Mandy Rosello and her husband Joe are truly living their dreams. The two enjoyed sailing and international travel, so they found a way to make a career of it. Together, they run Sailing Kuma Too, a sailing charter company operating a 47-foot catamaran out of Dunedin, Florida, just west of Tampa Bay. The business offers single- and multi-day charters, sunset cruises, and half-day excursions in the Tampa area. The Rosellos are excited to expand their business to the U.S. and British Virgin Islands soon.
Why did you start your business?
My husband and I started our careers in private and corporate aviation. We had a strong background in providing customer service for high-profile clientele. Then, I transitioned out of aviation and into healthcare administration. I was an office administrator at a surgery center that had multiple facilities around the country. I learned more administrative roles, regulations, basic accounting, and the financial side of business.
My husband and I both started sailing about 10 years ago as a hobby on small sailboats. We love to travel. It’s been a passion of ours since we met. As we would work our day-to-day jobs, we would save up for vacations. We’ve always wanted to live internationally and find a living doing what we love. It was on one of our vacations that we met someone making money off their sailboat by chartering. We got back from that vacation and made a plan and set a goal. We started working towards that goal and saved every penny to put a down payment on a catamaran that could eventually make us money and be our home. It could take us around the world from business and lifestyle standpoints.
How did you fund the business at the start?
We have always tried to make sure we had a hefty savings account. We financed the company all on our own dime. We took a loan on the actual asset, the boat itself. We’ve always had credit cards for perks and rewards, but we try not to carry a balance.
How do you manage cash flow?
As we started to see our savings account dwindle once we started the business, we put some of the larger purchases on zero-interest credit cards just to give us time to build our savings back up. We were lucky to be able to get these cards because of good credit in the past.
From a software standpoint, we use QuickBooks. We try to use cash more than credit and only use credit cards when we need to. If there’s a project that pops up that can wait until we have the cash for it, that’s how we manage it.
What’s the most challenging thing about running the business?
Managing our time was the biggest thing we had to learn. Our first year in business, we were always chasing our tails trying to get the next project done. Now, we have a much better routine and we’re better able to set goals for the day, month, and so on.
What’s the most rewarding thing about running the business?
We get to do something that we love every single day. We love interacting with our customers. It’s one of the main draws of doing what we do. We get to meet different people on our boat and many of our guests have turned into good friends. Making our living on a sailboat out on the water is hard work and exhausting, but I wouldn’t trade it for a minute.
What’s the biggest mistake you made at the start?
We hired a maritime attorney that cost about three times what he originally quoted us, so that was really scary financially. One of the areas that we thought he was going to be able to help us with was licensing. He was able to help us with licensing from a marine/boating standpoint, but he was not able to help us with our city licensing. We went to the city and got our licenses and thought we did everything to get setup perfectly. But, I ended up getting a call from the superintendent of the city telling me we were operating illegally out of the marina. She told me we needed an additional commercial operator’s permit. We had to cease business for 2-3 months before that got ironed out. It was a major mistake and really scary. But, it all worked out.
What’s the smartest thing you did at the start?
We hired a maritime attorney. We talked to other operators in our industry who shared advice and lessons they had learned with us. We did spend a lot of money on the maritime attorney, but we know it’s worth every penny because we are protecting our business.
What advice would you give to a new entrepreneur?
Do it! People settle working for others more than they should. I hear more often than not that people are not happy in their current jobs, but they’re comfortable and it’s easy. People are afraid to go out on a limb, but I don’t think they should be. If you’re willing to put in the hours and persevere, it’s always worth it.
What’s next for Sailing Kuma Too?
We are in the process of completing the additional licensing needed to start chartering in the British and U.S. Virgin Islands next season. That’s really big for us, because, although we love our hometown, our goal in buying a sailboat was not to stay here forever. We’re excited about our next step so we will be able to charter in the Virgin Islands during the winter season.
This article was originally written on May 17, 2019 and updated on January 27, 2021.