After graduating with a degree in English literature and a minor in history, he leaned towards becoming a literary, post-modernist writer and penned a couple of novels in that style, which went unpublished as Roberson realized that he "wasn't depressed enough for that line of work".

"[1]During this period, Roberson had a variety of day jobs, such as a product support engineer for Dell computers, a position he held for seven years and quit in 2003 to concentrate on his work as a writer and publisher.

After the dissolution of Clockwork Storybook, Roberson decided to focus on his career as a writer and soon after made his first professional sale with the short story for the Live without a Net anthology, edited by Lou Anders and published by Roc.

Roberson, who runs MonkeyBrain along with his business partner and spouse Allison Baker, decided early on that the company would deal exclusively in "traditional offset trade-paperbacks and hardcovers," distributed internationally, rather than printed on demand.

The mini-series, titled Cinderella: From Fabletown with Love and illustrated by Shawn McManus, was described by Roberson as featuring "spies, sex, and shoes.