Write a short re-engagement email for a newsletter that's about tips for starting an online business. Use a friendly tone.

12 upvotes

3 years and 9 months later

GPT-3.5

Hi there! We hope you're doing well and staying safe. We wanted to reach out and remind you about our newsletter that provides tips for starting an online business. If you're considering starting your own online business or have already taken the first steps, our newsletter is a great resource for you. We cover topics such as how tochoose a profitable niche, how to create a website, and how to market your business online. We understand that starting a business can be overwhelming, but with the right resources and support, it can also be incredibly rewarding. That's why we're here to help! If you're not already subscribed, we'd love for you to join our community and receive our weekly newsletters. Simply click the link below to sign up. [Insert link to newsletter sign-up page] Thank you for considering re engaging with our newsletter. We hope to see you on our subscriber list soon! Best regards, [Your name]

GPT-6 Astra

Subject: Still dreaming of starting your online business?

Hey [First Name],

It’s been a little while! If starting an online business is still on your mind, we’re here to help—one small step at a time.

From choosing an idea to finding your first customers, our newsletter shares practical tips to help you get moving.

[Keep the tips coming →]

Ready when you are,
[Your Name]

P.S. Taking a different path? You can [unsubscribe here]—no hard feelings.

76 words

What changed

GPT-3.5’s email is addressed to the wrong people. A re-engagement email goes to subscribers who have drifted away, but this one asks readers to sign up: “If you’re not already subscribed, we’d love for you to join our community.” It then closes by thanking them “for considering re engaging,” which sits oddly next to a sign-up link. The pandemic-era “staying safe” opener and the long paragraph about how business “can be overwhelming” add bulk without urgency.

Astra treats the reader as a lapsed subscriber from the first line: “It’s been a little while!” It adds a subject line, one clear button, and a P.S. offering an unsubscribe link with “no hard feelings,” a standard re-engagement move that cleans up the list. It is also genuinely short, as requested. GPT-3.5 does name more concrete topics, such as choosing “a profitable niche” and building a website, while Astra’s “practical tips” is vaguer. But Astra’s email is the one you could actually send.

From December 2022 to March 2023, visitors to LearnGPT, the earlier version of Emergent Mind, shared ChatGPT conversations they found useful or funny. On October 19, 2026, each prompt went to GPT-6 Astra exactly as it was shared: one message, no system prompt, default reasoning effort. Claude Opus 5.5 wrote the analysis under each pair after reading both answers. Original answers appear as the people who shared them pasted them. A few examples are left out because they depended on missing context or weren't appropriate to republish.

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