The Happiest Pirate In Town

What do you get when you take away the alcohol and violence associated with pirates? You have The Pleasant Pirate, a whole new take on beachwear. You won’t find any skulls or rum here, what you will find is a happy pirate that enjoys the beaches. There is no pillaging, just spending time with good friends.

Like many businesses before it, The Pleasant Pirate was born out of personal interest. Lynn Small wanted something different. So she created a design and, with the help of a friend, she put that design on a shirt for her own personal use. It was when people started to take notice that she realized the potential her idea had to become a viable business. Less than a year after the official launch, Lynn is preparing herself for what she hopes will be a busy summer in business.

Tell us a little about your business, The Pleasant Pirate, and what inspired it.

When on vacation last Summer, we happened upon a pirate festival. We wanted tee shirts as souvenirs, but were not thrilled at wearing a design with a menacing skull — especially for our two young boys. Although we understood the genre, we were still surprised we could not find any “pleasant” pirate t-shirts. It seemed that every pirate tee I found online shared the same theme of skulls and rum. So, I designed my own tee and had a friend heat press it on a shirt for me for my own enjoyment. I was overwhelmed at the compliments I received when wearing it. That’s when I knew I was on to something.

How many products are currently offered on your site?

We currently offer 16 different products in various colors and design combinations.

What are some of the top picks among customers?

The most popular products have been Men’s t-shirts with positive messages on them. In particular, our most popular is our logo shirt with “Happiness begins with a great latitude”.

What kind of growth have you seen in the months since you launched your business?

Since we sell primarily beachwear, we purposefully launched our business in the Fall season to prepare for what we’re hoping to be a big Spring and Summer. So growth has been slow but promising.

What goals do you still hope to accomplish before your first anniversary in October?

I personally want to see our company making enough money so that we can contribute to local charities in our community. It would be a personal highlight for our company to help other would-be entrepreneurs realize their dreams.

How long did it take to build The Pleasant Pirate from idea to launch? What was the process like for you?

It took about three months to bring our store online from the idea in my head. The process seemed to flow very naturally. Every time I had a question… or if an obstacle presented itself, I did not allow worry to enter my thought process. I would just picture people smiling while wearing my shirts, and somehow the situation would remedy itself and the business progressed.

What are some of the lessons your business has taught you?

1) Do not take business negotiations or transactions personally.

2) Be your own cheerleader.

3) Keep a notebook to write down all ideas.

4) If you keep envisioning the end result, things always workout.

How about your kids? Do they help out with the business in any way?

My kids do not directly help my business, but they certainly understand when I have to work on the website or talk to vendors. They offer to clean the kitchen, do laundry, etc. And it’s especially rewarding that they choose to wear my designs!

What tips or tricks help you balance your time between family and your business?

I believe very much in my boys, ages 11 and 10, becoming self sufficient so they are good at fixing themselves a nutritious breakfast in the morning while I check emails, orders and website statistics. I make sure to drive them to school and back every day…I find this is when my boys want to share about their day. When they come home from school, I am 100% Mom and the business takes a backseat. After they go to bed, I find time to tie up any loose ends I was not able to finish during the day.

Do you have any advice that you’d like to offer fellow stay at home moms that are also thinking about starting their own business?

Only start it if you absolutely 100% agree with what you’re doing or selling. Be excited about your product or service, not the fact of making money. The other night my husband and I were out to dinner and he was wearing a Pleasant Pirate shirt. A woman and her grandson kept pointing at it and smiling. That little boys smile was worth more to me than any dollars handed to me. And I couldn’t wait to get home and work again.

Also, while at home, turn off the television. It is so easy to get caught up in negative news stories or talk shows. Find motivational and inspirational stations on the internet or tapes from your local library. Feeling good about yourself opens the floodgates of ideas that can inspire others.

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