Word of the Day app started as a little experiment by a motley crew of developers launching random app ideas. Over time, it picked up thousands of loyal fans, then almost collapsed under its own weight.
No one saw the plot twist coming: a routine UX interview that opened up a whole new chapter for the app.
Listening to users turned out to be the one decision that changed everything.
This story is told by the Vocabulous US executive team:
Scrappy origins
With no marketing, funding, or editors — and zero expectations — the original team thought it would be fun to build a small app that showed users one English word a day, inspired by a paper calendar scene in the movie Alfie (yep, really).
The first version of the app was hilariously raw, so it was expected to fade away like the others. The prototype was put together in Xamarin, a cross-platform shortcut that the devs assumed would be good enough to get started.
The app had a calendar-style UI that showed users a single new word every day, the same word for every user, whatever words looked interesting from vocabulary lists on Pinterest. As a result, some of the words were off.
Dmitry: Let’s just say that little attention was paid to linguistic quality during that time.
Organic growth and early lessons
In spite of the bare-bones interface and weird words that occasionally popped up, Word of the Day started gaining traction, especially among US users. That was a surprise as it was aimed at the UK market (we had this vision of Brits learning fancy words over afternoon tea).
Turns out that a lot of Americans grew up getting word-of-the-day calendars for Christmas or watching their teachers write the word of the day on the chalkboard, so checking the app was something of a comforting tradition.
The app was free for the first two years, then the devs started monetizing by running ads. Users didn’t seem to mind, and installs grew steadily. The devs had also launched some other digital products that were picking up steam, so they hired a team to run Word of the Day.
Dmitry: I came on as product manager, and Tanya joined shortly after to conduct user interviews. I had a linguistics degree, and she spoke several languages, so this was a dream project for us.
Unexpectedly, the app took off, seemingly overnight. It was just organic growth: word of mouth, shares on Twitter, who knows where. Unfortunately, the Xamarin codebase that held the calendar together couldn’t stretch.
Vlad: Xamarin was trying to sit on two chairs at once, and when high traffic hit, both chairs snapped.
To capitalize on the moment, we had to rebuild from scratch. Vlad volunteered to learn Swift on the fly and rebuilt the iOS version with UIKit, Apple’s standard interface toolkit. Going native cut the extra layers that had slowed everything down and stopped the worst crashes.
Rebuilding with intention
The word nerds on the team had already been eager to add more robust content, so we decided to seize the opportunity.
Dmitry: We didn’t chase the first wave, it chased us. The rebuild was our chance to turn luck into a product that deserves its audience.
Mark Davies, the creator of English-Corpora.org, sold us extensive word and phrase data from the COCA corpus (the Corpus of Contemporary American English). Stefan Gries, a professor at UC Santa Barbara, came on as a consultant to help us structure and rank words intelligently.
We built an in-house editorial team to craft engaging content around the words, brought in illustrators to create handmade illustrations to match, and developed a clever UI for word discovery.
We also formed a marketing unit to focus on user acquisition and implemented a user feedback loop to boost retention. That turned out to be the decision that changed everything, though we didn’t realize it at the time.
A better product, a tougher crowd
When the new and improved Word of the Day hit the App Store, we quickly learned how attached people were to the old version. Overnight, the support inbox was filled with angry messages.
Tanya: I was sitting there with a newborn, fielding dozens of messages a week from users calling us idiots.
It wasn’t just one type of person either. Teenagers complained about losing their study tool, older people complained about their morning ritual being disrupted. We even heard from people recovering from brain surgery who had been using the app as a kind of brain training tool.
We realized that if we wanted to keep this thing alive, we’d have to get better at understanding who was out there and what they needed.
Turning feedback into progress
Our UX efforts had all been directed toward maintenance, but we began making a concerted effort to open a dialogue with users. We decided to add a Product Market Fit (PMF) survey straight into the app.
