This comedian thinks he can help founders pitch their startup—by roasting them publicly

Want to test your pitching skills? New York City comedian Noah Obstfeld has a challenge for you at his Shark Tank-comedy-roast mashup show, Pitch Roast Live.

“Come in, take a plunge in the ice-cold water. Every other dive after that is going to be a lot easier,” Obstfeld told Founder Brew. “I’ve heard from founders afterward—the scary investor Zoom call or live pitch in front of an audience is not nearly as difficult.”

Pitch Roast Live asks founders to pitch their business for five minutes with slides in front of a crowd—and a panel of three comedians and one investor. The onstage judges make jokes about the company and then crown a winning founder at the end of the night. Anchored monthly in New York, the show will also travel to San Francisco, Austin, Dallas, and Miami.

But this is not a free-for-all. Creator and host Obsterfeld, who worked in finance before becoming a full-time comedian, has road tested the format since December 2024 to find the right balance between the comedy and business bonafides.

First, he specifically asks the investor to bring hard questions, as if they were really investing. “I don’t want them to be nice just because it’s a comedy show,” he added.

Obstfeld also capped the number of comedians at three, ensuring no one has to fight over the spotlight, and doesn’t like when they joke about “not understanding something.”

And as for the founders themselves: They’re the clear centerpiece. Obstfeld meets with each selected founder for at least one 30-minute prep call to make sure they’re ready for the room.

“I really want to showcase founders. I really want to give them an opportunity. This is not Shark Tank. It’s not going to change your life yet, but there are going to be connections in the room that are valuable,” he told Founder Brew.

Who should apply

Any full-time founder is encouraged to apply through the website or reach out, but Obstfeld does have a specific vision. Companies should be accessible to a general audience—this is a comedy show after all. He prefers that companies aren’t too in the weeds of technical fields like AI, crypto, or B2B SaaS.

“B2B SaaS is not funny,” he said, though he admits he’s sometimes been wrong in the past.

Past guests of the show include an AI clothes try-on app, a fitness platform that synchronizes with menstrual cycles, and new software for Congress.

So far, there has been no shortage of founders ready to take the stage. But, maybe that isn’t too surprising.

“Founders are perfect for this because they’re already very risk forward people,” he said. “They hear about a challenge or something that they’ve never done before, something that could be perceived as scary, and a lot of them really want to face it.”

Know your audience

Morning Brew’s own Dan Toomey, host of the video series Good Work, has joined the judging panel twice. His advice for founders about to pitch is relevant to the stage and the boardroom: Know your audience and tailor your message to them.

“There are some people that treat it like they are pitching to a VC and don’t recognize that they’re in a basement where people are drinking,” Toomey told Founder Brew. “You should acknowledge the room that you are in and the audience will be on your side,”

In fact, Toomey says some of the best founders he’s seen have leaned into the roast format. They turned the tables and came prepared with roasts for the comedians on the panel, or even the host.

“Please roast Noah,” he advised.