7 min 58 sec

16-Year-Old Earns $10,000+ Selling Watches

After spotting an unusual watch design while on vacation in Aruba, this enterprising teen and a friend go on to hustle their way to making five-figures.
Manufacturing Reselling Student Hustles Unique Ideas

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What It's About

A trip to Aruba leads two high schoolers to an unlikely (and lucrative) side hustle.

Business Model
Skills Required
Ingenuity & Resourcefulness
Profit Potential

Words of Wisdom

Doug advises several young entrepreneurs and always recommends two things: that they carry a notebook with them at all times to jot down their thoughts or ideas, and that they talk about their idea or side hustle as much as possible before diving into it so they can get important feedback on whether their idea is actually needed and can generate a profit.

Fun Fact

Doug was barely 18 when he began promoting events, and he discovered that nightclubs were the perfect setting for promoting and selling his budding watch brand. They’d sell a few hundred watches a night in addition to what they made at the event: they’d charge a cover at the door and receive a percentage of the bar from the owner. So we’re talking $25 ticket sales for 500 to 600 people who typically spend between $25 to $150 at the bar each night, as well as a few hundred watch sales. Doug said he was making more than any college kid he knew!

Notes from Chris

Episode 275
Doug started his side hustle in an unlikely place—while on vacation in Aruba with his best friend Brendan. The security guard at their hotel was wearing a brightly colored watch with a silicone band. Doug had never seen a watch like at in the U.S. before, so he asked the guy wearing the watch how much it cost. The security guard told him he could have it for $5. Doug and Brendan thought it would cost around $20 and told him they’d be happy to pay the full retail price. The security guard told them the watches were only $3 in the shop down the street. When Doug went to the store, he found dozens of interchangeable bands and faces—and sure enough, they were $3.

The watch had the website ss.com imprinted on it, so when Doug and Brendan went home, they contacted ss.com and learned that they were not planning to enter the U.S. market. They offered to provide them the licensing rights to manufacture the product and sell it under their own name at no cost, so long as they used them as a manufacturer.

They got started by marketing and selling them at the high school they were enrolled at, but what started as a modest school side hustle for Doug and Brendan quickly developed into something so much more. After getting celebrity endorsements through YouTube influencers, the DBFLY Watches brand grew. Doug even got the watches distributed in Shop-rite and Urban Outfitters using connections he had with people in the retailing industry.

Doug and his cofounder made about $20,000 in profit from the watch company before they decided to switch their attention to their new startup, University Beyond. Not a bad little side hustle—especially for a couple of teenagers!

Don't you think it's time for you to start your new side hustle?


  • DBFLY Watches: While Doug and Brendan are no longer in the watch selling biz, you can still check out the watch brand they started on this website
  • University Beyond: The startup that Doug and Brendan run now that serves as a marketplace for students and brands to connect and collaborate
  • ss.com: The manufacturer for the DBFLY watches that allowed Doug and Brendan the option to sell the watches under their own name free of charge
  • ShopRite & Urban Outfitters: Two of the retail stores that Doug and Brendan sold their watches out of

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"From my advisors to clients, to other "hustlers" I've met along the way, it's inspiring to be surrounded by equally as motivated and often times more successful people every day. You are also learning every day from those peers which adds value to your day job, as well as your general business acumen."
—Doug Messer #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau