Dyna Moe studied at Wesleyan University and is a 2000 graduate of New York University. Since 1999, she has been a fixture at the Upright Citizens Brigade Theater in New York City, performing in hundreds of shows. Dyna wrote and starred in the live-action anime show NeoTokyo Girl Crush 2040 and wrote and performed a one-woman show, Riot Nrrd. She is also a Channel 102 producer and co-creator the popular web series Cakey: The Cake From Outer Space. She is a frequent collaborator with Mitch Magee, with whom she produces the cult web series Welcome To My Study.

In 2007, Mad Men star Rich Sommer commissioned her to design a custom Christmas card for the cast and crew of the show. From there, she began to illustrate one scene per episode and post it to her Flickr site. She was eventually hired by AMC to design madmenyourself.com, the show's custom avatar generator used to promote the premiere of Season 3.