How To Fail With Elizabeth Day - ON REALITY TV… With Dorinda Medley and Captain Sandy

Episode Date: November 10, 2025

If you know me at all, you’ll know that I am a huge advocate for reality TV. So what better reason to have a little trawl through my archives than to revisit some of my favourite interviews from reality TV stars? First, we hear from Dorinda Medley, known and adored from The Real Housewives of New York. Dorinda speaks about being approached to join Housewives shortly after losing her husband. She talks about her grief as a young widow and how the Bravo community supported her when she needed it most. Then, we turn to Captain Sandy from Below Deck Mediterranean. Sandy talks about life on board with production crews, the dynamics with her team, and - crucially - what she would put on her own preference sheet. Even if you’re not usually a reality TV fan, I hope this episode offers a glimpse into the humanity behind these shows - and how connection, vulnerability and growth can show up in the most unexpected places. Listen to Dorinda Medley’s full episode of How to Fail here: https://link.chtbl.com/Lf44HTRS Listen to Captain Sandy’s full episode of How to Fail here: swap.fm/l/CaptainSandy 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [e-mail] Learn more about your ad choices. Visit podcastchoices.com/adchoices

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That's the powerful backing of Amex. Conditions apply. be my PhD subject. Now, some people might mistakenly think it's just surface level fluff. But what great reality TV shows do is show people navigating the ups and downs of life. It makes us feel less alone, and it also entertains and provides some escapism and a break from daily routines. So this felt like a good week to listen back to some reality TV stars who have been on how to fail, given that in the next few days, I am heading to BravoCon. I know I'm so excited. And for those of you who don't know, BravoCon is an annual fan convention hosted by the TV network Bravo,

celebrating all of its reality shows and the castmates on them. And I am so excited. I can't even put it into words. First up, you're going to hear from Derinda Medley. You'll know her from the Real Housewives of New York. And we recorded this episode in New York earlier this year. Derinda talks about how she was recruited to appear on Housewives and the fact that she had just lost her husband at the time and how the reality TV community picked her up.

Secondly, we hear from a below-deck legend Captain Sandy. Sandy talks about what it's like with production staff on board the yacht, her favourite members of the team, her favourite members of the crew, and most crucially, what would be on her preference sheet. Even if you're not currently a fan of any reality TV, I mean, who even are you? I think you'll find this a fascinating peek behind the curtain of some of the world. biggest shows. And now, here's Derinda. So, you know, Ramona was always was a very dear friend, Luann, and all of them. I always stayed

in contact with them. And, you know, they had asked me previously to be on, and I would always be in the background and scenes. I don't know if you look at that. But yeah, don't you worry. So Ramona said to me one day, enough. Like, you need to do something now. And, you know, it would be great. You'd be great at house rights. You mean, you don't with everybody. You'd have been on and you know us. And just do houseways for a year and do something. And I thought, you know what? She said, you can be a friend. You can be a friend. And if you don't like it, you can leave. It's four months, four months of filming, right? And I thought, so I think I kind of did, you know, it's so funny because now it's much more of a bigger process. I had lunch

with Ramona and Lisa Shannon or wasn't even Lisa Shannon, one of the people. And they were like, You can be on. It was that simple. I don't remember thinking of it as auditioning. I'm thinking of, I'm going to do this. And your life changed and so did ours as viewers. And we're going to come back to Housewives as it pertains to one of your failures.

But your first failure is playing Superwoman. And as you put it to me, I played Superwoman so long, I forgot how to be vulnerable and allow outside people to help me. So tell me when you first realize this about yourself. after Richard died. And that's why I could do housewives. It all feeds because I knew that I came to New York City, you know,

without a lot of money, a lot of, not a lot of opportunity. And I was always, I never, I was very careful not to show too many flaws and keep it, you know, and do everything right and follow the rules and never be unhappy, you know, and mourn personally. And, you know, it's not that I was so. superficial. It's just that I wanted to appear strong. I can do everything. I even remember with Ralph, you know, my first husband, who, by the way, I still love today. And he's a great guy and he's very close to Hannah. And I attribute all of Hannah's, you know, a lot of, not all of Hannah's

success, because Hannah owns her own success, but her success, a lot of her success in her life, not just from me, but from both of us. But, you know, I even remember when we moved to London for the first time, I didn't know a soul. I mean, my best friends were at Peter Jones. I'd go visit people of Peter Jones. at the candled place. There was that florio brand, I think it was called. Yes. Yeah, it's still that.

I actually had lunch with them at Luriel one day because I just was looking for a friend, right? And, you know, I just studied how the women dressed and studied how they set tables and took a course at the lease school and really made sure if Ralph had to go to work at 5.50 in the morning, I was up waiting for him, made sure I knew when he came home, made sure I laid out his clothes,

So I took on this investment banker's wife, never looking scared or unknowledgeable. Like, I watched the way lady so-and-so did stuff. I watched the way people, you know, dressed their children when they were in the park. So I became a study of that. And I just always was afraid that I think I could do it. No, there was no, no, no. Absolutely. Are you tired?

No. Would you throw this? Absolutely. You know, everything was yes, yes. And, you know, the truth of the matter is when I look back at that now, I was afraid. I was young. I had no friends.

