The Underbelly of Luxury Travel Planning w/ Olivia Ferney

0:00Haley: Okay, we all love to romanticize being your own boss, but even when you have a team, you still end up being the bookkeeper, the marketing department, and the person rearranging appointments at 11 p.m. And that work isn't just annoying, it is expensive, and it's especially taxing for businesses that run on appointments. So if you own a business that takes bookings, this one's for you. Gloss Genius is a system that runs the operations for you behind the scenes. Scheduling, payments, admin, handled automatically. Payment processing is a flat rate with zero hidden fees. And check out Rebook's clients on the spot.

0:37Haley: Clients can book in seconds too, so there's no login or separate app necessary, so you actually get more appointments. 125 ,000 businesses already trust Gloss Genius to earn them more and save them time. Want to try it out for yourself? Go to glossgenius.com and use code financial for 50 % off your first two months of a premium plan. The other day I was going through my desk and I found a journal right from when I graduated and it had pen and paper how much I spent each day. At this time, I think I was making around$40 ,000 and access cash flow was pretty tight. So I had to watch every penny. I think about how far we've come with technology and advancements to help us with this stuff.

1:20Haley: We don't need a journal with pen and paper anymore. The answers are out there. And Monarch is one of those answers. Monarch is literally, it's like having a financial advisor in your pocket. So you can use AI to help see what you're spending. Monarch will help you have full visibility in your accounts. It will help you see your trends. It will help you set goals, map out big purchases. See if you're actually on track to where you wanted to be. You can ask a Monarch's AI assistant anything about your finances. Like, hey, how much did I spend on travel last summer? Can I afford this vacation without touching my savings?

1:56Haley: You can spot things you wouldn't think about before. Like, oh, hey, has my spending gone up or just inflation? I was using pen and paper. Now you can use tools like a full financial advisor in your pocket. And that's called Monarch. So what you want to do is you want to go to monarch.com, use code TRADING. the first year of Monarch Core is half off at just 50 bucks. That's 50 % off your first year. Just go to monarch.com with co-trading. The experience market is booming. I mean, Super Bowl is our Super Bowl. If you want to pay to put a stake on a private jet, like we can do it. It's a huge waste of money, in my opinion, but no problem.

2:40We'll get it done. I'll be out and these guys will come up to me and be like, hey, I want to be a client. I'm like, you probably can't afford it. Love you. I love telling them that you can't afford it. It's fantastic. And then they, I've had a couple of guys just pull out their bank account and be like, I'm good. Wait, stop. What's the number? Great.

2:54Haley: Like always 50 mil plus. This is Financial Tea. What's up, Sippers? Welcome back to Financial Tea. This is a podcast where I teach you how to build wealth with a side of market drama, money scandals, and of course, financial pop culture. And before we get into anything today, because we have a really good episode, I just want to remind you to rate, review, subscribe. It helps the show so much. And we'd love to hear from you. I read all your comments. So leave me something. Today, we have something very exciting in the chair who, honestly, I can't believe that she's even here IRL because she's usually pimping all over the world.

3:32Haley: It's crazy that you are in Dumbo right now. That's fair. We have got Olivia Fernie in the house. You've definitely seen her content. She is a luxury travel agent, content creator. she goes by travel with livy and she just every day going viral for these videos where she's talking to ultra wealthy clients about you know their travel demands she's seen it all so today I wanted to have her on the show just to learn more about what she does get the tea on the crazy things that you've seen get your tips because I feel like you have really good tips about travel and maybe you have some for us people traveling on a budget you're like no yeah you could also We'll see.

4:14Haley: But Olivia, welcome to Financial Tea. Thank you for having me. I'm so excited to be here. I'm so excited to have you. We are both Time 100 creators. My girl. My girl. So we're going to be reunited tonight as well. Looking fabulous. Before we jump in, we always do some rapid fire. So ready. What were your best and worst purchases of the week so far? And how much did they each cost? Oh my goodness. Yes. Well, I mean, as a group, we spent$266 ,000 on bottle service with a client like 72 hours ago, setting a Guinness World Record for the largest bottle service presentation in Vegas. So that was probably like the company largest spend, although it wasn't even through the company.

