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 live session expands on the story we shared earlier this week, going deeper into the behind-the-scenes details with Yana G.Y.
Read the post by Yana G.Y.
More on the project:
How Yana Earned Her First Digital Dollar on Substack and What Changed After
What happens after someone pays you for the first time, before you even know what you are selling?
In this Substack Live, Yana G.Y. , creator of Unplugged, breaks down the exact moment she earned her first $108 on Substack and why that moment scared her more than it excited her .
She shares the full, unpolished journey:
Starting on Medium with no clear monetization
Moving to Substack with only 60 imported subscribers
Turning on paid subscriptions without a clear offer
Watching three people upgrade immediately, purely on trust
That single moment forced a shift.
From writing casually to building a real subscription business.
In this conversation, we go deep into:
Why enabling paid subscriptions early works, even without a perfect strategy
The psychology behind trust, upgrades, and subscription retention
How Yana redesigned her About page more than 10 times to improve conversions
Why your About page and welcome flow must sell, quietly and consistently
The automation stack she uses to convert up to 70 percent of subscribers within the first month
How she thinks about customer journey, from free reader to paid member to VIP
The biggest fear holding creators back from turning on monetization, and why that fear is misplaced
Yana also shares hard numbers, real workflows, and uncomfortable truths about selling, losing non-buyers, and why subscription businesses outperform one-off digital products long term.
If you are:
Writing on Substack but hesitant to turn on paid subscriptions
Unsure what to sell or afraid you are not ready yet
Curious how real creators convert readers into paying subscribers
Thinking about systems, automation, and retention, not just growth
This session will challenge how you think about monetization.
Watch the recording to hear the full story, the reasoning behind every decision, and the lessons Yana wishes she could tell herself the day she earned her first digital dollar .
Awesome Quotes From The Live:
“I got paid before I even knew what I was selling. That scared me more than not getting paid.”
“Those three people didn’t pay for a product. They paid because they trusted I would figure it out.”
“Your About page is not a biography. It is part of your sales funnel, whether you like it or not.”
“If you don’t sell in the first month, you miss the most important window. Most people never recover from that.”
“You are not losing subscribers when you turn on paid. You are losing non-buyers, and that is a good thing.”
This Live is part of the First Digital Dollar Project, where solopreneurs share the real story behind their first online income.
Follow along:
Thank you Eric Mattie, Finn Tropy, How They Got Caught, and many others for tuning into my live video with Yana G.Y.!
Join me for my next live video in the app.
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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
