Dickie Bush: From Quitting Wall St. to Making $500K/mo Writing Online

Dickie Bush: From Quitting Wall St. to Making $500K/mo Writing Online

Dickie Bush: From Quitting Wall St. to Making $500K/mo Writing Online

This creator has a superpower.

One that helped him:

  • Turn pro at Call of Duty at 13

  • Play D1 football at high school and college

  • And amass 600K online followers in less than 4 years

This is a tale of obsession.

This is the story of Dickie Bush.

At 5 years old, Dickie read the sports pages in the newspaper every morning.

There wasn’t a fact or stat he didn’t know about his beloved baseball team, The Tampa Bay Rays.

By 8, he could complete a Rubik’s Cube in 19 seconds.

His secret? “Obsession-based learning.”

Fast-forward to 2018. 

Dickie graduated from Princeton University with a major in Math & Computer Science. He then landed his dream job at a global investment firm, BlackRock. For the next 4 years, he worked as a hedge fund trader in the bustling streets of Manhattan. 

He loved it!

However, 2 years in, Dickie looked around at the old guys and saw a future he didn’t want.

But one thing he admired about the powerful people at BlackRock was their ability to write. They all wrote in-depth educational emails, distilling their learnings for others.

Dickie hated writing at school. But seeing how influential real-world writing could be, opened his mind.

Dickie listened to podcasts while on-commute. He began writing to refine and share his learnings via an internal newsletter at BlackRock. Very quickly, 200 fellow employees were reading his stuff.

Then it hit him… If he could gain readers at work, why couldn’t he gain (even more) readers online?

“If you want to unlock opportunities, put yourself out there in some way” 

So in January 2020, Dickie committed to publishing a weekly newsletter for 52 weeks.

Worst case scenario, his writing would improve and he’d better understand the ideas he was sharing; best case scanario, it would transform his life.

After 9 months, nothing happened.

To accelerate his newsletter growth, he began posting on Twitter every day.

28 days went by… Still, crickets. 

A failed experiment, he thought. But before stopping, he committed to seeing out the full month on Twitter. On the evening of day 29, Dickie posted a Twitter thread before going to bed.

The next day, he awoke to find his post had 4,000+ likes. 

His newsletter subscribers more than doubled overnight. It took him 9 months to go from 0 to 400 subs, and 9 hours to go from 400 to 1000.

Rather than claim to be an expert, Dickie would study experts, then write to share his learnings with others. 

This simple strategy of learning in public is one he uses to this day.

"People confuse writing as a teaching tool when it's a learning tool." 

To capitalise on this newfound attention, Dickie compiled some of his podcast notes into a Notion Doc. He sold it for 19 bucks. Within days, he made $600. 

It was the first money he’d ever made online. It was a brain-breaking moment.

Soon after, a businessman asked whether he could distil some content on his behalf. 3 days later, Dickie delivered a document to the client. 

Thrilled with the result, the businessman asked how much to pay him. But with no idea how much to charge, Dickie told him to pay whatever he thought it was worth, expecting a couple of hundred bucks. 

The next day, $5K hit his account.

In no time, he was “ghostwriting” for others, all while working full-time at BlackRock.

Then, 2020 hit. 
New York went into lockdown. 
Dickie moved back to Tampa to live with his Mom. 

One evening, at the dinner table, he excitedly pitched a business idea to his parents: Ship 30 for 30, a writing accountability group.

At first, 50 people signed up at $49 a pop. Dickie spent every free hour he had on his new venture. 

After 30 days, he jumped on a call with all 50 customers to ask: 

  • What they enjoyed

  • What they didn’t enjoy

  • What could be improved

  • And what they’d wanted from the experience

Dickie knew the key to making Ship 30 for 30 a success was to build something people couldn’t help but tell their friends about.

In early 2021, he partnered with esteemed digital writer Nicolas Cole, and things really took off. Dickie left BlackRock later that year to put all his energy into Ship 30 for 30.

Each new cohort generated more feedback, which helped them continue to iterate and improve the customer experience.

The pair has since used this same approach to launch and grow a suite of digital writing products.

