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Lack of transparency in AI pricing
AI users face challenges with unclear usage limits and billing practices, often leading to unexpected charges. Token-based pricing lacks transparency, complicating cost management. While some providers are introducing controls to mitigate expenses, there’s a need for clearer metrics akin to traditional utilities, allowing users to predict costs and optimize usage effectively.
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Think like a CTO – Japanese Edition
Think Like a CTO has been translated and published into another language, Japanese.
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How AI Agents Will Change Ecommerce
The rise of the machine customer marks the end of the browser era. To win, platforms must move beyond UI and provide deterministic, AI ready APIs. Making your site agent friendly is no longer optional; it is your new competitive advantage.
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The Flaws in AI Customer Support Systems
My recent Logitech support experience highlights why context is king. A solid AI speech agent was ruined by a human handover that started from scratch. AI should be a connected workflow, not an isolated silo. If your latest improvement makes the service slower, you have failed the integration test.
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Rock me Amadeus (& Elvis)
Watching the new Amadeus series led me down a rabbit hole where I found a striking parallel between Mozart and Elvis. Both icons died broke, but their widows, Constanze and Priscilla, became the first accidental CEOs. They professionalized the legacies, cleared massive debts, and pioneered celebrity tourism to save the brands.
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2025 in review
With the 1st of January now rolling us into 2026, it’s time for my annual review of the year that has just closed. Another beautiful sunny day here in Virginia, warm and blue skies as I sit down and reflect on some of the stats and journals I have maintained this year.
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The Inevitable V3 Rewrite
Software rarely finds its feet until version three. Version one is an idealistic guess. Version two is a survival patch. Version three is the rewrite where you finally delete the noise and build what is actually needed. Real stability comes from subtraction, a lesson every architect learns the hard way.
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Double NAT, 40 Terabytes, and a Christmas Miracle
I spent my Christmas downtime replacing a fragile, port-forwarded network with a resilient Tailscale mesh. I managed to overcome double NAT headaches to sync Synology units peer-to-peer, fixed the inevitable MTU “black holes,” and automated the DSM 7 sandboxing hurdles to build a private, encrypted family network.
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“This ain’t no technological breakdown”
Honoring British rock legend Chris Rea, I recall 1989: a 16-year-old student in Paisley, wrestling with the guilt of spending my living grant on “The Road to Hell” vinyl. Purchased for £5.99 at Woolworths, it became the defining soundtrack of my university years. Thirty-five years later, the joy remains. RIP.
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The CTO’s Year-End Audit: Are You Building Your Vision or Just a Backlog?
December is the only quiet time you have. Don’t waste it clearing your inbox. Use this silence to audit your architecture against your Vision Document. Move beyond simple feature roadmaps and focus on building strategic capabilities. If your environment doesn’t support your 2026 goals, fix it now before the chaos returns.
the legend that is, Alan Williamson.
For over 20 years, I’ve shared my thoughts whenever the muse strikes. It’s unpredictable, honest, unedited, and occasionally witty. I’m living the best years of my life, working harder than ever, and enjoying every second.
Alan Williamson 