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How a lifelong watch enthusiast’s unexpected idea became a watch company—and why its first design began on a Harley.

Wayward Watch Company began with a question about motorcycles.

Through EvelRide, founder Davis Raine was already accustomed to people trading things toward their next bike. Old motorcycles, cars, trucks—even guns. As a watch enthusiast who had been collecting for decades, he saw another possibility.

Why not watches?

He began accepting high-end watches in trade toward new and used motorcycles and quickly discovered how many people were interested. A watch sitting in someone’s collection could become part of the deal that put them on their next motorcycle.

Wayward grew out of that exchange. Initially, it was a platform for selling pre-owned watches. But as more watches passed through Davis’s hands, the business began taking him somewhere he hadn’t expected.

He started thinking about making one.

From collecting to creating

Davis had built EvelRide around something he loved long before it became a business. His interest in watches followed a similar path, although this time he wanted to put his own ideas into the product itself.

He gravitated toward watches with larger cases and a strong presence on the wrist. As he explored the microbrand world more deeply, he struggled to find enough designs that reflected his taste. He also kept noticing familiar design cues, particularly among dive watches.

An artist with a habit of finding his own way, Davis began sketching.

The name Wayward already fit. It reflected an adventurous streak, a reluctance to stay on the beaten path, and a willingness to see where his own road might lead. What began as a name for a pre-owned watch business became a guiding idea for the watches he wanted to create.

The first would be the Open Water One.

A first watch with a personal history

The name reaches back to Davis’s childhood, when his father taught him to scuba dive and helped him work toward becoming a licensed diver.

Open Water One recalls that first level of learning: the beginning of a journey into an unfamiliar world. For Wayward’s first watch, it felt appropriate. It connected a memory of discovery with the experience of starting something new.

Its design, however, also owes a great deal to life above the water—specifically, time spent on a motorcycle.

One of its defining ideas came while Davis was riding his Harley.

Looking down at his wrist, he noticed that the watch dial appeared crooked from his natural riding position. The conventional orientation made sense when viewed straight on, but that wasn’t how he was encountering it.

That observation stayed with him. He began paying closer attention to how people actually checked the time: the angle of an arm, a quick glance, the small turn of a wrist.

For his own way of wearing a watch, he wanted to try something different. He rotated the dial 60 degrees clockwise, bringing the display into an orientation that felt more natural to him.

That decision gave the Open Water One a distinctive face, rooted in an everyday experience.

A bezel shaped by the road

Another feature came from a more specific frustration.

Davis often rode a custom, hand-built chopper without a fuel gauge. He used his watch bezel as a reference to help keep track of fuel stops. But the edge of his leather jacket sleeve would catch the external bezel and move it, disturbing the marker he had set.

His solution was to move the rotating bezel inside the watch.

The Open Water One’s internal rotating bezel grew directly from that experience. Bringing it beneath the crystal kept it out of the path of his jacket sleeve while preserving the function he wanted.

Together, the rotated dial and internal bezel began to give the watch its own identity. Both came from paying attention to something Davis wore and used, then asking how he would change it.

Drawing the watch he wanted to wear

Turning those observations into a complete design took repeated sketching and refinement.

Davis began in Procreate on his iPad, drawing the watch and working through its proportions. He then moved the artwork into Photoshop and Illustrator to tighten the details. As the design developed, he also used AI tools to explore color palettes, textures, and geometry from his sketches.

The process gave him ways to test ideas and keep refining what he saw in his head.

The turning point was personal: the designs had become watches he would buy himself without hesitation.

As he continued working, he saw an opportunity for Wayward to contribute something distinctive to the microbrand market. He wanted a dive watch with its own visual identity, one whose choices could be traced back to his experiences and preferences.

The Open Water One became the first expression of that ambition.

Where Wayward goes from here

Davis wants Wayward to grow into a brand worn by everyday people—people who appreciate a watch’s design and also want it to accompany them through their lives.

Adventure remains central to that vision. It runs through the company’s name, the childhood memory behind the Open Water One, and the riding experiences that shaped its features. It also informs his thinking about future models, including the On Reserve, conceived around people who are comfortable heading into unfamiliar territory and value practical capability along the way.

There is a familiar pattern here. With EvelRide, Davis began as a motorcycle enthusiast and built a brand around that passion. With Wayward, decades of collecting led first to trading watches, then selling them, and finally drawing one of his own.

The Open Water One brings those experiences together: a father teaching his son to dive, a glance at a watch from the seat of a Harley, a jacket sleeve moving a bezel, and an artist deciding to work through an idea.

It is Wayward’s first watch—and Davis’s next road.