How Dickie Bush built a $10M writing business from a Wall Street desk

Executive overview

Dickie Bush was a hedge fund trader making good money but with no leverage — extra effort produced zero extra reward. He started writing online while still employed, didn't quit until his side income matched his salary, and now runs four writing businesses on pace for $10M in 2024.

Writing is the highest-leverage skill available: it compounds across every product, platform, and business model.

From Wall Street to first dollar

• Watching a colleague ask permission to attend his son's little league game was the turning point — Dickie decided he wouldn't wait 14 years for the same outcome.
• He didn't quit immediately; staying employed removed scarcity pressure and gave him time to experiment.
• Started a newsletter inside BlackRock to build visibility, then moved to public social media to reach a wider audience.
• Committed to a 30-day daily publishing challenge — on day 27, a post got retweeted by Naval and Balaji, taking his newsletter from 250 to 1,000 subscribers overnight.
• Key lesson: you can't predict what goes viral — consistency is the only reliable input.

Landing the first $5,000

• The viral post was a "worldview creation thread"; readers began asking Dickie to write similar threads for them.
• His first paying client offered to name his own price — Dickie did 15 hours of work over a weekend and received $5,000 (he'd expected $250).
• That moment proved the link between writing-generated attention and real business income.
• Within two weeks he was on pace for $10K/month from ghost writing alone.

Building Ship 30 for 30

• Recognised ghost writing was hard to scale past $10K/month as a solo operator.
• Tweeted asking if others would join a 30-day writing challenge with him; response was overwhelming.
• Charged $50 with a money-back guarantee for completion; ran 50 one-on-one interviews to understand what people actually needed.
• Rebuilt the product properly, charged $99, and made $30K in December.
• Partnered with Nicholas Cole to expand Ship 30 into a full digital writing education; the course now does ~$3M/year.

Scaling while employed

• Daily routine while at BlackRock: 4:30 AM wake-up, two hours of writing, 7 AM work login, evenings back on Ship 30.
• By end of 2021, Ship 30 did ~$1M at ~90% margin — doubling his full-time salary.
• Only then did he quit, operating from abundance rather than desperation.

The writing business portfolio

• Ship 30 for 30 — community writing course for beginners: ~$3M/year.
• Premium Ghost Writing Academy — group coaching for freelance writers: ~$5M/year.
• Write with AI — paid newsletter on AI writing tools: on pace for $500K.
• TypeShare — SaaS with templates, analytics, and hosting for writers.

Why writing is the right skill to build

• Every piece of content — video, podcast, product — starts as writing; it transfers everywhere.
• Schools teach academic writing, not persuasive or online writing — the gap is a genuine opportunity.
• Write with an empathetic lens: the reader only cares what the writing does for them, not who wrote it or how long it took.

Fastest path to income as a writer

• Build the skill yourself, then borrow someone else's audience as a ghost writer.
• Ghost writing can generate $5–10K/month without requiring a large personal following.
• Operating from that income base lets you build your own audience without financial pressure.
• Avoid waiting for followers before monetising — Dickie had 1,000 when he earned his first $5,000.

Tools and working habits

• No complex system: Apple Notes for ideas, TypeShare for publishing, search his own Twitter to find old writing.
• Over-engineered note-taking and content calendars are productive procrastination — just publish.
• Two work modes: monk mode (5 AM start, everything scheduled, single outcome, 3–4 times per year) and maintenance mode (more sleep, less output, where the next sprint's ideas emerge).

Founder advice

• If doubling your effort in your current role produces no extra reward, find a different vehicle — don't wait two years to make that call.
• Stop learning "just in case"; start learning "just in time" — read only what a current project requires.
• Kill your "once's": "once I quit… once things slow down… once I move jobs" — that moment never arrives. Take one step today.
• The people you admire are not more talented; they've simply been at it longer.