1990: Made short comedy movies with brother on VHS.
1994: Attended magic camp.
1999: Diagnosed with clinical depression.
2000: Dropped out of high school. Fled to England. Lied about age. Directed Waiting for Godot. Returned to Boston. Met Josh and Elaine at summer camp.
2001: Directed Rosencrantz and Guildenstern Are Dead. Sold guitars. Telemarketed. Became Interim Artistic Director of the Lyric West Theatre. Moved in with Elaine.
2002: Moved to New York. Played Leonardo Da Vinci in children’s theater tour. Did extra work on Law and Order. Broke up with Elaine. Bummed around New York with Josh.
2003: Played village idiot at the New York Renaissance Faire. Directed plays at the Theatre Studio Inc. Took classes at the Atlantic Theater Company, New Actors Workshop, and HB Studio. Got back together with Elaine.
2004: Founded Dutch West, an internet comedy group, with Josh, Elaine, Vince and Matt. Made videos for CollegeHumor, Tribeca Films, and SuperDeluxe. Did improv in the basement of a bar. Took classes at UCB.
2006: Hired by CollegeHumor as Director of Original Content. Developed first web series, Street Fighter the Later Years and The Michael Showalter Showalter.
2007: Hired Josh and Vince. Developed Jake and Amir, Hardly Working, and Prank War. Broke the record for most watched internet content, beating out SuperDeluxe, Dot Comedy, and This Just In. Won an Aspen Rooftop Comedy Award and ECNY Award.
2009: EP’d, directed, and starred in The CollegeHumor Show on MTV. Promoted to President of Original Content.
2010: Wrote and directed Web Site Story. Won six Webby Awards. Co-created Elaine’s web series, Very Mary-Kate.
2011: Married Elaine.
2012: Named one of Forbes’ 30 Under 30.