Chen joined Gawker in November 2009 as a night shift editor, graduating from an internship position at Slate,[2] and has written extensively on Internet culture, especially virtual communities such as 4chan and Reddit.

In October 2012, Chen exposed the real name and details of Violentacrez (a moderator of several Reddit jailbait communities), a Texas Internet developer, who was subsequently fired from his job.

[9] In September 2012, Chen acquiesced to demands from Anonymous and posted images of himself dressed in a tutu with a shoe perched on his head.

The images had been demanded in exchange for interviews regarding an alleged leak of Apple iPhone and iPad user data from an FBI laptop.

[20][21] In June 2011, Chen wrote an exposé of Silk Road, a darknet market which facilitated online drug purchases.

[23] As a result of Chen's investigation, United States Senators Charles Schumer and Joe Manchin publicly called on U.S. Attorney General Eric Holder to shut the site down.

[35] The public outpouring of hostility towards Brutsch following the exposé prompted commentators such as danah boyd at Wired and Michelle Star of CNET to question the morality of outing as a way to enforce societal standards online.