Every day feels like Christmas to Johnny Earle. Perhaps it’s because he was voted America’s number one young entrepreneur by Business Week in 2008, or because what began as a hobby has turned into a million-dollar business, or maybe it’s because he makes money while he’s sleeping, through his online store.

But really, it’s because he gets to do what he loves.

“I took a risk, quit my job and put 110 per cent into my business,” Mr. Earle told a group of students on Wednesday at the regional high school. “If you guys ever start a business and want to mess around with a hobby you have, it’s very important to utilize your time and money the right way. You have to take some risks and try it out.”

Mr. Earle started the T-shirt company Johnny Cupcakes in 2000, when he was 19. In between designing new graphics and visiting his stores in Boston and Los Angeles (and London come spring), Mr. Earle gives lectures on his success story to school campuses across the country.

He has a special connection to the Vineyard; both of his parents are from here, and he grew up coming here during his summers. In August this year, Mr. Earle hosted a popup shop at the Dock Street Diner in Edgartown; he plans to make it an annual 10-day event.

Johnny Earle constantly found himself getting into trouble in school. He tried selling wholesale drinks to his classmates. When that didn’t work out, he turned to selling pranks, such as whoopee cushions, stink bombs and itching powder. But after a student had to be rushed to the hospital from an allergic reaction to the powder, Mr. Earle turned to selling candy.

“Selling candy was crazy, because if I sold 200 packages of candy a day at a dollar each,” Mr. Earel said with a slew of random Google images behind him on stage, “I was making $1,000 a week doing something legal. I was making more money than my friends who were selling drugs. And my friends were like, ‘Wait a minute, so I could sell something legal and make more money?’ They didn’t believe me.”

While the candy business didn’t last long once the school store found out, another business did. Mr. Earle tried a semester of college before landing at Newbury Comics in Boston. Working there he found himself nicknamed Johnny Cupcakes and made one shirt with his signature cupcake and crossbones emblem. Soon his T-shirts were a hit, a new business.

“A lot of my friends were going out partying,” Mr. Earle said, but he chose to save his money and grow his business instead.

“To this day I’ve never had a sip of beer in my life, never had any alcohol, never tried any drugs ... I’d rather buy a Shirley Temple with extra cherries, save a bunch of money, and not have like 10 babies the next day.”

The crowd broke out in hysterics.

“It just smells gross, it’s not for me. I don’t look down upon anyone who does it and still go out with my friends sometimes — usually I’m the designated driver.

“It just never made sense,” he added. “And I’ll tell you one thing, the amount of money and time that I saved over the years is incredible. There’s so much stuff you can do with your money, you can reinvest it.”

Mr. Earel encouraged the students to get together, working with friends who have different talents, to create a business plan during the off-season and during the summer months execute it, and maybe even petition their teachers for credit.

What has separated Johnny Cupcakes from similar graphic T-shirt companies is the experience customers receive. By constantly changing his product and keeping the buzz alive, Johnny Cupcakes needs little advertising; the man and his materials are mostly known by word of mouth.

His customers get an experience they can’t find anywhere else, whether it’s camping outside the store for a week to buy a one-of-a-kind T-shirt, walking into the store to find a faux bakery, or a surprise gift inside a shipped package.

“Doing something like this enables your company to have longevity. People want what they can’t have,” Mr. Earle said of having, per design, only a few hundred T-shirts circulating. “You have to realize everything in the world has been done before, which means we have a good chance of failing. It should challenge us and make us think. It’s important for when we start a business, it’s important for us to reinvent ourselves.”

On this trip down to the Island, Mr. Earle bought 60 advent calendars on his way, to place in random online orders. Sometimes his company even puts a $20 dollar bill into shipments, so every time that person sees a $20 bill they will share their story of Johnny Cupcakes.

“The real success is being happy and doing what you love, and usually the financial success follows,” Mr. Earl concluded. “If you’re doing something you love, it doesn’t feel like work and you find yourself working extra all the time.”