Before Testimonial.to, there were four other side projects. They were called Indielog, Howdy, Influeswer, and Backlogs.co. Together, they generated $1.99 in revenue.
That number — not zero, not a symbolic dollar, but $1.99 — is a precise, almost comic measure of how long an idea can fail to connect. Damon Chen kept four of those records before he built something people actually wanted to pay for.
Eight years and the itch
For eight years, Chen worked as a software engineer at Cisco. By his own account, it was stable work, the kind that most people around him regarded as a good outcome. He didn’t disagree — he just couldn’t stop building things on the side.
The four failures weren’t careless. Each was a genuine attempt at a product. Each one taught him something about what made software actually sell — or, more often, why it didn’t. But they made $1.99. The lesson wasn’t in the products themselves. It was accumulating underneath them.
In December 2020, he launched Testimonial.to: a tool that lets businesses collect video and text testimonials from customers and embed them on their websites or marketing pages. The problem it solved was small, visible, and annoying — and it was a problem Chen knew well, because he’d been trying to collect social proof for his own failed products and had no clean way to do it.
“One big reason I created Testimonial.to is to help myself sell,” he wrote on X. “I don’t know how to do marketing and sales. Using testimonials to convert prospects becomes a shortcut for me.”
The promise
When Testimonial hit $1,000 in monthly recurring revenue, Chen made a decision. He quit Cisco.
He also made a promise to his wife: if he couldn’t reach $100,000 in annual recurring revenue within a year, he’d go back to a regular job. It was a commitment with a real deadline and a real cost — the financial security of eight years at a company that paid reliably, in exchange for a year to find out if he could make this work.
“Quitting my day job is the best decision I’ve ever made in my whole adulthood,” he wrote publicly — “yet a tough and scary one.”
He reached $100K ARR in nine months.
Building in public
The mechanism Chen used to grow wasn’t advertising or outbound sales. He documented everything: what he was building, what was working, what wasn’t, how many customers he had and where they came from. He did it primarily on Twitter.
“Build in public on Twitter, kinda like flywheel marketing,” he described his approach — “keep shipping new features to make existing customers excited and get more exposure to potential customers.”
In March 2022, a thread highlighting Testimonial.to went viral, gathering over 1,600 retweets and 7,800 likes. The spike was real. But the distribution flywheel he’d built before it was what made the spike convert — potential customers already had a context for what the product did and who was behind it.
By 17 months after he quit Cisco, Testimonial had reached $300,000 in annual recurring revenue. The year he’d promised his wife had become a benchmark he had long since left behind.
Compounding the bet
As Testimonial crossed $1.3M and then $2.4M in ARR — still bootstrapped, still without outside funding — Chen started placing additional bets with the same logic that had built the first one: find a problem you know is real, build something to solve it, ship it fast.
He acquired PDF.ai, a tool for chatting with PDF documents, for $20,000. It had been a weekend project with no revenue when he bought it. He grew it past $1.5M in ARR.
The portfolio logic is deliberate. Each product solves a narrow, genuine problem for a specific kind of customer. None of them require a sales team, a marketing department, or a funding round to operate. What they require is a founder who knows what it costs to build something nobody buys — and what it feels like when the problem is real enough that they do.
What $1.99 actually buys you
The four failed products made $1.99. They also taught Chen what his customers look like, what buying decisions feel like from the outside, and what building in public sounds like when there’s nothing impressive to report.
When he built the fifth product, he built it for himself first. That’s a small distinction that makes all the difference. Testimonial.to existed because he needed it. The first paying customers existed because other people needed the same thing. The $100K ARR existed because the product actually worked.
The eight years at Cisco, the $1.99, the promise to his wife — they’re all part of the same story. Most founders want to skip the failures. Chen had four of them on the record before he got started.
Facts and milestones drawn from Damon Chen’s public Indie Hackers AMA, his posts on X (@damengchen), and reporting by Creator Economy and Tech Startups. ARR figures from Getlatka (2024).
