Dicky Bush
- Background and origin story
- Former Wall Street hedge fund trader working 60-hour weeks, initially making $90k/year, promoted to $180k/year by age 22
- Princeton alumnus: Played football, studied math and computer science, interned at BlackRock as a sophomore, joined full-time after graduation
- Grew unhappy due to misaligned incentives: Working harder or longer did not increase compensation
- Pivotal turning point: Witnessed a 37-38-year-old coworker get denied permission to attend his son’s little league game by his boss, realized he did not want to be in that position 14 years later
- Started an internal newsletter at BlackRock to build name recognition, launched a public newsletter in January 2020 to reach larger audiences
- Pivotal moments and turning points
- Committed to a 30-day daily writing challenge; day 27 post went viral after being retweeted by nval bology and other high-profile accounts, growing newsletter from 250 to 1000 subscribers
- First ghostwriting client paid $5000 for a single project, proving writing attention could convert to high-income opportunities
- Partnered with Nicholas Cole to scale a $99 Slack writing challenge into Ship 30 for 30, a full digital writing course
- Hit $1M in revenue from Ship 30 for 30 in 2021 with 90% margin, quit BlackRock when side income doubled his full-time salary
- Business growth, current status, or exit details
- Runs a portfolio of 4 writing-focused businesses, on pace to generate $10M in total revenue in 2024
- Maintained full-time job until side income exceeded salary to avoid operating from a scarcity mindset
Products and Offerings
- Core products (4 writing-focused businesses)
- Ship 30 for 30: Community-powered writing course for beginners to start writing online, generates ~$3M/year
- Premium Ghostwriting Academy: Evergreen group coaching model for beginner freelance writers to position as premium ghostwriters, generates ~$5M/year
- Write with AI: Paid newsletter training AI writing tools to act as personal writing interns, on pace for $500k in 2024
- Type Share: SaaS platform with templates, analytics, hosting, and all resources needed to start writing online
- Early experiments
- $50 30-day writing challenge with money-back guarantee for completion, later upgraded to a $99 paid product that generated $30k in December
Metrics and Financials
- Revenue milestones
- 2021: Ship 30 for 30 generated $1M in revenue with 90% margin
- Early $99 writing challenge product generated $30k in December of its launch year
- First ghostwriting project paid $5000
- Total portfolio on pace for $10M in annual revenue in 2024
- Individual business revenue:
- Ship 30 for 30: ~$3M/year
- Premium Ghostwriting Academy: ~$5M/year
- Write with AI: $500k projected for 2024
- Financial decisions
- Quit full-time BlackRock role only after side hustle income doubled his $180k/year salary to avoid scarcity mindset
- Ghostwriting can generate $5k–$10k/month in income with fewer than 40 hours of work weekly
Strategy and Growth
- Overall vision and positioning
- Build a portfolio of complementary writing-based businesses that leverage online writing as a core monetizable skill
- Position writing as the foundational skill for all content, products, and media
- Primary growth engine
- Consistent daily writing and publishing to social media, relying on viral posts to grow audience and inbound client leads
- Key tactics and routines
- Launched 30-day daily writing challenge to build writing habit and initial audience
- First monetized by ghostwriting for others with established audiences before building a personal audience
- Ran 50+ one-on-one interviews with users to refine paid course offerings
- 9-5 routine while working full-time: Woke up at 4:30 a.m. to write for 2 hours, logged into full-time job at 7:30 a.m., logged off early to build side business in evenings
- Current routine alternates between two modes:
- Monk mode: 5 a.m. wake-up, schedule down to the minute, 9 p.m. bedtime, 2 daily workouts, pre-planned meals, 3-4 times/year for intense sprints
- Maintenance mode: 9 hours of sleep, more leisure time (beach time) to generate ideas for future sprints
Tech Stack and Infrastructure
- Core tools
- Type Share: Proprietary SaaS for publishing tweets, long-form LinkedIn content, and Instagram carousels
- Apple Notes: Synced across phone and computer to capture ideas on the go
- Twitter search: Used to find past written content instead of complex note-taking systems
- Key technical decisions
- Avoids over-tooling: No complex content calendars, editing systems, or note-taking setups to prevent productive procrastination
- Publishes directly without waiting for perfect systems
Lessons and Advice
- General founder advice
- Leave any role where doubling your effort does not lead to more income or skill growth
- Avoid “productive procrastination” (reading books without a project to apply them to); adopt “just in time” learning instead of “just in case” learning
- People you admire are not more talented or special, only more experienced – extend your time horizon to reach goals
- There is no perfect time to start: Stop waiting for ideal circumstances (quitting a job, personal life events) to launch a project
- Kill “want-tos” (excuses) and take one small step forward daily
- Writing-specific advice
- Writing is the foundation of all content, products, videos, and podcasts; persuasive writing is a lifelong income skill
- Top resource: Nicholas Cole’s The Art and Business of Online Writing for social platform writing guidance
- Write with an empathetic lens: Focus on solving the reader’s problem quickly and concisely, not on personal effort or credentials
- Fastest way to monetize: Build writing skills first, then ghostwrite for others with established audiences to generate $5k–$10k/month before building your own audience
- Overcome fear of judgment: Peers are too focused on themselves to care about your writing; the bigger challenge is usually low engagement, not negative feedback
- Hard-won insights
- Viral content is unpredictable – consistent daily publishing is required to hit viral posts that grow your audience
- Ghostwriting is the most sustainable way to build initial writing income without working 40+ hours/week
- Scaling a solo ghostwriting side hustle beyond $5k–$10k/month is difficult; pivot to scalable products (courses, SaaS) instead