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.
More on the project and the list of contributors:
6 solopreneurs. 6 different paths. 1 shared truth.
Over the past two weeks, I’ve been running the First Digital Dollar Project on Solopreneur Code.
Each week, a solopreneur shares the honest story of how they earned their first dollar online.
Their real path from zero to one.
We’re six stories in.
And the patterns are starting to emerge.
I studied every post and every live session.
Here’s what I found…
Meet the 6 Contributors
Taylin John Simmonds built a ghostwriting business that pays $3K/month. Started by writing for free on Twitter.
Orel built WriteStack, a SaaS tool now earning $6K/month. Started after 18 months of failed products.
Timo Mason🤠 went from a single $25 sale to a full digital product ecosystem. Started as a military-to-Bali solopreneur.
Yana G.Y. runs a paid newsletter earning $5K to $10K/month. Started with 3 Medium subscribers who paid $108 total.
Khadejah J became a storytelling consultant. Started with $1.06 from the Medium Partner Program.
Sharyph sold a Data Analyst Roadmap for $700. Started as a student working retail.
Six different people.
Six different models.
Six different paths.
But when you line them up side by side, the similarities are impossible to ignore.
What They All Have in Common
1. They started before they were ready
Every single contributor launched without a polished product, a big audience, or a clear plan.
Yana changed her About page 10+ times.
Taylin’s first writing sample was on an embarrassing topic.
Sharyph built a roadmap for personal use with zero intent to sell.
None of them felt ready.
They started anyway.
2. The first dollar came from solving a real problem
Not from marketing tactics.
Not from a viral post.
Not from a course about courses.
Sharyph solved a problem for future data analysts.
Orel built a writing tool he needed himself.
Yana answered questions her readers kept asking.
The product was the byproduct of a personal need or a repeated question from their audience.
3. Consistency beat strategy
Taylin posted daily on Twitter before landing a single client.
Orel committed to a 6-month ultimatum.
Khadejah wrote every single day until a viral article found her niche.
None of them credit a clever funnel or growth hack.
They credit showing up.
4. One person changed everything
Taylin’s first ghostwriting client paid $3K/month.
Orel’s first customer paid $9 and validated the entire direction.
Yana’s first 3 Medium subscribers became her proof of concept.
In every case, one person saying “yes” collapsed months of uncertainty.
5. They talked to their audience directly
Orel DMed people one by one using the Alex Hormozi approach.
Yana and Khadejah both found their niche by answering reader questions.
Taylin built relationships by writing for free first.
The first dollar was earned through conversations, not campaigns.
Where They Differ
The 6 stories split into three clear paths:
Path A: Service-first (Taylin, Khadejah)
Wrote for free, then pitched paid work
Took weeks to months of free work before the first payment
Key lever: proof of work and reputation
Scaling move: raise prices and niche down
Path B: Product-first (Orel, Sharyph, Timo)
Built something, then shared it
Took days to weeks (Sharyph earned while studying for an exam)
Key lever: shipping fast and iterating on feedback
Scaling move: add features and expand the product line
Path C: Audience-first (Yana)
Published free content, then monetized readers
Took months of free content before turning on paid subscriptions
Key lever: trust and nurture sequences
Scaling move: automate email funnels and optimize conversion
There is no single right path.
But there is a right path for you, depending on your skills, timeline, and what you already have.
6 Key Learnings for You
1. “Ready” is a myth
Every contributor launched with doubt. Yana said her first sale felt like panic, not celebration.
You don’t get ready first. You get ready by starting.
2. Solve your own problem first
Sharyph’s $700 product was a roadmap built for personal use.
Orel’s SaaS was a tool he wished existed.
Your best product idea is probably sitting in your own workflow right now.
3. Proof collapses uncertainty
Taylin invested $5K in coaching (money he didn’t have) because he needed skin in the game.
One writing sample. One client. One payment.
That’s all it took to shift from “maybe” to “this works.”
You don’t need 100 customers. You need one.
4. Pick one lane. Change strategies within it
Orel spent 18 months jumping between ideas before committing to one.
Khadejah pivoted platforms (Medium to X to Substack) but never left writing.
The lane stays. The vehicle can change.
5. The less you focus on selling, the more you sell
Sharyph posted a helpful thread.
No pitch. No urgency. No scarcity tactics.
People bought because the value was obvious.
Yana’s 70% upgrade rate comes from a nurture sequence, not a hard sell.
Lead with value. The sales follow.
6. Your first dollar is a responsibility, not a trophy
Yana reframed her first $108 not as validation, but as a promise to deliver.
That mindset shift separates creators who earn once from creators who build a business.
The first dollar is not the finish line.
It’s the starting line.
The Bottom Line
Six different people. Six different models. One shared truth
The first digital dollar is never about the money.
It’s about proof that your work matters to someone.
Every contributor crossed that line the same way. They created something real, shared it with real people, and let one “yes” carry them forward.
If you’re still waiting for the perfect moment, the perfect idea, or the perfect plan, these six stories are your permission slip.
Start with what you have.
Share it with someone who needs it.
Let someone say ‘yes’.
That’s how every first digital dollar begins.
This Live is part of the First Digital Dollar Project, where solopreneurs share the real story behind their first online income.
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Thank you to everyone (all 341 of you!) who tuned into my live video!
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Thanks for reading! Ready for the next step?
Let’s crack the growth equation and build a thriving one-person business on your terms!
Anfernee
