Name: Ben Sheehan

Age: 35

Hometown: Washington, D.C.

Now Lives: In a two-bedroom condo in the Hancock Park section of Los Angeles, with his fiancée, Jackie, and his dog, Chooch.

Claim to Fame: Until 2016 Mr. Sheehan was the head of talent for the humor site Funny Or Die, in charge of concocting outrageous skits with celebrities, like when Michael Bolton starred as himself in a spoof screen test for “Office Space.” Now he’s using humor for civic education. His nonprofit, O.M.G. W.T.F. (it stands for “Ohio, Michigan, Georgia, Wisconsin, Texas, Florida”), explains how the government works to millennials and Gen Z-ers — “a.k.a., the people who have been deprived of civic education these last 20 years,” Mr. Sheehan said.

Big Break: In 2013, when he was a consultant for Funny or Die, charged with getting more musicians on the site, he ran into Scooter Braun, Justin Bieber’s manager, at a party. On the fly, Mr. Sheehan made up a story about how the site had wanted to book Mr. Bieber for the talk show “Between Two Ferns.” Before Mr. Braun got back to him, he told his bosses at Funny or Die that Mr. Bieber had said yes. His bluff wasn’t caught, he was hired full-time, and he picked up two Webby awards for pulling it off.

Latest Thing: To underscore what he believes is the absurdity of some oddly shaped congressional districts, Mr. Sheehan is selling jewelry in the shape of those gerrymandered districts. “We couldn’t even make a district in Ohio, OH9, because the jewelry kept breaking,” he said, referring to a district that is 120 miles long and connected at one part by a 20-yard-wide bridge. The jewelry was created for the 2018 midterm elections. He also published a book in April, “OMG WTF Does the Constitution Actually Say,” that got shout-outs by Chelsea Handler, Ilana Glazer and Hillary Clinton.

Next Thing: A “kid safe” version of the Constitution book. (Asked what “kid safe” meant, Mr. Sheehan said, “There won’t be profanity!”) The book was written by kids, and it has illustrations for them. Copies of the book will be sent to schools.

Side Gig: In his spare time, Mr. Sheehan plays guitar and sings backup in a 1990s cover band called Jumperwall (“We start with ‘Jumper’ from Third Eye Blind and usually end with Oasis’s ‘Wonderwall,’” he said, explaining the band’s name.) Darren Criss is the lead singer and performs occasionally with special guests. “The band kind of pools its contacts to see who we are friendly with, and who we can get to perform,” Mr. Sheehan said. In February, he emailed Weird Al Yankovic, “and he just said yes.”