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

Summary

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 in 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. Techcrunch event San Francisco | October 13-15, 2026 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, ba...