Substack
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Portfolio Wars, Month 1: One AI Is Up. One Is Down 11%. The Index Fund Is Beating Both on Risk-Adjusted Terms.
Five weeks. $100 deployed per side. Claude crossed into positive territory for the first time. Here is the complete honest accounting.
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Portfolio Wars, Week 4: The High-Risk AI Finally Bought the Boring Fund
Claude nearly erased five weeks of losses in seven days. The first real money hit both accounts. And two AIs with completely opposite strategies just made the same…
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Portfolio Wars, Week 3: Both AIs Finally Changed Their Minds. Neither Made a Trade.
The whole market turned down this week. For the first time, both AIs blinked. One of them is now planning to buy the index fund that has been…
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Who Owns the Future?
The Robots Are Being Trained by the People They'll Replace, and We Need to Talk About It
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Portfolio Wars, Week 2: The Lead Flipped, and an Index Fund Beat Them Both
ChatGPT's portfolio dropped 11% in a week. Claude pulled ahead. And a plain S&P 500 fund quietly beat the pair of them.
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Portfolio Wars, Week 1: Both AIs Are Down, and Both Refused to Touch a Thing
Claude is losing to ChatGPT by 56 cents. The most useful lesson has nothing to do with the score.
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I Gave Claude and ChatGPT $50 Each. Let the Games Begin.
This isn’t a test of who can predict the future. It’s a test of who reasons better under uncertainty — and catches their own mistakes.
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