My Interview With Captain Wendy Longman of Windsong Charters
If you think you’ve “made it” you’re not working hard enough!
Today, I am interviewing Captain Wendy Longman, the owner of Windsong Charters, a local charter boat company located in New Port Richey, FL. I met Wendy at the wonderful Sip restaurant in downtown New Port Richey while I was acting in Leading Ladies. One of my co-stars was asking her about what she did for a living, & she said she owned a charter boat company & got to sail boats FOR HER JOB. Doesn’t that sound awesome & like it would be a lot of fun? She sounded like she really enjoyed what she did for a living & I found that totally inspiring.
I love when I meet people who really love what they’re doing, especially if what they’re doing is an opportunity they created for themselves. So, when I came up with the idea of interviewing people & then sharing it on my blog, Wendy was honestly one of the first people I thought of. I reached out to her, we emailed back & forth a bit, & here we are with this awesome first interview for my blog.
Tell us a little bit about Windsong Charters & what they offer.
Windsong Charters & Boat Rentals offers private sailing charters, private fishing charters, pontoon boat rentals (drive yourself or hire a captain), and paddle craft rentals (kayaks, canoes, and stand up paddleboards). We also do weddings, memorial services / ash scatterings, island BBQ parties on Anclote Key (bachelor, bachelorette, sweet 16, anniversary, quinceanera, etc), corporate team building…anything you can do on land, we make it more fun on the water or an island.
How did you end up starting your business? Was there a specific moment that made you say, “I need to start a boat charter company”?
LOL! There was no “A-HA” moment. Windsong actually started by accident drinking cheap beers and smoking cheaper cigars sitting on the island back in 2002. We met a retired aerospace engineer from San Diego and he wanted to start a “little retirement business”. He was an accomplished sailor and my husband and I were currently in marketing working for Corporate America. Hubby came up with the name and the deal was, we do the marketing (website, sales, collateral) and he taught us how to sail.
When the 2004 hurricanes played havoc with the area, he decided to move back to San Diego as he wasn’t overly fond of Florida. We had since bought our own personal sailboat and he asked if we could take over the existing bookings. I basically said sign everything over to me…state, county and city licensing. We had our personal sailboat commercially documented by the US Coast Guard, obtained our US Coast Guard Captain’s Licenses, and the rest is history!
What is your favorite part about owning your business?
What kinds of things did you do initially to attract customers? Was there a specific thing you did that really seemed to help?
How did you get to where you are today? Walk us through the steps you took & tell us what happened.
It’s been a crazy wave of high and low tides! Where we are today is the result of a TON of literal blood, sweat, and tears. I could have never done this without my best friend and partner in life, my husband Bruce. We both had full time jobs when I took the company over and both of us were travelling a lot for work. Once the business made about 1/2 of what I was making in Corporate America, I left my job to market and build Windsong full time. So to go step-by-step over that past 15 years will take more space than I’m allotted in this blog. LOL.
How did it feel when you started getting more customers? Was there a moment when you realized you’d “made it” & that your business was working out the way you hoped it would?
Growing Pains in any company can make or break you. It’s a delicate balance of who to hire and when without sacrificing quality and ability to pay your mortgage. We hired some fantastic people who are still with Windsong today, to people that are sitting in jail today. Owning your own business is the hardest you will ever work in your life – EVER!!! As far as “Made it” – am I there yet?
What do you know now that you wish you’d known when you started?
Not to hire the people that screwed me. But hey, if I didn’t have the opportunity to learn THAT critical lesson, Windsong might be in a very different place today. Things happen for a reason. These life lessons, whether business or personal, cannot be rushed or avoided. Life lessons are exactly that – you learn the lesson and move forward being better and striving for the best. Or you wallow and never grow.
Who or what are some of your biggest influences? Tell us about some of the people, books/movies/songs, or events that have inspired you the most & why.
My mom. She’s my rock. She’s my inspiration. She’s my everything. She is truly the strongest person I know (three bouts of cancer and chemo in 15 years). She’s a fighter. She’s Polly-Anna. She’s AWESOME SAUCE!!! I didn’t spend a lot of time in Corporate America, but the few “real” jobs I had, all three of my bosses made me the person I am today. They were wonderfully fair and insightful.
What’s something interesting about boats that most people don’t know?
Boats are a total pain in the ass!
What is the best advice you have ever received?
From my Gramma: “You’ll know better when you’re 25”. At the tender age of 24 years and 364 days old, I wrote her a long letter (remember that ancient art of a piece of paper and a pen? Then you fold the papers that you’ve spent hours pouring your soul upon, stuff it in and envelope and mail it?) Anyhoo…I wrote her this long 10-page letter explaining how I know better and all the things I’ve learned.
