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June 11, 2025 30 mins

In this Pride Month special, Rebekah speaks with Captain Jen and Captain Janet of Sundog Sailing about their journey as queer women in the sailing and tourism industry. They share how they built a business rooted in inclusion, hospitality, and joy all while creating a safe space on the water for everyone.

Together, they reflect on the importance of visibility and representation in tourism, the personal stories that shaped their business, and how being themselves has been the most powerful form of leadership.

Captain Jen and Captain Janet encourage donations to the following organizations:

This episode must-listen for queer entrepreneurs and anyone who’s ever built something from the ground up with heart.

Listen wherever you get your podcasts, or watch the full episode on YouTube!

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Rebekah Costley (00:02.324)Okay, and it looks like we are recording which I am so happy about because it is my favorite time of year. I love Christmas. I love fall. I love Halloween, but what I especially love is World Pride Month. It is so much fun. There's so much color. There's so much personality. There's so much celebration, so much remembrance and being

(00:01):
of the two women that I have on the podcast today is something that I am certainly proud of and I've met them multiple times. At Spark, I've met them I think a couple times in Charleston. They are the life of the party. They bring life to every room that they go in, laughter and light into every room that they go in. I am happy to have co-owners and captains
Captain Jen and Captain Janet of Sun Dog Sailing. Thank you so much for being here. How are you both doing today?
Janet (01:03.361)Very good, very good. thank you for having us today.
Rebekah Costley (01:10.318)Of course, like I said in the intro, I'm just so excited to have you on this episode of Growth Powered by FareHarbor We at FareHarbor really love celebrating pride and I was like, I would really like to highlight some queer owners that utilize FareHarbor on our podcast this month and I was like, who has a great personality, who's super funny and who has an awesome boat that many of my team members have been on before.
And it was like, my gosh, Sundogs Sailing, hands down, we gotta have them on. And we already have B-roll, I think, as well, of being on your tour. And I haven't been on it, but I've heard great things. So I'm just super excited to have you on. Thank you both for being here again. Can you give our listeners who aren't familiar with you a little rundown of Sundogs Sailing, where you're located, maybe some fun facts about both of you and what tour Sundog offers?
Janet (02:08.905)Awesome. Yeah, let's see. We are Sundog Sailing here in Charleston. We are very fortunate to have a 50 foot sailboat and a 21 foot center console. So we're really excited about getting people, visitors and locals out on the water here in Charleston. We're women owned, women operated. And I mean, that is amazing. You you show up to a charter.
And you're excited about seeing what your area has to offer. And it's just so neat to see people do a double take. And they're like, wait, there are two women on this boat. We're departing the dock. We are communicating with the bridge tenders. And we're women. And we're doing it. And so that is awesome. Sundog Sailing is a really neat platform, awesome opportunity for everybody. We're inclusive. We want it to be.
We want it to be an experience that, you know, they take pictures, people laugh about. Remember when we went sailing? Yeah, that was such an awesome time. We heard people say that it was a highlight of their visit here. So to show them not only a beautiful city full of history, but to show it through the lens of women, women owned, women operated from the deck of a sailboat. Yeah, we're lesbians. We're a couple. People get to see two people, two married people.
working on a boat and doing very well with their, you know, just working together, you know, as a team. Let me show other people that they can do that too.
