You only need one client
First Digital Dollar Project | Taylin John Simmonds
Welcome to the First Digital Dollar Project
Every week, a solopreneur shares the honest story of how they earned their first dollar online. They also join me on Substack Live to dive deeper into their journey.
Each story follows one path from idea to struggle to income. You will see the doubts they faced, the pivots they made, and the exact steps that led to that first sale.
Whether you are still searching for your breakthrough or already building momentum, these stories show you what is possible when you take action.
This post is a guest contribution from Taylin John Simmonds , a fellow solopreneur sharing the story of that first sale.
More on the project:
Check out my Substack Live with Taylin:
You only need one client
My first ghostwriting client made me rich.
Not with the money they paid me.
But with the mindset shift they created in me.
To explain why that matters, I have to take you back to a version of my life where the future felt... closed.
Nothing worked... Not even me
In 2021, I was teaching college and making about $3,000 a month Canadian (basically $5 per month USD LOL)
I was $30,000 in credit card debt from business ideas I’d labeled “learning experiences.”
My girlfriend lived in Europe. I couldn’t afford to travel to see her. I couldn’t even afford to buy Kindle books once a month.
What scared me wasn’t panic—it was the quiet certainty that if nothing changed, this would just become my life.
Permanently.
I didn’t need motivation.
I needed a way to earn on the internet.
And I didn’t have one…
Suspicion
A friend recommended I meet a guy named Liam at a coffee shop.
At some point, Liam casually mentioned he was making $30,000 a month teaching people how to start cleaning businesses...
... On Twitter (da fuq?).
I smiled and nodded.
But in my mind, I thought, there’s no way this is real.
So he pulled out his laptop.
Stripe screenshots. Backend dashboards. Numbers that didn’t change just because I didn’t believe.
Then he said something simple:
“This is also possible for you.”
He told me to write on Twitter every day for a year. Said it would change my life.
Did I believe him? No.
Who would?
But I didn’t have a better plan.
So the next day, I posted my first tweet.
Liam liked it. Reposted it.
Aaaaannnndddd.... that was it.
No viral post. No income. Just a crack in an outdated worldview that still held its shape.
Bleak
I kept writing.
After work. Late at night. Through heavy eyes.
Most days, nothing happened.
Little engagement. Not much attention. Just the kind of silence that makes you wonder if you’re not just failing, but embarrassing yourself publicly.
I started asking questions I didn’t like.
Is this just the next thing I’ll quit?
Am I saying no to friends for this?
Am I giving up things I love to fail at yet another business?
Every other business idea I’d tried had failed.
So what evidence did I have that this would be different?
None.
Just faith. And even that was thinning out…
The opportunity
One of those early tweets got seen by Dakota Robertson.
At the time, he was making $10K–$20K a month ghostwriting on Twitter.
He reached out. We talked. He mentioned ghostwriting was real.
Not a pitch. Just a helping hand in the form of information.
And suddenly I had a new problem (cause I needed more of those).
Because now the question wasn’t “Is there a way out?”
It was “What if the way out requires skills I don’t have?”
I wasn’t good yet. My posts didn’t get more than 10 likes. And I’m still too embarrassed to mention how little followers they got...
Getting paid to write for someone felt like fighting against gravity.
So instead of aiming for a client, I aimed lower.
Much lower…
Embarrassment
I asked another ghostwriter if I could write for him for free.
He laughed. Said I wasn’t good enough (lol true).
But I was embarrassingly persistent. Borderline pathetic actually.
Eventually, he agreed.
Under one condition.
The topic was humiliating:
Christian semen retention.
... Huh?
I opened my laptop in a Starbucks and immediately felt like everyone could see my screen. I angled it away. Then worried people walking by could still see I was writing about how to not cum.
It was absurd.
But I wrote it carefully. Seriously. Like I was getting a PHD and this was my dissertation.
I sent it off expecting nothing.
He replied: “This is actually pretty good.”
I thought: “The only thing more embarrassing them writing about semen is being good at it.”
He asked me to write two more posts that week.
For free.
Maybe my life had changed...
From a tragedy to a comedy.
A little less fake
The ghostwriter lived in Europe. I lived in Western Canada.
To hit deadlines, I wrote after teaching. Some days I woke up at 2 or 3 am, wrote posts, sent them off, then grabbed an hour of sleep before work.
My body was always slightly behind my life.
The sleep deprivation alone was bordering on depressive.
So why did I keep doing it?
Because I needed experience and proof.
I screenshotted everything. Every post. Every like. Every tiny win.
Not only because I needed it to land clients—but because I desperately needed any sliver of confidence to keep pushing.
After 3 months of this, I still wasn’t successful.
But I felt a little less fake…
The finish line failure
Dakota—from earlier—later offered to coach me on starting a ghostwriting business.
It cost $5,000 USD.
Money I didn’t have. Debt I didn’t need.
But I maxed out my last credit card anyways. (I don’t recommend this; It was irresponsible).
But something in my gut said this would work.
Months later, Dak said, “You’re ready,” and referred me a client he didn’t want.
On the call, my voice sounded calm.
But my body wasn’t. I felt nauseous. I was experiencing slight vertigo from the anxiety.
I threw out $3,000 a month. High enough to sound legit. Low enough that I didn’t feel like a complete imposter.
The client said it was too expensive.
I didn’t budge.
Neither did he.
I told Dakota I’d get the next one.
But privately, I was relieved.
Familiar pain felt safer than public failure.
The email
The next day, an email came in.
The client said he’d thought it over. Asked if we could do $0.50 per follower instead.
Dakota said it was a great deal.
I was scared shitless but with Dakota holding me accountable, I couldn’t think of a logical way to get out of it.
Thirty days later, $3,000 USD hit my bank account.
I stared at it.
Did I just make more money ghostwriting part-time for one client than I did teaching full-time?
That’s when something snapped.
What actually changed
Yes, the money mattered.
But what changed was this:
I no longer had to wonder if this was possible for me.
That doubt that silently lived in the corners of my subconscious mind—the one draining energy from every effort—got a lot quieter.
I didn’t need faith anymore.
I had proof.
And proof speaks.
It changes how you stand. What risks you take. What you believe you’re allowed to want without being crazy.
That client didn’t just pay me.
He collapsed my uncertainty.
And once uncertainty shrinks, effort compounds a lot faster.
That’s why my first ghostwriting client made me rich (and has the potential to make you rich as well).
Not by paying our bills.
But by paying off our doubts.
If I were starting again from 0, here’s what I’d do
Pick a niche I’m obsessed with
Study hook writing daily
Grow my own audience to acquire skills
Write for free to gain experience
Share results on socials to attract my first client
— Taylin
The Vision of First Digital Dollar Project
By the end of 6 months, we’ll have created more than content.
We’ll have built proof that there are infinite ways to start.
That your background doesn’t determine your future.
That the first dollar is possible for anyone willing to ship, learn, and iterate.
Your story matters.
Your first dollar was a turning point.
Let’s celebrate it together.
Find out how 20 solopreneurs with different products, different offers, different strategies, different paths earn their first digital dollars.
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Appreciate you featuring my story for this project man. Much love to ya 🙏
Good job on this :)