One Cold Email Changed Everything: How Clipbook Landed $3M from Mark Cuban

In a world where startup founders obsess over warm introductions and networking events, Adam Joseph did something almost unthinkable. He grabbed a beer for courage one evening in late 2024, opened his laptop, and sent a cold email to billionaire investor Mark Cuban. No connection. No mutual friends. Just a one-page pitch and a whole lot of guts.

That email just turned into a $3 million seed round.

Clipbook, the AI-powered media monitoring startup Joseph founded, announced in December 2025 it closed funding co-led by the Shark Tank star, along with Commonweal Ventures and Carpenter Capital. The deal proves that even billionaires still read their inbox when the right pitch lands.

The Bold Strategy That Worked

By late 2024, Joseph had bootstrapped Clipbook to $1 million in annual recurring revenue with over 200 clients, including major names like Weber Shandwick and Boston Consulting Group. It was time to scale.

The billionaire’s media empire spans networks, Shark Tank fame, and his own ventures like CostPlus Drugs. If anyone could grasp the value of automated media intelligence, it would be him.

So Joseph sent his one-page pitch to everyone on the list. 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 told TechCrunch. Despite his packed schedule, the Shark Tank investor still scans his inbox hunting for his next big deal.

The Shark Tank-Style Interrogation

Getting a response was only the beginning. Cuban’s first reply hit Joseph with what he called “the most skeptical 20 questions that he could ever ask.”

“When I start to pepper them, they wilt, right? They wilt or they get angry,” Cuban explained. “But Adam was just like, bam, bam, bam, bam, bam.”

Joseph answered every question thoroughly and confidently. That resilience earned him a real-world test: produce a comprehensive media monitoring report for CostPlus Drugs, Cuban’s online pharmacy that sells medications 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 said.

Within days, Joseph delivered. The report not only captured relevant references but also uncovered a previously unknown podcast about pharmacy benefit services, exactly the kind of hidden insight that makes media monitoring truly valuable.

After reviewing the proof and negotiating for a few days, Cuban sent over a term sheet. The deal was done.

What Makes Clipbook Different?

The media monitoring space isn’t new. Established players have dominated for years. So what makes Clipbook special enough to attract a billionaire investor through a cold email?

Clipbook is AI-native from the ground up, not a traditional tool with AI bolted on as an afterthought. This fundamental difference is everything.

Traditional media monitoring tools scan for keywords. If you’re tracking “Apple,” they’ll show you every mention, the tech company, the fruit, or someone named Apple. You drown in noise while missing what actually matters.

Clipbook’s AI understands context. It knows the difference between a reference to “cost” and a mention of “CostPlus.” It can parse audio and video content from podcasts and broadcasts, not just written text. It aggregates data from over 1 million sources news, TV, radio, social media, podcasts, and policy documents, then surfaces only actionable intelligence.

Joseph built this from experience. He previously worked at Boston Consulting Group doing PR work and felt the pain of media sentiment research firsthand. Clipbook solves what the company calls the “Derek problem”, every communications team relying on a junior intern to manually monitor media.

The platform doesn’t just dump raw data on users. It automatically filters out irrelevant content, ranks insights by importance, and formats reports visually. Users get a dynamic, searchable archive automatically tagged and organized by stakeholder, topic, or region.

The Technology Behind the Success

Clipbook’s AI can disambiguate names distinguishing which “Adam Joseph” in the media is the founder versus any other person with the same name. It understands sentiment and tone, identifies emerging trends before they go mainstream, and creates custom briefings tailored to specific team goals.

For PR agencies, this is transformative. They can deliver enterprise-grade media insights without enterprise-grade budgets or team sizes. Small boutique firms can compete with major players because Clipbook levels the playing field.

For corporate communications teams, it means responding faster when narratives shift, understanding what stakeholders are saying in real-time, and making strategic decisions based on comprehensive intelligence rather than scattered Google searches.

“AI is a tectonic shift, and communications is one of the largest professional services segments globally,” Joseph said. “PR teams that just aggregate Google results are dead.”

Who’s Using Clipbook?

Clipbook now serves over 200 corporate customers across multiple sectors. PR firms monitor client coverage and competitive landscapes. Political campaigns track opponents and policy discourse. Consulting firms like Boston Consulting Group use it for strategic intelligence. Financial institutions monitor market sentiment and regulatory developments.

The platform has been particularly popular in political and public affairs spaces. The South Carolina Democratic Party, for example, has used Clipbook to supercharge their communications program.

Customer feedback highlights the value: “Clipbook has made monitoring press and mentions easier than ever. I look forward to seeing it in my inbox every morning!” Another noted: “Our clients see enterprise-grade media insights from a boutique firm. We’re able to punch above our weight because of Clipbook.”

Star-Studded Investor Support

While Cuban co-led the round and grabbed headlines, the full investor roster includes Danny Werfel, former IRS Commissioner and Boston Consulting Group’s Global Head of Public Sector, and Dan Pfeiffer, former White House Communications Director.

These aren’t just check-writers, they’re operators who understand communications, media, and government.

“Clipbook is changing how organizations understand and respond to the world around them,” Werfel said. “Throughout my work in consulting and government, I saw how fragmented information hinders effective decision-making. Clipbook delivers clarity, speed, and actionable insight.”

Cuban’s endorsement was equally strong: “Clipbook keeps me informed. The right intelligence is invaluable to a business, and Clipbook takes that intelligence and makes it actionable. Backing Adam Joseph and the Clipbook team was a no-brainer.”

What’s Next for Clipbook?

With $3 million in fresh funding, Clipbook plans to invest across product development, engineering, and go-to-market strategies. The goal is to expand its position as the leading vertical AI player in communications.

Joseph, a PRWeek “40 Under 40” honoree and Milken Institute Young Leaders Circle member, has ambitious plans. “We bootstrapped to rapid scale, and with this capital, we will supercharge our profitable growth to join the fastest growing enterprise AI businesses in the world,” he said.

The company is well-positioned in a massive market. Communications and public relations represent one of the largest professional services segments globally, and AI is fundamentally transforming how that work gets done.

The Bigger Lesson: Bold Moves Still Work

Perhaps the most inspiring part isn’t the technology or funding amount, it’s the reminder that cold outreach can still work if you do it right.

Joseph didn’t have insider connections. He just identified the right investor, crafted a compelling pitch, and hit send. Cuban’s willingness to read cold emails and invest from them has created multiple unicorns over the years.

For founders watching from the sidelines, the lesson is clear: make your list of ideal investors, craft your best pitch, and hit send. The worst they can do is not respond. The best? Write you a multi-million dollar check.

Just make sure you grab that beer first for courage, and be ready to answer 20 very hard questions.