Since 2014, Dunn has hosted the YouTube comedy show and podcast Just Between Us with fellow former BuzzFeed writer Allison Raskin.
Dunn also hosts the podcast Bad with Money, which launched in 2016 and which primarily focuses on personal finances, while also discussing subjects including poverty and economic oppression.
[2][3] His debut young adult novel I Hate Everyone but You, co-authored with Raskin, was published in 2017 and made The New York Times Best Seller list.
[6] Dunn began performing during his first year at Emerson with the sketch comedy troupe Chocolate Cake City (CCC).
At the time he considered himself a better writer than actor, and working in CCC allowed him to do both, since members were expected to write and perform their own sketches.
He worked the 6:30 pm – 2:30 am shift, using a police scanner to monitor potential news items, and then driving to the scene of the crime to write about it.
Interview subjects included a transgender person, a rocket scientist, an Abraham Lincoln expert, and Stephen Colbert.
[11] Dunn's attempts to gain wider exposure for what he called his "diary journalism"[12] were initially met with rejection.
[13] Dunn has been recognized as a success case of the use of social media for self-promotion,[9] particularly via Tumblr, the micro-blogging service and web application platform through which he initially self-published his interviews, and Twitter.
[19][4] The young adult fiction novel follows two college freshmen and best friends, and is told through emails and text messages exchanged between the two.
[21] In January 2019, Dunn published Bad With Money: The Imperfect Art of Getting Your Financial Sh*t Together, a book based on the podcast.
[25] In April 2014, Dunn created a comedic variety YouTube show with his best friend Allison Raskin called Just Between Us.
[26] In 2020, Dunn created, wrote, and starred in Apocalypse Untreated, a post-apocalyptic fiction podcast about teenagers in a wilderness rehab and troubled teen program trying to survive after a meteor strike.