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A daily-writing habit turned into a portfolio of writing courses, coaching, a paid newsletter and SaaS, on pace for $10M in 2024 — started from a $50 Slack accountability channel.
Premium Ghostwriting Academy ~$5M/yr · Ship 30 for 30 ~$3M/yr · Write With AI on pace for $500K · Ship 30 did $1M in 2021 at ~90% margin · first ghostwriting job paid $5,000
Not knowing what to charge for his first ghostwritten thread, he said "pay me what it was worth" (he had planned to ask $250) and received $5,000 — then turned the 30-day writing challenge that got him noticed into a $50 Slack group, a $99 course and a $3M-a-year business.
Fewer bars = easier, cheaper, or faster for an AI-assisted solo builder. Editorial judgments based on the case details.
Dickie Bush was working at BlackRock when he decided a job where extra effort earned nothing extra was a trap. He started an internal newsletter, then a public one in January 2020, and stalled at about 250 subscribers. He committed to publishing something every day for 30 days. On day 27 a post got zero engagement, until overnight it was retweeted by Naval, Balaji and others, reached four to five thousand likes and took his newsletter from 250 to about 1,000 subscribers. That post led to his first ghostwriting client, who paid $5,000 for a thread. Instead of scaling ghostwriting, he tweeted an invitation to join his next 30-day challenge: a $50 Slack accountability group, refundable if you finished. After 50-plus customer interviews it became Ship 30 for 30, a $99 course that made $30,000 that December. With Nicolas Cole as partner it did $1 million in 2021 at about 90% margin, and he left BlackRock. Today the portfolio — Ship 30 for 30, Premium Ghostwriting Academy, the Write With AI paid newsletter and Typeshare software — is on pace for $10 million in 2024.
His first customers came from his own writing, but only after a stretch of near-zero results. With about 250 newsletter subscribers, he publicly committed to a 30-day writing challenge and published every day.
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Data credibility: Dickie Bush states every figure himself in a Starter Story interview: the portfolio is on pace for $10M in 2024, Premium Ghostwriting Academy does about $5M a year, Ship 30 for 30 about $3M, Write With AI is on pace for $500K, and Ship 30 did $1M in 2021 at roughly 90% margin. No dashboards are shown and 'on pace' figures are projections. Auto-captions garble the first payment as $55,000; he twice says it was $5,000. Typeshare, the SaaS, is not given a revenue figure.
The first dollar was a $5,000 ghostwriting payment. After his viral breakdown thread, someone asked him to write a similar thread about them.
The flywheel is writing feeding products that teach writing. Daily public posts build an audience; the audience buys Ship 30 for 30; students who learn to write online publish more, which advertises the course and the brand.
Dickie's quiet stretch was the months of newsletters to about 250 subscribers and a 30-day challenge that, by day 27, had produced nothing. He says the bigger fear early on is what old friends will think; the real problem, once you publish, is that nobody cares yet.
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