Rudder was the creative voice of TheSpark.com,[3] which was the viral content arm of SparkNotes during the site's early rise to popularity.

[4] From 2009 - 2011, OkCupid published statistical observations and analysis of members' preferences and connections; the blog posts were written by Rudder and gained widespread media attention.

[6] After the sale to IAC, Rudder assumed day-to-day control of OkCupid as President and General Manager until he left in 2015.

[8][9][10] Rudder played guitar in the hardcore punk band Pissed Officers and indie rock group Bishop Allen, both with Justin Rice on bass and Rudder and Rice sharing songwriting and vocal duties.

[13] Through Bishop Allen, Rudder has contributed to the soundtracks of the movies Saved, Sleepwalk with Me, No Strings Attached, Nick and Norah's Infinite Playlist, Bully, and several other smaller films and commercials.