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.
Startups, finance, business and strategy.
Reflections on building Jamie, an AI assistant for email, and the decision to wind down Pragmatic after not finding product-market fit.
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.
Reflections on meeting a team of scrappy, multi-faceted engineers and what makes the best startups work
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.
A founder's warning about why early-stage startups should ignore cloud vendor sales calls and keep infrastructure simple to preserve runway and focus on shipping product.
How unnecessary CAPTCHAs, cookie prompts, and popup modals are driving customers away from websites, with practical advice on reducing friction.
Why VCs should back focused tools that integrate well with existing platforms instead of chasing the next monolithic unicorn that tries to do everything.
Why product teams need to embrace simplicity over complexity, focusing on clear blueprints and agility rather than endless documentation and rigid processes.
How a single bad hire can become cultural rot, fracturing teams, slowing delivery, and driving away top talent through bureaucratic chaos and toxic behavior.
Why the most successful B2B SaaS products like Canva, Shopify, and Notion started as beloved consumer tools before conquering enterprise markets.