Rebekah Costley (03:47.97)That's so incredible! How did you two meet?
Janet (03:51.9)I'll let Janet answer this one. No, you can answer it. We met as volunteers and Bird of Prey Rehab Center in Charleston. And we're both very silly people. We just kind of hit it off as friends like many, many moons ago. OK, that was Janet's version. Now there's another side of the story. We take care of we were we were responsible for taking care of these like beautiful raptors who come in.
No eye contact, you're not supposed to look at them, you might be a predator. And that was my first challenge because I was just enamored by these beautiful birds. And so Janet and I had to separate out the food that like a bald eagle or a great horned owl would eat. We would have to put medicine, tuck it behind the kidney or the liver to make sure that they didn't spit out their daily meds. And so we were sorting these mice, we called them ooglies.
And we were sorting the ooglies and there was one ooglie that was like a little furry Russian hat. And it was a little mouse and his little frozen friend was a Russian hat on his friend's head. And so I started making them dance and making Janet laugh. And we got to talk and we got to share our love of birds. The flight of a bird in the sky is somewhat similar to what we experience when we sail. Everybody has that magical feeling of sailing.
And so that was kind of a close thing on our terrestrial side. So it was neat to develop like a sailing relationship, going out on the river. We go out on a Friday night and we wouldn't be back till Sunday night looking at the tide. Was the tide right? If it wasn't, we'd just anchor out, have a little bit more red wine and play Yahtzee until the tide was perfect to bring our sailboat into the harbor safely and just go back out there.
wait for the week and then Friday would happen and we do it all over. So we're sort of addicted to being out on the water. It's a beautiful place to be.
Rebekah Costley (06:01.076)It really is. I think that even though the people who may not have like, like, for instance, I can't swim, which is embarrassing. I probably shouldn't say that on a on a public platform. But people like me who are so scared of the water, is so comforting when I do tours in my line of work that are on a boat of some kind or a canoe or a paddleboard. And my guide or my captain is just so
I feel so safe. I feel so like incredibly taken care of. I'm having a good time no matter what happens. I know that I have an experienced professional and I think also having the layer of inclusivity on a tour like that of being like, feel like I belong here and I feel like I'm good to be myself here and I can have a great time without worrying about judgment.
I can just be who I am. I think that's a really freeing feeling that unfortunately not everyone gets to feel like they can be their authentic selves all the time and maybe the only point they get to have that type of experience is on vacation. So I think what you provide is really special and exciting in that way. My next question for you is, it sounds like the passion, you have this deep passion for the water.
and for sailing, when was the moment you both realized together, we can actually make this a business? What did that look like?
Janet (07:36.982)Wow. Well, there's several. Like, I was a tour guide on Keowa Island. They rely heavily on nature. Nature is what people go there to see. It's a beautiful resort island, but it's cloaked in the maritime forest. You've got bobcats, you know, sitting in the shadows waiting for all the busy people to go to sleep. And then they pop out, you know, so doing like night tours.
watching sea turtles, taking people and sharing with them the magic of the sea turtles that nest on our barrier islands here. Just the platform turned into not a bicycle, not walking, but like, wow, on a sailboat. That's a whole nother level of nature. And it's amazing. mean, the number of people that have gone out with us that have not been sailing before, that's kind of critical.

