[3] Rees grew up in Chapel Hill, North Carolina,[citation needed] and was an avid reader of Rex Morgan, M.D.

[6] When the follow-up volume, Get Your War On II was published, Rees donated all the royalties of both books (more than $100,000) to Adopt-a-Minefield,[7] an organization that works to remove landmines from post-conflict areas.

In 2010, Rees worked as a civil servant for the United States Census Bureau, a position that revitalized his interest in pencils.

Rees claimed to be a craftsman in "the age-old art of manual pencil sharpening", saying his “artisanal service is perfect for artists, writers, and standardized test takers."

[9][10][11] According to The New Yorker, "This was before parody menus of farm-to-table restaurants had come out, before it was a cliché to make jokes about Mason jars and pickle-making, and artisanal culture desperately needed to be mocked.

The New York Times called it a methodical, deliberate and gleeful subversion and satire that "capture[s] the inherently joyless tedium of conveying specialized instructional information, while tipping off the reader that the cod liver oil is laced with laughing gas."

The show featured Rees humorously investigating the science and process behind very basic tasks such as making ice, lighting matches and the tying of shoelaces.

[16] Rees hosts the weekly podcast Election Profit Makers with his childhood friend Jon Kimball and Starlee Kine in which they discuss the prediction market website PredictIt.org.

Rees co-created the animated television series Dicktown with John Hodgman, and starred as the character David Purefoy.