Lieb was raised in Columbia, South Carolina, and graduated from Harvard, where he was an editor of The Lampoon, the college humor magazine.
After graduation, he found work writing for Twisted Puppet Theater, The Jon Stewart Show, and NewsRadio.
He subsequently worked as a producer on many shows including The Simpsons, Drawn Together, What We Do in The Shadows, Silicon Valley, and Who is America?
Lieb's tenure at The Daily Show lasted from 2006 to 2010, during which he also served as executive producer of The Rally to Restore Sanity And/Or Fear and as co-editor and co-author of Earth: The Book.
Stars featured in the shorts included Matt Damon, Jessica Biel, Sir Richard Branson, and Bono.