How John Annetti started his Johnny Vacay T-shirt business and keeps it going

(Editor's note: John Annetti is the person behind the brand JohnnyVacay.com. He took his passion for photography and travel and created a T-shirt and lifestyle brand. He shared with "Good Morning America" how he got started and the ups and downs of pursuing his dreams.)

In 2013, fueled by my love for photography and an interest in travel, I booked a one-way flight to the Caribbean island of St. John. With $800 in my pocket, my life in my backpack and the contact information of a friend of a friend, I headed to paradise.

Although I made it to my destination, the first couple of months were rough. I slept on a half-inflated air mattress in a hot, mosquito infested apartment, worked odd jobs to pay for rent, food and plenty of rum.

But my luck soon changed when I met the owner of the biggest surf shop on island. He offered me a job screen printing T-shirts for his shop. I asked if I could print some of my photographs on the shirts and put them in his store.

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They quickly sold out, and I realized I was onto something.

For the next five years, I traveled from island to island, taking thousands of pictures, creating new designs and selling the Johnny Vacay brand. I never spent more than seven months in one place, expanding the brand throughout St. John, Martha's Vineyard, Cape Cod, Nantucket and Malibu.

Today, my day-to-day is different than it was five years ago. When I first started out, I was screen printing all of my own T-shirts by hand while working a full-time job at hotels while traveling and spending six months at a time in various destinations.

My day-to-day evolves, but the constant is the ever-expanding To-Do list. The exciting thing is, my days are always changing. Running a clothing business has seasonal tasks -- especially mine, since most of my business is done in the summer.

For the past two years, I have been spending my summers on Nantucket selling and meeting customers at my wholesale account -- Nantucket Surf Co. I open the store with the owner and spend most of the day selling.

I take off to explore the island, taking photos and creating new designs, and of course, stopping by my largest account -- Cisco Brewers -- for a cold one!

After the summer ends, the fall transition means it's time to reach out to new accounts. I travel around the region looking for new business and exploring new areas to make new designs.

The fall quickly becomes the holiday season, which is packed with marketing and promotion. Packing orders and customer service is a huge part of my job as well.

After the holidays comes trade show season. This is the time to sell for the next summer.

Once the trade shows are done, it's time to get orders in to the manufacturer and tie up loose ends for the next summer.

Spring comes around, which is when stores start to receive their products. Hopefully, everything goes well and there are no returns. Spring turns to summer and we do it all over again.

The ups and down the past couple of years seem to be very up and very down.

The best ups for me consist of a few things: Opening new wholesale accounts and having them do well is the best for me. It shows me people are resonating with the brand. It's a big moral boost that gets me excited to keep moving forward.

I recently got my first press coverage in the Aspen Times. That was an amazing way to end the year.

One of the most constant ups for me, as an artist, is finishing a new T-shirt design. They are difficult to make so when one comes to fruition -- from concept to final product -- it's a great feeling.

The downs hurt. They can hurt moral and they can hurt the bank account. I’m not sure which one is worse. Last season, we used a new manufacturer in China. There was a huge mistake made and I ended up with 2500 women's T-shirts instead of men's. That one hurt the bank account.

The hardest down to deal with is getting into new wholesale accounts. As a young brand, store owners are hesitant to take a chance on you. They like to see success in other stores and markets before they give you a their money. The business is very relationship-based, so cold calling and emailing without success can hurt moral.

I've learned when you're pursuing your dreams, patience is not only a virtue, but a necessity.