Sometimes the boldest moves pay off. Clipbook just announced a $3 million seed round co-led by Mark Cuban after founder Adam Joseph sent a cold email that turned into an investment - proving that even billionaire Shark Tank judges still read their inbox when the pitch hits right.
Clipbook founder Adam Joseph never expected his Hail Mary email to work. But when Mark Cuban replied with what Joseph calls "the most skeptical 20 questions that he could ever ask," he knew he had a shot at something big. On Monday, the AI-powered media monitoring startup announced a $3 million seed round co-led by Cuban, marking one of the most unconventional investor courtships in recent memory.
The story starts with Joseph's pragmatic approach to fundraising. After bootstrapping Clipbook to $1 million in annual recurring revenue by 2024, he felt ready for institutional capital. "I literally made a list of the top five media investors in the world," Joseph told TechCrunch. His AI platform helps companies track media mentions across press, podcasts, and social media, so he wanted investors who understood that landscape.
Cuban topped the list. The billionaire's media empire spans networks, "Shark Tank," books, movies, and constant TV appearances. So one evening in late 2024, Joseph grabbed a beer for courage and fired off a one-page pitch to his entire list. No warm introductions, no mutual connections - just a founder betting everything on a cold email.
Only Cuban responded. "I have literally invested tens of millions of dollars from emails, and a lot of them have paid off, turned into unicorns," Cuban explained to TechCrunch. Despite his packed schedule and constant pitch bombardment, the Shark Tank star still scans his own inbox hunting for his next deal.
But Cuban wasn't writing checks yet. His first response hit Joseph like a "Shark Tank" interrogation. "When I start to pepper them, they wilt, right? They wilt or they get angry at a certain level," Cuban said. "It's their baby. They don't like to be questioned, yeah? But Adam was just like, bam, bam, bam, bam, bam."
Surviving the question gauntlet earned Joseph a real test: produce a comprehensive media report for Cuban's CostPlus Drugs, the online pharmacy he co-founded in 2022 that sells medications at cost plus 15%. Cuban knew firsthand how painful PR research could be. "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," he explained.