Tanya: I started reaching out to everyone who answered they’d be “very disappointed” to lose the app. The first few tries, nobody replied. It took a while to refine my pitch.
Eventually, people started answering. We booked two or three calls a day with users and started really listening. Why they had downloaded the app, when they used it, where they used it… We wanted to know everything.
This wasn’t just a research project. We took what we learned and started feeding it right back into the product.
[Callout Box] Tanya’s Pro-tips for user outreach
- Strike the right tone. When you’re contacting users, sound as approachable and friendly in your emails as you can. Don’t overthink it. Like you’re messaging an old friend to catch up. Corporation lingo kills your outreach.
- Segment your most engaged users. The people who would be “very disappointed” aren’t just happy customers, they’re your product evangelists. Understanding their specific use cases reveals expansion opportunities.
- Let insights drive product decisions. User feedback directly influenced our editorial strategy, monetization approach, and feature development. Don’t just collect feedback. Act on it.
The call that changed everything
Despite the initial backlash, internally, the numbers looked better: session length rose, crash logs flattened, and retention inched upward each week. Our App Store rating climbed to 4.8. We also caught the attention of potential investors.
The app had years of words banked, meaning it could essentially operate with a skeleton crew in perpetuity. The devs who’d built the first version had other projects taking off and were ready to sell it, take their profit, and move on. Us word nerds wanted to grow the product, add more features, and see how far we could take it.
That was the state of things when a colleague came to Tanya about an interesting guy she had just interviewed who wanted to speak with the person in charge.
Tanya: His name was John Steuart, and he was a veteran Silicon Valley entrepreneur with decades of experience co-founding and investing in startups.
Tanya forwarded the request to Dmitry because he understood the app better than anybody. He was busy, but his instincts told him it would be smart to take the call.
The conversation lasted more than an hour and covered a lot of ground, from the evolution of the app to John’s background and investment philosophy.
John: I’m at a point in my life where I’m thinking about making the world better, and how to do that through technology. I want to support businesses that I believe have that potential.
When John asked about future plans for the app, Dmitry told him a bit about the internal conflict the team was facing.
Dmitry: I jokingly said something like, “Don’t suppose you’re looking for one more company to believe in?”
But when John replied “Perhaps,” he was not joking at all.
John: I’m always looking for entrepreneurial opportunities. That’s always in the back of my mind. So it was not a spontaneous response in that sense.
That first call led to a second. Tanya joined the third call. The fourth included Vlad. A deal began to take shape.
John made an offer to buy the app, but only if the core team agreed to keep running it. He would work alongside us and offer guidance on scaling, with an expanded mission to build language learning tools beyond the mobile platform.
The next chapter
With John, we’ve formed a new company called Vocabulous US and are working on building an ecosystem of vocabulary learning products, both online and offline.
We’re also continuing to grow our flagship product, the Word of the Day app, which has been downloaded more than 4 million times.
Nowadays, users take an adaptive, personalized vocabulary assessment as part of the onboarding process. Not just about what they know, but what they’re curious about. This allows for personalized word feeds, which aligns with our mandate of putting users’ needs first.
Tanya: We’re not trying to replace test-prep platforms. We want to be something lighter and more insight-driven that makes people feel sharp and capable without rote memorization.
Knowing that some users rely on the app to keep their minds sharp, we’re designing with that in mind. We’ve introduced gamification, on-device progress tracking, and context-aware delivery.
Three lessons we learned:
- Success is a stress test. Build slack in both code and people before the spike.
- Rewrite sooner than feels safe. Waiting would have embedded tech debt and slowed every future experiment.
- Get to know your users. As we’ve discovered, they’re more loyal and intelligent than you could ever imagine.
The Word of the Day app started as a random experiment, but it became a sustainable business when we started treating users as partners in product development. That became the foundation of everything we built afterward.
Sometimes the most powerful product insights come from asking users what they think. And maybe, if you’re lucky, one of those users will set your company on a whole new course.
