Born to Mom, Clare Dalton, and Dad, Robert Reich, in Boston, Massachusetts.

Get really into Weird Al Yankovic.

Make comedy shorts with brother, Adam, on VHS.

Learn one great card trick at magic camp.

Diagnosed with clinical depression. 

Drop out of high school. Enroll in program for troubled kids in England. 

Lie about age. Direct "Waiting for Godot" at the Burton Taylor Theater. 

Return to Boston. Meet Josh and Elaine at summer camp.

Direct Rosencrantz and Guildenstern are Dead in Boston. Cast find out about age, angry, write article in Improper Bostonian with headline "BUSTED." 

Sell guitars and do telemarketing. Move in with Elaine. 

Follow Elaine to New York. 

Play Leonardo Da Vinci in a children's theater tour. Do background work on "Law and Order."

Break up with Elaine. Bum around New York doing comedy with Josh. 

Play a village idiot at the New York Renaissance Faire. 

Take acting classes at the Atlantic Theater Company, New Actors Workshop, and HB Studio.

Get back together with Elaine. Direct Josh, Elaine, and Matt in plays at the Theatre Studio, Inc.

Found Dutch West, an internet-based sketch comedy group, with Josh, Elaine, Vince, Matt. Make videos for CollegeHumor, SuperDeluxe, and Comedy Central.

Note neighbor comedy group, Olde English, featuring Adam Conover. 

Do improv in the basement of a bar. Take classes at UCB. 

Get hired by CollegeHumor as Director of Original Content. 

Develop first web series: "Street Fighter the Later Years" and "The Michael Showalter Showalter."

Develop more web series: "Prank War," "Hardly Working," and "Jake and Amir." Break record for most-watched internet content, beating out SuperDeluxe, Dot Comedy, and This Just In. 

Win Aspen Rooftop Comedy and ENCY Awards.

Adopt a cat, Mr. Hammers.

EP, direct, and star in "The CollegeHumor Show" on MTV. Show is quickly cancelled. 

Promoted to President of Original Content. 

Co-create, co-write, direct, and edit Elaine's web series "Very Mary-Kate." Series is profiled in the Washington Post and Wall Street Journal.

Win a bunch of Webby Awards.

Elope with Elaine in Las Vegas. Make Very Mary-Kate episodes while there.

Named a Forbes "30 Under 30" in the Media category. 

Develop more web series: "Troopers," "Badman," "The Adventures of Kim Jong Un," "Hello My Name Is." Also co-create, co-write, direct, and edit "Precious Plum," starring Josh and Elaine. 

Hire Adam Conover as a writer-performer. 

Win a bunch of Telly Awards. Named an MCN "40 Under 40."

Move to LA to form Big Breakfast, CollegeHumor's offshoot production company. 

Create "The Britishes," a sketch series for DirecTV, co-starring Elaine and Josh. Win pilots for "Middle of the Night Show" on MTV and "Adam Ruins Everything" (with Adam Conover) on TruTV. 

Make Weird Al's music video, "FOIL."

"MOTNS" and "Adam" both picked up for series.

EP "The Comedy Music Hall of Fame" on IFC, "Fatal Decision" on go90, and "Bad Internet" on YouTube Red. 

Make a music video with First Lady Michele Obama. 

"MOTNS" cancelled. "ARE" becomes #2 show on truTV. 

EP "Time Traveling Bong" on Comedy Central, "Rhett and Link's Buddy System" on YouTube Red, and "I Want My Phone Back" on Watchable / Facebook Watch.

Adopt a dog, Finnegan.

"Hot Date," starring CH cast members Emily and Murph, picked up by POP.

"Adam" enters into its second season.

Announce DROPOUT, CH's new subscription platform, worked on in secret for two years.

For DROPOUT, write and direct "See Plum Run," a rebooted "Precious Plum," starring Josh and Elaine. Also EP "Cartoon Hell," with intro vocals by Weird Al.

"Adam" enters into its third season.

With Dropout, launch a new title per month: "WTF 101," "Dimension 20," "Um Actually," "Total Forgiveness," and more.

Create and host "Game Changer," a game show in which the players don't know the rules.

"Adam" enters into its fourth season and "Hot Date" into its second.

IAC shuts down CollegeHumor and lays everyone off.

Make a quick deal to purchase CollegeHumor from IAC.

The pandemic hits two days later.

CollegeHumor survives.

Dimension 20, Game Changer, Um Actually, and Breaking News all get subsequent seasons.

A Kickstarter for Um Actually's home game raises $400k in 24 hours.