At this comedy show, tech workers are the butt of every joke

A second man chimes in: "How does it feel for your entire department to be a punchline?"'

This exchange would be horrifically rude in nearly every context. But comments like these are par for the course at Socially Inept, a comedy show hosted by former tech employees who make the audience — which is largely made up of tech workers themselves — the material.

I was introduced to Socially Inept a few months ago at a pitch "speed dating" event, where an early-stage AI founder and I bonded over our love of comedy. "You have to see these guys," the founder told me. Their entire act is roasting volunteers from the audience who work in tech. They uncover dirt about founders in real time and make fun of them onstage.

The concept was intriguing. Not only did this seem incredibly entertaining, but putting founders through a roast sounds like a fantastic form of due diligence. Can you pitch under pressure? Can you win over an audience? Can your company withstand a cursory Google search?

Lucky for me, Socially Inept was coming to New York for two nights in late April, so I bought my ticket and eventually headed to a show at the Peter Jay Sharp Theater on the Upper West Side. It was an interesting location choice: when I think of tech hot spots in the city, my mind goes to the Flatiron District, where VC firms like Union Square Ventures and Thrive Capital have set up shop, or Hudson Square, a downtown neighborhood on the west side of Manhattan where Google recently opened a $2.1 billion headquarters.

The uptown venue didn't seem to deter techies, though, as both the Friday and Saturday night shows were sold out. Arriving felt like I had been transported to happy hour at an SF-based tech conference, and I pushed through a lively crowd of people, most of whom looked to be in their early to mid-20s dressed in uniforms of t-shirts, jeans, sneakers, and glasses. As I settled into my seat, people around me sipped Liquid Death water, cracked open canned cocktails, and gossiped about which of their friends were leaving their Big Tech jobs to become startup founders.

Waiting for the show to start, I knew only the basics. Socially Inept was founded by Jesse Warren and Austin Nasso, two former Big Tech employees. Alongside co-host Nikita Oster, they host shows in tech hot spots around the country — New York, San Francisco, LA, Miami, Boston — lampooning the tech industry and using engineers, founders, VCs, and interns in the audience for their material.

The trio met back in 2018 when they were all living in Seattle. Although Warren and Nasso are both Big Tech alums — Warren interned at Microsoft and SpaceX and worked at an AI startup, while Nasso was a software engineer at Microsoft — the three ended up meeting through the city's comedy circuit, doing standup at bars and clubs in the area. At the time, the Seattle comedy scene was going through a "roast" phase, where many shows and open mics focused on making fun of specific people — think Comedy Central's legendary celebrity roasts of Justin Bieber, James Franco, and, recently, Tom Brady.

In a similar fashion, the entire first hour at Socially Inept was devoted to seemingly random attacks on audience members. Warren, Nasso, and Oster took to the stage wearing all black while crew members trolled the audience with video cameras and microphones, searching for the trio's next victim.

As an audience member, you need some tech savvy to fully appreciate the show: jokes are largely improvised reactions to tech stereotypes. Often, a person's job, résumé, or startup idea is what elicits laughs in the first place; the hosts' responses are just icing on the cake.

At a recent show in LA, the trio singled out a startup founder building VR concert experiences.

"Oh God, that sounds so stupid," Warren said as a crew member pulled up the company's website on the stage's big screen for the audience to make fun of. "I have to see how stupid this is."

At another show, the hosts brought onstage a former Silicon Valley Bank employee who now works for Microsoft building mixed-reality headsets for the Army.

"Imagine having a Windows gun," Nasso said as the audience laughed. "How shitty would that be?"

The rapid-fire roast format was incredibly funny, but my stomach was in knots for the duration of the 90-minute show as I feared being called on and subsequently humiliated for being a tech journalist. Many people there, however, seemed to revel in the chance to be made fun of and volunteered themselves.

At my show, an eager university student raised their hand at one point. When the microphone and camera came their way, they announced they had just landed a summer internship at eBay, prompting laughter and cheers from the audience.

The response from the stage: "Is eBay even a tech company?"

In roasting techies on the spot, Socially Inept has found a formula blending crowd work and audience participation with improvisation. The trio also has a knack for focusing their jokes on the humor in situations themselves rather than making someone feel really terrible about something they did or who they are as a person. It makes it seem like you're in on the joke, even when you're also kind of the butt of the joke.

The trio also actively solicits feedback via a form emailed to attendees and takes that advice to heart to ensure their comedy doesn't cross over to become mean-spirited.

"It's a difficult thing to navigate in public performance because there's a sort of economy of hurtfulness and the probability of hurting someone with the things you say, even if you have a right to say it," Oster said. "After every show, we debrief together and talk about the things that went well and the things that might have been uncomfortable.

Of course, it also helps that Socially Inept is largely punching up by poking fun at a coveted industry known for its high salaries and generous perks. And for the most part, it seemed like tech workers in the audience were very self-aware and took their roasts in stride. In an industry that at times seems so driven by public image, large compensation packages, impressive resumes, and thought leadership, it was really refreshing that people in the tech industry were so eager to make fun of themselves and, in some cases, were actively seeking out opportunities to be humbled.

'Tech people are just so wild, and there are so many different sub-cultures in it," Nasso said.

"And then it constantly changes, right?" Warren added. "They're doing one thing for a year, and then the next year, they're onto the next. So we can talk about that, and it's always fresh."