Is Glenn Shephard, the ‘Below Deck Sailing Yacht’ Captain, the Nicest Guy on Reality TV?

The boat, as Below Deck Sailing Yacht fans know, has finally hit the dock.

All season long, show trailers have built up to the moment, and the crunch of the good ship Parsifal against smashing, displaced stone. The much-hyped collision happened at the end of Monday night’s episode (“Crash Boom Bang!”) of the Bravo reality show, now 11 episodes into its second season and a spinoff of the incredibly popular Downton Abbey-at-sea Below Deck franchise in which the stars are not the rich guests on board, but the telegenic, horny crew serving them in between hookups and fights.

The surprising thing is not the crash—it looks expensive, rather than life-threatening—but the loss of cool of Captain Glenn Shephard, the only adult on board the vessel of hard-working, hard-drinking, bed-hopping young crew. “Captain Glenn”— all the Below Deck captains are known with the C-descriptor, “Captain Sandy,” “Captain Lee”—is a rare character not just in the seven-year-old, now multi-tentacled franchise, but in reality TV itself.

He seems (famous last words) wholly nice, polite, and un-glacial to his staff, efficient and no-nonsense but with a twinkle in his eye. He helps with passenger luggage, he shares quarters with the crew. He is a boss who clearly likes to work just as hard and collectively as those around him. He is kind and unflappable.

Below Deck Sailing Yacht’s Captain Glenn on the COVID Scare That Nearly Sabotaged the Season

But the jolting impact of boat on stone changes him, at least momentarily. As the credits rolled, we saw Shephard get understandably angry, and start swearing. This coming Monday night (episode title, “Total Ship Show”) will reveal the extent of the damage and the extent of that anger. Should we be worried? Could this be just the start of a Lou Ferrigno-becomes-the-Hulk transformation? Has Captain Glenn—who really does not like to be called Captain Glenn, by the way; more of this later—gone mean?

Shudder.

Thankfully, when we Zoom, the captain is twinkling and smiling as normal. He is seated in the living quarters of his own “little boat” in the north of the Spanish island of Majorca. It is 13 meters, compared to Parsifal’s 54 meters, a modest 10 tons versus 460. And presumably, there are no tear-stained twentysomething love triangles raging upstairs.

He laughs when asked about appearing to be the nicest person on reality television. “A few people online have said that. Those are big shoes to fill. I think of myself as a nice guy wrapped in a thin veneer of asshole. Once in a while I will throw my toys out of the pram. But generally, I try to be a nice person. My style of management is to try to keep the team happy. I don’t want to come down too hard on them. There are moments when I have to, but I try to set the tone and keep the mood pleasant.”

But the jetty, the meltdown…

It was an “easily avoidable screw-up,” says the 61-year-old captain. “I made some mistakes, but it was also stuff beyond my control. The computer on board and throttles had a malfunction, so there was nothing I could do. It was stressful. It was the first time something like that had happened in a 20-year career, and 12 years on this boat. It was shocking. People could get hurt. It could be the end of the season, it could be a lot of things. It’s sort of like if your brakes were to fail and you smashed your best friend’s car into a wall. Imagine how upset you would be. It’s not a minor thing. I would be surprised if anyone in that situation stayed completely calm. We’re all human, right?”

Now the angry genie has been briefly released, is it going to be more present?

“It’s a brief glimpse of me at my most angry,” Shephard assures the Sailing Yacht faithful. “At the point you see me react I don’t even know how bad it is yet, I feel the shock. I thought the throttles were forward. There are no brakes. The throttles are the brakes. So you keep going forward till something stops you, which was the dock.”

He declines to reveal what the extent of the damage is—he’s gotta keep us tuning in after all—but notes, “I can say if you hit a dock like that you’re definitely going to have some kind of repairs. The question is whether it’s structural or simply cosmetic. These kinds of boats are built out of steel and aluminium, but because they’re flash boats and need to look sexy, they have a thick layer of filler and are made to look glossy and shiny. That’s a costly repair, but it’s not structural. It’s cosmetic.”

