Where Silicon Valley Roasts Itself

Austin Nasso, Nikita Oster, and Jesse Warren spent years toiling in the tech mines, racking up paychecks and blitzing through code while attempting to ignore the dull, aching feeling of existential boredom. 

Warren interned at SpaceX and Microsoft before joining a San Francisco startup as a software engineer. Nasso spent years coding for Microsoft, and Oster — a Russian immigrant who graduated high school when he was just 13 — recalls long nights as an independent game developer, falling asleep in his chair with his Oculus headset still affixed to his face. 

It’s no wonder their comedic barbs hit so close to home when they roast other tech workers, live on stage in front of a crowd. One of their most popular clips on social media features a software engineer named Neil, who works at Squarespace and lives in San Francisco. It’s almost too easy of a hit for Nasso. 

“Neil follows the Jain religion, which believes the path to enlightenment is reducing harm to living things. As long as those living things aren’t low-income families he pushed out of the Mission,” Nasso says in the clip, eliciting a wince from Neil and oooooohs from the audience. “You say you have imposter syndrome. Makes sense. All of your neighbors know you’re not the family that used to live there.” 

This public flagellation is the heart of the Socially Inept Tech Roast Show, which is touring across the country and seeking techies brave enough to be picked apart for a laugh. The 90-minute production flits between improvised punchlines, social commentary and teasing of tech tropes, with an undercurrent of wink-wink in-jokes that reinforce the comics’ understanding of Silicon Valley culture. 

“We were like you once, living from 12k paycheck to 12k paycheck at soul-sucking tech companies,” the Tech Roast Show website says. “One day after breaking production, we decided we had enough.”

Yet the show offers more than easy mockery of America’s most culturally dominant industry, and the well-monied tech workers who comprise a modern petit bourgeoisie. There is a dose of mockery, of course. But the troupe demonstrates a keen sympathetic streak with its humor, making the show feel as much a toast as a roast—consensual sadomasochism for a self-aware crowd. 

“Having been in the trenches of tech, and really questioning my purpose, there’s a shared experience with our audience,” Warren told me after their Dec. 10 show.

Nasso and Warren devised the concept for their live show in August 2018 while still working in tech during the day, shortly after producing a one-night-only roast of the Seattle comedy scene. Looking for a clever angle for their next event, the duo turned inward to examine their day jobs. Could a takedown of Seattle’s booming tech industry draw a crowd? Uncertain but inspired, they spent hundreds of dollars on Facebook ads to spread the word. 

Nasso and Warren were shocked when they sold out an October show at the 200-person Laughs Comedy Club in Seattle. They took this as a sign that the project would be  successful in the long-term and added more shows: small roasts in Seattle, and two San Francisco events in early 2019. That summer, Warren and Nasso brought on Lee Yang, a comp-sci whiz whom Warren had met in an improv class, to serve as a full-time producer. The final piece was Oster, a former game developer and a familiar face in the Seattle stand-up scene.

The early successes proved the value of their premise. Tech continues to be an “all encompassing, ever-expanding” imposition on our lives whether we like it or not, Nasso said. That includes the absurd ways the industry has warped wealth for a small subset of the population: “Straight out of college, I remember like my buddies were getting $70,000 sign-on bonuses with like $60,000, $120,000, $240,000 in stock,” Nasso said. “It’s just this insane thing where these college grads are making more than what both of their parents were making combined after 20-year careers. And there's just a lot of ridiculousness that comes with that terrain.”

Warren nodded, noting that the sudden cash often fails to solve the “existential dread” of tech-work monotony. 

“Now you're like, ‘What am I passionate about?’ This is a common dilemma in our audience,” Warren said. “It seems like every time we do a show, people come up to me and they say, ‘Hey man, I secretly want to be a sushi chef, but I'm in tech’s golden handcuffs.’ ‘I'd like to be an experimental DJ, but it makes no sense.’ And I think that they like that we actually bailed.” 

