Q&A with Cara Joyce, Owner of Urban Pirates

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Urban Pirates

Cara JoyceName / Title: Cara Joyce, CEO, Urban Pirates

First job: I delivered newspapers around my neighborhood as a kid and I worked at The Kite Loft at the Inner Harbor, Baltimore.

Best advice for aspiring entrepreneurs: Seek advice, do your homework and ask a lot of questions. Make sure your business has a fresh look, keep your consumers in mind when developing your business, invest in your team and be fearless.

Favorite pastime: Being active. I love to watch my kids play sports and I enjoy participating myself. Swimming, soccer, baseball, tennis and ice hockey are my favorites (I currently play in an adult ice hockey league)!


Congratulations on your recent retirement as a schoolteacher! How did your experience as a teacher impact your decision to start a family-friendly pirate-themed cruise?

I got the idea to start Urban Pirates after attending a pirate-themed birthday party with my son, who was three at the time. I said, “This is what I’m going to do for the rest of my life – bring fun to other families in an affordable way.” To me, teaching is entertaining kids. We want kids to have fun, but also learn something through the experience. We hope that we’re encouraging children to be creative while celebrating the story of historic Fell’s Point.

What was your biggest business challenge and how did you overcome it?

Like many new businesses, the initial funding of the company vision was the toughest part. I requested capital from at least 10 different banks, but no one wanted to finance a pirate boat – so we decided to use credit cards for the initial funding. Looking back, I don’t know what I was thinking but to be honest, I never once thought that the business wouldn’t succeed. We got lucky – our pirate adventures were a hit and now, we’re in a great financial position.

Urban Pirates

You were recently selected as a Bizwomen mentor by the Baltimore Business Journal. As a mother, what advice would you give to other women who are balancing career and family?

It can be really stressful trying to balance it all. The best advice I could give to others is this 1) Never be afraid to ask for help. I count on my “little village” of people who are there to support me and offer to help when I have too much on my plate. And 2) Always try to dedicate a little time out of each day to take care of yourself – even if it’s only a few minutes.

Impressively, the Urban Pirates’ ship FEARLESS was custom built from raw materials. How long did the boat take to complete, and who came up with the design?

The original concept was just a little sketch on a piece of paper. We found an amazing builder here in Maryland and he worked with us to complete our vision. The project started in January, and was completed in April in time for its debut during Fell’s Point’s annual Privateer Festival. A four-month completion is an incredibly impressive feat for a 52×18 foot boat – and all of the painting on the boat was airbrushed by hand.

We had a contest with over 5,000 entries to help us decide on the name of the boat. The second entry that came in was FEARLESS – the reasoning? “The people who started the business and the people who board have to be fearless.” I loved that, and I’ve adopted that mantra. I think being fearless resonates with anyone who is starting his or her own business – risk-taking is what will ultimately lead to success.

Urban Pirates

Urban Pirates has become decidedly recognizable along the Fell’s Point waterfront. How much advertising do you invest into the business now as opposed to when it was started in 2008?

During our first year we spent around $100,000. Now, we spend half of that. Online advertising has really transformed our business. It’s great because we can measure clicks and actually see our ROI. Social media has been huge for us – we’re very active on Facebook and are ranked #1 on TripAdvisor for Baltimore activities. We also hold promotions through daily deal sites once a year. In our first year with Groupon, we actually became their best-selling activity in the area. One year alone, we sold out of our 8,000 available tickets in four hours.

Also, the FEARLESS is pretty unique, so I make sure it’s out on the water during Ravens games in case we can get into an aerial shot – free national advertising!

Your chartered cruises have been embraced by local businesses as excellent team-building excursions. What benefits do your cruises offer to business owners looking to boost employee morale?

The cruise is great for interpersonal relations, employee morale and good ol’ fashioned fun. Many major local businesses participate in and benefit from the cruise – in fact, corporate events are one of our biggest sources of revenue. It’s fun seeing a difference in employee attitudes. You’ll watch employees in nice suits board the ship a little hesitant and uncomfortable, but they always return smiling and laughing and saying they had a great time.

Any plans for an Urban Pirates expansion into other cities?

We’re in the planning stages of expanding into other markets and building another ship. I have a few cities in mind but choosing the right location is key. Also, Urban Pirates does have licensing opportunities available.

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