While most 16-year-olds were worrying about homework and prom, one student turned a vacation discovery into a profitable watch business that made him $10,000—and taught him the power of entrepreneurship early on.
Challenge
When Doug M. went on vacation to Aruba, he wasn’t thinking about business. He was a high school junior on break, hanging out with his best friend Brendan. But a single conversation with a hotel security guard changed everything.
Doug noticed the man’s bright, colorful silicone watch and asked where it came from. The guard smiled and said he could sell it for five dollars.
Doug was surprised—it looked far more expensive. Curious, he visited the nearby store where the watch was sold and discovered rows of interchangeable watch faces and bands, all priced at just three dollars each.
At that moment, he saw opportunity.
When Doug returned home to New York, he couldn’t stop thinking about it. The watches were stylish, affordable, and totally different from what his friends wore in the U.S. If he could bring them to America, he might just have something special.
Action
Doug found a website printed on the back of the watch and reached out to the company. To his surprise, they weren’t planning to enter the U.S. market—but they were open to letting him sell the watches under his own brand, as long as he used them as the manufacturer.
It was the perfect arrangement.
Doug and Brendan pooled their savings and borrowed $2,000 from their parents to place their first order. Then, they got creative with marketing.
Instead of relying on ads or retail stores, they built a student sales network. They recruited student reps from nearby high schools—club presidents, team captains, cheerleaders—people who were already influential among their peers.
These student reps worked on commission only, earning a cut of every watch they sold. Doug also kept them motivated with weekly sales competitions and cash bonuses.
To build buzz, they made sure the watches matched school colors and emphasized their interchangeable design. It was part fashion statement, part status symbol—and it caught on fast.
Soon, students across multiple schools were wearing Doug’s watches. Sales grew so quickly that they began receiving attention from unexpected places.
A friend spotted one of their watches in a YouTube influencer’s video, which they used to approach more creators and artist managers. They offered free samples in exchange for exposure—an early example of influencer marketing done right.
Then, a lucky break catapulted them to the next level.
A friend’s parent who worked at People magazine noticed the watches and asked for samples. The next month, they were featured in the magazine’s Style section, right next to luxury brands.
That one placement changed everything. Their watches were soon carried in ShopRite stores, then in Urban Outfitters—a dream for any teenage entrepreneur.
Result
By the time Doug turned 18, he and Brendan had sold thousands of watches and earned $10,000 each in profit.
Doug didn’t stop there. He used the experience to launch new ventures, including an event promotion business. During his college years, he hosted shows for local artists, charging admission and taking a percentage of the bar revenue—while also selling his watches at every event.
Each project taught him something new: how to market, negotiate, and manage money.
The watch hustle eventually wound down, but the lessons stayed with him. Doug went on to co-found University Beyond, a platform connecting students and brands—a natural evolution of the ambassador network he’d built years earlier.
Lesson
Doug’s story proves that entrepreneurship has no age limit. At 16, he didn’t wait for permission or experience—he saw an idea, took action, and learned by doing.
His approach was simple but powerful:
- Find something unique.
- Start small.
- Leverage your network.
- Keep learning as you go.
He didn’t just sell watches—he built confidence, business acumen, and momentum that carried into everything he did next.
Sometimes, the smartest thing you can do is to treat your curiosity like an opportunity—and just start.
Inspired by a true story originally featured on Side Hustle School by Chris Guillebeau. This rewritten version is independently produced and fully original.