As storylines like Gary, Alli, and Sydney’s love/lust triangle become ever more excruciating, and the drinking and partying continue when the boat is not on charter, the genial captain is nowhere to be seen. We assume he is in his cabin, reading, sleeping, earplugs in, but not necessarily.

“Unless it’s getting too out of hand, I try and stay out of their way, because I don’t want to be the schoolmaster,” the captain says. “I’m not a spring chicken. I did all that 20, 30 years ago, so you don’t see me doing that. These guys work really hard and need to recharge their batteries and blow off steam and come back happy for the next charter. I am mostly in my cabin chilling out. Occasionally, I go to a hotel nearby, get a room, take a nice hot bath, watch football highlights on my iPad, or interesting videos. I chill for an hour. That’s my way of relaxing.”

He doesn’t seem to involve himself in any of the gossip and intrigues. Does he secretly know all the shenanigans going on around him?

“We work in a really small space. I don’t want anybody to come and snitch to me unless it’s a safety issue or serious work-related issue I need to know about. I don’t need to know about all the details of the romances, although I get the big picture. I’ve worked with a lot of couples. Some of them came on board as couples, like (season 1’s) Paget and Ciara, and some who became couples on board. To be honest, if you can have that job and all the great parts of what we do for a living, and have a partner with you—that’s a great thing. I’m willing to cut those people a little bit of slack so they can have all that.

“On some boats it’s different—it’s ‘no way, no couples,’ and if you hook up on board it’s big trouble. Then you’re just hiding it, you know? Some boats don’t hire smokers, and say ‘Don’t smoke,’ and then you see people having a sneaky cigarette. This season it was a little bit complicated for Gary and Sydney to get together because they work in the same department. But there was no coercion involved, and if anything like that happened I would be right on top of it and say, ‘Stop that instantly.’ Generally, I don’t want all the juicy details, I keep my distance, I definitely care, and I hear more maybe than what you see.”

The captain says that in season 1, he didn’t know all that was going on in the on-off relationship between (chef) Adam and (chief stewardess) Jenna. “I probably would have said more if I had known because their thing was a little bit negative and negative towards other people, particularly in Jenna’s department.”

This season not much he has seen on screen has surprised him, apart from details like the number of times guest cabins were used for crew hookups. “Some of the stuff they put on TV, I don’t want my mom to see, and she’s a big fan of the show,” he laughs. “Using the cabins is a no-no, but it’s not something that would get you immediately thrown off the boat. They shouldn’t really be doing it. They all have their own cabins on board, but on the other hand, they can’t sneak off to a hotel if they wanted to because of the COVID restrictions we were operating under.”

Again, Shephard defends the crew. “They have a job to do, but they also have a life, and their home is on the boat. Wherever you work, your boss doesn’t get to tell you what to do when you go home. I have to manage that, and give them a little bit of freedom. They work for me, but they don’t live their lives for me.”

More than we see on camera, the young people confide in the captain, and ask his opinion. “I’m not just a boss, but also a friend who has experience in yachting and also in life as an older person. But they also want to figure it out on their own also.”

His humility seems genuine. It is certainly a constant in our conversation, where he will say something, then put forward a qualifier or opposing point of view. He seems so odd in a reality show, not just because of his apparent decency, but also because he doesn’t seem to care about making a good impression. He just gets on with his job.

Like any reality show, the viewer’s assumption is Below Deck Sailing Yacht producers are manipulating the drama on-screen, but Shephard insists not.

“Before I got involved, I thought the same. I thought a producer would come in in the morning, and say, ‘OK, today you’re going to fight with that guy and you’re going to sleep with that girl.’ I didn’t really like reality TV. I thought it was unscripted drama where you didn’t want to pay the writer. I’m sure some of the shows do it. But on Below Deck, at least on Sailing Yacht, they don’t do that at all.”

He says he first brought his concerns up when the production initially reached out to him, looking for a sailboat. He suggested the Parsifal, but didn’t think he should be involved, “because I’m not an actor.” A producer told him, “No, we don’t do any of that. We just get people together and film it.” Despite reality TV being a buzzing hive of manipulations and contrivances, the captain says Sailing Yacht remains, at least in its filming methods, pure.

“There’s nothing like that. No one says, ‘Gary, you need to go kiss Sydney.’ It is just us doing our jobs. Yes, you have to factor in we know the cameras are there. The only way you could get true reality is if you had a total hidden ‘Candid Camera’ set-up, but I don’t think it would be much different to what you see.”

Shephard says that, unless one burrowed into individuals’ subconscious, there is no way of knowing if anyone is acting up to the cameras. “I’m probably on my best behavior, but I am running a boat.” He recalls in season 1, for the first few days it was “weird” being filmed, “but then you forget they are there. Everything you see really happens. Nothing is made up, or asked for by them.”

“I love Downton Abbey, and the dynamic of our show is exactly that,” says the captain. “It’s average people, the crew, interacting with people who are mega-rich, and the locales and dishes, and the interaction of people under stress to achieve a goal. Obviously, there is a lot of drama on the show, but I hope it inspires young people to work on super-yachts as a career and think, ‘Oh, I can do that.’”

He doesn’t think deckhand Sydney—whose seeming infatuation with her boss, first mate Gary, and now understandable anger having Gary and stewardess Alli parade their relationship in front of her—is psychologically suffering. “I’m not worried about Sydney’s mental state. I think she’s fine. She has her moments, especially if she’s been drinking. Overall, I’ve been really impressed by how she handled herself, and how she got on doing her job, working with Gary when she was no longer in a relationship with Gary. I thought she handled it very professionally. Maybe there’s some hurt there which comes up when she’s drunk. She’s a good crew member, understands sailing, and I would love to have her back if we come back.”

What about the production encouraging all the boozing? Doesn’t that count as manipulation?

“Well, they are all adults. They are legally allowed to drink,” says Shephard. “I have a strict policy that if it’s self-inflicted it doesn’t get any mercy from me. I’ve seen crazy stuff in my career, people so drunk they can barely get back to their bunks. I haven’t had that happen in season 1 or 2. If that happened, I would hope someone would say, ‘Hey, we’ve got a serious problem.’ Super-yachties drink a lot. I don’t drink much. I’ve had moments when I’ve been drunk, but luckily nothing unsafe happened.” He doesn’t think the cast drink dangerously either.

The captain is looking forward to meeting Captain Sandy Yawn and Captain Lee Rosbach—from the first Below Deck franchises—in person, and talked to them both before starting the show. He and Yawn did an Instagram event together recently. (Before the show he didn’t have an Instagram account; now he does and has over 50,000 followers.) “Before the first season, they both told me, ‘Be yourself. Don’t try and do anything different other than to be who you are. Don’t try to act for the cameras. Be yourself, and you will be fine.’ It was good advice.”

“I’m not celibate. OK, I’ll say that.”

Reality TV fame is strange for Shephard, but not unpleasant. “I’m not an attention-seeker. I feel a bit awkward about it all.” Living in Europe, Captain Glenn has only been recognized a few times. It might be different if he were in America, he says. “I’m not getting a big head about it. I’m just a dude, just a guy, who has an interesting job. I’m a traveler. Sailing is the perfect job for me, and I feel very fortunate to be able to do it. All of a sudden. I’m on television, which is really weird, but it is what it is.”

He insists TV has not made him vain. “I’m not metrosexual at all. I use a 3-in-1 shampoo for everything. I do try and use sunscreen. You will notice there is a bimini on the boat where I stand, but there is a lot of reflected light so I get a farmer’s tan. One thing I have changed is, you may have noticed I wore ankle socks in season 1. You have to wear socks, or your shoes get stinky. But after seeing how the ankle socks looked, now I have short socks.”

