#35 - Context > Data: Building Trust in the Agentic Web | Brendan Norman, Co-Founder & CEO of Classify

In this episode of The Digital Diaries, Peter sits down with Brendan Norman, Co-Founder & CEO of Classify, to unpack one of the most overlooked forces shaping the future of AI, advertising, and digital trust: context.

Brendan’s career spans founding client partner roles at Facebook, strategic supply leadership at Unity Technologies, and years advising startups on go-to-market strategy. Today, he’s building infrastructure for what he calls the agentic web — a world where AI agents don’t just assist humans but actively retrieve information, make decisions, and interact across digital systems.

But here’s the catch: without contextual intelligence, even the most advanced systems can misfire — breaking user trust, wasting ad spend, and damaging brands.

🔍 What We Explore in This EpisodeWhy Context > Data

Brendan explains the difference between raw data and contextual intelligence — and why simply knowing who someone is isn’t enough. Timing, mindset, semantic understanding, and nuance matter just as much as behavioral data.

Drawing from his experience helping build Facebook’s Audience Network, Brendan shares what large-scale platforms taught him about:

• Advertiser value

• Publisher monetization

• User experience

• And the fragile nature of digital trust

We unpack:

• AI agents retrieving and synthesizing information in real time

• Agents interacting with other agents via backend protocols

• How advertising may integrate into AI-powered workflows

• Why agentic attention is the next frontier of monetization

As AI agents scale, so do risks:

• Fraud traffic
• Misplaced ads
• Broken user experiences
• Brand safety issues

Brendan shares how Classify approaches contextual targeting without using cookies or personal identity data — focusing purely on content-level intelligence.

For operators unsure where to start:

• Experiment in controlled environments

• Use AI as a coach, not a replacement

• Learn by building

• Avoid handing over your API keys

Advice for Founders Overwhelmed by AI