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Mike Loukides would like to direct your attention to some of tech’s most interesting exploits in his September index. Here’s a few to whet your appetite.

If you’re tired of ChatGPT’s relentless bonhomie, you can choose an edgier assistant like the “cynic,” or several other new personalities, to align its responses with your mood—apparently, OpenAI is still working on the “mansplainer.” Also, thanks to Gemma 3 270M, you can tell a bedtime story without taxing your imagination: for example, a soon-to-be classic where a brave squirrel, in a giant’s boot, uncovers a secret door! And in the “sorry, not sorry” category, we know AI can express guilt, but there’s no framework yet for making it sincere. On a more serious note, if you want to head off bias in your AI, FairSense’s simulations can assess your system’s potential for a breakdown in objectivity. More news at the link below.

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Tim O’Reilly and Claire Vo

Live event: Claire Vo Live with Tim O’Reilly—September 22

Tim sits down with ChatPRD founder Claire Vo to talk about GPT-5—what its lukewarm reception means for the industry, what tasks it’s good at (despite that reception), and where we’re headed next.

If you’re an O’Reilly member, register here. If not, register for free below.

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book cover: AI Management Framework

Book: AI Management Framework—Practical Solutions for Ethical AI Deployment and Continuous Improvement

Amid the whirlwind pace of AI growth, this book can serve as a steady guide to preparing your organization for AI, developing and operating AI systems, and continuously assessing and improving your AI ecosystem.

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book cover: Writing, Presenting, and Communicating with Confidence