4:51It was just something we were a part of. Personally, I mean, I flew out my whole team to come see that just because I felt like they had to be there. It was such a monumental moment for our entire team. So how big is your team? 10 of us. Wow. Yeah. Full time. Yeah. Yeah. So we brought everybody in. Everybody came to watch. And we had also just people outside of the team as well. We had like management, just people like friends and family. Everybody was there. We had a couple of clients. So hotel rooms, dinners, flights. That was a little bit expensive. But you needed people there to drink all the champagne.

5:23Of course.

5:24Haley: Yes. Did you finish all of it? There were no full bottles left. Whoa. So it was all gone. How was the hangover? Horrific. But we're fine. Worst purchase of the week, honestly, New York City Ubers. I know. Suck. You just got here. Like, you were like, why does it take an hour to get everywhere? Why does it take an hour to get everywhere? I feel like your next endeavor is going to be like a helicopter. Helicopter drop lift everywhere. Yeah. I will pay$1 ,000 to go anywhere. That's fine. Just drop me where I need to go. I can't sit in traffic. Yes. The traffic is horrible. It's insane. You learn how to make the car like your office, though.

5:57Haley: What is the most expensive trip you've ever planned? And how did that cost break down? I cannot go over the most expensive ones I've had. I can tell you they're in the many, many millions. I am NDA'd like crazy for those trips, so I can't break them down per se. But last week, for example, we had a million dollar yacht charter, and that was just the charter. And then to get there, that particular client owns his own plane, so that cost was not included. But if you were to charter to there, that would be$200 ,000 to$300 ,000 minimum up to a million plus, depending on what plane you're getting. And then, of course, dinners every night south of France, you're looking at probably$5 ,000 to$15 ,000 minimum.

6:33And then another$40 ,000 to$75 ,000,$100 ,000 plus for bottle service usually every night because they're going out as well. So very easily that becomes like a 1.5++ trip. That's for how many people?

6:44Haley: That was, I think, eight of them. I just am seeing so many – like celebrities are obsessed with going on yachts, right? Like I just saw Jennifer Aniston is on a yacht in Mallorca, you know, Selena Gomez is on a yacht. They're all on freaking yacht charters. And so, but I was looking up the economics of it because like my financial brain was cooking and I was like, what's going on? And it is like 500K to a million dollars a week, right? It's a fortune. Yeah. It is a fortune. Like that was a beautiful boat, but some of the big like Jeff Bezos style boats, you're looking at millions of dollars before like APA and all these other fees.

7:16So like your flat rate for a boat, you also have to pay about a 30 % charge for gas, for food, for provisions, like all that stuff. And then the tip is also huge, right? A huge tip. I mean, you can be an a-hole and not tip, but you know, you should be a good guy in that industry because it'll get around really quickly.

7:33Haley: So you have to tip really well. And we've all seen below deck. That's a big part of it. So Olivia, for my listeners who aren't familiar with your content, can you just explain what it is that you do? Because you're a content creator, but you have a business. Yeah. And like talk us through the whole Olivia empire. So many moving pieces nowadays. Yeah. I mean, it really started. So we can dive into this a little bit more as we go through. But when I met Troy Arnold, who's now my amazing fiance, he had this spectacular business. We met at an event. I hate talking about this. Called Model Volleyball.

8:04You were a model? I was not. Troy likes to say he was. He also was not. We were, it's like models play volleyball on the beach and you pay for bottle service around to watch them play bad volleyball for like 19 hours straight and you get wasted. So Miami. But it was really fun at the time. I was drunk. Troy came up to me and then we slowly started getting to know each other. But that was like the original meet cute, I guess. Okay, cute. But when he told me about his business, I was like, I just can't help but get involved in everybody's business. Apparently, I have a background in digital marketing.

