Phil Simon
Phil Simon
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I write about AI, the future of work, low-code/no-code, collaboration, communication, technology, and other topics. I pepper my posts with humor and pop-culture references. Oh, and I freakin’ despise jargon and weak writing. Since 2008, I’ve penned thousands of posts, more than 1,300 of which live on this site.

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Battle of the LLMs
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Battle of the LLMs

To answer a simple basketball question, I pitted Claude and ChatGPT-5 against each other. Let's see which tool won and what we can learn from the exercise.
ChatGPT-5 Still Makes Egregious Errors
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ChatGPT-5 Still Makes Egregious Errors

OpenAI's new model is supposed to represent an improvement over its predecessor. Maybe it is, but it's nowhere near perfect.
Moving From WordPress to Ghost: The Verdict
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Moving From WordPress to Ghost: The Verdict

The new content management system has rekindled my love of writing.
Will AI Make Us All Line Judges?
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Will AI Make Us All Line Judges?

Not that long ago, the idea of a machine making tennis calls seemed far fetched. Now, thanks to a narrow form of AI, it's the norm.
The Nvidia Arrow
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The Nvidia Arrow

What if we're looking at the relationship between company success and remote work wrong?
The AI Goldilocks Test
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The AI Goldilocks Test

Thoughts on the right way to use Claude, Perplexity, Gemini, and ChatGPT.
One AI Tool, One Simple Question, Two Different Answers
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One AI Tool, One Simple Question, Two Different Answers

A simple exercise undermines a fundamental, scary LLM limitation.
On Thermostats and AI Hallucinations
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On Thermostats and AI Hallucinations

A recent interaction with Claude left me profoundly perplexed.
The Forthcoming Wave of AI Mop-Up Jobs
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The Forthcoming Wave of AI Mop-Up Jobs

Get your buckets ready. Plenty of rework is coming.
The Harold Baines AI Hallucination
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The Harold Baines AI Hallucination

A recent experiment only underscores the need to question LLMs' responses.
AI Dataviz Abominations
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AI Dataviz Abominations

Claude knows a great many things, but it conveniently ignores the basics of creating simple charts.
AI's Promethean Moment
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AI's Promethean Moment

As a 2023 tragedy manifsted, we're not remotely prepared for what's here, never mind what's coming.
Lessons From My Accounting System's Sudden Crash
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Lessons From My Accounting System's Sudden Crash

A case study in how not to run a software company and the current limitations of AI.
Web Browsing Is About to Get Much More Interesting
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Web Browsing Is About to Get Much More Interesting

Forget the marginal improvements we've seen over the past decade. Big changes are coming.
What Every Software Vendor Should Learn From This Glorious Ghost Alert
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What Every Software Vendor Should Learn From This Glorious Ghost Alert

Recent notifications from Google Gemini and Notion prove that they are generally a hot mess. There's hope, though: it's a fixable problem.
The Generative AI Tool That's Blowing My Mind
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The Generative AI Tool That's Blowing My Mind

Citizen developers' toolboxes just exploded. Arthur C. Clarke's words are ringing truer than ever.
I Asked AI How My Writing Has Evolved Since 2009. Here's What It Found.
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I Asked AI How My Writing Has Evolved Since 2009. Here's What It Found.

Claude weighs in on my nearly 1,500 blog my posts. Its findings were scary accurate.
How AI Eased My Recent Website Migration
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How AI Eased My Recent Website Migration

A long post about how our robot overlords saved me considerable time and money.