There was no phones. I couldn't barely contact my family, you know, because there was no cell phones, no FaceTime. There were a lot of times when Rich Ralph was, thankfully, working 12, 14 hours a day and gone three days a week. And I had a brand new baby that I wanted my mother. Yes. But I couldn't do that. So I didn't reach out to a lot of people and say, and when my mother would call and be like, how are you doing? I'm like, I'm fine.

It's great. It's wonderful. just moved into a place, and I'm so excited we're going to the Venice. Like, it was all that. Yeah. And now I feel like I'm much more, I'm much more saying, I don't want, that frightens me. Like, and I need your help. Can I talk to you? I even texted someone the other day. And after I texted, I thought, oh, should I put that in text? I said, listen, can I, if you get

time, can you call me back? I'm feeling sad today. And after I sent it, I kind of, has, I sent a flaw. Oh, well done for sending the text, first of all. Yeah. And thank you so much for talking about this, because it's so relatable. And this is the thing. We connect as humans through our vulnerability. That's it.

It makes you more lovable. It makes me feel closer to you when you do me the honor of sharing something like that. And that's what housewife all right me. So when you go full circle, all of a sudden, because I didn't really give a shit anymore, you know, and I was still grieving, For me, I wasn't great at therapy. I mean, I went to it like three times. I was like, I don't want to talk about him. Like, I wasn't great at it.

And I found myself getting very insular and angry. A lot of people mourned by crying a lot and stuff, I was angry. I was lost. I felt like I got cheated. So it was a great way for me to work through my really housewives. And I always thank Andy Cohen for this and the Bravo world. It was really a place where I was able to. to go through a lot of my morning. I met Carol, Rosuel, who we had that incredible bonding scene

with in London. I remember. It opened up a bigger world. And I just was able to be vulnerable and not care. I'm going to ask you some very niche questions now, because this is the only opportunity I'll get. Do the crew that are being filmed always sleep on the boat? Do they ever have a night off the boat during charge of season? No, they sleep on the boat every night. And you sleep on the boat every night. Yes. Okay. We wake up together and we go to, not all together, but you know what I mean.

It's just like breakfast, lunch and dinner. You're with each other 24-7. And how does it work with the production crew? Because it's a very confined area below deck. It must not. You've got all these extra people that we never see as viewers who are filming the whole thing. That's right. When do they sleep?

They sleep off the boat. Okay. So they have another boat that transport them to and from the hotel. but at the same time the combined spaces right so the stairwells are very narrow like they're running up those stairs with those cameras and you'll see the the people carrying the mic box whenever the camera comes around or we're walking and you start to feel bad because they have to duck really fast or they run out of the camera shot and I go oh my gosh why didn't I use the other door now I'm like messing with their their movement do you have to consult with the production when you want to fire someone I do, but I don't have to, but of course they got to line other people up because we have to require a certain amount of people on board to be able to leave the dock. It's called a safe manning document. So the insurance companies require that and the flag state requires that. I can't just drive a boat off the dock without a certain amount of crew with the certifications.

Okay. I want to ask about some specific incidents. Namely, I want to ask about the chef Mila and those nachos. Now, she licked a steak too. Did you see that? Did she want to say? She licked the steak. I did not see that. She licked the steak.

Yes. And when it was in the microwave, that she microwaves. And then she smelled it and licked it. Was she actually a chef? Was she on her CV? It said she was a chef. I believe her. I believe everyone.

Yeah. Until they show me otherwise. And then I'm like, why did I believe them? Who for you has been the best chief stew you've ever were? with on the TV show? The best? They all bring different elements, right? I wouldn't say the best.

Natasha was very polarizing, watching it with Chef Dave, but she was fine dining. Yes. She was really excellent. Like, I really admired her ability to serve and the kind of service that I would want as a super yacht captain. They're all great. But they all bring different elements. So I don't really have one.

I thought you did a great job of managing Frasier in the last season. And you ended up, it felt like the two of you with such mutual respect. Yes, you know, when I come as a captain, I come with years of experience with former crew. Some of the best crew I had a chief stewardess who served the queen of England. Like, she's the finest, like apart from the TV show, she was Irish, Ifa, and she was my chief stew. And I actually had a client complain about her that she was too formal. I go, that's a great complaint. I mean, it's okay.

So Fraser, I see that he didn't have a lot of experience. It was really about that. And when you don't know how to manage people, that's really a disservice to the client and to yourself. To learn management skills, you have to remain teachable. to think that you know everything about everything is really ego. Your failure, right? So sometimes you just have to let them know, no, that's not how you do it. Maybe you're not here to make friends.

You're here to do a job. I want to go back to your life before you got into the maritime industry in a minute. But just finally on the below deck questions, have you ever imagined? So again, for anyone who hasn't watched it, the clients come and the primary will give a preference sheet and say their likes and dislikes and that they want an all-white-dressed theme party, an 80s disco, and they can't eat gluten. What would be on your preference sheet? Oh, my gosh. I would say get the grill up.

Okay. Everything on the grill. Yeah. You know, honestly, I love grilled food. And I would, all the toys in the water. The slide. I'm desperate to try that slide. I know that the deck who always hate having to put it out.

Yeah. So I would be in the water the whole time. and then want to come out and eat grilled food. Okay. Grilled fish, grilled lobster. Like, I'm not a lobster. So grilled fish, grilled burgers, grilled steak. Like, yes.

Everything on the grill. Please do follow how to fail to get new episodes as they land. On Apple Podcast, Spotify, Amazon Music, or wherever you get your podcasts, please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening. Thank you.

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