Holly and Ewan Are Working On It Podcast
Holly and Ewan Are Working On It is a podcast hosted by Holly and Ewan. They discuss technology and digital transformation, with a focus on financial services and related industries. Episodes explore how change affects businesses, people, and the wider world. The show blends conversation and insight for listeners interested in innovation and transformation.
Episodes
Epsiode 23: Live - 9 Months with Agentic AI
Recorded live in front of an audience at the W Hotel in Abu Dhabi, the second half of Holly and Ewan's evening goes back to where it started: the end of 2025, when OpenClaw launched and people were handing an AI agent the keys to their computers. Ewan, who works with regulated institutions, spent December dithering. Holly dived in. Nine months on, how are they actually living with their agents
Episode 22: Live - Reviewing the AI Summer
Season three opens with Holly and Ewan's first ever live show, recorded in front of an audience at the W Hotel in Abu Dhabi, and they have a lot of catching up to do. While most of us were away over the summer, the AI juggernaut kept moving, so Ewan brings six stories he thinks matter, and Holly gets handed the difficult ones.They start with geopolitics. For years the hosts have asked boardroo
Episode 21: AI Fluency for Executives - Learn by Playing
It's a slightly different episode today - in this one, we're talking about how we're helping executives develop AI fluency with one of the services we're offering, AI Fluency Coach. Here's the overview: Senior leaders are being asked to make enormous decisions about AI, on investment, direction and ethics, while quietly admitting to themselves that they don't really underst
Episode 20: OpenClaw: The Always-On AI Agent
After listeners said they felt a little short-changed by an earlier mention of OpenClaw, Holly Joint hands Ewan MacLeod the floor to properly explain what it is, why people are so excited about it, and where the real dangers lie. The result is the season's most practical deep-dive into agentic AI, grounded in how Ewan and even his wife are actually using it day to day.Stripped to its essential
Episode 19: The Board You Can Actually Afford
In this hands-on episode, Ewan MacLeod turns interviewer again to find out exactly what Holly Joint has been building with AI, and the answer has moved well beyond the games and chief-of-staff tool from earlier in the season. What emerges is a practical picture of how a non-engineer is now creating real, deployable software simply by describing what she wants in plain language.Holly's flagship
Episode 18: Drones, Defence and Misinformation
This is a different kind of episode. Holly Joint joins from a region now living under daily missile alerts, and the conversation with Ewan MacLeod turns from the usual workplace-and-AI territory to something far more immediate: how technology shapes life, safety and truth in a conflict zone. It is, by both hosts' admission, a difficult subject, but one they feel matters too much to skip.Holly
Episode 17: When Big Tech Pulls the Plug
Some technologies fail not because they don't work, but because the world never quite wants them, or because the bill simply never makes sense. In this episode Holly Joint and Ewan MacLeod use a striking month of tech news as a jumping-off point to ask what it really takes for a technology to survive, and why even brilliant, well-funded ideas end up in the graveyard.The numbers do a lot of the
Episode 16: Am I Right? AI and the Sycophancy Problem
We've all noticed it: ask an AI whether you're in the right, and it tends to reassure you that you are. This episode digs into why that matters far more than it first appears, and what it might be doing to the way we think, argue, and take responsibility.Holly Joint opens with a deceptively light framing, the "am I being unreasonable" and "am I the asshole" posts famili
Episode 15: The One-Person Billion-Dollar Company
Twenty-five years ago, building a tech company meant teaching yourself to code, surviving on pizza and caffeine, and hacking through the night to have something to show a client by morning. Ewan MacLeod lived that life as a dot-com entrepreneur, and in this episode Holly Joint uses his story as a lens on a simple but disorienting question: what would that journey look like for a twenty-one-year-ol
Episode 14: Why HR Can't Sit Out the AI Conversation
AI tends to be guarded by the technology function, treated as the natural property of CTOs and engineers. Holly Joint and Ewan MacLeod think that is a mistake, and this episode makes the case that the people who shape how AI affects our working lives shouldn't be the last ones in the room.The starting point is a talk Ewan gave with their colleague Mike, an HR specialist, to a roomful of senior
Episode 13: The Shadow AI Problem
If you run a company and believe AI isn't being used inside it, Holly Joint and Ewan MacLeod have unwelcome news: it almost certainly is, just not in ways you can see. This episode turns from their personal experiments toward the harder question of what AI is actually doing inside organisations, and why the gap between what employees do and what leaders know has become a serious problem.The co
Episode 12: Building Your Own Chief of Staff
