Offcuts

On this episode I sit down with Alex O'Byrne, an independent writer, builder and investor focused on AI-first companies, and my former co-founder at the Shopify agency we built and sold together. Alex now runs Alpha Factory, an AI investment company, from Miami. This is his fourth time on Offcuts.

This time we go deep on what happened after he built an AI hedge fund, Money Monster, that read earnings transcripts to try to predict stock moves, and took real losses when the Iran war broke its macro signals. He walks me through how he rebuilt it as Alpha Factory, multi-strategy, multi-instrument, and increasingly run without him, after realising his own risk calls were often the weak link in the system.

From there we get into the organisation of the future: why Alex thinks the one-person billion-dollar company is mostly rage bait, what he thinks is actually achievable solo, and the role he calls the orchestrator, the generalist who directs a stack of AI agents and supplies the taste the machines still can't fake.

We also get into why he thinks frontier labs' safety messaging is more political positioning than genuine alarm, and what a dog park in Miami taught him about how obsolete the standard thirty-minute Zoom call is starting to feel.

Enjoy the show.

On this episode I sit down with Alister Hewitt, Technology and Operations Director at Rat & Boa and co-founder of Prebuy.

Alister has been with the brand since the very beginning. He built the first website for a friend launching a clothing label, and within a couple of months the orders were flying in.

He describes what Rat & Boa actually is: born on Instagram in 2014, back when the platform had no product tags and no stories and brands used it as a mood board, built around the founders' aesthetic, worn organically by the likes of Bella Hadid and Alexa Chung, and still run by a far smaller team than people assume.

Most of the conversation is about the problem that comes with being a viral brand. Collections sell out in a couple of days, the rebuy window runs six to eight weeks and sometimes ten, and back-in-stock alerts were only converting at five to ten per cent. Alister's view is that preorders look like a product page feature and are really a supply chain one. Change the CTA and you just push the problem into the warehouse, the merch team and the customer service inbox. That is where Prebuy came from.

The second half is about how far AI has gone inside the business. A dev team that is almost AI native, with Cursor as the harness. A CRO audit skill the digital team built themselves. Gorgias and Shopify MCPs in customer service. A server in the building running local models, because the token bill is climbing. And why Alister thinks agentic shopping is sitting exactly where mobile commerce sat a decade ago.

Enjoy the show.

On this episode I sit down with Eleanor Warnock, a writer, journalist and communications expert based in London who has worked for The Wall Street Journal, the Financial Times's Sifted, and the Reid Hoffman-backed AI company Every. She's currently an advisor to Bek Ventures, ranked the top-performing VC firm globally since 2010 by HEC-Dow Jones, and holds an MBA from INSEAD.

Eleanor is about to launch her own venture, and this conversation ranges across the state of journalism's business model, the myth of the one-person billion-dollar AI company, and where AI and taste collide.

We get into why she thinks journalism is heading toward a handful of consolidated giants and a long tail of one-person outlets, why Every's hybrid of media and consulting works, and why even she needed a lawyer to check the incorporation documents Claude wrote for her. We also dig into taste: why she thinks it's really about cultural status, why the tech world wants it and can't build it, and where in her own daily workflow she lets Claude in and where she keeps it firmly out.

Enjoy the show.

On this episode I sit down with Olivier Legris, co-founder of Alter, a native macOS AI assistant that refuses to bet on any single model, and founder of Clauders, the global Claude Ambassador community.

Olivier's thesis is simple: the model doesn't matter to most people, the task does. Alter started as a frustration with Siri and has become a Mac-native, model-agnostic assistant with its own router, Best, that picks the right model for the job. When Alter shipped that router, Olivier expected a fight over which model was best. Instead, barely 10% of users ever touch the model picker. They just want the task done.

We get into why Mac is quietly the best platform for building AI products, the challenge of building on a market that moves faster than any roadmap can keep up with, and Olivier's read on the "Linux of AI" moment happening with agent frameworks right now, powerful, but still too complicated for anyone outside the bleeding edge.

We also talk about the Clauders community, how it grew from 50 ambassadors to a genuine cross-border network, and the 90/9/1 rule that keeps it alive. And we close on the big picture: open source versus proprietary models, on-device AI, and whether Anthropic and OpenAI will actually IPO this year.

Enjoy the show.

On this episode, I sit down with Nico Willson, co-founder of Futsol, to talk about what happens when you look at the world's most popular sport and decide the brands serving it are getting it completely wrong.

Futsol started from a simple observation: every other sport - cycling, running, boxing - had developed a culture and community around it that people actually wanted to belong to. Football hadn't. Nico and his co-founders set out to build the brand that changed that. We get into how they avoided the trap of competing with Nike and Adidas on performance, why the vast majority of their customers wear Futsol to watch football rather than play it, and how jersey culture - once their hero product - has now been taken over by every brand from Gap to Palace, forcing them to think about what comes next.

We also talk about the World Cup moment: how a small independent brand navigates a global tournament without getting drowned out, why they went evergreen instead of chasing the flash, and the Bloomsbury charity partnership and City Guides zine they built around it instead.

