The Admiral Pattern Recognition Story: How a VC-Turned-Founder Spotted the Privacy Wave Before It Hit

 

The Admiral Pattern Recognition Story: How a VC-Turned-Founder Spotted the Privacy Wave Before It Hit

Grooveshark had reached 100 million users. The music streaming pioneer had 120 employees and a substantial business. Dan Rua had helped build it, then sold it to the music labels. Most operators would take the win, rest, maybe join another company as an executive.

Dan grabbed the product team and immediately started hunting for the next problem. But he wasn’t searching blindly. Two decades in venture capital had given him a specific lens for spotting disruption: he knew what the boardroom view looked like across 40 different companies.

In a recent episode of Category Visionaries, Dan Rua, CEO of Admiral, explained how that dual operator-investor perspective helped him see a massive wave coming—one that would fundamentally break the internet’s business model and create the need for an entirely new category.

The Boardroom Pattern That Revealed the Gap

Dan’s VC background at Draper Fisher Jurvetson had exposed him to a specific ritual that happens in every SaaS board meeting. The head of marketing walks in. They share visitor numbers. Then comes the critical question: how many email addresses, leads, conversions did those visitors generate?

“Picture the average SaaS company and you’re at the board meeting and the head of marketing comes in and says, hey, we got 15 million visitors last month. And you’re like, holy crap, that’s phenomenal. And you ask, you say, so how’d we do on getting email addresses or leads or what did that mean in terms of lead? And imagine the marketer says, well, no, we didn’t do anything like that,” Dan explains.

For a SaaS company, this answer would be unthinkable. It would trigger immediate concern about the marketing function’s competence. The entire infrastructure of modern B2B marketing—HubSpot, Marketo, Salesforce—exists because capturing and nurturing visitor relationships is obviously essential.

But when Dan looked at media publishers after Grooveshark, he saw exactly this scenario playing out. Publishers celebrated traffic numbers without any comparable infrastructure for building visitor relationships. They had analytics to measure ad impressions but nothing resembling the relationship management tools SaaS companies considered table stakes.

This wasn’t ignorance. It was because the old business model didn’t require it. Track visitors around the internet, serve them ads, collect revenue. No relationship necessary. The gap was invisible until you’d seen both worlds.

Seeing the Wave Before It Broke

The operator-investor lens did something else: it helped Dan spot converging trends that individually seemed manageable but together represented existential disruption.

“There was a disruptive wave coming through that was around privacy user empowerment, really disrupting the core business model of the Internet, starting with ad blockers,” Dan explains.

Ad blockers alone would have been a solvable problem. Publishers could have treated them as an annoyance, implemented basic countermeasures, moved on. But Dan’s pattern recognition told him this was just the leading edge.

“It’s ad blockers, it’s data blockers, it’s death of the cookie, where the browsers are killing off the tracking. It’s privacy consent like GDPR and ccpa. And all of that is a massive wave that’s just kind of undercutting the traditional business model of the Internet,” he adds.

This is where the VC pattern recognition becomes valuable. When you’ve watched 40 companies respond to market shifts, you develop intuition for which trends are isolated events versus fundamental restructurings. You learn to ask: if this continues, what becomes impossible? What new capabilities become necessary?

The answer was clear: websites would no longer be able to just track people around the internet and serve them ads. They’d actually have to build relationships. Which meant they’d need relationship management tools. Which didn’t exist.

The AdTech Versus MarTech Distinction

Dan’s investment experience revealed another critical pattern: billions of dollars had poured into AdTech, but that category was optimizing for the wrong future.

“AdTech is there to shoot ads very efficiently, whereas martech, or marketing automation is how do you talk to people and build some sort of relationship and hopefully some sort of value exchange over time that sticks,” Dan notes.

This distinction seems obvious once stated, but it requires cross-category experience to see clearly. AdTech investors and founders were focused on incrementally improving ad targeting, bidding, and delivery. They were optimizing the existing model.

What they missed was that the model itself was dying. Browser companies were actively killing third-party cookies. Legislators were passing privacy laws. Users were installing blockers. The infrastructure supporting programmatic advertising—the tracking, the behavioral targeting, the retargeting—was being systematically dismantled.