Today, Dickie has:

  • 4 digital writing businesses

  • 578K+ followers across all platforms (incl 117K on LinkedIn)

  • And he’s on a mission to help 1,000,000 people start writing online

This creator has a superpower.

One that helped him:

  • Turn pro at Call of Duty at 13

  • Play D1 football at high school and college

  • And amass 600K online followers in less than 4 years

This is a tale of obsession.

This is the story of Dickie Bush.

At 5 years old, Dickie read the sports pages in the newspaper every morning.

There wasn’t a fact or stat he didn’t know about his beloved baseball team, The Tampa Bay Rays.

By 8, he could complete a Rubik’s Cube in 19 seconds.

His secret? “Obsession-based learning.”

Fast-forward to 2018. 

Dickie graduated from Princeton University with a major in Math & Computer Science. He then landed his dream job at a global investment firm, BlackRock. For the next 4 years, he worked as a hedge fund trader in the bustling streets of Manhattan. 

He loved it!

However, 2 years in, Dickie looked around at the old guys and saw a future he didn’t want.

But one thing he admired about the powerful people at BlackRock was their ability to write. They all wrote in-depth educational emails, distilling their learnings for others.

Dickie hated writing at school. But seeing how influential real-world writing could be, opened his mind.

Dickie listened to podcasts while on-commute. He began writing to refine and share his learnings via an internal newsletter at BlackRock. Very quickly, 200 fellow employees were reading his stuff.

Then it hit him… If he could gain readers at work, why couldn’t he gain (even more) readers online?

“If you want to unlock opportunities, put yourself out there in some way” 

So in January 2020, Dickie committed to publishing a weekly newsletter for 52 weeks.

Worst case scenario, his writing would improve and he’d better understand the ideas he was sharing; best case scanario, it would transform his life.

After 9 months, nothing happened.

To accelerate his newsletter growth, he began posting on Twitter every day.

28 days went by… Still, crickets. 

A failed experiment, he thought. But before stopping, he committed to seeing out the full month on Twitter. On the evening of day 29, Dickie posted a Twitter thread before going to bed.

The next day, he awoke to find his post had 4,000+ likes. 

His newsletter subscribers more than doubled overnight. It took him 9 months to go from 0 to 400 subs, and 9 hours to go from 400 to 1000.

Rather than claim to be an expert, Dickie would study experts, then write to share his learnings with others. 

This simple strategy of learning in public is one he uses to this day.

"People confuse writing as a teaching tool when it's a learning tool." 

To capitalise on this newfound attention, Dickie compiled some of his podcast notes into a Notion Doc. He sold it for 19 bucks. Within days, he made $600. 

It was the first money he’d ever made online. It was a brain-breaking moment.

Soon after, a businessman asked whether he could distil some content on his behalf. 3 days later, Dickie delivered a document to the client. 

Thrilled with the result, the businessman asked how much to pay him. But with no idea how much to charge, Dickie told him to pay whatever he thought it was worth, expecting a couple of hundred bucks. 

The next day, $5K hit his account.

In no time, he was “ghostwriting” for others, all while working full-time at BlackRock.

Then, 2020 hit. 
New York went into lockdown. 
Dickie moved back to Tampa to live with his Mom. 

One evening, at the dinner table, he excitedly pitched a business idea to his parents: Ship 30 for 30, a writing accountability group.

At first, 50 people signed up at $49 a pop. Dickie spent every free hour he had on his new venture. 

After 30 days, he jumped on a call with all 50 customers to ask: 

  • What they enjoyed

  • What they didn’t enjoy

  • What could be improved

  • And what they’d wanted from the experience

Dickie knew the key to making Ship 30 for 30 a success was to build something people couldn’t help but tell their friends about.

In early 2021, he partnered with esteemed digital writer Nicolas Cole, and things really took off. Dickie left BlackRock later that year to put all his energy into Ship 30 for 30.

Each new cohort generated more feedback, which helped them continue to iterate and improve the customer experience.

The pair has since used this same approach to launch and grow a suite of digital writing products.

Today, Dickie has:

  • 4 digital writing businesses

  • 578K+ followers across all platforms (incl 117K on LinkedIn)

  • And he’s on a mission to help 1,000,000 people start writing online

This creator has a superpower.

