How Dickie Bush Built a $10 Million Writing Business While Working a 9-to-5 Job
In this inspiring story, we’ll explore how Dickie Bush transformed his career from a Wall Street hedge fund trader to a successful online writer and entrepreneur.
His journey demonstrates that with dedication, the right skills, and a strategic approach, it’s possible to build a thriving business while maintaining a full-time job. Let’s learn how to make money writing online from his journey.
Meet Dickie Bush
Dickie Bush’s story is a testament to the power of online writing and entrepreneurship.
In just three years, he went from a Wall Street trader working 60-hour weeks to running a portfolio of writing-based businesses on track to generate $10 million in 2024.
His business portfolio includes:
- Ship 30 for 30: A community-powered writing course ($3 million/year)
- Premium Ghost Writing Academy: Group coaching for freelance writers ($5 million/year)
- Write with AI: A paid newsletter for AI writing tools ($500k/year)
- TypeShare: A SaaS platform for online writers
The Turning Point
Despite having what many would consider a dream job on Wall Street, Dickie found himself unfulfilled.
The lack of correlation between effort and reward in his corporate role left him searching for something more.
“I witnessed someone I worked with asked for permission to go to their son’s little league game and he was probably 37, 38 years old and his boss said no. So if I do everything right for 14 more years, I might be sitting here having to ask for permission to go to my kid’s little league game. Uh oh, I got to get out of here.”
This realization led Dickie to explore new opportunities, but he didn’t quit his job immediately.
Instead, he started looking for ways to passively pursue new ventures.
The Early Days of Writing Online
Dickie’s journey into online writing began with a simple newsletter inside BlackRock. After a few months, he realized he could reach a much larger audience through social media and the internet.
His breakthrough came when he committed to a 30-day personal writing challenge:
- Write and publish something every day for 30 days
- On day 27, with no engagement, he almost gave up
- The next day, his post went viral, gaining thousands of likes and retweets
- His newsletter subscribers jumped from 250 to 1,000
The key takeaway: Consistency is crucial. You never know what will resonate with your audience, so keep showing up and hitting publish.
Monetizing Writing Skills
Dickie’s first significant earnings came from an unexpected source.
After his viral post, someone reached out asking him to write a thread about them. Unsure of what to charge, Dickie let the client determine the value.
The result? A $5,000 payment for a weekend’s work.
“That was the very first time in many years I felt that I again had something where more effort, more intensity led to more results, and that completely broke my brain.”
This experience taught Dickie two valuable lessons:
- The attention generated from writing can lead to lucrative business opportunities
- There’s a market for high-quality, personalized content
Scaling Up: From Side Hustle to Full-Time Business
Recognizing the potential of his 30-day writing challenge, Dickie decided to turn it into a product.
Here’s how he developed it:
- Tweeted about his experience and asked if others would join him
- Initially charged $50, with a money-back guarantee for completing all 30 days
- Conducted over 50 one-on-one interviews to improve the product
- Partnered with Nicholas Cole to create a comprehensive 30-day digital writing education program
- Priced the new program at $99
The result? By the end of 2021, Ship 30 for 30 had generated $1 million in revenue with a 90% profit margin.
Balancing a 9-to-5 Job and a Side Hustle
Dickie’s daily routine while building his business alongside his full-time job:
- Wake up at 4:30 AM
- Write for 2 hours
- Start BlackRock work at 7:30 AM
- Log off as soon as possible
- Build Ship 30 for 30 in the evenings
This rigorous schedule allowed Dickie to double his full-time job income from his side hustle before eventually leaving his corporate role.
The Importance of Writing Skills
Dickie emphasizes that writing is the foundation for all content creation:
“When you recognize that the foundation for every single piece of content, every product, every video, every podcast is writing… it’s the most applicable skill.”
He argues that mastering persuasive and compelling writing can open doors to numerous opportunities across various industries and ventures.
Advice for Becoming a Better Writer
Dickie offers the following tips for aspiring writers:
- Read “The Art and Business of Online Writing” by Nicholas Cole
- Write with an empathetic lens, focusing on solving readers’ problems
- Create content that provides value in the most concise, clear, and compelling way possible
Monetizing Writing Skills Quickly
For writers looking to make money quickly, Dickie recommends:
- Build your writing skills
- Borrow someone else’s audience by ghost writing for them
- Use this approach to build a sustainable income of $5,000 to $10,000 per month
- Use the financial stability to work on building your own audience and passion projects
Writing Tools and Workflow
Dickie keeps his writing process simple:
- Uses Apple Notes for jotting down ideas
- Avoids complex organizational systems
- Utilizes TypeShare for publishing content across platforms
- Emphasizes the importance of writing consistently rather than getting caught up in productivity tools
A Day in the Life of Dickie Bush
Dickie alternates between two modes:
- Build Mode (Monk Mode):
- Wake up at 5 AM
- Strictly scheduled day, including two workouts
- Meals planned in advance
- 9 PM bedtime
- Focused on achieving a specific outcome
- Occurs 3-4 times per year
- Maintenance Mode:
- 9 hours of sleep
- More relaxed schedule
- Time for idea generation and reflection
Overcoming Struggles
One of the biggest challenges Dickie faced was overcoming the fear of judgment:
“If there’s anything that’s holding someone back from creating on the internet more than any other factor, it’s what their high school friends are going to think about them if they see them on Twitter like writing.”
He realized that most people are too busy thinking about themselves to pay attention to what others are doing online.
This mindset shift allowed him to start publishing without fear.
Advice for Aspiring Entrepreneurs
Dickie offers the following advice for those starting their entrepreneurial journey:
- If your current situation doesn’t lead to more income or skill development when you double your effort, find something else.
- Avoid “productive procrastination” – focus on learning skills that directly apply to your current projects.
- Remember that successful people aren’t necessarily more talented; they’ve likely been working at it longer.
- There’s never a perfect time to start. Take action today rather than waiting for ideal circumstances.
“If you can’t get started on something today thinking there’ll be a better time in the future, that’s never going to come. So anytime you can just throw all that out and say how can I take one step forward on it today… if you can kill all the ‘whens’ in your life, you’ll be in a better spot.”
Key Takeaways on How to Make Money Writing
- Consistency is crucial in content creation and business building.
- Writing is a foundational skill that can open doors to numerous opportunities.
- Start monetizing your skills by offering services to established audiences.
- Balance your day job and side hustle by creating a strict schedule and maximizing productivity.
- Overcome the fear of judgment by focusing on providing value to your audience.
- Take action today rather than waiting for the perfect moment to start your entrepreneurial journey.
Dickie Bush’s story demonstrates that with dedication, the right skills, and a strategic approach, it’s possible to build a thriving online business while maintaining a full-time job.
By focusing on developing your writing skills and consistently creating valuable content, you too can unlock new opportunities and potentially build a multi-million dollar business.
The key is to start small, remain consistent, and be willing to adapt and learn as you go.
Whether you’re looking to start a side hustle or completely change your career path, Dickie’s journey offers valuable insights and inspiration for aspiring entrepreneurs and content creators.
(Source: The “Starter Story” Youtube Channel’s vide on Dickie Bush)