Most conversations about AI focus on what the technology can do. This one is about what a person can do once they stop being a passive user and start directing the tools themselves.Holly Joint tells the story of her own leap: from running Claude and ChatGPT on a desktop to standing up a dedicated server and building software with nothing but natural language. Ewan MacLeod, the self-confessed geek
Episode 11: AI Optimists and the Permission Problem
Season two opens with a simple question: what has actually changed since the end of 2025? For Holly Joint and Ewan MacLeod, the answer is a lot, and not always in the direction they expected.The headline shift is capability. A new generation of models has moved AI from a useful novelty into something closer to a working colleague, and both hosts find themselves using it far more, and paying far mo
Episode 10: The AI Risks We’re Not Ready For
In this episode, Holly and Ewan deliberately shift tone to explore the risks, power dynamics, and uncomfortable questions surrounding AI, from superintelligence fears to geopolitics, cyber warfare, and who really controls the technology shaping our lives.Ewan opens with a stark provocation from the book If Anyone Builds It, Everyone Dies, which argues that the creation of superintelligent AI could
Episode 9: The Year AI Went Mainstream
In this episode, Holly and Ewan look back on 2025 as a defining year in technology, exploring what really changed (and what didn’t) in the most transformative period since generative AI emerged. They begin with the obvious headline: ChatGPT’s rise into the top five most-visited websites on Earth, a staggering shift for a product only three years old. Ewan reflects on the moment AI moved from novel
Episode 8: Inside the AI Agent Revolution
In this episode, Holly and Ewan explore one of the most hyped (yet deeply misunderstood) topics in AI today: AI agents. Holly opens with the big question: What actually is an AI agent? Ewan explains why definitions vary wildly, but broadly defines an AI agent as any system that can operate independently on your behalf to complete tasks. That could be a coaching assistant, a financial helper, or ev
Episode 7: Are you buying a $499 home robot?
In this episode, Holly and Ewan debate the arrival of the $499-a-month X1 Neo humanoid robot: A domestic helper that promises to tidy, load the dishwasher, and even put away groceries. Ewan’s enthusiasm meets Holly’s positive skepticism as they unpack the hype, the marketing fluff (“machine-washable knit suit,” anyone?), and the uneasy question of who’s really in control when a human operator can
Episode 6: How We Actually Use AI Every Day
In this episode of We’re Working On It, Holly and Ewan get personal about their real-world use of AI: Not the hype, but how these tools actually fit into their daily routines.Ewan breaks down his $300-a-month AI stack, from ChatGPT Plus and ChatGPT Pro with ChatGPT Pulse to Anthropic’s Claude and his WhatsApp-accessible assistant Martin. He explains how each shapes his productivity, workflow, and
Episode 5: Why AI can't be creative (yet)
In this episode, Holly and Ewan explore whether artificial intelligence can ever truly be creative. They discuss how large language models tend to produce the most probable (and often bland) responses, why human creativity is driven by risk, emotion, and purpose, and how AI’s so-called “hallucinations” might be the closest it gets to genuine imagination. Along the way they touch on philosophy, art
Episode 4: The AI 'Work Slop' Problem
In this episode, Holly and Ewan explore the concept of 'work slop', a term they use to describe the inadequate work produced by AI. They talk about how AI affects writing, why maintaining personal style matters, and how AI-generated content erodes trust in communication. The conversation also covers the responsible use of AI tools, the value of idea generation, and what the future holds fo
Episode 3: Making the Final Quarter Count
In this episode, Holly and Ewan dive into the realities of getting through Q4 - that busy, make-or-break time of year for many organisations. They share practical insights on planning ahead, staying disciplined, and keeping teams open to change. Along the way, they discuss how good decisions, self-awareness, and solid governance can turn year-end pressure into real progress.TakeawaysQ4 is a critic
Episode 2: Paper Photos in a Digital World - UK vs UAE Tech Tales
In this episode, Holly and Ewan discuss the challenges of obtaining a season ticket in the UK, highlighting the outdated processes that require physical photos in a digital age. They contrast this experience with the seamless digital services available in the UAE, particularly in public transport and government services. The conversation touches on the future of digital identification and the bure
Episode 1: Pilots, MVPs and Proof of Concepts
In this episode, Holly and Ewan explore the concepts of MVPs, prototypes, and pilots, discussing their importance in product development and the challenges faced in implementing them, particularly in the context of AI and financial services. They emphasize the need for accountability, structured processes, and the value of learning from failures to drive innovation and improve outcomes.TakeawaysMV
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