8:36So he had no marketing whatsoever on any front. I felt like it was being done wrong a lot on social media. So I started to experiment a little bit. And of course we hit the ground running within a month. We had like 400 ,000 followers within eight months. We had a million plus and our whole lives have changed. Now, as all of that was happening, I was getting really, really just like aware of what was going on in the business. I was becoming a salesperson for the company. I was becoming a marketing person for the company. I was becoming a travel agent all at the same time and educating like crazy and learning what it's like to work with this level of clientele.

9:09And then while the social media was blowing up, of course, our client base started exploding. And then we had to expand really, really quickly.

9:15Haley: The thing I think is really interesting about the ultra wealthy is that, you know, as dupe culture has become so prevalent, like we, you can, you don't need diamonds, you can get a lab diamond or you can get any bag from China or, you know what I mean? Like what they, the new currency is experiences because that's something that cannot be replicated, but more with your clients who are legitimately wealthy like if you've seen that difference for them because there is like a peacocking to that echelon a person and so instead of being like hey look at my new watch that's 750 000 it's more like i just went to this part of africa that no one's been in except for like you know the people who you know have lived there for thousands of years and like we were airdropped in by Olivia Fernie and like, you know, we had caviar with like whatever, you know, I don't know.

10:09Haley: Yeah. I would say we've seen a huge influx over the last like year and a half, two years. It's always been a thing, but now that COVID is completely wiped out, obviously there was a little bit of a dip there. The experience market is kabooming. I saw that. So we really hone in. I mean, Superbowl is our Superbowl, like the private suites, the hotel rooms, we buy millions of dollars of inventory just to have access for our clients that they can get the best suite when they're a couple of weeks out and they find out their team is going, or when all the suites are sold out at the arena and then we can get them the suite.

10:38So yeah, it's, it's definitely, uh, I mean, F1s, tennis events, golf, anything that people can actually go to has become very high in demand.

10:47Haley: Cause you go to these dinner parties or whatever, and you're like, that's what you want to talk about. You know, it's, that's the flex. It's a social currency for sure. This is the financial tea. So we always ask for the numbers. So how does it break down? Like what is your salary? What does your commission look like? You know, how does that work? So we actually don't take traditional travel agent commissions. Those usually look like 10 % across the board. Anybody that's going to become a travel agent, whether you're, you know, low tier or top tier. And for us, we charge a hundred thousand dollars for the year flat.

11:19And that's just to get access to our team. Oh, smart. So it's a subscription service. Yes. So it's a yearly subscription. We'll call it a membership.

11:26Haley: And do you also do reservations? Cause like I have a And there's a million, our friend in New York who, and there's obviously New York, it's so hard to get reservations. And she's like, Oh, want to go to corner store tomorrow? Want to go to like the 86? Like, and she pays for one of these and it's just like, they got you in wherever that you can do that too. Yeah. Okay. I need your number. Do you do it for friends? Only, only special friends. Of course. Always text me. Um, so yeah, we, we pay a hundred, it's a hundred thousand dollars for the year is the model. And then usually we have a minimum spend of like 1.5 million for the year.

11:57Whoa. None of our clients ever come close to that. usually it's way above. We're looking at four to five mil a year minimum, especially for bigger families. I mean, as I just said, we had a yacht charter that was a million dollars last week. So that's one trip if you just take three or four of those throughout the year. And then our service actually becomes very cheap for those clients. And we're also saving them a ton of money. When it comes to jets, that is the biggest waste of money. I see a lot of people, a lot of like our clients will spend with other people and that's why they come over to us, if that makes

12:26Haley: any sense and even for the ultra rich it's like you're still looking for value yeah you know what i mean of course yeah yeah everybody should i think you'd be stupid just to be throwing out money like 100 and why what is isn't there some insane statistic about people that win the lottery it's like 70 of them blow it within the 100 yeah because you have to be smart to keep your money no matter how much you have and that's what i always say when people i always give advice when i say if you're going to win the lottery keep your mouth shut got a good lawyer don't tell anyone claim it under an anonymous name it really should be like legally um you should have to get a financial advisor yeah you should and a lawyer and a lawyer yeah you need and don't tell anyone because it's also like for these clients like if i'm jeff bezos and i'm negotiating something i'm automatically gonna charge jeff bezos like if he comes to my lemonade stand i'm like oh the lemonade that's 40 dollars yes 40 more like 400 like sorry inflation is crazy these days jeff but It's like, you know, if Olivia comes to me and says it's a client, he wants lemonade.

