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How I made my first $200,000 writing online – Part 1

The secrets to my success

You’re crazy, I get it…

You’d rather read instead of watch the video.

I love it. Here’s the text version:

The Broke, Broken Batman

“I f*cked up.”

I was 28 years old. With $50,000 of credit card debt.

And only making $32,000 Canadian per year – Colleges don’t pay teachers as well as you think.

Each month I paid my monthly bills and was left with a big fat $0 in my account.

I was trapped.
I knew it.
I felt it.

It was like being stuck in the pit from the Dark Knight Returns.

But unlike Batman, I had no money to come back to if I escaped.

That was, until Dakota Robertson taught me how to make internet money.

Fast forward 18 months and I’m running a $500,000 per year content marketing agency.

Where people will pay me $1,000 for an hour of my time.

(That seemed impossible 12 months ago).

Some call me an outlier.
They say my transformation is rare and doesn’t work for other people.


They are also stuck in the pit.
And people in the pit don’t like seeing others leave it.

No matter where you’re at, you can be free in 6-12 months.

You just need to play the “internet money” game correctly.

Gary V’s Got a Point

Yesterday, I was scrolling IG, procrastinating writing this newsletter – yes, I’m human.

And this short from Gary V video got my thinking.

To paraphrase it, he said: If the internet existed when he was a kid, he’d already own the New York Jets.

Before you call this crazy, let me explain.

One path to riches is to own a piece of a business.

And all successful businesses have 1 thing in common:
They exchange value for money.

The more people willing to give you money for what you offer, the more successful your business will be.

In theory, all business is this simple – but it’s not easy.

So let’s bend our minds with a thought experiment.

Imagine starting a business in a small city without the internet.

Your earning potential is limited by your customer base.

For me that would be 100,000 people in the small city of Kelowna, Canada.

Where only a fraction of them will want what I offer.

Now imagine trying to expand to other cities in this pre-internet era.

It would take A LOT of money, connections, and infrastructure.

And these connections wouldn’t be easy to make without physically traveling.

I refer to this era as “business on hard mode.”

But then the internet pulled a modern Pokémon on us.

And started to make the games easier…

Start a “Chinese Record Shop”

“Bard AI, what’s the population of China?”

“China is estimated to be 1,425,671,352 people. Making up 17.72% of the total world population.”

This might not seem relevant but here’s the thing.

In China, an entrepreneur can open up a small store selling ONLY 1980s rock records and turn a profit.


Because the population is large enough to support a niche record shop’s customer base.

Now expand this scope to the internet.

Which has 5.19 BILLION people on it.

With that many potential customers you can create million dollar empires within the smallest of niches.

  • Ghostwriting agencies
  • Creative SaaS products
  • Direct to consumer semi healthy chocolate bars – Feastables.

No matter where you’re at in your entrepreneurial journey, you’re only a few shares away from millions of people.

Millions of potential customers!

What’s the point of all this?

Speedy scale to be exact.

With the right skills you can build multi 6 figure companies in 6 to 12 months.

The only limit to your scale is your skills, beliefs, and ability to consistently execute.

Still don’t believe me?

Here’s what it would take for you to make $100,000 this year:

Sell 100 people a product for $1,000.
Sell 40 people a product for $2,500.
Sell 20 people a product for $5,000.

In theory, it’s that easy.

The problem is, most people don’t know where to start.

They lack experience.

And a road map to get them there.

That road map is what Dakota gave me 18 months ago…

Making Your First 6 Figures (Without Any Experience)

In hindsight, I had 2 major problems when I started my online business:

  • No one knew I existed
  • No one would pay me $3,000+ / mo

I used to think these problems were impossible to solve.

But if this is true, how come so many 20 year olds are making 6 figures online?

They’re young.
Have little life experience.
But they’re crushing it.

And you can be one of them.

If you can solve the above 2 problems.

Problem 1: No one knows you exist

As of writing this, I have 68,000 Twitter followers.
7500 LinkedIn followers.
And 228 followers on Threads – I’m clearly crushing it on this platform, I know.

But it wasn’t always this way.

My first 6 months on Twitter I only grew to 2,000 followers.

No one took me seriously.

I struggled each week to get eyes on my content.

But I found a solution.

I “borrowed” influence.

• Paid for retweets (reach)
• Commented under big accounts (reach)

With a single retweet from Dakota, I could reach 10,000+ people.

Main Lesson: Borrow influence while you build your own.
(All big creators grew this way, btw).

Problem 2: No one will pay you $3,000+ / mo

People will pay you high ticket prices…
If you solve the right problem.

But most creators focus on solving the wrong ones.

“The amount of money you make is equal to the size of problems you solve.”

My business mentor used to tell me that.

The big problems that need solving aren’t in:

  • Mindset
  • Productivity
  • Self improvement

People usually only pay a few hundred dollars for these.

Making it hard for you to make big money if you have a small audience
(more on this in a future issue).

Big money problems tend to exist in the world of business:


  • SEO
  • Ghostwriting
  • Cold outreach


  • Appointment setting
  • High ticket closing
  • Sales training

Develop skills in these areas and you can make 6 figures online with a small audience.

I took the marketing route.

Learning copywriting / ghostwriting from:

  • Books – The Ad Week Copywriting Handbook
  • Mentorships – Growth Ghost Cohort
  • Courses – Digital Economics

(No affiliations btw).

It all starts with skills.

Pick your high income vehicle and start learning.

That’s part 1.

In part 2, we’ll break down my multi 6 figure playbook.

The exact system I used to scale my agency to $500K ARR.

It’s beginner friendly.
Focusing on core business principles that apply to any niche.

See you in the next issue,


Keep reading
Taylin Simmonds
About the author

Retired educator turned creator and consultant, I took my ghostwriting agency to $500K/year. Now I guide other creators toward achieving similar results.

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