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

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

The deal happened because Clipbook’s 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 bootstrapped it to a million dollars in annual recurring revenue, he said. At that point, about a year ago, he felt he was ready to find investors.

“I literally made a list of the top five media investors in the world,” Joseph recalled. His product uses AI to help companies track what the world says about them and their competitors in the press, across podcasts and social media. So he wanted investors who understood that scene.

Mark Cuban, who has founded media networks, starred on “Shark Tank,” written books, produced movies and is regularly interviewed on TV, was at the top of Joseph’s list.

So, one evening in late 2024, Joseph drank a beer for courage and sent a one-page investment pitch via cold email to everyone on the list. No warm intro.

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

But before Cuban cracked open his checkbook, he put Joseph through a series of tests. His first email response “was the most skeptical 20 questions that he could ever ask,” Joseph recalled.

Cuban admits he’s fairly famous for that from “Shark Tank.”

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

After answering every question to Cuban’s satisfaction, the billionaire then asked Joseph to prove the product by producing a report for Cuban’s own baby: CostPlus Drugs. That’s an online pharmacy and public benefit corporation he co-founded in 2022 that prices drugs affordably at cost plus 15%.

“I know what a pain in the ass it is to do the research for PR and for marketing, and to learn about [competitor] companies, and to find out what people are saying about your own company,” Cuban explained.

Not that Clipbook doesn’t have plenty of competitors that also do this work. Sprinklr is among the best known, but others include Sprout Social, Emplify, Hootsuite, and more.

Joseph contends that Clipbook is different because it was built from the ground up to be AI native. That means it doesn’t just scan for keywords, but it understands the context of how those words are used. It knows that media references to “cost” and “drugs” is not the same as looking for CostPlus Drugs. It knows the difference between any person named “Adam Joseph” and the one who is the founder of Clipbook.

Being AI native (not an AI bolt–on) also helps it search where other products struggle to go, such as audio and video references in podcasts, Joseph contends. He built this product after doing PR work for Boston Consulting Group and so experienced the pain of media sentiment research firsthand, he said.

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

After a few days of negotiating, 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 figures with TechCrunch from since his seed round closed — except to say the company has grown since its first million. But the company now counts 200 companies as customers, including Weber Shandwick and his old employer, the Boston Consulting Group, he says.