Five Minutes to Lose Twenty Years of Trust

Domain names were the first NFTs. Non-fungible digital assets, tradable and potentially valuable if you spotted the right trend before it broke. My Dad even bought me a URL for my birthday once - NikNak.com which is remarkably close to TikTok! I sold it ten years ago… I’m not much of a gambler or speculator though, but I’ve always enjoyed buying a domain or two as a kind of conceptual bookmarking for ideas and projects I might realise some day. I bought FastFoodForThought.com 19 years ago and only started using it to host this very Substack a few months back. I still hold Prototypist.com and Synthfluencer.com from a startup idea I was pitching 6 years ago, (a bit ahead of its time). And some bookmarks for business ideas I haven’t realised yet, like Cyk.co for a circular lifestyle brand with a nice subversive attitude. And a few more amusing ones, like Turbanoutfitters.com.

I’m not a trader so don’t have a massive portfolio, but hold around 50 domains. After migrating them from gandi.net, one of the OG cut-price registrars, 20 years ago, they’ve been with a company whose name I’ll protect by giving them the pseudonym StopMummy.

To manage the annual renewal budget I’d subscribed to a bulk domain buying club a few years back, which pulled the costs down substantially. But this year I looked at the renewal price and thought it was going a bit crazy. I briefly wondered if the Strait of Hormuz had something to do with it, but then remembered URLs don’t rely on fossil fuels for distribution. To do any meaningful comparison with alternatives would have taken me hours, different TLDs coded differently, bulk discounts to factor in, then comparing all of that against other registrars with their own costing structures entirely.

But we live in a world now where the LLMs are only too happy to assist. I don’t know why, but I’ve always felt Gemini is just that bit mathsier. Probably some weird prejudice in my lizard brain, but that’s where I go for these kinds of inquiries. Maths isn’t my strong suit. It’s not even my strong pyjamas.

So into Gemini went all my figures from my StopMummy account, and within less than 5 minutes I had a comparison chart showing the annualised financial picture of my account, with the features of each registrar option laid out clearly alongside it. It literally halved my annual costs and gave me a migration plan to follow. Clear, actionable guidance.

So many companies, in as many categories, have been able to hide behind a similar complexity. The inertia it creates for consumers is where fat margins sit happily for years, as mine had with StopMummy. But the LLMs are going to kill these comfy categories fast if the models behind them aren’t rethought in anticipation of the greater transparency now being imposed on them. Where obfuscation and high margins have thrived until now, the new conditions will favour the efficient and the transparent. That’s a commercial challenge, a brand challenge and a reputational one.

The moment I saw the comparison laid out so clearly, my feelings about StopMummy flipped abruptly. The OG value URL operator I’d been loyal to for so many years had become my exploiter. A Truman Show moment when the reality I had trusted up until that point melted away to show the uncomfortable truth beyond its boundary. I lost all respect and trust for them in 5 minutes. All loyalty, gone, just like that. I’m transferring everything over, and I don’t have any of the usual awkward pangs you get moving an account somewhere new after a long relationship. It feels like retribution.

At Sideways , where I work on trust as a discipline in its own right, the conversation about LLMs and trust usually starts with AI slop, the flood of synthetic images that’s made people doubt almost everything they see. But my StopMummy story is a different kind of trust erosion, and I suspect a bigger one for many enterprises. If you’re running a business that depends on a trustworthy reputation, but rely on a few margin-rich, low-integrity skeletons hiding behind complexity in your closet, it’s probably time to deal with them, before they come out and start breakdancing on your reputation.