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

on monday, ClipboardAn AI-powered platform that helps companies monitor their media coverage, has announced a $3 million seed funding round co-led by Mark Cuban, Commonweal Ventures, and Carpenter Capital.

The deal happened because Clipbook founder Adam Joseph took a long shot with a cold email that he never thought anyone would read, he told TechCrunch.

Joseph launched Clipbook in 2023 and generated $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 artificial intelligence to help companies track what the world is saying about them and their competitors in the press, via podcasts, and social media. So he wanted investors who understood this landscape.

Mark Cuban, who has founded media networks, starred in Shark Tank, written books, produced films, and conducted regular interviews on television, was at the top of Joseph’s list.

So, One evening in late 2024, Joseph drank a beer for courage and cold-mailed a one-page investment pitch to everyone on the list. There is no warm introduction.

The Cuban answered alone. It turns out he’s busy and inundated with pitches, and Cuban is still clearing his emails. He’s always looking for his next deal. “I’ve literally invested tens of millions of dollars in emails, and a lot of them have paid off and turned into unicorns,” Cuban tells TechCrunch about why he answered Clipbook.

But before Cuban opened his checkbook, he subjected Joseph to a series of tests. His first email response “was the 20 most skeptical questions he could ever ask,” Joseph recalls.

Cuban admits that he is somewhat famous because of the movie Shark Tank.

“When I start seasoning them with pepper, they wilt, right? They wilt or get angry at a certain level,” Cuban explained. “It’s their baby. They don’t like to be questioned, right? But Adam was like, bam, bam, bam, bam, bam.”

After answering each question to Cuba’s satisfaction, the billionaire asked Joseph to prove the product by preparing a report for a Cuban child: Cost Plus Medicines. It is an online pharmacy and public benefit corporation he co-founded in 2022 that prices medications at affordable prices with a 15% markup.

“I know how difficult it is to do PR and marketing research, learn about (competing) companies, and find out what people are saying about your own company,” Cuban explained.

That’s not to say that Clipbook doesn’t have plenty of competitors doing this work, too. Sprinkler is among the most famous, but others include social sprout, embodiment, Hootsuite, and more.

Joseph emphasizes that Clipbook is different because it was built from the ground up to be native with AI technology. This means that it doesn’t just look for keywords, but it understands the context of how those words are used. She knows that media references to “cost” and “drugs” are not the same as searching for CostPlus medications. He knows the difference between someone named “Adam Joseph” and someone who is the founder of Clipbook.

Joseph stresses that being native (rather than AI-powered) also helps it look for places other products struggle to reach, such as audio and video references in podcasts. He said he built this product after doing public relations work at Boston Consulting Group, so he experienced the pain of media sentiment research firsthand.

Joseph quickly produced the report for Cuba that “fixed” the relevant references, Cuban says. He was particularly impressed when he discovered a previously unknown podcast conversation about pharmacy benefits services.

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

Joseph declined to share updated ARR numbers with TechCrunch since closing his seed round — except to say that the company has grown since its first million. But the company now counts 200 companies as clients, including Weber Shandwick and his old employer, Boston Consulting Group, he says.