In 2006, Cleveland created and starred as the character Nick Chiapetta in The Temp Life, a comedy web series[1] which debuted on YouTube on November 29, 2006 and ended January 24, 2011 after 5 seasons.

[3] Cleveland created,[4] executive produced and starred in[5] Suite 7, a seven-episode branded web series sponsored by the Better Sleep Council and distributed by Lifetime.

[6] Cleveland is the co-creator, executive producer and co-star of Leap Year,[7] a comedy-drama series about five former co-workers starting a tech company in Silicon Valley, that aired for two seasons on Hulu from 2011 to 2012.

Cleveland, himself openly gay, explained in a June 28, 2013 NewMediaRockstars interview, "I wanted Derek’s sexuality to be a subtle layer to the character" and "not make it some big plot twist or its own storyline.

[19] Cleveland has also appeared in 3 episodes of Annoying Orange, has been a guest host for DNews,[20] and is the creator and executive producer of Courageous Leaders.