Robert Greiner
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Overview
Skip to the bio Robert Greiner Essays Archive About Subscribe Hi, I'm Robert. For the past decade, I’ve architected technology strategies for Fortune 500 companies, led teams through digital transformations, and watched technology reshape entire industries.
News
Shadow AI Is the Strategy
Most companies are running two AI strategies. The official one lives in slide decks, steering committees, and enterprise agreements. The real AI strategy runs in the tabs that get minimized when the boss walks by. After letting teams run wild with expensi
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The 1% Error That Ruins Everything
In 2025, 42% of companies abandoned most of their AI initiatives - up from just 17% the year before. The culprit wasn't bad implementation or insufficient data. It was math: a 99% accurate AI agent performing 50 sequential steps succeeds only 60% of the t
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Believe the Checkbook
Anthropic's AI agent was the most prolific code contributor to Bun's GitHub repository, submitting more merged pull requests than any human developer. Then Anthropic paid millions to acquire the human team anyway. The code was MIT-licensed; they could hav
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The Most Expensive Wall in Software
Palantir didn't have a working product for the first several years. What they had were brilliant engineers building custom solutions on customer sites. Somehow that "broken" model made them worth nearly $500 billion. The company that couldn't ship softwar
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The Breaker Box Economy
During a summer blackout when I was a kid, a neighbor ran an orange extension cord across the street so our freezer wouldn't thaw. It looked absurd: this thin line humming with borrowed power, keeping the lasagna alive. But it worked. In a pinch, you buil
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