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How AI PR startup Clipbook landed Mark Cuban’s investment via cold email

TechBrunchBy TechBrunchDecember 1, 20254 Mins Read
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On Monday, Clipbook, an AI-powered platform that helps companies monitor media coverage, announced a $3 million seed round co-led by Mark Cuban, Commonweal Ventures, and Carpenter Capital.

The partnership came about because Clipbook founder Adam Joseph made a fiasco with a cold email that he didn't expect anyone to read, he told TechCrunch.

Joseph launched Clipbook in 2023 and has grown it to $1 million in annual recurring revenue, he said. At that point, about a year ago, he felt ready to find investors.

“I literally made a list of the top five media investors in the world,” Joseph recalls. His product uses AI to help companies track what the public is saying about them and their competitors in the press, podcasts, and social media. So he was looking for an investor who understood the situation.

Mark Cuban, who founded a media network, starred on “Shark Tank,” writes books, produces movies and is regularly interviewed on TV, was at the top of Joseph's list.

So one night in late 2024, Joseph plucked up the courage to grab a beer and cold email everyone on his list with a one-page investment pitch. There is no warm intro.

Only Cuban answered. It turns out that even though Cuban is busy and inundated with sales pitches, he still looks through his email. He's always looking for his next contract. “I've literally invested tens of millions of dollars into email, and a lot of it paid off and became a unicorn,” Cuban told TechCrunch of his reasons for responding to Clipbook.

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But before Cuban pried open the checkbook, he put Joseph through a series of tests. The first email response was “20 of the most skeptical questions you could ever ask,” Joseph recalls.

Cuban admits that he became quite famous on “Shark Tank.”

“When you start peppering it, it wilts, right? When it wilts or it gets to a certain level, it gets angry,” Cuban explained. “It's their baby. They don't like being questioned, right? But Adam was just like, bam, bam, bam, bam, bam.”

After all the questions were answered to Cuban's satisfaction, the billionaire asked Joseph to produce a report for Cuban's own baby to prove the product, Cost Plus Drugs. It is an online pharmacy and public interest corporation that he co-founded in 2022, and sells medicines at affordable prices at 15% above cost.

“I do research for PR and marketing, [competitor] It’s about finding out what people are saying about your company,” Cuban explained.

Image credit: TechCrunch

That's not to say Clipbook doesn't have a number of competitors doing similar things. Sprinklr is the most well-known, but others include Sprout Social, Emplify, Hootsuite, and more.

Joseph claims that Clipbook is different because it is built from the ground up to be AI-native. That means we don't just scan for keywords, we also understand the context of how those words are used. The company knows that media references to “cost” and “drugs” are not the same as looking for cost-plus drugs. It knows the difference between someone named “Adam Joseph” and the founder of Clipbook.

Being AI-native (not an AI bolt-on) also helps search for places where other products struggle, such as audio and video references within podcasts, Joseph argues. He built the product after working in PR at Boston Consulting Group, so he experienced first-hand the pain of media sentiment research, he said.

Joseph quickly produced a report for Cuban that really “nailed” the relevant references, Cuban says. He was particularly impressed when he unearthed a previously unknown podcast conversation about pharmacy benefit services.

After several days of negotiations, Cuban agreed to send Joseph a term sheet. The first part of that seed round closed in early 2025, with other investors pouring in over the next few months.

Joseph declined to share the latest ARR numbers with TechCrunch since the seed round closed, but said the company has grown from its initial 1 million. But the company now counts 200 clients, including Weber Shandwick and his former employer, Boston Consulting Group, he said.



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