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He Quit His Job And Makes $10M/Year Writing Online | Starter Story

August 13, 2026

AI Summary

5 min read

Dickie Bush was a hedge fund trader on Wall Street who woke up at 4:30 a.m. to write for two hours before his day job, then built a portfolio of writing-based businesses on pace to do $10 million in 2024. He did not quit his job until his side income hit a million dollars a year. The turning point came when he saw a 37-year-old colleague ask permission to attend his son's Little League game and get denied. Bush realized that even if he did everything right for another 14 years, he would still be asking for permission. Instead of quitting immediately, he started writing online while still employed.

The first $5,000 and the ghostwriting blueprint

Bush committed to a 30-day personal writing challenge, publishing something every day. On day 27, a post got zero engagement overnight, but by morning it had been retweeted by Naval Ravikant and others, picking up thousands of likes. His newsletter grew from 250 to 1,000 subscribers. The lesson: "You never know what's gonna go viral. You just have to keep showing up and hitting publish."

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What you'll learn

  • 1 (01:01) **Introduction & The $10M Writing Portfolio** - Dickie Bush describes his transition from Wall Street hedge fund trader to full-time writer, and breaks down the four businesses that are on pace to do $10M in 2024: Ship 30 for 30 ($3M/yr), Premium Ghostwriting Academy ($5M/yr), Write with AI ($500K/yr), and TypeShare (SaaS).
  • 2 (03:55) **Backstory: From Princeton & BlackRock to Feeling Trapped** - Dickie traces his path from playing football at Princeton, studying math and CS, to landing his "dream job" at BlackRock and then a hedge fund, only to realize his effort wasn't rewarded.
  • 3 (04:57) **The Turning Point: Asking for Permission** - Dickie describes witnessing a 37-year-old colleague ask for permission to attend his son's Little League game and being denied, which triggered his exit strategy.
  • 4 (06:42) **The Early Days: Zero Traction & The 30-Day Challenge** - Dickie describes cutting his Wall Street work hours from 12 to 3-4 per day to learn and write, but only having 250 subscribers on his newsletter.
  • 5 (09:01) **The Viral Breakthrough** - The post from Day 27 went viral overnight after being retweeted by Naval Ravikant, taking him from 250 to 1,000 subscribers.
  • 6 (09:26) **First $5,000: Ghostwriting with No Price** - A follower asked Dickie to write a "worldview creation thread" for him, and Dickie, unsure of what to charge, asked the client to pay whatever they thought it was worth.
  • 7 (11:04) **Scaling Beyond Ghostwriting: Ship 30 for 30** - Dickie realized ghostwriting was hard to scale past $5-10K/month, so he zoomed out to identify the input that created the opportunity: the 30-day writing challenge.

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Guests on this episode

Show Notes

He Quit His Job And Makes $10M/Year Writing Online

This is the breakdown of how Dickie Bush makes over $10M/year as a digital writer.

📚 FREE Sheet of 160+ Solopreneur Business Ideas → https://www.starterstory.com/solopreneur?utm_campaign=dickie&utm_source=youtube

Follow Dickie 🐦 Twitter - https://x.com/dickiebush 🖥️ Website - https://www.dickiebush.com/

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