(00:22):
You have to make sure that everybody feels comfortable and that they, you know, the anxiety, you watch people, they sit at the beginning of the, of the trip and they're a little stiff and they're formal and everybody's there. know, within minutes, you know, I, I, I try to make people as comfortable as they can be and make sailing. If this is their first experience, something they can remember as a positive thing. So yeah, just making sure that everybody feels secure. You watch people just break down.
Within minutes and then after three hours of that, know, people have broken down. There's no there's no guard. Everybody lets their guard down and opens up. They open themselves up to receiving the beautiful nature that's there already. And our job is to maybe point it out or, you know, like help interpret the nature that they're seeing. But it's like everybody's experiencing the same thing. Whether it's like there's a bald eagle. Wow, that's amazing. Or look at the.
stingrays as they swim along the surface and their little wing tips like break the surface. I mean, I see it. I'm excited. I want somebody else to see that and be, you know, share the childlike joy that everybody has inside of them. it just seemed like a perfect platform to combine the sailing with the tour, nature tours, history tours. Charleston is such a rich place and not only ecosystems, but history, archaeology, geology. There's just
Janet (09:58.125)It's just layers. It's lots and lots of layers. And we wanted to share that with people. as you said, inclusivity is a very big part of it. were when I started sailing here, I don't know that there were other women sailors. Now there's a lot, a lot more women on the water. Still not equal to men. There's still yacht clubs that don't allow women in this city. But so it is very important for us to be out there, be in our authentic selves and allowing other people.
to have that relaxation and that peace to have a place where they can belong and they could be that has been excluded to them for so long. It's like we open an invisible door. I had no idea that there was a door there. just, boop, open the door, pop in, and let's share this world that everybody's equal, that everybody, like, you know, enjoys letting your guard down. So I think that is rare in today's world.
And we're so proud to be able to be good, like a leader in our community, you know, a leader in sailing. We have like four, I'm interviewing another young woman tomorrow for a deckhand position. We've had five ladies reach out to us here in Charleston. They're sailors. They want more hours on the water. They want, you know, more of that good good. And, you know, they've reached out to us and said, Hey, look, there are
There are businesses here that are run by men and the men have said openly that they are not going to hire female captains. And so I'm excited that we have an opportunity that we can hire these young ladies. They can get their sea time. In order to be a captain, you have to have so many hours on the water. And if these women are just being hired as deckhands and not as captains, then that's a failure of society.
And if I can fix that or provide an opportunity for a young woman, if she's gay, if she's straight, if she wants to sail, I want her to come on our boat. I want her to be at the helm and feel it. It's a wonderful paralyzing anxiety when you realize you're in charge of these souls on board. And it's a beautiful thing to show people that you can be strong. A woman can be strong. A woman can navigate.
Janet (12:23.768)A woman can sail, a woman can own a business, a woman can be successful. And I'm so proud that we're here in Charleston and that we're able to do what we do. We're very grateful.
Rebekah Costley (12:38.38)Wow, my only response to that unfortunately isn't very professional. It just makes me want to say, hell yeah. Hell yeah, that's what I like. I love that. And before we started recording, we were talking about your relationship with FareHarbor and with each other and with your business. And you've summed it up as like, we are proud.
Janet (12:46.304)Yeah.
That is very professing.
Rebekah Costley (13:05.774)We're proud of ourselves, we're proud of FareHarbor, we're proud of our business. And I hear that passion in our conversation and I'm just elated to hear you're providing this environment for women of all orientations to be able to thrive in their professions and in their passions. And that's really important and I think mentorship is incredibly important. I'm curious to hear...
Janet (13:23.267)Bye.
Rebekah Costley (13:33.826)the inclusivity portion of men and mentorship. How important do you think it is for other queer people to see other queer people succeed, but also in your niche on a boat? How important do you think it is for queer people who want a career on the water, whether they want to be captains, deckhands, what have you?
How important do you think it is to have that representation? And did you have anyone like that to look up to or to mentor you as in your journey in your sexuality, as well as being female captains?
Janet (14:20.024)Wow, we are, we are gay, we are proud. It was a big deal. My hound dog is also proud. We're proud to be out there. It wasn't like a scary thing to do, but in generations past, even being out at all, I mean, you know, that was like life threatening. And in some cases it could still be, you know, we don't know it. We're just happy go lucky. We're ourselves.
out there and we're not holding back. We're not going to hold back. know, I mean, we're proud people at our Marina, you know, they're like, wow, these two ladies, they take that boat out all the time and they're sailors and they want to improve themselves. You know, we have like a lesbian couple that I think we're hiring them for the summer. You know, I mean, they have a job. You know, they're a lesbian couple. We are a lesbian couple. like we're we we we are in a role.
that I never expected to be in, but I'm very proud and happy to fulfill. And visibility is key to see other gay people, LGBTQIA people out there. I mean, we've gone out of town and we've gone on a charter with a lesbian, civil charter in Massachusetts. Yes, absolutely. Absolutely. We chose her. You know, and it's neat to have that choice.
You know what I mean? I mean, if you've got a choice and we're out there, why not choose all the colors of the rainbow? know, chocolate and vanilla is, you know, lovely, but like, let's have some strawberry. Yes. And back to the yacht clubs, there's women can only be in there as a wife of a man. So if you're a lesbian couple, you'll never, you'll never be part of the Carolina yacht club. It was established in 1883. And to this day, dog is upset as well.
Rebekah Costley (15:55.854)You

