PrintCash with AI
EasyServiceFrontierClear niche and buyerAI model/API accessPayments via Stripe
Operator-Reported

Paid Newsletter Teaching AI Writing

Paid Substack newsletter of ChatGPT and Claude prompts and methods for writers; #2 education newsletter on Substack at the time.

In plain English

Write With AI is a paid email newsletter that teaches people how to write better with ChatGPT and Claude. Each issue shares ready-to-use prompts and examples. Readers pay a monthly or yearly subscription for the full content. The two founders are well-known online writers.

Automation60%
Startup costNot disclosed
Time to first $Not disclosed
Monthly range*$33,333 Annual ÷ 12

~$400K annual recurring revenue (founder-reported, Mar 2025)

DifficultyEasy
SourceWrite With AI - Our $400K/year newsletter strategy ↗

Operator: Nicolas Cole and Dickie Bush

Operator-Reported

A named, real operator ran this and shared results publicly. The figures are their own.

Not disclosed.

The tool stack

Stripe ↗
2.9% + 30¢ per charge

Payments

 Beehiiv ↗ affiliate link
Free tier; paid plans

Newsletter platform

 OpenAI API ↗
Pay per token

LLM / vision

Prices are the vendors' published list prices as researched in Oct 2026 and change often — always check the vendor's pricing page.

Step-by-step setup

  1. Pick a niche and language with underserved readers.
  2. Write a consistent paid newsletter; AI helps research.
  3. Free tier to build the list, paid tier for depth.
  4. Grow through social and cross-promotions.

What's automated vs. the human 40%

The machine does

  • Core AI generation/analysis
  • Billing and onboarding

You still do

  • Product quality and support
  • Distribution and marketing
  • Compliance and edge cases

Overview

Paid Substack newsletter of ChatGPT and Claude prompts and methods for writers; #2 education newsletter on Substack at the time.

Operator: Nicolas Cole and Dickie Bush. Website: https://writewithai.substack.com/

Estimated split: about 60% of the work automated, 40% human.

Realistic income

Nicolas Cole and Dickie Bush wrote: “We’re at $400K ARR” and the #2 education newsletter on Substack (Mar 2025). This figure is operator-reported and not independently verified. This is one operator’s result, often after months or years of work, and doesn’t predict yours. Check the live source — numbers change.

Risks

  • Writer-dependent; hard to step away.
  • Slow audience growth at first.
  • Startup cost and time to first dollar are not disclosed.

*Income figures are illustrative ranges based on public pricing and typical outcomes reported by practitioners, not guarantees. Most new online businesses earn little or nothing at first. Not financial, legal or tax advice.

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