Inside the Sailing Education Startup That Out-Executed the Category and Won Two Golds

Inside the Sailing Education Startup That Out-Executed the Category and Won Two Golds.

Nick Leonardo, an expert in education technology, explains how a beginner-first approach resulted in a distinct way to teach sailing and two Gold Stevie Awards.

Modern sailing education still carries a contradiction. The water demands precision, yet the theory that prepares newcomers for that precision is often delivered in formats that assume patience rather than comprehension. Printed manuals, lengthy video lectures, and classroom explanations that rely on jargon favor experienced learners. Beginners, meanwhile, end up doing parallel work. They pause lessons to google terminology. They rewatch sections to catch what was not explained clearly the first time. They show up to practice with gaps that instructors have to patch on board.

In other words, the issue is not a lack of information. It is a mismatch between how sailing theory is usually taught and how people actually learn complex systems. Nick Leonardo’s sailing education app, Yapp.pro, was built from that insight. He built a learning experience with a product designer’s obsession for sequencing, clarity, and interaction. The outcome has been remarkable for a small startup built with a handful of freelancers — a 60% trial-to-paid conversion rate and 20% of paid users retained through month four, without the use of ads. The app is used in 25-plus countries, including sailing hubs such as the UK, Denmark, Australia, France, and the US. In August 2025, his app won two Gold Stevie Awards at the International Business Awards, one in the Learning and Education category and another for Best User Experience. In the UX category, second and third place were awarded to the large-scale Istanbul Kart and First Abu Dhabi Bank apps.

What does it look like when seamanship is taught as UX?

Most introductory sailing materials jump too fast into terminology and rules. While learning yachting himself, he noticed the pattern that many newcomers recognize.

“Great captains are not always great teachers,” Nick shares. “I have watched a simple question turn into a chain of terms, and each new term needs another explanation. If you are a beginner, you are basically trying to build the whole picture in your head by yourself, while the conversation keeps running ahead,” the expert adds.

Leonardo’s approach begins with structure. He designed the course as 140-plus short, minute-long lessons, each acting as a step in a system. Instead of asking learners to sit through long explanations, the experience is built around microlearning: small, focused segments that teach one idea at a time, then immediately show where it fits in the water. The learner is guided through a sequence that reduces cognitive overload and limits the number of new terms introduced at once.

This is what UX looks like in education. It is not visual polish alone, but a deliberate reduction of ambiguity.

Interactivity is treated as comprehension insurance, not as decoration

Passive learning fails. People think they understand until they need to apply the knowledge. Leonardo built the course so that learning is not just about watching. It responds, taps through, and confirms understanding through interaction. The practical value here is that mistakes are revealed early, while the cost of being wrong is still relatively low.

“Interactivity is my way of preventing false confidence. After a section, you get a quick knowledge check or quiz, so you find out immediately what you missed while it is still easy to correct. That is the whole point: catch the gap on the phone, not later on deck,” the expert says.

For yachting, that matters. Better theory comprehension improves the efficiency of practical sessions, lowers the risk of beginners improvising on the water, and directly addresses operator inexperience, a factor the U.S. Coast Guard highlights among the leading contributors to recreational boating incidents.

However, to create that sophisticated system, the founder, Nick Leonardo, came across some challenges. The biggest one was visual accuracy. In sailing education, an illustration is not decoration but instruction. If a diagram is polished but technically wrong, it teaches the wrong reflex, and it breaks trust faster than any rough sketch ever could.

“I honestly did not expect this to be the hardest part,” Nick says. “You can find talented illustrators, but finding someone who can draw boats and sailing situations correctly, every time, is a different story. In this niche, a beautiful picture that is slightly wrong is worse than a simple drawing that is right, because beginners will remember the image.”

So he handled the visuals the way an experienced product lead handles a design system. Instead of treating each illustration as a one-off, he managed the visual language as a component library with rules. He wrote detailed briefs, standardized angles and conventions, and reviewed images as if they were product UI elements, rejecting anything that looked good but failed the seamanship test.

He wrote briefs for more than 1,000 illustrations and, in many cases, personally adjusted them in vector software until they accurately conveyed the intended meaning and met the standard. This is not typical founder behavior, but it explains why the product reads as coherent. The same logic, proportions, and visual conventions repeat throughout the course, which reduces the mental effort required to interpret each new frame.

Execution discipline showed up in places readers rarely see

The early build phase did not go smoothly. Leonardo describes a period when progress stalled because the initial technical approach could not support the level of interaction and polish the course demanded. The reset was a switch from React Native to Flutter, a cross-platform development framework used to build fast, consistent mobile apps, which provided the product with a sturdy foundation to meet the quality bar he had in mind. For readers in the yachting industry, the parallel is familiar. Boats reward the good system choices early. If the foundation is wrong, every downstream improvement becomes expensive.

Once that technical constraint was removed, execution discipline showed up in places users rarely see. Product UX is often decided by details that are invisible when done well. Leonardo personally set the timing for each lesson, down to the exact moment when subtitles appear, when an image changes, and when a button becomes available. He also co-wrote every lesson script with an instructor, spending over a month developing the content line by line. The recording process took another month in studio conditions, with repeated takes when phrasing or pacing did not meet the standard.

“As soon as we had the recordings, one of the key tasks was the assembly,” the expert says. “I personally cut and trimmed the lesson clips, built the timed visuals on top of them, and designed the quizzes and small activities that keep you present. Then we ran QA, and users immediately showed us where friction still existed, such as wanting to zoom in on an illustration or needing smarter playback so they could replay a moment without losing the flow. You do not notice these details when they are right, but you feel them the second they are missing.” That same attention to execution is also why Leonardo was later selected as a judge for the 2025 Women in Business Awards in the New Product and Service category.

This is also how an education product earns retention. It respects attention, anticipates confusion, and removes small sources of friction that compound over time. According to Yapp Sailing Course’s internal analytics, 84% of new users return, indicating that the experience is not merely sampled once and abandoned. Public feedback echoes the same point from the learner’s side: “Brand new to sailing, this course has me feeling 1,000x more confident,” one App Store reviewer wrote. Additionally, analytics indicate an average session time of 10 minutes.

Nick Leonardo remains an active sailor, training year-round and competing in local regattas, including winter sessions. In a credibility-driven domain, that proximity matters. It keeps the work anchored in real-world conditions: instructions come quickly, situations change rapidly, and beginners often have to make sense of unfamiliar language under time pressure.

That practical grounding leads to the broader lesson his story illustrates about learning design. In 2026, the constraint is not access to information. It is whether the learning experience can turn information into usable judgment. The strongest training products behave like well-designed systems. They introduce concepts in an order that builds a mental model. They use interaction to surface misunderstandings early. They treat visuals as technical language, not decoration. They remove friction in timing, wording, and pacing because attention is a finite resource.

That is why this project reads as more than a sailing course. It is a blueprint for how competence can be built in any skills-based sport or high-responsibility hobby, where “knowing” is meaningless until it translates into informed decisions. The Learning and Education recognition reinforced that the underlying instructional design is effective and transferable beyond sailing, while the Best User Experience recognition served as a strong external signal that the bar he set is high and competitive under the same UX standards serious consumer platforms are judged by.

Written by Daria Iv