Today we won’t be discussing a typical startup story that goes from struggles to fortunes, but rather a humble story of a man finding financial independence. Dickie Bush is the co-founder of Ghostwriting Academy, Write With AI, Typeshare, and Ship 30 for 30. 

These are all the multiple sources of income he’s built over time, but his actual journey started in 2019 in his early-mid 20s. 

Bush was living the dream, at least on paper. A prestigious Wall Street job, a six-figure salary, and a “clear” path to career success. But deep down, he felt trapped. The long hours, the fluorescent lights, the lack of control over his time, everything he didn’t want. 

He needed an escape, but he didn’t quit right away. Instead, he took a different approach: he started writing online. Fast-forward a few years, and that decision turned into a $10 million business. 

The path wasn’t glamorous or overnight. It required strategy, consistency, and a willingness to put ideas out into the world before they were perfect. Here’s how he did it.

A Wake-up Call - A Deep Realization!

Dickie’s wake-up call came when he saw a 37-year-old coworker ask for permission to attend his son’s little league game. The boss said no. That was the moment Dicky realized he didn’t want that future. 

But instead of quitting his job in frustration (a mistake many people make), he focused on building something sustainable on the side.

He started by writing a simple newsletter for his coworkers at BlackRock. Then, he thought, “Why limit myself to a corporate audience when the internet gives me access to millions?” That’s when he shifted to publishing online, using platforms like Twitter to build an audience.

The 4:30 AM Routine That Built a Business

Dickie didn’t quit his job overnight. He didn’t throw caution to the wind and dive into writing with no plan. Instead, he used a structured approach that balanced his full-time job with his side hustle.

• 4:30 AM – Wake up and write for two hours.
• 7:00 AM – Start his hedge fund job.
• Evenings – Build his writing business.

“I went from working 12-hour days down to 3 or 4 and spent the rest of a 10-hour workday learning, reading, immersing myself into different things and then writing about that in my newsletter.” - Dickie Bush, Starter Story

Most people underestimate what they can achieve in their spare time. Dickie knew that small, consistent efforts would compound over time.

And then, one tweet changed everything.

Writing Every Day and Finding a Breakthrough

Dickie committed to writing and publishing something every day for 30 days. Most posts went unnoticed, but on day 27, everything changed. A tweet he wrote got picked up by well-known entrepreneur Naval Ravikant and went viral. His newsletter exploded from 250 subscribers to 1,000 overnight.

That’s when he realized: virality isn’t predictable. The only way to win is to keep publishing until something takes off.

Making His First $5,000

With newfound attention, people started reaching out, asking if he’d write for them. One potential client asked, “How much do you charge?”

Dickie had no idea. Instead of throwing out a number, he said, “I’ll do it for free, just pay me what you think it’s worth afterward.” He was expecting maybe $250. Instead, the client sent him $5,000. That moment shattered his perception of money and value.

The takeaway? You often undervalue your own skills. Letting the market speak can help you find the true worth of your work. Dickie assumed his work was worth $250, but his client saw it as worth 20x more. Once he realized that people would pay big money for high-quality work, he started thinking bigger.

Success in business often follows a simple formula: get a win, capitalize on it, and keep pushing forward.

More requests started coming in, and within a few weeks, he was on track to make $10,000 a month of ghostwriting. But ghostwriting alone wasn’t scalable. He needed something bigger. That shows how rooted in reality yet ambitious Bush was. 

Scaling Up with a Writing Challenge

Looking back at what led to his success, Dickie realized that writing consistently for 30 days had been the key. So, he put out the following simple tweet.

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The response was overwhelming. He set up a Slack group and charged $50 to join, refunding participants who completed all 30 days. The challenge took off, and people loved it. He refined it, added more structure, and rebranded it as Ship 30 for 30, a writing community designed to help beginners build a writing habit. That first iteration made $30,000 in a month.

Turning a Side Hustle Into a Business Empire

Dickie didn’t stop at Ship 30 for 30. He partnered with Nicholas Cole to expand it into a full-scale writing education program, increasing its price and value. Meanwhile, he launched new projects:

• Ship 30 for 30: A structured writing course that now generates $3M a year.
• The Premium Ghostwriting Academy: Teaching freelance writers how to become high-paid ghostwriters ($5M a year).
• Write with AI: A paid newsletter on AI writing tools ($500K a year).
• Typeshare: A SaaS platform for writing and publishing online.

These businesses all fed into each other, creating a self-reinforcing ecosystem around writing. In total, they’re projected to bring in $10M in 2025.

Final Thoughts: Key Lessons for Aspiring Writers and Entrepreneurs

Dickie’s success isn’t random but a blueprint that both writers and entrepreneurs can follow. His journey highlights principles that apply to anyone looking to build an online presence, monetize skills, and grow a business. 

One of the most important takeaways is to start creating online. Whether you're a writer, a consultant, or an entrepreneur, the internet rewards those who consistently put out valuable content. Sharing insights, lessons, or expertise attracts attention, builds credibility, and opens doors to opportunities.

You don’t need a massive audience to make money. Dickie Bush earned $5,000 from ghostwriting before hitting 1,000 followers. Entrepreneurs, too, can generate revenue early by focusing on high-value clients rather than chasing large followings. A small but engaged audience is often more profitable than a big but passive one.

The fastest way to monetize? Sell a skill. Writing is one example, but the principle applies broadly. Whether it’s marketing, design, coding, consulting, or coaching, offering a service is the easiest way to start making money. Selling a skill generates cash flow, builds your reputation, and can eventually evolve into scalable products or businesses.

Test small and scale up. Dickie’s Ship 30 for 30 started as a $50 challenge in a Slack group before becoming a multi-million-dollar course. Entrepreneurs should take the same approach and validate ideas with small experiments, refine what works, and scale strategically. The best businesses start with a simple solution to a real problem.

Finally, consistency beats talent. Dickie’s breakthrough came on day 27 of his writing challenge. The same applies to business. Success isn’t about one big moment, but about showing up every day, learning from failures, and improving over time. Those who stay in the game the longest tend to win.

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