The captain accepts that becoming famous may be a motivation for some of the crew, but it isn’t lucrative. “I’m not getting rich because I’m in a TV show. But if a sunglasses company approached me to promote their brand, then great.”

His nascent celebrity hasn’t changed him, he thinks. “I like to think I’m the same person. It’s interesting and funny. It’s not something I wanted to do all my life, but I can see the benefits of it. I think it would be different if I was in America meeting people regularly.”

He’s handsome too; what’s it like becoming a pin-up? Shephard laughs. “I definitely don’t consider myself handsome. I think if people see someone on TV, and they think that person is attractive and nice. I think that’s great. It’s an honor to be in that situation. Before this show, I was just an average guy. It wasn’t an issue. Now, all of a sudden, I have a lot of nice people reaching out to say, ‘Hey captain, we like what you do on the show.’ A lot of people think I’m an idiot, and I just ignore those people. I don’t drink the Kool-Aid. I am who I am. If people like it, great. If people don’t, that’s fine too.”

Is he single? A pause. “Yes. That’s kind of a private part of my life I like to keep private, but I can tell you I’m not married.” Is he straight, gay, something else? “I’m straight. But I have a lot of gay friends. I have no issues about it, and I think the community is fantastic. I fully support it.” Is he happier being single than in a relationship? “I’m not celibate. OK, I’ll say that. How can I say this? Working in this industry, especially for someone my age, there are some beautiful people, but they’re half my age. I’m not chasing stewardesses. When you’re constantly moving around, it’s hard to have a relationship unless you’re with a chef or maybe a chief stewardess.

“It’s hard. I’ve been a traveler all my life. I very much believe in the idea of monogamous relationships. I’m not single because I want to play the field. I want to be with the right person. I don’t need to be in a relationship. I want to be in one, and I like to be in one. But settling down in that whole marriage/big wedding stuff is not really me.”

He has not missed being married or having children. “If not in my next life, I would definitely like to have kids after that, but I can borrow my brother and sister’s kids, my nephews and nieces, to get my kid fix.” He laughs. “I’m relieved to hand them back. Really, I love kids, I love spending time with kids, but I don’t know if I have patience for it. It’s a long commitment and kind of dictates the rest of your life. I still have a lot of travel I want to do. I get so excited when I see all the books in a Barnes & Noble travel section. I want to go to all those places. In an exotic place, I always think about the next exotic place. I would love to be a dad, but I don’t think I’m cut out for it now.”

He wonders if a child would like being “dragged” around the world—frankly, this sounds like a potentially pretty amazing parenting option if Shephard was doing the dragging, as he clearly loves traveling so much. But he worries about falling short, then worries he’s being selfish by making such a choice.

A surprising thing, and this again apparently is rooted in his humility, is that Captain Glenn doesn’t like to be called “Captain Glenn.”

His attitude is that he has a job to do and gets that the position needs to be respected as part of the job, and he doesn’t want to talk down those who hold the descriptor-name dear. But he never introduces himself as “Captain Glenn.” He doesn’t like it when the crew says, “This is my captain.” He doesn’t like to be pretentious about it. He feels he is no better than any other crew member, it’s just that his role comes with more responsibility.

“It’s fine, referring to me as ‘Captain Glenn,’” he says. “‘Can I speak with Glenn’ is fine too. But it’s a bit weird being attached to ‘Captain Glenn’ if you’re not on my boat because I’m not your captain. If fans of the show say, ‘Hey, that’s Captain Glenn,’ that’s OK because that’s what the show calls me. I am ‘Captain Glenn’ on my Facebook page. It’s fine, but normally when I’m away from the boat I don’t introduce myself as ‘Captain Glenn.’ I don’t think every captain does. It depends on the situation. For me, it’s not a big deal.”

