Benjamin was born in Chicago and moved around a lot in his youth, living in places such as Florida and Mississippi before settling in Minneapolis. 
Benjamin made his break by appearing in season 20 of America's Next Top Model, earning a spot as a finalist.  He would win the inaugural season of the show Scared Famous (TV series).  Benjamin is a rapper whose music has been aggregated in the media. His song "Across the Sky" has appeared on Big Brother, America's Next Top Model, and programs on MTV. The song earned a spot on the iTunes Overall Top Songs chart.
Benjamin started dating Liane Valenzuela in 2015.  After two years of dating, they decided to document their relationship on their YouTube channel, Forever Us. As of April 2018, the channel has over 64k subscribers. In addition, they released the song together "No One" in Januray 2018.
Benjamin is represented by Wihelmina for print opportunities and the Don Buchwald Agency for theatrical opportunities.