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Analyze a Substack newsletter export with ChatGPT agent mode

WorkedEvidence: Described by posterPosted Last checked

Clint Cain merged a Substack export with ChatGPT Agent Mode and got blunt advice: stay on 1 topic and use fewer CTAs.

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  4. Send it, then read the answer before acting on it.
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Prompt

Original prompt

The prompt as the person shared it in the source.

What the prompt labels mean

These are the person's own words, as shared in the source.

For each row in posts.csv, use the post_id value to find the matching HTML file(s). Extract the plain‑text content from that HTML file and add it to a new column called post_content in the CSV. If no matching HTML file exists for a row, leave post_content blank. The result should be an updated CSV where every post has its associated text content (stripped of HTML markup) in the post_content column of the final file as post_content.csv .

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Optional stronger version

Our rewrite with extra checks. The poster didn't test it.

Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish.

Goal: Combine my newsletter export into one spreadsheet, then review my writing and give honest, specific feedback.

Questions to ask me first:
- Which platform is the export from?
- Have you removed files with subscriber emails or other personal data?
- What do you most want to improve: topics, hooks, calls to action or format?

Inputs (fill in or confirm):
- Posts list: [UPLOAD POSTS CSV]
- Post files with no subscriber data: [UPLOAD COMPRESSED FOLDER]
- My goals and audience: [GOALS / AUDIENCE]

Rules:
- First, match each post to its file and add the plain text in a new column; list any posts with no match.
- Don't open or use any file with subscriber names or email addresses; tell me if you find one.
- Base every finding on specific posts, and quote short lines as examples.
- Give 3 keep doing and 3 stop doing points, ranked by impact.
- Don't invent numbers like open rates; say what's missing if you need data I didn't give.

Checkpoint: After building the merged file, show me row counts and any missing matches before the analysis.

If you get stuck: If a file won't open or match, tell me which one and why, then continue with the rest.

Verify before you finish: Check that the merged file has one row per post and no HTML tags in the text.

Output: The merged CSV, then a short report with examples from my posts.

Done when: I have one clean spreadsheet and a short list of changes for my next posts.

AI tool

ChatGPT agent

Outcome

Clint Cain of Tech Wing Management exported a Substack newsletter's data, then deleted the per-post deliveries and opens CSV files first, because they contain subscriber email addresses that shouldn't be shared with AI. In ChatGPT's Agent Mode, Cain attached posts.csv and a compressed folder of the post HTML files and asked it to pull the plain text of each post into a new post_content column, matched by post_id. In the same chat, Cain then attached the merged file and asked it, as a newsletter analyst, about the most valuable content, voice consistency, hooks, calls to action, 3 recommendations, similar publications and 3 keep doing and 3 stop doing items. ChatGPT 'almost hurt my feelings,' Cain wrote: stay on 1 topic, cut back on too many CTAs, ask real-world questions, restructure the articles and share the YouTube video.

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Source

Posted
by Clint Cain (Tech Wing Management)
Last checked
Method:
How we verify

https://techwingman.substack.com/p/i-replaced-my-substack-data-analyst

Context: Cain removed the files with subscriber email addresses before uploading anything; do the same with any export.

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