13:23Okay. $4, you know.

13:25Haley: So it's good. So you own the business with your husband or with your fiance. And so how many clients do you, like how big is the business, I guess, instead of, because you're all going to tell me the salary. So how big is the business? Yeah. So right now we always keep our Concierge Plus group under 50. So even if we, when we fill up, we will take people away or not take them away. We'll wait and see if they want to. So far, we just started the Concierge Plus membership eight months ago, I think, eight or nine months ago. So that's the 100K. Yes, that's the 100K. And we're just 5 mil right there.

13:54Yeah, we're keeping it really, really tight for now. I mean, we'll see over the next couple of years, but we are quality over quantity right now. I do not want a bazillion clients. Not everybody is the right client. We say no to people all the time. And it's kind of nice having a wait list of people.

14:07Haley: Yeah, that is a cheat. It's good, yeah. So that's one revenue. Where are the other revenue streams for you? So we do also do corporate stuff outside. um so we are helping like large corporations with large hotel blocks um some of those are huge bookings so we try not to say no to those we do have a separate team that handles all that stuff obviously there is only so many hours of the day so myself and like our higher level team and troy are dealing with our concierge plus members and then we have another team that helps with you know the big buyouts are doing massive activations yeah yeah yeah which are really fun and good for content as well yeah and then of course there's the influencing side which pays very well.

14:41I know.

14:42Haley: People don't realize. I know. We could really make a good buck around here. Yeah. So what has that been looking at? Like how are, how do you monetize your content? How much have you been making as an influencer? So, I mean, all together looks like I'm going to make a million plus this year, which is great. She's a seven figure lady, which is very exciting. Okay, girl. Yeah. Coming from, but you have to put a lot into, cause I know also you're now investing a lot more in your look too. Yeah. Which I love. I want to talk, well, talk to us more about the money, but then I want to talk about the look stuff.

15:09Yeah. I mean, the money stuff is confusing. I am a violent saver, I will say. So I don't spend a dime on myself. Did you grow up with like, like what was your money relationship growing up? Two parent teachers who told me to be terrified of losing everything I had. Exactly. So it's all in there from like when you're seven. Correct. Yeah. And it is very obvious. I'm spending money on myself is like the most embarrassing thing to my core. I struggle with it a lot, which is great that I'm an influencer now because everything's free. Yeah. So it can make sense. I invest every penny I have, either back into the business or into my, I just have a financial advisor that kind of handles everything else for me.

15:44Haley: When you first started your content, you were really like workout clothes, just like chill, whatever. And now it's like you are a glamorous model diva. Thank you. You know, like you look really, I mean, you've always looked amazing, but it's like, you're definitely, I mean, you see it with every influencer that it's like - Slow. Yeah, I know. The glow up does happen, but it's like the glow up costs money. So how much are you spending on like becoming Travel with Livy? It really, it's crazy to say, but like it, I haven't really spent any money on it. I, Oh, you're just getting sent clothes and stuff.

