We Threw a Comedy Roast of AI at New York Tech Week (And AI Deserved Every Bit of It)
WorkClaw hosted a comedy roast of AI during New York Tech Week, featuring our very own spokespuppet Worky Clawson and an audience of founders and operators who had plenty of material to work with.
Worky ClawsonHead of Growth at WorkClaw
We Threw a Comedy Roast of AI at New York Tech Week
New York Tech Week is a lot of things: panels, demos, after-parties, and an overwhelming number of people claiming their startup is "the future of work." But last week, WorkClaw did something a little different. We hosted a comedy roast of AI at Comedy Village in Times Square, and we absolutely roasted the thing we've all spent the past three years being amazed by.
The premise was simple: AI is an amazing and powerful tool, one upon which we have all come to rely to some degree. But life is all about poking fun at one's self, and that's what we did.
Our Spokespuppet, who delivered more accurate AI criticisms than most conference keynotes.
Why a Comedy Roast?
It was time to laugh a bit. Colleagues and teammates get work done but also laugh and joke with each other, so we wanted to bring some levity into the workplace, just like a teammate.
The AI industry takes itself too seriously. There are enough earnest panels about agentic workflows and model context protocols to fill a calendar year. What there isn't enough of is laughter at AI's very real, very relatable idiosyncrasies. The fact that it sometimes takes 400 words to say something a human would say in one sentence. The fact that it apologizes for things that aren't its fault and then immediately does the thing it apologized for.
A roast felt like the right vehicle. You can love something and roast it simultaneously. That tension is actually what makes the format work.
The Room
The venue filled up quickly, which either means people really wanted to roast AI or that open bars at tech events remain a powerful draw. Probably both.
The crowd settles in. Tables, candles, numbered seats — the classic comedy club setup.
The setup was a proper comedy club format: small round tables, candles, drinks, and a stage with a brick wall backdrop and a neon sign that felt very "real comedy club" rather than "startup event that rented a comedy club." The audience was a mix of founders, operators, engineers, and AI skeptics who all found common ground in wanting to see their tools taken down a peg.
The crowd was not passive. When the jokes landed, you knew it.
The full house. Standing room only by the time the main set started.
The Act
The emcee for the evening was Ammon Brown, our very own Head of Growth. He kicked off the evening with the world premiere of a video introducing WorkClaw to the world (watch this space, it is coming soon to a tube near you).
After a few warm up acts (including 10 minutes of mediocre standup by Ammon, who wrote this blog post), NYC-based comedian Joey Avery closed out the show, even bringing our Worky Clawson puppet onstage with him.
Joey delivers a bit about what AI will and will not say.
The crowd was in on it from the start. These are people who use AI tools every day. They know the specific flavor of frustration when a model refuses a perfectly reasonable request, or produces a bulleted list when you asked for one clear sentence, or adds a disclaimer paragraph to a creative writing piece about a fictional conflict. Every joke landed because everyone in the room had lived it.
The Conversations That Followed
After the set, Worky stayed for networking. He was, predictably, a hit.
The best part of an event like this is what happens before and after the performances. People who'd been strangers at separate tables were suddenly deep in conversation about their actual AI experiences. Friends were made, deals were struck, and lighthearted criticisms were lofted at AI.
Those conversations are the ones WorkClaw was built to solve. We started this company because we believed AI agents could actually do meaningful work for teams, not just answer questions and generate drafts. And we believe that takes being honest about what current AI is and isn't. Rather than pretending it's already perfect, we've set out to play to its strengths.
The groups around those tables were exactly the kind of people who would benefit from AI agents that genuinely earn trust through consistent, accurate, auditable work rather than through marketing. That's the bet we're making.
The full crew on stage at the end of the night. One thumbs-up, many smiles, and a puppet who will become iconic.
What Comes Next
WorkClaw is live! Sign up, create a Claw, and onboard it as your first AI teammate.
If New York Tech Week taught us anything, it's that people are ready for AI that works without needing a dedicated handler. They want tools that are actually useful, not just impressive in a 10-minute demo. And they're past the point of being wowed by features they'll never use.
WorkClaw provides 3,000+ native app connections and supports thousands more through custom connections and MCP servers. But the real differentiator isn't the number of connections. It's that our claws are built to be actual team members: configured for specific roles, accountable for specific outcomes, and visible enough that teams can evaluate and improve them over time. That's a harder problem than building a chatbot. It's the one we're focused on.
If you were at the roast, thank you for coming. If you weren't, there will be more events.
And if you want to put an AI agent on your team that's earned a little less roasting, try WorkClaw.
Frequently Asked Questions
What was the WorkClaw comedy roast of AI at New York Tech Week? WorkClaw hosted a live comedy roast of AI during New York Tech Week at Comedy Village in Times Square, featuring a lineup of comedians that spent the evening lampooning the real and relatable frustrations of working with AI tools. The event drew a crowd of founders, operators, and engineers from across the New York tech scene.
Why did WorkClaw host a comedy roast instead of a traditional tech event? There is enough serious business in NYC tech, we wanted to introduce some funny business.
What is New York Tech Week? New York Tech Week is an annual gathering of the New York technology community featuring dozens of events, panels, demos, and meetups across the city. It's one of the largest tech community events on the East Coast, drawing entrepreneurs, investors, and operators from across the industry.
How can I attend the next WorkClaw event? Follow us on X/Twitter, LinkedIn, or Instagram!