatta in Florida.