16:14Yeah. It's a lot of that. It's just a lot of like the right brands that I've always been wearing. And honestly, I haven't been showing a lot of that either. I feel like I have had great business style most of my life. I've always dressed very corporate. So that side of me, I just wasn't really filming. So I'm starting to show that a little bit more, but the day-to-day fashion side, like I do have a stylist now, you know, we just pay by every meeting I would say, but a lot of those brands are just like and when you pay the stylist they have connections which is awesome she's a beast yeah yeah her name is Danielle she's from the UK she is like I don't even know how I found her but she is God's gift to earth like she shows up well she sends people because she's in the UK obviously but like we had boxes and boxes and boxes of stuff just brought in yesterday like filled up the whole room oh my god yeah she gets it like she wants business batty and she's like she'll tell me to you no no no you need to elevate this because of this and this is the comment I read so let's change this get out of the workout clothes girl like it's time

17:11Haley: to it's image shaping it's like it was a diet with law roach where it's like he's not her stylist he's like her like image like sculpt consultant it's like PR and stylist and dusty all in one I know it's interesting that your clients find you on social media though I mean it makes so much sense but it's also like then you sort of know when you sign up with you that okay if I I have this crazy call with her or something. It might end up in a video. So what is the permission structure like? Like obviously discretion is a huge part of working with ultra wealthy, but you're blasting it a little. How do you get away with that?

17:44Haley: You know what? It's something that I still would like to know the answer to, to be honest. It's been so interesting. A lot of people are like, why are your clients not offended? Who's looking at this? Like you're making fun of me. But a lot of people that see the content either relate to it. They're like, she can pull this off and I struggle with this issue and no shame on them. Like these people are paying millions of dollars to travel. I would be asking for a lobster from a different ocean if I didn't like one who was in that ocean. Like I totally get it. So just trying to move without any judgment there.

18:11But when it comes to talking to people about the calls, you know, right away, to be honest, when I get on a phone call, first off, depending on what industry they're in, I'm likely not going to ask if it's somebody that's just going to NDA me. And some of these phone calls, like I know from the alias, they're going to give me an NDA before I even get on the initial call to potentially sign them up for Concierge Plus. Those people will never be on calls. Their vacations will never be spoken about. I have other clients who own businesses that are like, hey, would love to maybe advertise with you if we could do a call about this.

18:43Or they find their situation really funny and they love the content. So like change the name, you're good. Or live, oh my God, you'll never believe what happened today. You have to do a call about this. So I think there's like a really big split of of clients and like we're just able to respect it and it's just knowing the relationship and

18:58Haley: and working with it so you mentioned the lobster from a different ocean which I'll let you explain that but I obviously want to know the craziest client request because this was when you had yeah a client who asked for lobster from a different ocean yeah I would say I mean the the one that really got me because I felt like a bit of a rude person for judging this was the Lyme situation. I don't know if you ever saw that one. So we had a woman that was, of course, food in general. We have tons of food requests. We have so many people with preferences, allergies, things that they're just really particular about.

19:31I personally am allergic to gluten and dairy and it's very frustrating when I don't have options. So I hear the frustration and also people are nightmarish when they're hangry. So add those two things together. So I deal with a lot of food related stuff. We had a woman that had, she was allergic to Lyme's that were from that particular region. And I brought off the phone and I made fun of her like fully. And I've talked about it on podcasts. I'm like, that was crazy. That was insane. That was a preference. That was not an allergy. A doctor picked it up and blasted me online and was like, he wasn't mean about it, but he's like, you're wrong.

20:05This is fully an allergy. This is very possible. When something like that happens, we just have, I mean, we have amazing people at the hotels that can help us handle those situations. So that one happened rather late at night. I had to go to bed, but we were able to literally source another lime. It's also produce. You might be on an island, but they have produce from other parts of the world always ready to go. So that was quite easy to actually solve. We just had to kind of figure out how we were going to do it and then just bring in the limes for her and keep them there for the week. So the craziest requests are really the food-related ones.

20:34Haley: I would say food-related ones. Yeah. So you get lobster from a different ocean, limes from a different region, those sort of ones. those kinds of things for sure. And it's just last minute too. And like, we've had people that want certain types of beef flown in and like stuff can happen to food when you're moving it. Right. So if you show up and your steak's gone bad and it flew in from like six hours away, you got to right away and it's expensive, but it's possible if you want to pay to put a steak on a private jet, like we can do it. It's a huge waste of money, in my opinion, but no problem.