By the start of 2020, the show stood on the cusp of crucial growth. Then COVID hit, and everything skidded to a stop as tour venues shut down. Desperate, the quartet pivoted to hosting shows via Zoom and recording custom roasts by request, Cameo-style  — an “innovative” but ultimately clumsy alternative, Warren said. 

Gassed and demoralized, they put the project into a deep hibernation. 

“We completely, umm, failed the company and didn't do anything, to Lee's dismay and anger,” Nasso said with a sarcastic laugh. 

Bored and understimulated, Nasso and Warren turned their attention toward a shorter form of content: TikTok. Nasso gained more than 400,000 followers by pumping out Trump impressions throughout 2020. Warren went far more niche, building a cult fandom by masquerading as a shirtless self-help dragon named “Bartholomew the Terrible.” Yet despite the early highs of going viral, it wasn’t long before the repetitive nature of bowing to the TikTok algorithm led to burnout. 

(Meanwhile, Oster had already beaten them to the exhaustion stage of the hiatus. He recalled 2020 simply: “I was severely depressed and writing jokes for Russian television.”) 

A full year passed before they reconvened in March 2021, when large indoor venues started to reopen. They remained worried about the loss of momentum during the pandemic as they planned a fall tour. Even worse, the Facebook ads that had been so crucial to their ticket sales were now ineffectual and more expensive. Something about the algorithm had changed, and with their marketing strategy in flames, the group hemorrhaged money and fought over what to do. Nasso even admitted he had “one foot out the door.” 

What saved them, ironically, was pivoting their act to social media. Nasso and Warren were adamantly against the idea — “I think I’m still scarred by the dragon thing,” Warren says — but Yang urged them along, posting clips of past roasts as well as new comedy bits and man-on-the-street interviews. Slowly, their follower count on TikTok and Instagram rose. As of writing, the Tech Roast Show Instagram account has 229,000 followers, and their TikTok videos have gotten 4.5 million likes. Today, they’re able to sell out shows without spending a single cent on ads.

Social media helped sell their unique personalities and group chemistry, which has only improved with time. Nasso is the bruiser of the bunch, serving up deadpanned punchlines that cut like proper insults. Warren has a more sly charm, often resisting a smile as he weaves tech references into his bits. Oster shines as the weary philosopher-cynic — wry criticism, made hilarious through context. Yang directs the production from behind the scenes, including picking through roast nominees for each show and interviewing them at length to harvest comic material. 

As for how bloody that roast gets, well, your mileage may vary. The guest of honor at the Dec. 10 show in Mountain View, California, was a cherubic twentysomething named Nijat, who chuckled and nodded as the trio lobbed their barbs. They teased him for losing a pricey Steph Curry NFT when the cryptocurrency exchange FTX crumbled. They roasted his role as a project manager at corporate video game goliath Electronic Arts, making light of how it was once dubbed “worst company in America.” Elsewhere, Nasso riffed on Nijat’s love of playing the EA franchise FIFA: “EA stock is as flat as the 600 people who died building FIFA stadiums in Qatar for the World Cup,” he said, eliciting a burst of awkward laughs from the crowd. 

All in all, a gentle affair, and nothing to sway Nijat from tech, given how assuredly he told the crowd that, despite the mockery, he still finds his career in tech to be “fantastic.” 

Perhaps more effective was a skit pitting awkward techies against ChatGPT, which the New York Times dubbed “the best artificial intelligence chatbot ever released to the general public.” Warren played the role of a distraught friend who had lost their job; the volunteers were tasked with giving a more empathetic reply than the chatbot. 

Easier said than done: “Yeaaaauuuh, one hundred percent,” one preppy blond engineer blurted out after a pregnant pause. “Maybe you want to work for me? Or like, go to a coding bootcamp?” 

That offering paled in comparison to the more nuanced response on the screen above the stage from ChatGPT: “I can’t imagine how hard this must be. I want you to think about the fact that, while you may have to put in a bit of extra work, you can overcome this.” The crowd burst into cackling laughter, seemingly satisfied with a joke about tech workers being more robotic and out-of-touch than a literal chatbot. 