(00:43):
Janet (16:12.534)Us too, Bella, us too. We can't tie our boat up out there dock. We can't have access. We just watched a beautiful interview. I don't know if you're familiar with Cole Brower, but she's a 30-year-old young lady that has sailed around the world. She was the first woman. American woman to sail nonstop around the world. she won a race. She won. And she had an experience here in
Rebekah Costley (16:14.188)you
Janet (16:42.175)Charleston, think one of the yacht clubs. don't necessarily need to say their names, or the James Island Yacht Club. He was kicked out because her boyfriend, she wasn't married to him and and that he wasn't present. And it's just it's it's just important. That's why we chose to buy our boat to start our own company.
instead of trying to work with other people and having the same stories the women are telling us. We just be a deck We're just like, we're going to do it ourselves. We're going to do it our way. And we're going to include everybody's welcome. That's the difference that everyone is welcome. Right. All right. Yeah. And this is 2025. I mean, we're like role models. We're setting trends here in the South, in the United States of our America. And we are in the South of it.
And I mean, like opportunities for young women sailors up North, maybe they don't have the same challenges. So I didn't realize that we picked a battle here in Charleston. It seems to be a battleground for more than just, you know, rights. It's rights for everybody. Everybody is equal, should be seen as equal. And that's our main job is to show equality and strength.
equality and strength.
Rebekah Costley (18:02.19)Absolutely. Wow, that's really powerful and thanks for sharing that with me. Why do you think in that power and strength can come a lot of, I think it takes time to get there. As a queer person myself who comes from a very, an area where it was difficult to know like, oh, is this, oh, I'm not like,
weird, like this is queerness. And it's okay to say that out loud and it's okay to like, you know, for me that my queerness was rooted in surrounding myself with other queer people and being like, I'm not alone. And that was a real blessing to me as a young woman growing up, especially in my younger 20s.
I'm interested to know, like, how did finding your love of sailing help you find your power, help you find your pride? How did the water really nurture those parts of yourselves?
Janet (19:11.018)I'm interested in Janet's response. Well, it's like our own little island. We are on this boat and we create the environment that we want, that we maybe haven't seen and we didn't have role models. So we have to take that on ourselves and we're, you know, creating our own environment and hopefully inspiring other people of all diversities and of all queer people.
all races and genders and just let's all just go together and enjoy sailing. Yeah, sailing is a platform that like once again, it breaks down barriers. And so, you know, I mean, you break down your own barriers. You know, I mean, how many gay people in their lives have questioned being here at all? You know, I mean, do we want to even be on this island? Like, you know, it's a club. Do you want to be in it? And this is such a valid place to be in. There's so many beautiful things.
to, there's so many great reasons to be here. And so like being gay isn't a bad thing. It's not something for self torture. You should be proud of who you are and seeing other people proud of themselves facilitates your own pride. You're like, wow, that makes me proud. Why did that make me proud? Don't even realize that you needed that. You have no idea that you just needed that strength. And so sailing, it just like, it calls on.
a lot of strengths. You know, you can't cry. If you're 60 miles offshore and the boom breaks, I looked at Janet, well, maybe we did cry a little bit, but we did put on our big girl sailing pants and we stood right up there and we hand sailed our sailboat in a storm 19 hours back to land. And that was amazing. We looked at each other. We didn't get fussy. We just knew that our vessel would take us home.
And if you have your strength inside of yourself, your vessel's driving every day. You're making choices. You're making gay choices. You're making straight choices. You're making choices. And, you know, I mean, like we want everybody to find their own inner strength. That's important. That's important for everybody. You know, all of our diverse, beautiful selves. We're the color of a rainbow. And, you know, you can't have a rainbow without every single color in it. It's not a rainbow. It's just monotone.
Janet (21:37.328)And that kind of gets boring. So we provide a choice. We provide a chance to express ourselves and for other people to express their selves. Everybody's got a little sailor girl in there. You know, we all want to be big sailor girls. And so to put on your pants and wear them proudly, let's be gay and let's sail. You know, we're strong women. We're showing other people how to be strong and they're doing it. These women are reaching out to us and we are so pleased and so
honored. Kind of shocked. It's like a new pair of shoes. It's like, how do you wear these shoes? How do you be a mentor? Don't put a lot of pressure on yourself, but just be your true genuine self. Everybody's got a beautiful self in there. And we should rejoice and share that pride. Yeah, that's a spiritual experience to be out there sailing.
Janet (22:32.678)Yeah.
Rebekah Costley (22:34.414)Absolutely. That's a perfect segue into my next question. How has being out and visible changed how you connect with the guests on your tours and the guests in your community? I'm so sorry. Can you still hear me? I think my microphone just died.
Janet (22:54.168)still. Yeah, we can hear you. Yep, you seem like you're still on track.
Rebekah Costley (22:58.326)Okay. Okay, cool. I'm going to react.
Rebekah Costley (23:04.398)That's a perfect segue into my next question, which is how has being out and visible and proud, as you say, how has that changed the way you connect with your guests and the way that you connect with your community?