21:00Haley: We'll get it done. If you got finances to do it, it's okay. So you're saying the standard budget rate for the trips you plan, it sounds like it's like a million plus per trip. I mean, it's all over the place. We have tons of people that are taking like 50 to 150 a year, sorry, 50 to 150 per trip. Really depends. If it's like an individual business guy that's just coming to New York for two days, you're going to be on the lower end. And some of those clients don't always want the penthouse, which always gets it down there as well. But the family trips usually are insane. So there is quite a bit of a range, I would say, when it comes to individual trips.

22:01Haley: When you're building a company, you learn that trust is what closes deals. You may have the best product, but buyers won't sign without proof that your product is secure, especially if it has AI. Vanta gets you compliant fast with SOC 2, ISO 27001, and more, and keeps you secure with continuous monitoring. Hyperbound, a YC-backed startup, used Vanta to unlock the Fortune 100 in under a year. Snowfire got audit ready in a month and closed a multi-million dollar deal. Trust matters. Get started at Vanta.com. so you talk a lot about the kids of the ultra rich and on mrs dow jones i talk a lot about generational wealth and it's sort of funny because people are obsessed with growing generational wealth for their kids like they want to have rich kids but as a culture we hate nepo babies and we hate rich kids isn't that funny it's like this dichotomy yeah so i just wonder sort of like what your experience has been with these children, what your feelings are about generational wealth.

23:02Haley: You know, you could pass on money, but you can't pass on financial literacy. That's fair. And, you know, by the second generation, 80 % of generational wealth is gone, 90%. And when you hear your calls, you sort of get why, because these kids seem like they're just blowing through it. They blow through it. Yeah. It's funny to actually look at it globally because different areas don't struggle with that the way that North America does. Like you look at the families in Dubai and they're on seven, eight, nine generations and it's just growing and growing. But yet somehow they have so much principle that I feel like it's, it's just different.

23:39Haley: Yeah. It's just a different level. Like when you got that oil money, it's like, if they're going to spend a million dollars on whatever. You actually can't even run through that. Yeah. They're like, try, try. Yeah. Maybe sports gambling or something. Yeah. And they're just much more, I mean, there's just so much more regimented things going on over there. So it just doesn't happen. But here, yeah, of course, we see so many third generation. It's always gone. Working with these kids. I mean, first off, something to note for us, we are really trying to tap into this because there are trillions of dollars that are going to go into these younger kids within the next couple of years.

24:12You know, we've got a lot of - The great wealth transfer.

24:14Haley: The great wealth transfer. Yeah. It is coming and these kids love our content. So, you know, it is nice that we're targeting them and hopefully they want to come work with us as they come into billions and billions of dollars over the next, you know, several years. So working with them is great. I am a part-time family therapist for a lot of these people. They love to get in trouble. It does seem like that. Yeah. So what's like the craziest request that you've heard from kids? Just like they just get in trouble. I've had to deal with people getting the cops called on them who've been stuck in jail.

24:43For what? Just like, I can't, I can't talk about it, but just like, they just do, they do stupid teenage stuff. Yeah. Just add a couple hundred thousand dollars onto the stupid thing that they did. Yeah. And they, they get in trouble. They go out to the night clubs, they get drunk, they're underage sometimes. Like they're just, they're just running around like the city's theirs because it is. Yeah. No one says no to them. So they're not used to hearing that. And then they do stupid stuff and they get in trouble. And that's, so I'm just dealing with stuff like that a lot of the times. Yeah. And I just overall, it is tough sometimes to try and tell them no.

25:16They don't hear it. A lot of these parents are scared of their kids. Yeah.

25:19Haley: That's what I've noticed is that they want you to be the bad cop. Yeah. Yeah. Which is interesting. But also, I mean, it's what we get paid to do. Do you think it's like this outsourcing of childcare? Like there's this romanticization of, oh, I'm going to have a kid and have a nanny who raises them or whatever. And then it's like, you sort of like fill in that role a little bit and it's you, you know, like they're sort of pushing it off onto you. It's different per family. Um, I know a lot of families we work with are so tight with their kids and just like, they value that core group more than anything in the whole world.