One that helped him:

  • Turn pro at Call of Duty at 13

  • Play D1 football at high school and college

  • And amass 600K online followers in less than 4 years

This is a tale of obsession.

This is the story of Dickie Bush.

At 5 years old, Dickie read the sports pages in the newspaper every morning.

There wasn’t a fact or stat he didn’t know about his beloved baseball team, The Tampa Bay Rays.

By 8, he could complete a Rubik’s Cube in 19 seconds.

His secret? “Obsession-based learning.”

Fast-forward to 2018. 

Dickie graduated from Princeton University with a major in Math & Computer Science. He then landed his dream job at a global investment firm, BlackRock. For the next 4 years, he worked as a hedge fund trader in the bustling streets of Manhattan. 

He loved it!

However, 2 years in, Dickie looked around at the old guys and saw a future he didn’t want.

But one thing he admired about the powerful people at BlackRock was their ability to write. They all wrote in-depth educational emails, distilling their learnings for others.

Dickie hated writing at school. But seeing how influential real-world writing could be, opened his mind.

Dickie listened to podcasts while on-commute. He began writing to refine and share his learnings via an internal newsletter at BlackRock. Very quickly, 200 fellow employees were reading his stuff.

Then it hit him… If he could gain readers at work, why couldn’t he gain (even more) readers online?

“If you want to unlock opportunities, put yourself out there in some way” 

So in January 2020, Dickie committed to publishing a weekly newsletter for 52 weeks.

Worst case scenario, his writing would improve and he’d better understand the ideas he was sharing; best case scanario, it would transform his life.

After 9 months, nothing happened.

To accelerate his newsletter growth, he began posting on Twitter every day.

28 days went by… Still, crickets. 

A failed experiment, he thought. But before stopping, he committed to seeing out the full month on Twitter. On the evening of day 29, Dickie posted a Twitter thread before going to bed.

The next day, he awoke to find his post had 4,000+ likes. 

His newsletter subscribers more than doubled overnight. It took him 9 months to go from 0 to 400 subs, and 9 hours to go from 400 to 1000.

Rather than claim to be an expert, Dickie would study experts, then write to share his learnings with others. 

This simple strategy of learning in public is one he uses to this day.

"People confuse writing as a teaching tool when it's a learning tool." 

To capitalise on this newfound attention, Dickie compiled some of his podcast notes into a Notion Doc. He sold it for 19 bucks. Within days, he made $600. 

It was the first money he’d ever made online. It was a brain-breaking moment.

Soon after, a businessman asked whether he could distil some content on his behalf. 3 days later, Dickie delivered a document to the client. 

Thrilled with the result, the businessman asked how much to pay him. But with no idea how much to charge, Dickie told him to pay whatever he thought it was worth, expecting a couple of hundred bucks. 

The next day, $5K hit his account.

In no time, he was “ghostwriting” for others, all while working full-time at BlackRock.

Then, 2020 hit. 
New York went into lockdown. 
Dickie moved back to Tampa to live with his Mom. 

One evening, at the dinner table, he excitedly pitched a business idea to his parents: Ship 30 for 30, a writing accountability group.

At first, 50 people signed up at $49 a pop. Dickie spent every free hour he had on his new venture. 

After 30 days, he jumped on a call with all 50 customers to ask: 

  • What they enjoyed

  • What they didn’t enjoy

  • What could be improved

  • And what they’d wanted from the experience

Dickie knew the key to making Ship 30 for 30 a success was to build something people couldn’t help but tell their friends about.

In early 2021, he partnered with esteemed digital writer Nicolas Cole, and things really took off. Dickie left BlackRock later that year to put all his energy into Ship 30 for 30.

Each new cohort generated more feedback, which helped them continue to iterate and improve the customer experience.

The pair has since used this same approach to launch and grow a suite of digital writing products.

Today, Dickie has:

  • 4 digital writing businesses

  • 578K+ followers across all platforms (incl 117K on LinkedIn)

  • And he’s on a mission to help 1,000,000 people start writing online

Level up your LinkedIn game. Install Kleo for free.

Level up your LinkedIn game. Install Kleo for free.

Level up your LinkedIn game. Install Kleo for free.

© 2023 Kleo

© 2023 Kleo