The Ruffian

The Ruffian

Why I Won’t Reply To Your AI-Generated Email

The Email Exchange That Radicalised Me

Ian Leslie's avatar
Ian Leslie
Sep 05, 2026
∙ Paid
Ernest Hemingway left his typewriter behind when he visited Los Angeles in 1937.
Ernest Hemingway sending me a nice email about John & Paul

Catch-up service:
Why Introverts Make the Best Extroverts
Politics Is Making Academia Stupid
Einstein, Churchill, and AI
The Great and Unfortunate Story of Jason Arday
The Last Lunch
Young Churchill


John & Paul is now out in paperback in the US, and I am absolutely thrilled to say that it’s a Barnes & Noble Monthly Pick for September! Please buy a copy for yourself and everyone you know. I’ve written a blog post for B&N about why and how I wrote J&P.


You’ll be excited to learn that I have added a couple of sentences to my Gmail signature. You know, the bit at the bottom of the email in which you can hawk your wares. After advertising John & Paul and this newsletter, it now includes this:

This email is 100% human-generated. If yours is not, don't expect a reply.

I’m not particularly proud of it. It’s a little snippy and sanctimonious. But a recent email exchange with someone who should know better made me feel that I had to say it.

Here’s what triggered me.

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