At times it may be difficult to tell from his demeanor — the nervous pace of his speech, the often self-deprecating edge to his humor, the trademark baseball cap and horn-rimmed glasses — but so far, Josh Gondelman has actually acclimated quite well to adult life.
“I consider myself a pretty well-adjusted person, but I certainly have insecurities and anxieties,” Gondelman, 30, tells the Voice. “I guess I’m an extrovert with strong introvert sympathies.”
Since joining Twitter in 2009, Gondelman has been one of the few Internet personalities able to leverage a wry and witty social media presence into an actual career as a comedy writer and performer. His personal Twitter account was named one of the best feeds of 2012 by Paste magazine, and Modern Seinfeld — an account he co-created that same year which has the famed sitcom’s iconic characters squabbling over the present-day absurdities of online dating and millennial slang — currently boasts more than 868,000 followers.
The strength of Gondelman’s Twitter presence ultimately landed him a gig on HBO’s Last Week Tonight with John Oliver as a web producer and staff writer. And on Tuesday his debut book, You Blew It!: An Awkward Look at the Many Ways in Which You’ve Already Ruined Your Life, was released through Plume, an imprint of Penguin Random House.
“[You Blew It!] is like an etiquette guide that basically says, ‘You’ve already screwed up; you’re going to screw up again; life is a nightmare; you’ll always get it wrong, and that’s kind of fine,’” explains Gondelman, who co-wrote the book with Fast Company editor Joe Berkowitz. “‘That’s just what living is.’”
Despite his ability to help steer a wildly popular television program, or perform stand-up comedy five nights a week in New York City, Gondelman still seems to be hopelessly preoccupied by the small, everyday tortures of real-life human interaction. In many ways, You Blew It! reads like a continuation of Modern Seinfeld — a look at how average New Yorkers might navigate the awkward social contracts of dating, friendship and employment in 2015 — just without the characters of Jerry, George, Elaine and Kramer to help guide the neurosis along with their familiar banter.
With chapters that address important life skills such as breaking off plans with old pals, skipping out on house parties, and avoiding family members on social media like the plague, You Blew It! is, in essence, a book about nothing.
“It’s like Seinfeld in the sense that it’s very universal, but universal to people who live in cities in the present day and are of a relatively similar age bracket,” says Gondelman, who recently moved from Harlem to Williamsburg with his girlfriend, Slaughterhouse90210 creator Maris Kreizman. Despite his aversion to social gatherings, a launch party for his book will take place at Powerhouse Arena in Dumbo on October 13. “It’s not universal in the same way that when you have a kid you’ll love him more than you can understand — like that kind of universal, cultural, biological truth. It’s universal in the way of, like, when your mom joins Facebook your life becomes more complicated.”
Born and raised in the small, Boston suburb of Stoneham, Massachusetts, Gondelman began writing and performing sketch comedy while studying English at Brandeis University in Waltham. After graduating in 2007, he started working the Boston comedy club circuit, hoping to hone his stand-up chops while forging connections within the industry. But for how much technology has confused and complicated social interaction over the years — providing a great deal of fodder for Gondelman’s book — it was the Internet that ultimately gave him the platform he needed to break into humor writing.
“I wasn’t great at comedy by the time I graduated, and I didn’t have an especially strong network of people in show business,” Gondelman remembers. “[Twitter] helped me get my writing seen by people that otherwise wouldn’t have seen it. It helped me make friends with comedians and writers that I otherwise wouldn’t be acquainted with. And honestly, it helped me get my job at Last Week Tonight.”
With the rising popularity of Last Week Tonight as both a laugh-out-loud comedy series and surprisingly hard-hitting news program (John Oliver’s most recent tirade on the mental health debate is a must watch), Gondelman’s stature as a writer has steadily begun to grow, too. Now, with a gig on a hit TV show and a new book in stores, he is emerging as an unlikely star in the world of comedic writing.
Still, as a high-functioning neurotic, Gondelman seems most concerned with making others feel comfortable while trapped inside their own personal hells of social ineptitude.
“I guess the people I’m writing for are the people who are kind of chasing that dragon of, ‘Is this fun? Am I doing it right? Did I just screw up?’” he explains. “The people who are trying, but never quite feel like they nailed it.”