According to Business Insider, startup founder Adam Joseph secured a seven-figure investment from billionaire Mark Cuban for his AI-powered PR agency, Clipbook, entirely through a series of emails over the past 12 months. Joseph, who never appeared on “Shark Tank,” initiated the process with cold outreach, mentioning backing from Dan Pfeiffer of “Pod Save America.” Cuban responded the same day after a follow-up, requesting a sample report for his own name and asking how Clipbook differed from Google Alerts. The founder said the deal moved “more aggressively and faster” than expected, culminating after a few emails and a call where Cuban intensely pressure-tested both the business and Joseph himself as an entrepreneur.
Cuban’s email playbook
Here’s the thing about this whole exchange: it’s a masterclass in what a time-poor, savvy investor actually cares about. Cuban didn’t ask for a 50-page deck first. He asked for a tangible, immediate product demo—a report on himself. That’s genius. It tests the tech’s speed, accuracy, and relevance all at once. And his question about differentiation from Google Alerts? That’s the billion-dollar question for any SaaS startup, isn’t it? Basically, he cut straight through the fluff to the core value proposition. Joseph’s move to name-drop a credible backer like Pfeiffer in the follow-up was the nudge that probably got the reply. It’s social proof in its purest, most efficient form.
The founder vs. the business
What’s really telling is Joseph’s reflection that Cuban was vetting him, maybe even more than the business. “He had come in pretty hot with some pretty aggressive questions,” Joseph said, seeing that as a positive signal. That tracks. For early-stage bets, especially in a crowded field like AI, the investor is betting on the jockey, not just the horse. Can this person execute? Can they handle pressure? Will they fold when things get tough? Cuban’s email grilling was a mini version of the “Shark Tank” hot seat, designed to see how Joseph thought on his feet. Seems like he passed.
Cold email isn’t dead
This whole story is a massive counter-narrative to the idea that you need a warm intro to reach top-tier investors. Cuban has famously said he lives in his inbox. Joseph proved that if your pitch is sharp, your concept is clear, and you can demonstrate value instantly, the door can still swing open. But let’s be real—this is the exception, not the rule. For every Joseph, there are probably ten thousand emails Cuban ignores or archives. The pitch worked because it was specific, showed an understanding of a real pain point (PR sentiment tracking is a nightmare), and leveraged AI for a concrete solution. It wasn’t just “an AI for X” vaporware.
The AI-PR gold rush
Joseph’s insight that ChatGPT’s launch made it “immediately obvious” AI could transform PR is spot-on, and he’s far from alone. We’re seeing a flood of tools aiming to automate media monitoring, press release writing, and sentiment analysis. The race is on to own the workflow. Clipbook’s bet is that being more sophisticated than a simple alert—providing analysis, synthesis, and actionable insights—is where the real business value is. The hard part, as with all AI tools, will be moving from a clever demo to an indispensable, scalable platform that clients rely on daily. Cuban’s investment is a vote of confidence that this team might just pull it off. Now the real pressure test begins.