Meanwhile, in the SaaS world Dan knew from VC, an entire ecosystem of MarTech companies had built multi-billion dollar businesses on the premise that you need to build relationships with your audience. The tools existed. They just weren’t designed for publishers.

The Roller Coaster Education

Dan’s first company launch came during the late 1990s internet explosion. He joined Draper to launch their first East Coast fund in 1999—right before the dot-com crash.

“It was a roller coaster to be sure. There was massive growth and explosive growth. You know, there was one deal that I led that we did the seed round on it and within 18 months it sold for 10x plus. It was just a just massive value creation. But then we also, you know, we’re on the flip side of the dot com crash,” Dan recalls.

This experience—seeing both the euphoria and the collapse—taught pattern recognition lessons that most operators never learn. When business models shift, the companies that die aren’t always the ones with bad execution. Sometimes they’re the ones solving yesterday’s problem brilliantly while tomorrow’s problem goes unaddressed.

Vice and BuzzFeed had great content and massive audiences. What they didn’t have was direct relationships with those audiences when the platforms changed their algorithms. “If you built your model on viral social content and you had no sort of relationship with the visitor, you were just hoping that you were gonna always gonna get viral clicks from Twitter or Facebook and all of a sudden that changes, or you thought you were always gonna get search traffic from Google and that changes. Well then absolutely, you will have a rollercoaster ride of fortunes because you don’t control your most valuable asset, which is the visitors,” Dan explains.

The contrast: The New York Times and Washington Post invested in subscriber relationships and thrived through the same platform shifts.

Why VCs Make Different Founders

Dan’s path from investor to operator created advantages that pure operators or pure investors don’t have. Operators know execution deeply but sometimes miss market-level patterns. Investors see patterns across many companies but often lack the operational muscle memory to build.

The combination creates something specific: the ability to spot disruption early and the confidence to act on it before the evidence is overwhelming.

When Admiral started in 2015, the privacy wave was visible but not yet obvious. GDPR was still three years away. Safari’s Intelligent Tracking Prevention didn’t exist yet. The death of the third-party cookie was a rumor, not a roadmap.

Building for this future required conviction that came from pattern recognition, not proof points. “We felt, you know, that’s really what the Internet needs. If we’re shifting to this kind of privacy user empowerment world, then Websites need a way to build those relationships with their visitors. It didn’t exist already, right. There was no kind of HubSpot or Marketo or Salesforce built for media publishers to talk to their visitors,” Dan explains.

The Prediction Playing Out

Dan’s prediction about the future has become increasingly validated. “The sites that are going to be the winners, they’re going to look a lot like, you know, registered relationship based sites instead of transient, you know, viral sites hoping for traffic hits,” he says.

This isn’t hindsight—it was the founding thesis. The business model shift from tracking-based ads to relationship-based monetization would fundamentally change which publishers survived. Those who controlled their visitor relationships would thrive. Those dependent on platform distribution would struggle.

The pattern recognition that led to Admiral offers lessons for any founder trying to spot the next wave: spend time in multiple contexts to see patterns that single-context operators miss, watch for converging trends that individually seem manageable but together are existential, identify when existing categories are optimizing for a dying model, and find the gap between what one industry has and another industry desperately needs.

What Founders Can Learn About Pattern Recognition

The Admiral founding story isn’t about having a crystal ball. It’s about developing pattern recognition through diverse exposure. Dan saw publisher board meetings through a VC lens calibrated by SaaS company norms. The gap became obvious.

Most founders don’t have two decades of VC experience. But the principle applies: cross-pollinate your context. If you’re building for enterprise, study consumer. If you’re in fintech, understand healthcare. If you’re in one industry, study the adjacent ones.

The biggest opportunities often sit at the intersection of “this industry has a problem” and “that industry has a solution.” Admiral’s entire category exists because SaaS companies solved visitor relationship management and publishers desperately needed it but didn’t know to ask.

As Dan frames it, the disruption was visible if you knew where to look: a massive wave reshaping internet business models from tracking to relationships. Admiral didn’t create that wave. They just saw it coming and built the infrastructure publishers would need to survive it.