(01:04):
Janet (23:20.801)Well, I've been amazed. mean, we've had mostly very positive response. People seem to be very supportive, whether they're straight or gay. Yes. And I know that we're probably the first time anyone's seen, I don't, know, lesbian captains or whatever. So we've we've really been happy that we've had positive, positive reactions.
We even have like parents that will come on board and once again we've already broken down the ice, we've broken down the barriers and they're comfortable enough to talk to us about their son or their daughter and that they are gay or lesbian. And so to be able to tell them, you need to talk to your kids. Don't not talk about these things called gay. Don't not talk about it. This is a perfect platform. So they ask us.
and we're able to talk to them. And as a child with parents, and my parents have struggled with their acceptance of who their daughter is. And my mom, she calls us her girls. She loves us. And I am so grateful to have accepting parents and to be able to be a role model in that way, to talk to the parents, to their side of it, their kids up front. And their mom is struggling with it. It's like, you can struggle with it. Everybody has struggles of acceptance.
But why not find love and find a way to talk to them about it, that it's perfectly acceptable to be a gay person and be a beautiful color in the rainbow and that we should shine brightly. And you shouldn't diminish or shade out or snuff out or put it back in the closet. Talk to your kids. Kids, talk to your parents. Like, let's be honest about who we are. Be proud of who we are. It's nothing embarrassing. It's a beautiful thing.
to be a color of the rainbow.
Rebekah Costley (25:22.72)Absolutely. Can you speak to why it's so important to support queer-owned businesses, not just during Pride Month, but any day of the year?
Janet (25:36.848)Always. Yes, we'd love to see examples and visibility of other businesses out there and makes us feel good to support those businesses. Yeah, we choose them. You know what I mean? I mean, sometimes it's neat once again to be looking at the menu of, here's some tours. And then I read about who's giving the tour and that's just as important as the tour itself.
The dates of history are wonderful, but like the person providing that information you want to connect with your tour guide you want to see yourself as you know living and understanding what this person is trying to show us, you know a tour through whatever so to be To be a lesbian and to choose other lesbian or gay owned community members, you know, that's just showing pride
You know, and we definitely would love, know, like when we see there's a rainbow or a chance. I mean, you you like want to talk to them about it and tell them that we appreciate the fact that they are showing their selves, their true selves. And I'll have a more genuine time on their tour, knowing that it's, that's the true selves providing their insight and a safe space also safe place. It's comforting to us. then.
We want to support those businesses over other businesses that may not have a welcoming atmosphere to people like us. Definitely would rather support the ones that support us. Yeah, it's a small part of the community. I mean, if you look at the number of gay and lesbian owned businesses, that's small. There's small business and then there's even small sector of people that are rainbows and that
It's critical. got to support each other. And that just gives everybody confidence. know, confidence that, this is a five-star business right here we're going to. know, I mean, they're lesbian-owned. Wow, look at that. They're women. They're all of these things. They're captains. They're sailors. Wow, just blowing the glass ceiling right out of this place.
Rebekah Costley (27:49.474)Yes, yes, to shatter that glass ceiling. Absolutely. My next question to you would be why we talked a lot in this episode as we close down here, we talked a lot of in this episode about, I heard a lot of the word comfort. And in that is like inclusivity. Like it's so important for us as humans to feel comfortable and for our
guests on our tours to feel comfortable, to be themselves, be who they are. And as you said earlier, there's some people who don't get that chance, unfortunately, even in 2025, in their day to day to be themselves. So providing that space, especially when on their vacations to be themselves is something that's really special. Do you think it's important for operators to publicize this inclusivity?
in part of their tours and why do you think that is?
Janet (28:50.297)Yeah, I guess it depends on the safety of where you live and what the climate is because sometimes it could be to your detriment, but it's wonderful when people are brave and do that and put it out there. That's very important. Yeah, because the more you see, the more like it's being shown, you know, and it's a beautiful thing to be seen. You know, it's just it is you like, look and say, hey, look, I can go there. I could be myself.
You know, I can ask questions. You know, if you're curious or whatever, you know, let's show the community that we are beautiful leaders, we're educators, we're sailors, we're captains, we're lesbian. Those are all wonderful things to say about a person. people should see that and recognize that. And the more they see it, the more they say it and the more they do it and the more they can become it and be proud of who they are.
Rebekah Costley (29:51.658)Absolutely. And speaking of proud, at the end of every episode, I like to ask all of my operators, it's interesting because especially if I have a female guest, it's so hard for me to get them to brag. So I like to call this my not so humble brag and ask, what are you most proud of? And if you want to make it, you know, I know it's special that I have like a
couple on the podcast. So I think maybe it'd be fun for you to say what you're proud of for each other, and maybe yourselves as well. And it can be personal, professional, whatever you feel comfortable. But I would love to know what is your not so humble brag in one another and in yourself?
Janet (30:22.903)Bye!
Janet (30:46.113)We are dos capitanas. You're not even supposed to have bananas or women on a boat. And you got two ladies that are just so enthusiastic about what they're doing that you don't forget. I mean, just like, don't even make it a thing. Wow. Wow. There's a bunch of bananas. And hey, wait, there's two lady captains. you know, I mean, we sailed to Cuba. And when we pulled up to the customs, like dock, everybody was chasing our friend around.
Rebekah Costley (30:50.926)you

