Nicolas Cole and Dickie Bush were not first-time founders when they started Write With AI in early 2023. They had already built Ship 30 for 30, a digital writing course, and Premium Ghostwriting Academy, a higher-ticket coaching business. That meant they came in with a large existing audience on Twitter/X and a habit of publishing daily, so the newsletter started with built-in distribution rather than a cold start.

By their own account, Write With AI was a fun side project meant to capitalize on the early ChatGPT moment, and it grew to about $100,000 in revenue in its first year. The pair largely ignored it through 2024 while focusing on their bigger businesses, and revenue hovered around $300,000 in annual recurring revenue. The interesting part is what happened when they decided to actually pay attention to it again at the start of 2025.

They wrote up five concrete changes that pushed the newsletter past $400,000 in ARR. The biggest lever was quarterly digital product drops: one single product release added about $90,000 in revenue, roughly a third of the newsletter's yearly total. They paired that with a $350 founding member tier that bundles every past and future product, so each new launch doubles as an upsell. They also ramped up Substack Notes (posting two to four times a day, which now drives over a third of new subscribers), built an organized content library sorted by reader problem, and added a welcome email with a free gift and a $49 upsell that quietly adds a few thousand dollars a month.

According to Nicolas Cole, the paid newsletter reached number one in Substack's Education category in 598 days, runs no ads, and had over 67,000 total subscribers as of mid-2025. The founders frame the newsletter not as a standalone product but as the front end of a wider AI writing business they expect to grow into seven figures through product upsells.