The show films for a couple of months, the length of a typical charter season. The production team “are working even harder than we are,” says Shephard. “We don’t interact with them. They don’t want us to acknowledge them. They really are like a fly on the wall. When nothing is happening, we can talk to them but when they’re doing their jobs the fourth wall stays up.” Is there a shadow set of workers helping the crew? “No, nobody is helping JL or Sydney clean the deck in the middle of the night.” (As fans know, JL isn’t too good at this particular task anyway.)

The money shot in Sailing Yacht is when the wind gets up, and the boat actually sails at an angle to the sea which looks exhilarating, and also a little funny as inside the crew desperately try to stop glasses and plates crashing down. The captain isn’t sure he has ever worked with anyone as tall as his roommate, deckhand Jean-Luc, who infamously lacks a bunk large enough to contain him.

He was “pretty amazed” filming on the second season went ahead, filmed under strict protocols as COVID raged all around. “Having that in the background added a bit more stress, but with the right precautions we were fine.”

One mystery was the complete erasure of the season 1 cast for season 2, which features a totally new crew. Shephard says he “can’t get into details,” but says, “There is a fine line between banter and bickering. Maybe season 1 went more towards bickering. It was a little too negative.” Did he or the production think they were not hot or dramatic enough? The captain demurs. “Maybe it was a combination of all those people together. Maybe people were busy. Maybe we wanted to mix it up, and bring in new faces.”

“When I lived this crazy life my family never said, ‘Why don’t you settle down?’”

Shephard grew up in Montreal, Canada. His father worked at an airport, and he recalls his dad taking him and his brother to work on their birthdays as a treat. It’s where the travel bug first bit, he says. They would look at planes, and sit in the control tower.

The family got standby passes, and traveled a lot all over Canada and to Florida. As a boy, he wasn’t too focused on his studies, but after high school—he didn’t go to college—he took an interest, “fascinated by consciousness and free will,” in physics, quantum mechanics, and astronomy. “I was kind of a bit of a science nerd. As a teenager, I enjoyed going to the library reading up on different subjects.”

It was an idyllic childhood, says the captain. His parents were married for 67 years. His father died recently, and his mom is 90. The family went for winter holidays in the Caribbean (“The only problem with Montreal for me is that it’s too cold in winter, too brutal”), and sailed on a few boats, but the young Glenn didn’t dream of becoming a captain.

In the early '80s, Shephard’s traveling began in earnest. He left Canada and went to live in Los Angeles, which first seemed “like the center of the universe. But then I realized it wasn’t that LA that was so cool, it was being somewhere new.” He scoped a few boat shows there. In Rome, he saw a notice for crew wanted for a boat cruising in the Aeolian Islands off Sicily. “That’s when I became hooked on boating for my whole life. It was the best summer. I knew right away I wanted my own boat. I didn’t know I wanted to work on yachts right away. Just because you like golf doesn’t mean you want to become a caddy. It doesn’t work that way. I wasn’t sure if working on super-yachts would ruin boats for me.”

In Tokyo, where he managed an English school for five years, he saved money and bought his first boat with a woman he entered into a long-term relationship with. In 2000, he decided to go to Fort Lauderdale to try day work on a 40-meter motor yacht, and thought, “Yeah, this is what I want to do.” He traveled to Monaco, and saw sailing yachts like the Parsifal and it has been “big sailboats” ever since.

“When I lived this crazy life my family never said, ‘Why don’t you settle down and have a family? Why are you traveling all over the place?’” says Shephard. “They were always supportive, and visited wherever I was, like Hong Kong and Australia.”

He has traveled to 50 countries, he says, and tells tales of underground caves in Turkey, the pyramids, Istanbul, and the arts, history, and architecture of Europe. When he taught, he would tell students to imagine being in the Star Wars cantina, sitting next to an alien, who when they ask where you are from and you reply “Earth,” and they ask to know what is cool on earth, “ensure that you’re able to tell them not just about the place you’re from, but provide a greater picture of this wonderful planet.”