But if anyone in the crowd expected an evisceration, they didn’t get it—and maybe that’s the point. While the commentary can hit hard, Socially Inept’s show is clearly a roast for people in tech, not one for those who hold serious grudges against the industry and its sins. They’ve even drawn interest from some bigger Silicon Valley figures, too; on Dec. 10, the crowd buzzed with excitement as Kyum Kim, co-founder of the anonymous professional networking app Blind, took the stage for a voluntary roasting that felt more like a softball interview. 

“For techies, it’s a very intimate relationship they have with these giant, non-human entities. And it can be very isolating to have your lifestyle and social circle be in large part determined by your relationship to that non-human thing, if that makes sense,” Oster said. “I think we try to be as empathetic as we can be to people. Of course a roast is supposed to be punchy. But it wouldn’t work if we were simply mean.”

“I think a majority of our audience feels trapped, in a way,” Nasso said. “They don't feel fulfilled by the work they're doing. They have other facets of their personality that they want to explore. But for whatever reason, they're afraid to.” 

He paused for a beat. “Is it egotistical to think that we broke out of that?” 

Warren shakes his head firmly. “We’re still afraid to break out… well, I’m still afraid!”

Perhaps their closeness to the material, and their audience, is why the roast can feel like a bloodless affair — enough to draw ooohs from the crowd, but not so incisive as to turn them off. It’s a delicate balance to strike, especially when tech remains one of the most divisive topics in the American zeitgeist — fueled by the promise of a disruptive utopia, but riddled with dubious ethics, profit motives, and cultural blind spots. 

There’s certainly no dearth of things to roast when it comes to Silicon Valley’s boom, which Warren aptly compares to the oil rush of the early 20th century. Its well-paid workers are forced to push a wheel of presumed progress, too often at the whim of egomaniacs with a propensity for exploitation, bullying, and excess. The Zuckerbergs and Thiels of the world just keep throwing their weight around; meanwhile, ground-floor techies are wrangling burnout and getting laid off en masse. 

Elsewhere, the industry remains dominated by white men, while women and Black and brown workers suffer disproportionate rates of harassment and lower wages. And even though tech workers tend to lean politically liberal, the cohort can seem clueless (or just unrepentant) about the people they’ve displaced in regions like the Bay Area, even as they watch tent encampments pass from the cabin of their private company bus.

Nasso, Oster and Warren clearly want to satirize this meld of slapdash ambition, dystopian infrastructure, and deep-seated greed that runs rife in tech. But you can sense a limit to the subversion, too. Revealing techies’ “total compensation” (the insider word for one’s base salary plus benefits like bonuses) is a favorite running gag for the crew, both in live shows and their roaming street interviews. But is it effective comedy if the most common reaction from the audience is merely aspiration? 

To be fair, the group isn’t actually trying to push people out of tech. In a turn of meta irony, they’re using their social media gains to do paid partnership content for Hired.com—quite literally recruiting more people into tech. Nasso, Oster and Warren are adamant they remain believers in the potential of tech innovation; the troupe is more intrigued by self-awareness than an industry exodus, Oster said. 

“There is a gradual misalignment that can happen if your interests are constantly intertwined with a big tech company. It can take you to a cold space,” he said. “So I like to think that by making fun of these corporate, sometimes robotic traits people develop while working in this culture, we’re urging them toward a warmer, more human place.”

It was obvious that there were more grins than soul-searching cringe in the crowd as cheery fans lined up for photos with the comics after the Dec. 10 roast. What would the trio do if someone truly wretched — say, a Sam Bankman-Fried or Elizabeth Holmes — appeared in the audience one day? 

The question sparked a flurry of debate on whether they would ever bring such a figure onstage, as well as how savage the jokes could get. For now, however, there are no such targets apparent in the audience. “We roast people we don’t believe to be truly sinister,” Nasso points out. 

Perhaps that will change one day, as the Tech Roast Show continues to grow in visibility and appeal, especially to Silicon Valley’s elite. 

“It’s all a ridiculous feast, and it really needs a jester,” Oster said.