After receiving his master's degree in the same field from Columbia University, he went to work for Rolling Stone, beginning as an executive assistant before being promoted.

[7] On December 18, 2017, Skipper revealed that he had been struggling with substance addiction, and announced that he would be resigning as president of ESPN in order to focus on treatment.

[4] In the wake of Skipper's announcement, the New York Times reported that he "didn't have a reputation for partying or erratic behavior" among coworkers at ESPN or confidants in his personal life.

[7] After his resignation, many current and former ESPN staffers, including Jemele Hill, Michele Steele, and Keith Olbermann, applauded Skipper's past work and the decision to focus on his personal life.

[9][10] On May 8, 2018, it was announced that Skipper had been hired as executive chairman of DAZN Group, a British international sports media company.

"[15][16] In January 2021, Skipper joined former ESPN personality Dan Le Batard to launch Meadowlark Media, a content company focused on sports.

"[22] During Skipper's tenure, ESPN lost nearly 15% of its subscribers as consumers moved to streaming and over-the-top (OTT) options and laid off more than 500 employees as all traditional media companies were impacted by cable's decline.