On AI, Nico draws a clear line - operationally yes, creatively no. For a brand built on sun-faded fabrics, block printing, and tactile craft, the question of where AI belongs is anything but abstract.

Enjoy the show.

On this episode, I sit down with Annica Rantala, CEO of Rapunzel of Sweden, to talk about what happens when you take a category dominated by professionals and salons and hand it directly to the consumer.

Rapunzel is a Nordic pioneer in hair extensions - built on a direct-to-consumer model from day one, with 81% of revenue through their own e-commerce. We get into how that model works in practice: the education-first approach to new customers, why micro-creators with 2,000–10,000 followers consistently outperform big names on return, and how the brand thinks about its dual audience of end users and hairstylist key opinion leaders.

We also talk about Annica's journey from board member to operating CEO - what you think you can see from a board seat, and what you can't - and the lessons from her time scaling Stronger through and beyond the pandemic.

On AI, Annica makes a point I hadn't heard put quite this way before: you can take a people-first approach to AI adoption, a brand-first approach, or a technology-first approach and most companies are getting it wrong by defaulting to the last one and locking it down to the tech team.

Enjoy the show.

On this episode, we did something different - Offcuts went live in Stockholm in front of a room of commerce operators.

I'm joined by two people who've each spent the best part of two decades inside consumer brands: Erik Arnewing, CTO at Stellar Equipment and twenty years at Sneakersnstuff before that, and Ola Ekerhov, who ran ecommerce at Acne Studios for sixteen years and now advises mid-sized brands.

We split the conversation in two. First, external AI - how customers now discover and buy through a layer you don't control. We get into why AI search reads structured data rather than brand vibe, the test you can run on your own phone in thirty seconds, and what happens to brands built on culture when the discovery surface stops caring about culture. Then, internal AI - the gap between the 76% of businesses using it and the 14% who say it works. Erik walks through querying his entire stack in plain English; Ola is sharp on where it makes teams faster and sloppier.

We also get into agentic shopping, who should actually own AI inside a company, and why attribution is getting harder, not easier.

Recorded live with our partners on this episode, Centra and DEMA.

Enjoy the show.

On this episode, I ask whether a brand built entirely on restraint and considered growth can have a coherent relationship with AI. I sit down with Andrew Cottington, Director of Digital at Studio Nicholson, the London-based fashion brand known for its modular wardrobe, fabric-led design, and a customer base that tends to find it rather than be found.

We dig into how a brand that deliberately avoids chasing scale thinks about customer acquisition and where performance marketing fits. We get into the loyalty programme they rebuilt after deciding fixed discounts were too transactional for their customer. We tackle the agentic storefront they launched in February with Swap, and something Andrew noticed that I thought was sharp: it was their most loyal customers, not new ones, who embraced it first. And we get into what considered growth actually looks like when the tools you're being asked to adopt are moving faster than anyone can predict.

If you're running or marketing a brand that leads with taste and is trying to figure out where AI fits without compromising what makes the brand worth following, this one's for you.

This episode is sponsored by Swap - if you want to see what the future of storefronts looks like, book a demo at swap-commerce.com/offcuts

On this episode, I sit down with Sam Atkinson, co-founder of Swap, to get into one of the more interesting infrastructure stories in commerce right now. How do you build the back office that nobody wants to think about, and use it as the foundation for something that changes how people shop entirely?

Sam played semi-professional football for West Brom until 18, studied law, worked at McKinsey, ran his own DTC business, and joined a fintech before co-founding Swap in 2023. The through line is someone who kept getting close enough to the hard problems in e-commerce to eventually decide to go and solve them.

We get into what Swap actually is, the back office suite covering cross-border, returns, tax, compliance and demand planning, and why building that first gave them something most agentic commerce players don't have: the data, the integrations, and the customer trust to move fast.

We talk about the agentic storefront they are already running live, the stats on conversion and returns, how they think about high intent versus low intent shoppers, and why they want to be the agent powering experiences like Brunello Cucinelli rather than replace what great brand teams do.

And then the fundraising journey, what it actually looks like to raise capital across multiple rounds, and the state of the fund raising market in 2025 and 2026.

Enjoy the show.

Book a free demo at: swap-commerce.com/offcuts

On this episode, I sit down with Jojo Regan, co-founder of MANORS Golf, to get into one of the more interesting brand building stories in British commerce right now. How do you take a sport with one of the strongest aesthetic traditions in the world and completely rewrite what it looks like?

We get into the cultural moment golf is having, why they backed a creator over a tour pro, the 90s nostalgia driving the aesthetic, and what it means to sell adventure rather than apparel. The pivot that defined the business, a fundraise with Andy Murray involved, and whether Manors ever steps outside of golf.

And then AI: where Jojo is actually placing bets, why the agentic website is already live and what the dot com of the future looks like for a brand built on culture and storytelling.

Enjoy the show.

This episode is sponsored by Swap - if you want to see what the future of storefronts looks like, book a demo at swap-commerce.com/offcuts