TechCrunch Startup News How AI PR startup Clipbook won Mark Cuban’s investment from a cold email
Dec 1, 2025
Adam Joseph shares his remarkable journey of reaching out to Mark Cuban with a cold email that sparked a series of probing questions. The discussion highlights Clipbook's innovative AI-driven media monitoring capabilities, outperforming traditional tools. Cuban's legendary diligence put Joseph to the test, leading to a successful validation report that helped seal a $3M investment. Since then, Clipbook has rapidly expanded, serving a growing list of clients and proving its value in the competitive landscape.
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Cold Email Turned Into A Term Sheet
- Adam Joseph sent a cold one-page investment pitch to five top media investors after bootstrapping Clipbook to $1M ARR.
- Mark Cuban was the only responder and began the conversation that led to investment.
Bootstrap First To Strengthen Your Ask
- Clipbook grew organically to $1M ARR before seeking outside capital.
- Bootstrapping gave Adam credibility and a clear milestone before fundraising.
Pitch Investors Who Know Your Industry
- When fundraising, target investors who understand your vertical and product use cases.
- Adam Joseph prioritized top media investors because Clipbook addresses press, podcasts, and social monitoring.