This transcript was generated from the episode audio and may contain minor errors.
What's up, Side Hustle School listeners? Welcome back. My name is Chris Guillebeau. We are beginning a brand new week. Excited to bring you a new episode every day featuring a new story every day.
A true story of someone who goes out to create a side hustle that is in fact an income generating project. Something that makes you money, creates more security for yourself, a backup plan. And something awesome that brings you more options, even if you love your job. Now this week I am coming to you live from London. That is London, England, not London, Ontario, not London, Kansas, not any other London.
But in fact, the world's biggest and most well-known London came in a couple of days ago after a transatlantic flight from New York. I will be here for the next couple of days doing events and media, including a public event that you are invited to, at least if you happen to be in London and you're listening in real time. If you're listening later, I guess I was in London this week. If you had a good week, wherever you were. That public event is October 3rd.
You can sign up at sidehustleschool.com/tour and at the end of the week, I'll get back to the US. I'll be in Atlanta, Miami, and Phoenix. Those details are on that same website, sidehustleschool.com/tour. Now I've got a great story for you as we begin the week. This is about a teenage side hustler who becomes a full-time entrepreneur.
He's doing some cool stuff now, but of course we're interested in the side hustle. At the time of this guy's story, he's actually 16 years old and he makes some money selling watches. Why is that interesting? Well, because he actually makes more than $10,000 selling watches. He's not just a great salesperson, although he seems like he's that as well.
He actually did something pretty creative and smart to source these watches in the first place. I'll tell you all about how he got his idea of what he did and what happened along the way in just a moment after this quick shout-out to our sponsor. Today's story comes from Doug Messer in New York City. He now runs a startup called University Beyond, which is a marketplace for students and brands to connect and collaborate, but Doug has had multiple side hustles. He's hosted events during holidays and ran a small consulting business helping brands with marketing.
The first hustle he started was 8 years ago when he was just 16. It involved selling interchangeable silicone watches to his high school friends, and then eventually a lot of other people. In addition to running this watch company, he also hosted events to earn extra cash and promote the brand. Now here's how it worked. Doug started the watch hustle 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 that in the US before, so he asked the guy wearing it how much it cost. The security guard said he could have it for $5. Doug and Brendan thought that was actually too cheap. They were expecting something like $20 at least.
When they told the guard they'd be happy to pay the full retail price, he told them the watches were only $3 in the shop down the street. And when Doug went to the store, he found dozens of interchangeable bands and faces. And sure enough, they were just $3. The watch had a website URL imprinted on the back. So when Doug and Brendan went home, they contacted the company that ran that website and learned that they were not planning to enter the US market.
This company offered to provide them the licensing rights to sell it under their own name at no cost, as long as they used them as a manufacturer. So Doug and Brendan asked their parents for a $2,000 loan. They used that loan to place their first order and began marketing the brand at different high schools in the area. And they had a creative idea for this too. They hired student sales reps to help promote their new brand at their school.
At first, this was a challenge. How do you find students who are not only trustworthy, but also able to actually sell the watches? Almost nobody had job experience, so they picked people based on their extracurricular involvement. They knew that presidents of clubs, captains of sports teams, cheerleaders, et cetera, would be able to reach an audience who would take their product recommendations seriously. And they also thought that student leaders could set trends.
They began with a commission-only program, where students would get paid a commission for selling the watches. They also created weekly sales competitions with cash bonuses as an added incentive. Doug said the watches were a pretty easy sell to high school students since they had never been seen in the US before. Also because they were interchangeable, they could be matched to the students' school colors. As they kept marketing and reaching out to people, they even got some endorsements from YouTube celebrities.
One day a friend of Doug sent him a photo of one of their favorite YouTube influencers wearing one of their watches in some of his videos. Once they had a few people doing this, they leveraged the photos they had to reach out to other artist managers asking if they wanted the product for free. This early success soon grew into something much greater. One day a friend of Doug's had some watches sitting around his house, and a friend of that friend's parents worked for People magazine. She picked up the watches and said, "These are interesting, I've never seen anything like this before." She requested some samples, and the next month, Doug and Brendan's watches were featured in the Style section of People, next to some of the biggest watch brands in the world.
This also led them to getting the watches distributed in Shoprite and Urban Outfitters. Remember, they're still in high school, and once Doug was 18, he began promoting events. This was essentially another side hustle. He was doing an internship at a small record label in Manhattan, and as part of a job he would meet with venue managers while trying to source bookings for artists. As a result of all the outreach he was doing, and all the people he got to know, he was soon promoting his own shows to all of his friends on Facebook.
And naturally, once he started doing his own shows, he brought in his watches to sell at the shows as well. And in fact, they were the only sponsor allowed. Doug would charge a cover at the door and receive a percentage of the bar from the owner. In addition to that, he would sell dozens of watches, sometimes more, at every show. Like a lot of side hustles, this one didn't last forever.
Doug and Brendan eventually wanted to work on other projects, for a while they switched full-time to working on a startup together, and then because Doug really likes to start new projects, he began two more. Before the watch hustle wound down, Doug and Brendan each made about $10,000 in profit. This experience and the lessons they learned gave them confidence as they moved on to other things. It was a profitable, helpful, and yes, timely side hustle. I related to this story personally because I got my start as a young entrepreneur as well.
I wasn't selling watches, but I had some stories myself of things like this, and I always like paying attention to the connection pieces. Like very often in the side hustle world, whether you're 16 or 60, once you start going down this road, one thing tends to lead to another. So in this case, they had the watch business, which made $10,000 each. Huge success on its own, and then Doug kind of transitions or connects that to his next thing, producing events, and all along the way, he's acquiring skills. Most of the time that you go through high school and college, you're acquiring skills along the way, but you're not usually getting paid for it, which is exactly what's happening here.
That's why I sometimes say a good side hustle is like a hobby. It's something you look forward to doing. You actually enjoy a lot of pieces of it. But unlike most hobbies, which usually end up costing you money, this is a hobby that brings you money. Anyway, congratulations to Doug and Brendan.
They're both still really young, so I'm sure they have a lot of side hustles ahead of them. And for you over there, I hope you enjoyed this story. I am heading out to do a number of events and interviews in London. I'll sign off by saying inspiration is good, but inspiration with action is better. And today's show notes are online at sidehustleschool.com/275.
That's right, episode 275. We are cruising along. I'll be back tomorrow and each day this week. I'm Chris Guillebeau for Side Hustle School.
