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 Timo Masonš¤
Read the post by Timo Masonš¤
More on the project:
Live recap: From first digital dollar to repeatable systems
In this Substack Live, I sat down with Timo Masonš¤ to unpack how his first digital sale happened, and what changed after that moment.
This was not a polished success story.
It was a real breakdown of experiments, wrong turns, and small wins that compounded.
We covered:
How Timo went from zero to his first $25 sale with a simple Notion template, built to solve his own problem.
Why his early attempts failed, including SEO content that nobody read, and what that taught him about distribution.
How one working product turned into an ecosystem, by duplicating, niching, and stacking offers instead of starting from scratch every time.
The role of social proof, especially how one viral thread unlocked confidence and sales for his AI product.
Why he moved beyond templates into custom GPTs, not as a pivot, but as an expansion for the same audience.
The honest psychology of the first sale, why it creates hunger instead of satisfaction.
Tactical thinking on giveaways, Substack Notes, followers vs subscribers, and growth experiments that can be measured.
The lifestyle side of solopreneurship, living in Bali, Vietnam, Bangkok, and how location choices tie back to focus and work.
A clear piece of advice for anyone stuck hesitating, based on a one-way ticket decision he made at 21.
If you are trying to earn your first digital dollar, or turn one small win into something repeatable, this conversation will give you practical signals on what matters and what does not.
Watch the full recording to hear the details, the numbers, and the thinking behind each decision.
Next week, the series continues with the first female contributor in the First Digital Dollar project.
She brings a very different path, shaped by clarity, self-trust, and intentional choices rather than chasing tactics.
If you think there is only one way to start, her story will challenge that assumption.
Follow along:
Thank you š»šš šŖššššššš šŖšššššššš, Justin, and many others for tuning into my live video with Timo Masonš¤ !
Join me for my next live video in the app.
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