Having his own boat, he smiles ruefully, can feel like “standing in a cold shower tearing up $100 bills, but when it’s good it’s worth it and anybody who is a sailor will tell you the same thing. It’s like being a sea turtle, with a home on your back. They say that sailing is the most expensive way of getting somewhere for free.”

The captain reckons he has crossed the Atlantic 21 times in sailing yachts like Parsifal. The weather can be challenging, and so “you always feel a sense of achievement getting to the next place.” Even in bad storms, he has never felt “this is my last day on this planet. Boats like Parsifal are strong and pretty safe.” He laughs that sailing yacht crew who become motorboat crew are known as “going over to the dark side,” because it’s seen as the easier, more plush option compared to the romance and closer-to-the-waves nature of actual sailing. In return, motor yachts’ folks make fun of sail yachts’ folks as “blow-boaters.”

Is there anywhere he hasn’t sailed that he would like to? “I am not a sailor who has to prove things to people. I am not going to circumnavigate the world. But I’d love to go to Tahiti, Tonga, New Zealand, and the Caribbean on my own time, not working.”

Like many Below Deck fans, this reporter marvels at the superhuman patience and restraint the crew shows towards occasionally obnoxious, rich guests.

“I’ve had a couple of Russians who were not pleasant, but mostly on sailboats, the guests tend to be very pleasant people. They’re paying top dollar. It’s meant to be 5-star floating hotel service, and we have to provide that. I’ve met a lot of billionaires and famous people. I don’t envy them. I’m glad they can afford and enjoy the experience, and we just want to give them the best experience we can.”

On one boat where he was a mate, a guest tried to grope the captain’s wife, who did massages. Another time, a rich Russian guest was furious when his wife went off with their son on a tender. But really, says the captain, most guests are respectful and sailing yacht guests more so than motor yacht—they have deliberately bought the experience of sails-up yachting. It’s less formal and stiff. Some guests have taken all the crew to dinner. On one Christmas cruise, the wife of the primary handed out $1,000 on Christmas Day to each of the crew; the end tip was multiples of that.

Relationships with customers are “pretty verboten, but I did come close one time.” But as a captain, says Shephard, “you want to set an example for the crew and it’s a line you shouldn’t cross. Innocent flirting is OK, as long as you don’t overdo it and mislead someone.”

“That question is like, ‘Name your 3 favorite children.’ These guys are like family. I love them all.”

Shephard doesn’t think about aging or retirement, apart from in the context of things he still wants to do and places he still wants to see. He is about to start something called “rotation,” where he and another captain can share duties, ensuring they have regular time off every two months. He hopes there will be a third season of Sailing Yacht, and to participate in it. He doesn’t totally live on the water, also owning an apartment in the suburbs of Palma.

An official announcement about season 3 has not been made yet but presuming it goes ahead, Shephard would like to feature some season 2 cast, including first mate Gary, who he says is a “great guy.” Indeed, asking him to say who he would like to take part in season 3 merits an anguished moan.

“That question is like, ‘Name your three favorite children.’ These guys are like family. Season 1 and Season 2, I love them all.” He chats to the cast from season 1, and “loves” everyone from season 2. He names each cast member and speaks positively of each one.

Parsifal is presently moored in Genoa, Italy, and Shephard will be reunited with her when the cruising season begins again. And then, if there is a season 3 of Sailing Yacht, we will see him and her together again on screen.

Whether we will see Angry Captain Glenn again after this Monday night remains to be seen, but c’mon, seems very unlikely.

“I do lay down the law sometimes, but I try to do it as little as possible,” says Shephard, chuckling. “I try not to do it if I am having a bad day, and I try not to lose my temper in front of the crew. I don’t think you’ll see a huge change in my personality if there are future seasons of the show. I am not going to change. Maybe the network wants me to be more stern, but I can only be myself. If they like it, that’s great. I can’t start acting. I’m no good at acting. I’m great at being myself.”

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