25:48And then I have other families that are like, you know, their kids are just kind of off on their own and they don't have that relationship that's as strong. So it's totally, it's yeah, it's totally different per family. Um, but yeah, some of them do have a lot of nannies and some of the kids think of their nannies as like their, their parents or their second parents.

26:05Haley: They see them more. what are the craziest requests that you've gotten from the kids and where you're like where you're like like are they like will you get me coke oh my god oh my god so we we do a lot of people ask you to do like illegal stuff yeah of course of course oh my gosh I love that you asked that question we never talk about this so often I cut my surfaces off at like 12 o 'clock at night I was like I say nothing good happens after 12 o 'clock usually it's I know it's nothing good happens after two but anybody in any major city when the kids are out when the parents are out if I I have new clients who are like, boys trips, girls trips.

26:37I'm going to get the text in the morning. Usually I'm sleeping. And then I'll get a, hey, by the way, do you know anybody? And then at 7 a.m., they're like, hey, I'm so sorry about last night. We don't do anything like that. We usually just ignore those texts. I would like to keep my hands clean for as long as we can. Yeah, I mean, people like to have fun. And no shame in that. Go nuts. There's a lot of crazy things happening in these worlds. But we are not the people to help you with that. Yeah. So they got to find it on their own.

27:06Haley: What about like sex workers or like bringing girls, not even sex workers, like maybe just like getting like yacht girls. Those are, yeah, those are like a promoter. Oh, a promoter. So you have a person for it. So I'm like, Liv, I'm going on a yacht this weekend. I want to have like - There's a million people that do that. Yeah. But you could connect me if I needed like a lot of hot guys on a yacht. Yeah. Yeah. Yeah. Cool. We'd put you in contact with somebody that might be able to help you. Awesome. Because I definitely feel like that's something that I want to do. Just for me, you know, like - Yeah.

27:31There's people that do that. I'm, you know, we try and focus in what we're very good at and not handle all the messy stuff. But there's tons of people in New York, Vegas, all the major cities have like nightlife guys and promoters that can fill the tables with hot guys. And, you know, I make sure you're having a

27:44Haley: good time. I love it. What is the most personal thing anyone has let you in on or like asked them to do? We are, I really sometimes am a full blown therapist. There's been a lot of like, just like personal stuff. You know, you might call me and be like, Like a divorce? There's, yeah. Surrogacy? There's a, you know, I'm worried that someone's going to hide money. We're going through a divorce. I'm worried that they're, you know, I'm making the wrong decisions. Can you help set me up with somebody? I'm thinking of losing my husband. You're sort of a financial advisor too. Yes and no. I have phenomenal people that I work with on the financial side that we kind of just help facilitate.

28:19I honestly am a facilitator of relationships. Yeah, that's, you're like a broker. I kind of am. Yeah. But a safe broker.

28:25Haley: Safe broker. Yeah. So you're not going to be like, I'm the broker and you're going to have to spend all these other fees because I'm giving you to all these people who are going to try and like get a buck off you. No, people trust me. And that's huge for me is there's a million people a day trying to become that person that I go to. I am so protective of my clients. Like even we had a reporter the other day that was like, I need all this information on your client. I was like, sorry, I'm not going to risk my business for your article. Well, what I think is amazing about your business is that, yes, you're going to make like a million dollars, it sounds like, off of influencing this year, which that's correct, right?

28:58Haley: Yeah. But that doesn't really hold a candle to how much you're making off of the actual business. And so when you have money, it gives you the power to say no. You know, like I was thinking about this with LeBron James that he just took this like four million or whatever. Like he took a 93 % pay. He's coming to the Philly. I'm so excited. But he took this huge pay cut and it's like, oh, how can you do that? And it's because like he has fuck you money. He can say. It doesn't matter. And he can go for something bigger. And so it's the same thing for you. You don't have to pimp yourself out for these like small fry things because you have the financial security of this like bigger business that that you realize that that's the bigger picture.

