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

Victor Varnado is a creative technologist, comedian, filmmaker, and founder of Supreme Robot — a studio building projects that sit at the intersection of culture, technology, and social impact.

In this episode of The Digital Diaries, we explore what it actually means to create in a world where everyone has tools, platforms, and opinions — but very few are willing to build.

Victor shares hard-earned insights from a career spanning comedy, film, AI, entrepreneurship, and experimental media. We talk about why taste is becoming more valuable than talent, why critiquing is easier than creating, and how AI is changing creativity — without replacing it.

This conversation isn’t about hype or fear. It’s about responsibility, curiosity, and the courage required to put real work into the world.

• Why AI enhances creativity but can’t replace human judgment

• The difference between building vs. critiquing

• Why taste is the real competitive advantage

• The risks of truth-telling in modern comedy and culture

• How personal branding is evolving in the digital age

• The responsibility creators have to their audience and society

Victor is also the showrunner of The Great Fantasy Debate — a genre-bending series exploring imagination, fandom, and debate through a cultural lens.
🎬 Learn more here: https://www.imdb.com/title/tt17506798/

If you’re navigating creativity, leadership, or identity in a rapidly changing digital world — this episode is for you.

In this episode, we explore:

AI Without Losing Your Human Edge (A conversation with Jenna Nelson)

Are small businesses about to be left behind by AI — or are they uniquely positioned to win?

In this episode of The Digital Diaries, Peter Woods sits down with AI strategist and brand consultant Jenna Nelson to unpack one of the most urgent questions facing founders today: how to adopt AI without losing trust, authenticity, or your human edge.

Jenna works directly with female founders and service-based businesses to turn AI from a buzzword into a practical advantage. Together, Peter and Jenna explore what thoughtful AI adoption actually looks like — beyond hype, fear, and flashy tools.

This is not a conversation about replacing people.

It’s about empowering them.

🌐 Website: https://heraigency.com