(01:25):
Janet (31:15.199)and going Capitan, Capitan. And he's like, no, Capitanas. We're two women. We sailed to Cuba. And even Cuba was like, wait, what are these two women doing driving this boat? And also, what are these bananas doing? So, I mean, we're beautiful people. We're so proud of ourselves. We're proud of the ladies that are wanting to work with us and work for us and make it still the number one, the best sailing charter in Charleston, women owned, women operated.
know, we're on queer operated. That's it. We're proud. Everyone is welcome. Very inclusive, very inclusive. No age restrictions, no, no rainbow color restrictions, just everybody who wants to go sailing. Let's let's get out there on the water and let's like share this a beautiful place because you're only on earth once. So we might as well have a good time while we're here and let's let's go sailing.
Rebekah Costley (32:15.694)I love that. you for sharing that. Well, thank you both so much for being on my from smiling my cheeks hurt. My my face from from the joy you both. thank you. And we love you. Thank you.
Janet (32:24.055)I know, I know, this has been a pleasure.
We love you so much.
Right on, right on. Well, we love you so much. Yeah, you guys have good energy.
Rebekah Costley (32:39.758)thank you. I think that what you're doing comes out of a place of so much, yes, pride, but also so much joy. And I think that queer joy is so incredibly important to publicize and to show. And for those who are listening, I hope that listening to this episode brings you comfort in what brings you joy and makes you proud of who you are, no matter who you are, no matter how you identify.
And it sounds like I think I can speak for Sundog Sailing if you need a place to be yourself. It sounds like the boat's open for you. And I'm so glad that it is. And I hope I can find myself on it somewhere soon. So thank you so much, Captain Janet Thank you so much, Captain Jen, for being on.
Janet (33:24.572)Yes. I hope so. Yes.
Rebekah Costley (33:32.428)I'm just elated to have you here and I can't wait to see you again hopefully at Spark this year. Thank you all for listening. You can find us wherever you get your podcasts. You can watch this episode and many more on YouTube. If you enjoy the episode, please leave us a great rating, maybe a comment as well of your favorite queer businesses. And I forgot to ask you both if you would like to shout out your favorite. I love the heart.
Janet (33:52.423)Right through the heart.
Rebekah Costley (33:59.038)I forgot to ask you both if you want to shout out your favorite LGBTQIA plus charity. I would love to also include that on the episode if there's one that calls to you.
Janet (34:10.963)I'm well i've always loved the trevor project because we all know what the struggles like when we're growing up clear in the small town or small southern town or wherever you are in the big city is just this just a challenge and the boys supported trevor project p flag and. many others human rights campaign so there's so many. We have a local.
We have a local group here called We Are Team Jake. They're not exclusively LGBTQ, but they are all representation anti-suicide group.
Rebekah Costley (34:54.968)Perfect, that's amazing. I'll be sure to include all those links in the description to donate to those. I especially am a huge fan of the Treasure Project as well. Thank you so much for sharing that. Thank you again for being here. Thank you all for listening. I'll be sure to catch you next time and I hope you guys have a great day. Thank you, Captains. It was lovely having you.
Janet (35:16.467)Thank you. Thank you so much. Happy Pride Month. Happy Pride.
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