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Straub went on to co-produced Blamimation and the Kris and Scott’s Scott and Kris Show for Penny Arcade TV. In 2012, ShiftyLook announced that Straub and Kurtz were co-producing a new animated web series, Mappy: The Beat, in which they also voice all the characters. The series premiered in July 2013 and aired for 13 episodes.

In 2016, from July to December, Straub co-hosted horror podcast Scared Yet? with cartoonist Abby Howard. It lasted 6 episodes, with Straub and Howard discussing horror storytelling, writing advice, personal favorite horror stories, as well as personal experiences with writing horror.

From 2009 to 2012, Straub also hosted comedy internet radio talk show Tweet Me Harder with David Malki. The show was recorded live and had the hosts interact with a Twitter feed of listeners' reactions to the broadcast, occasionally using comments as a springboard for their conversations. Following Tweet Me Harder, Straub then co-hosted Chainsawsuit: The Podcast with Mikey Neumann. The show began in April 2013 and spanned to December 2014 and included contents such as comedic sketches, satire, movie reviews, and general discussion. Beginning in January 2015, Straub and Neumann began hosting Morning Rush, which ended in June 2015 after 16 episodes.

In 2007, leading up to the release of How To Make Webcomics, Straub - alongside the books co-authors, Scott Kurtz, Brad Guigar, and Dave Kellett - produced the podcast Webcomics Weekly. The show featured comic industry news, techniques and general advice on how to create and maintain a successful comic online. In this same time period, Straub and Kurtz also produced two joint podcasts, The Kris and Scott Power Hour and Daily Affirmation.

In December 2006, Straub was named co-writer and co-producer alongside Scott Kurtz on PvP: The Series, a series of animated shorts featuring the PvP characters. In 2007, to coincide with his move to Dallas, Straub repurposed the Halfpixel site to serve as a hub for his and Kurtz's joint creative projects. Halfpixel later expanded to include webcartoonists Brad Guigar and Dave Kellett of the comics Evil Inc. and Sheldon, respectively. The four published How To Make Webcomics through Image Comics in the first quarter of 2008. The book covers a variety of topics of interest for beginning and intermediate webcartoonists.

In 2005, Straub began creating Starslip, a daily science fiction/comedy webcomic. Starslip Crisis was first set in the 3440s, aboard the starship IDS Fuseli, named after painter Henry Fuseli. The Fuseli was a former luxury warship which has been converted into a starship museum. It is still capable of military activities. The Fuseli travelled from system to system with its exhibits (using a faster than light "starslip drive"), the comic chronicling the adventures of the crew. Much of the art featured upon the Fuseli dated from the 20th or 21st centuries. Starslip Crisis was part of the webcomics cooperation collective Blank Label Comics, until Straub split away from Blank Label to merge Starslip with his new collective, Halfpixel, in November 2007.

The comic initially ran under the name Starshift Crisis. The nearly identical Starslip Crisis appeared early in the strip's run, with its own website and associated content, differing only in that the term "starslip" replaced "starshift". The two ran in parallel, until a strip in August 2005 which definitively ended the plot of Starshift Crisis, but which played out differently in Starslip Crisis. Reportedly the name change was caused by a legal issue.

In 2005, while part of the comic collective Blank Label Comics, Straub and Dave Kellett co-hosted the Blank Label Comics Podcast. The podcast interviewed fellow webcomic creators about their comics and creative process.

Straub launched his first comic, Checkerboard Nightmare, online in 2000. The strip was self-aware, using metahumour extensively, and the title character, Checkerboard Nightmare (Chex) being obsessed with gaining fame as a webcomic character and willing to do anything necessary to achieve it.