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

What does real, sustainable growth look like — beyond tactics and noise?

In this episode of The Digital Diaries, Peter Woods sits down with Neil Ateem, founder of Multiplier Agency, to unpack what actually drives scale in subscription businesses.

Neil has helped generate over $300M in revenue across SaaS, fintech, online education, and digital products. He previously led subscription growth at Mindvalley, building their membership model from zero to $20M annually — and he did it by focusing on clarity, customer feedback, and doubling down on what works.

This isn’t a conversation about hacks.

It’s about:

• The sacrifice behind early-stage entrepreneurship

• Why most founders spread themselves too thin

• How to balance acquisition and retention in subscription models

• Why brand credibility compounds over time

• The real role of AI — and why the human element still wins

Neil also shares the behind-the-scenes reality of building during scale: broken systems, customer complaints, iteration cycles, and the discipline required to stay focused on one lever at a time.

If you’re building a product, scaling a subscription, or trying to cut through digital overwhelm — this episode will sharpen your thinking.

What if the reason growth feels hard isn’t because you’re missing a tactic — but because the structure you’re operating inside is broken?

In this episode of The Digital Diaries, Peter Woods sits down with Justin Michael, executive coach and bestselling author of The Frame, to unpack why most revenue and performance problems aren’t tactical at all — they’re structural.

Justin challenges the hustle-heavy narratives most professionals inherit and introduces the idea of frame: the invisible structure that determines how pressure, authority, and decision-making show up in both business and life. From high-stakes sales conversations to personal relationships, the frame you hold often decides the outcome before words are ever spoken.

Drawing from decades inside enterprise sales and coaching operators carrying real accountability, Justin explains why durability matters more than speed, why authority compounds when it’s earned correctly, and how executive presence is built — not performed.

This conversation is for anyone who feels like they’re doing the work, showing up consistently, but still pushing uphill. It’s not about motivation. It’s about responsibility, clarity, and building a frame that can actually hold under pressure.

Panelists

Neda Jawad | CEO & Founder of Itremai

Jamie McGrane | GTM and Leadership Advisor

Rishi Sharma | Head of Sales & Revenue Enebalement at Stout

Summary

In this conversation, Rishi Sharma emphasizes the critical role of leadership in driving organizational change, particularly in the context of CRM usage. He discusses the importance of a systematic approach to logging activities and how this can create a trickle-down effect throughout the organization. The conversation highlights the need for leaders to be methodical and to communicate the value of these practices to ensure buy-in from all levels of the organization.

Summary

In this episode, Dr. Tamara Patzer discusses the intersection of AI, visibility, and trust in the digital age. She introduces the concept of AI suggestibility, emphasising the importance of permanent records and digital identity. The conversation explores the challenges of merging identities in AI, the significance of building trust online, and the role of media literacy. Dr. Patzer shares insights on using AI as a reflection tool and the importance of authenticity in a rapidly evolving digital landscape. She also offers advice for navigating professional transitions and creating a lasting legacy through digital records.

Connect with Tami on LinkedIn

Summary

In this episode of Digital Diaries, Peter Woods interviews Dave Boyce, EVP of Winning by Design, who shares his extensive experience in building and selling five SaaS companies. The conversation delves into the motivations behind entrepreneurship, the evolution of SaaS and AI in business, and the concept of factory thinking in revenue generation. Dave emphasizes the importance of courage in corporate culture and discusses the balance between automating predictable tasks and maintaining the human touch in business. The episode concludes with personal insights and aspirations from Dave, including his thoughts on the future of AI in the workplace.