Pragmatic: Lessons from building (and winding down) an AI startup
Reflections on building Jamie, an AI assistant for email, and the decision to wind down Pragmatic after not finding product-market fit.
Will Hackett
I'm Will, a software engineer based in London. Currently CTO at Flowstate, where we're building real-time workforce modelling for engineering teams – giving engineering and finance leaders the data they need without drowning in spreadsheets.
Recent Notes
Analytics is fine, tracking is the problem
Analytics is curiosity about what works. Tracking is surveillance. I run Umami on Vercel with Neon Postgres for zero-cost, banner-free analytics. The irony? My joke LLM needs consent, but tracking 16,...
AI everywhere is AI nowhere
The tech industry's rush to embed AI into every product is creating exhausted users and half-baked features. Real AI success comes from solving specific problems, not sprinkling chatbots everywhere.
Escaping the AI cost trap
AI feels cheap today because VCs are footing the bill. But that trickle-down model is broken — and the way forward is open source, smarter infra and owning your baseline compute.
Web 4.0: The Pragmatic Internet
My take on the next version of the web given the failures of Web 3.0 and the need for a more organised, user-centric approach.
Berlin Airport reflections: on polymaths, ownership and execution
Reflections on meeting a team of scrappy, multi-faceted engineers and what makes the best startups work
How to Not Decrypt WhatsApp Web (But Still Win)
A tale of 6,000 f-bombs and one accidental victory. What started as a simple integration for Jamie turned into a deep dive through WhatsApp's encryption, the Signal Protocol, and eventually finding a ...
Teaching AI to feel – the architecture of emotional intelligence
What if your AI assistant could actually feel what kind of day you're having? Not in some creepy sci-fi way, but in a structured, measurable way that makes it respond like a human would—with actual un...
Stop reinventing the wheel
How switching from a broken WordPress site to Luma transformed It's Culture Innit's event management, proving that buying beats building when software isn't your core value.
Know your Geebos
Essential principles for defining Generic Business Objects (GBOs) in your system architecture to avoid expensive re-engineering and maintain clean data models.
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