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Author: Jake

Capability Is Easy. Integration Is the Work.
February 9, 2026 CIO/CTO

Capability Is Easy. Integration Is the Work.

Last week was full of impressive AI headlines. New models from OpenAI and Anthropic. New benchmarks. Even stories about AI writing compilers that can run games like Doom. That level of capability is remarkable. The […]

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Systems That Survive the Winter
February 1, 2026 Artificial Intelligence

Systems That Survive the Winter

Winter has a way of exposing weak systems. Pipes freeze.Roads fail.Schedules fall apart. It’s rarely because someone didn’t work hard enough.It’s because the system assumed ideal conditions. Software systems behave the same way. Everything looks […]

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The Cost of Shipping ‘Almost’ Working Software
January 18, 2026 APIs

The Cost of Shipping ‘Almost’ Working Software

Before going any further, I’ll name the product I’ve been circling to and hinting at the past several posts. The system I’m building is called CoffeeBreak. It’s a human-in-the-loop AI teammate designed to assist across […]

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Why the First Users Shouldn’t Be the Loudest Ones
January 11, 2026 Leadership

Why the First Users Shouldn’t Be the Loudest Ones

Every product has early users. The question is whether they’re chosen intentionally or show up by default. Too often, early access is treated like a reward. The loudest voices get in first. Feedback comes quickly. […]

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The Problem Most Teams Are Trying To Solve Without Naming It
January 4, 2026 APIs

The Problem Most Teams Are Trying to Solve Without Naming It

Most software teams aren’t short on tools. They have ticketing systems, CI/CD pipelines, observability dashboards, documentation platforms, chat tools, and now a growing set of AI-powered assistants layered on top of everything else. And yet, […]

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