What does the future of shopping, media and affiliate marketing actually look like in an AI-driven world?
In this episode of Marketing Over Milkshakes, we are joined by Stuart Miles - founder of Pocket-lint and Squirrel - to unpack the evolution of affiliate commerce, publisher monetisation, tech journalism, AI in media, and why trust is still the most valuable asset in digital publishing.
Having spent more than 20 years at the heart of the tech industry, Stuart has seen it all up close - from the launch of Google and the rise of the iPhone to conversations with Steve Jobs, Elon Musk, and some of the biggest names in global technology. He now brings that experience into Squirrel, a platform helping publishers automate product feeds, price comparison, affiliate links, and commerce content at scale.
The conversation explores how publishers can survive in a world of zero-click search, AI-generated content, shrinking editorial teams and changing consumer habits. Stuart explains why editorial trust, storytelling, and real relationships still matter more than ever, even as AI transforms how people discover, compare and buy products online.
In this episode, we cover:
The journey from Pocket-lint to building Squirrel
How affiliate marketing has changed for publishers
Why trust is the foundation of commerce content
The real future of AI shopping and AI-assisted buying journeys
What publishers need to do to survive Google zero-click search
Why storytelling will matter more in the age of AI
The difference between good AI use and bad AI use
Founder lessons on decision-making, resilience and momentum
What brands are still getting wrong about outreach, PR and relationships
Key Moments:
00:00 – Intro to Stuart Miles, Pocket‑lint, big tech names (Steve Jobs, Elon Musk) and the future of tech and media
05:38 – From Pocket‑lint to Squirrel: how Stuart built and sold a global tech publisher then launched affiliate tech for publishers
13:19 – Inside Squirrel: 30,000 product feeds, 13 billion offers and fixing classic affiliate problems like dead links and bad pricing
21:29 – Trust, honest reviews and content strategy: avoiding clickbait, bad influencer habits and the programmatic race to the bottom
32:24 – PR vs commerce content: how publishers monetise with affiliates while still serving readers and brands
39:10 – How publishers really use AI: good vs bad use cases in journalism, writing and operations
43:26 – Meeting Elon Musk and Steve Jobs: what top founders teach us about focus, decisions and product
48:03 – Founder mindset: resilience, failing fast, making decisions and letting go as your business scales
51:53 – Future of devices and AI: AR/VR, companion hardware, quantified self and how AI will reshape shopping
59:17 – AI in commerce and discovery: boring repeat buys vs emotional purchases and the lasting role of publishers
1:05:51 – AI coding, no‑code tools and why senior human expertise still matters in development
1:20:12 – Personal lessons: being nice, long‑term relationships, leadership as removing obstacles and networking without an agenda