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    Home»Startups»How AI PR startup Clipbook won Mark Cuban’s investment with a cold email
    Startups

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

    PineapplesUpdateBy PineapplesUpdateDecember 1, 2025No Comments4 Mins Read
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    How AI PR startup Clipbook won Mark Cuban’s investment with a cold email
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    on monday, ClipbookThe 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 launches Clipbook in 2023 and aims to reach $1 million in annual recurring revenue, he said. At that time, 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. Their product uses AI to help companies track what the world says about them and their competitors in the press, podcasts, and social media. So he wanted investors who understood that view.

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

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

    Cuba alone replied. It turns out that despite the busy and busy pitches, Cuban still scans his emails. He’s always looking for his next deal. “I’ve literally invested millions of dollars from email, and a lot of them have paid off, turning into unicorns,” Cuban told TechCrunch about why he responded to Clipbook.

    techcrunch event

    san francisco
    ,
    October 13-15, 2026

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

    Cuban admits he’s pretty famous from “Shark Tank.”

    “When I start putting pepper on them, they blanch, okay? They blanch or they get angry at a certain level,” Cuban explained. “It’s their baby. They don’t like to be interrogated, yes? But Adam was just like, bam, bam, bam, bam, bam.”

    After answering every question to Cuban’s satisfaction, the billionaire asked Joseph to prove the product by preparing a report for Cuban’s own child: CostPlus DrugsIt is an online pharmacy and public benefit corporation, which he co-founded in 2022, that keeps drug prices affordable at 15% above cost,

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

    How AI PR startup Clipbook won Mark Cuban’s investment with a cold email
    Image Credit:techcrunch

    That’s not to say ClipBook doesn’t have plenty of competitors that do the same thing. Sprinklr is one of the most famous, but others include Sprout Social, Amplify, Hootsuite, and more.

    Joseph argues that ClipBook is different because it was originally created as an AI native. This means that it doesn’t just scan keywords, but it also understands the context in which those words are used. Know that references to “cost” and “drugs” in the media are not the same as looking for costplus drugs. It knows the difference between anyone named “Adam Joseph” and the founder of ClipBook.

    Joseph argues that being AI-native (not an AI bolt-on) also helps find where other products struggle to go, like audio and video context in podcasts. He said he created the product after doing PR work for Boston Consulting Group and experiencing the pain of media sentiment research firsthand.

    Cuban says that Joseph rapidly prepared the report for Cuba, which actually “tossed out” relevant references. He was particularly impressed when it revealed a previously unknown podcast conversation about pharmacy benefit services.

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

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

    Clipbook cold Cubans email investment Mark startup won
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