I didn’t hear back from her for weeks and all of a sudden there is a postcard in the mail. No “Dear Wendy”, no “Love, Gram”, just the following written in RED PEN (like when I was in school!!!)…”You’ll know better when you’re 30”. OMG! I FAILED! WTH??!!!!
When I gave her eulogy I relayed this story. She wanted me to be ME first. Get my career and my life in order FIRST and NEVER make any major life decisions until you are at least 25. I relay this story to the youngsters I hire, friends’ kids, and to the youth I mentor in the community. You really WILL know better when you’re 25 and you’ll know even MORE when you’re 30. Never sacrifice YOU!
When you were a kid, what did you want to be when you grew up? Does any aspect of it relate to what you do now?
I wanted to be an interpreter for the UN. By the time I graduated with my first degree, I spoke five languages. The UN thing never happened because I didn’t have the courtesy to actually listen to my Gramma about the 25-year-old thing. However, Windsong hosts guests from all over the world and my language skills have definitely come in handy.
I bet you’ve got a great story about something that happened while you were chartering a boat. What’s one of your favorite stories?
You really want to hear about being on a 44′ sailboat in the BVI (British Virgin Islands) during Category I Hurricane Olga? That sucked. The worst part was not being able to drink a beer because the barometric pressure and the winds just schlurped the beer up my nose. Most annoying. In all reality, it was one of the best learning experience of my life. (Wo)Man vs Mother Nature and the delicate dance of respecting her. Every day was trying to save the vessel. If you don’t have a vessel, you don’t have a safe haven. When my guests come in from a 15-minute Florida “micro storm” and complain about the “major hurricane” they experienced…I feel bad laughing at them, but they really have no clue.
Is there a previous job or business you’ve had that prepared you or inspired you to be where you are today?
My entire 49 years of life from shoveling sidewalks at 8 years old for $2 to getting fired from my first “real” adult job after college has been the greatest ride of life.
What was your biggest challenge or setback, & how did you handle it? How did it help make you/your business stronger & more resilient?
The “’Great’ Recession” of 2007 – 2009 was a challenge to say the least. Groupon contacted Windsong and we opened the Tampa market for 1/2 off Kayaks rentals. That helped get Windsong a lot of exposure. Because so many people lost their boats due to repo, we were able to gain that market. The pontoon boat rental company at our marina was closing their doors and gave me their blessings to “have at it in the rental biz”. I went into my nest egg, bought four pontoon boats, and started the rental side of the business. Many people back then could not afford a $500 boat payment on top of gas and insurance, but they could get a group of friends together, split the costs, and still afford a great day on the water.
Then we had the BP oil spill of 2010. It NEVER effected Tampa, but because of the insane media, the world was told we were a total loss in Tampa. We lost a lot of business. We tightened our bootstraps and learned to operate very, very lean. No one was laid off, but a lot of sacrifices were made by all.
Why do you do what you do?
To pay the mortgage. 😉
What drives you to be successful & keeps you interested in what you do?
My staff. If they don’t have jobs, they don’t pay their rent. I feel a sense of duty and responsibility to them. It also doesn’t help I’ve been an overachiever my whole life.
What is your favorite quote & how does it relate to or inspire your approach to your business?
Never regret the things you’ve done…only the things you haven’t. I don’t want to live my life with should have’s, could have’s, and would have’s. There are a few of things we tried that failed miserably at Windsong (such as starting the Jet Ski Tours division). If we didn’t at least try – we wouldn’t have known it would be a failure and then we would have wondered and obsessed incessantly about the “What If’s”. By the way, it failed not because we suck, but because the insurance was so insanely cost prohibitive that it would have been fiscally irresponsible to move forward.
What advice would you give to someone someone who’s just getting started with their own business?
Be prepared for 80+ hour work weeks, no time off, no vacation, and no life for the first 5 years. Have a great attorney and an even better CPA. Pinot Grigio will become your best friend.
What’s next for your business? What do you hope to accomplish with it over the next few years?
The sky is the limit! Personally, I would like to take a small step back from the day-to-day operations at the marina so I can team with County and State Tourism officials to re-open scalloping in this county for sustainable recreational harvesting. This would be a significant tourism boost and create very much needed jobs in this area. I would also like to focus more on events, corporate team building, and increase our number of weddings. The past couple of years have been training really amazing Manager Trainees to help with the goals of expansion.
Is there anything else you’d like to add?
When you’re in Florida, come float our boat! 😃
You can learn more about Windsong Charters at:
5015 U.S. Highway 19, New Port Richey, FL 34652
Open 9am – 5pm.
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