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 SquirrelHow affiliate marketing has changed for publishersWhy trust is the foundation of commerce contentThe real future of AI shopping and AI-assisted buying journeysWhat publishers need to do to survive Google zero-click searchWhy storytelling will matter more in the age of AIThe difference between good AI use and bad AI useFounder lessons on decision-making, resilience and momentumWhat 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