Holland attended Bishop Chatard High School in Indianapolis, where he played football, basketball, and ran track.
As a senior, Holland was named all-state, Indianapolis City Player of the Year and All-North Football Player of the Year after rushing for 2,048 yards on 239 carries and 35 touchdowns and added nine receptions for 153 yards (17.0 average) and one touchdown.
After redshirting his first year, Holland moved from safety to outside linebacker during training camp in 2008.
[2] On November 14, 2012, the Tampa Bay Buccaneers signed Holland to their practice squad.
[3] On August 22, 2013, the San Francisco 49ers claimed Holland off waivers from the Tampa Bay Buccaneers.
Holland's cousin, Danny Etling, won Super Bowl LIII with the New England Patriots and current plays for the Michigan Panthers of the United Football League.