29:42Now I have been there. Like when I started with Troy, I remember going and sitting at almost like a hooker. You go to those big, nice, fancy restaurants and you're just sitting there by yourself until you meet somebody that has a lot of money. But then of course you got to switch it right into business and be like, Hey, by the way, who plans your travels? All the things. So at the beginning, how did you get those clients? It was a nightmare. It was an absolute nightmare. I literally was, I was going to the one hotel. I was going to Faena. I was going to like addition and satay everywhere on, on Miami beach and just waiting for clientele.

30:15And of course it didn't work. I was taking any trip I could get. I was booking like a honeymoon for$20 ,000 where I made negative a thousand and it was so much work that my hair was falling out. It was horrible. It's not fun. But then of course I was hustling so hard in that avenue that while the social media was kind of blowing up, I wasn't even paying attention. And then all of a sudden we looked and we're like, oh my God, the New York Times is calling us. Oh my God, Wall Street Journal is calling us. Oh my gosh, somebody wants to pay us$100 ,000 to do an ad. It was just boom, boom, boom, boom, boom.

30:44And then next thing you know, I'm getting a DM from ex-billionaire and I'm like, oh no, what did we do?

30:49Haley: So you sort of figured out how to get that, the marketing pipeline. Yeah. And that was, and I still think even if like the social media stuff didn't blow up, I was starting to see returns. You know, like sales, usually it's going to take you a year, especially in luxury sales to see even one return. You got to put in time with those relationships. You got to do a lot of dinners, a lot of chalising. And they have to trust you, especially when it's that caliber of clientele. Well, that's, I mean, so if I'm a billionaire and I'm at the Faena and you come up to me and you're like, hey, can I plan your trip?

31:19Haley: I wouldn't really trust you. But if I'm on social media and I see your page and it's clear that you're working with all these other rich clients and I want a piece of that life. Now it's completely different. Yeah. Now it's a different conversation. Now we have people, I'll be out and these guys will come up to me and be like, hey, I want to be a client. I'm like, you probably can't afford it. Love you. I love telling them that you can't afford it. It's fantastic. And then they, I've had a couple of guys just pull out their bank account and be like, I'm good. Wait, stop. What's the number? Great.

31:44Like always 50 mil plus.

31:46Haley: Wait, in the bank account? Which first off - No, the investment account. It's an investment account. You know what? I actually haven't looked for that close. I hope to God it's an investment account. No, that's my biggest - Because that much cash should never be saved up in your bank account. I know. But yeah, we've had tons that are just like, we'll flash it. And I'm like, all right. It still doesn't mean you're a great client, but now we can at least have a conversation. But yeah, I mean, I do. I never want to tell people that it's not possible without social media. Because I do believe that at this point, I hopefully would have a good client base.

32:13I don't know if I'd have billionaires yet, but I think I'd still be doing pretty well just because like I was out there hustling every single day, like hands in the dirt, just meeting people and trying to build those relationships. But you're still doing that. You're just doing it digitally. But now I'm doing it digitally and in person. And now people are walking up to me. So, you know, of course. Such a good feeling when it switches. It's great. And thank God we have the social. But I never want to like deter anybody away from thinking that it can't happen without social media because I think that in like real life sales is still very much a thing and people can crush.

32:41You just got to really work at it. Yeah.

32:43Haley: I mean, but I think it's also like work smarter, not harder. If you can. Absolutely. but with your clients we were fired a client oh yes many what's like the worst thing that they've done um it's just a is level of respect across the board anybody that we've gotten rid of it's just the way that they talk to us you don't always see it and sometimes they are very good at hiding it they will come in in the first couple interviews they're like i'm such a good guy i care about you guys i think you're lovely people they speak very high level energy which is like you read me like a book if you speak like that i'm like oh you're great but that yeah it there's a flip usually after the first trip where they just start swearing.

33:19You guys suck. I don't know why I paid you. I want a refund. But then they still want to stay. It's just that constant level of insanity and almost like emotional switch. And that, for me, I've seen several times.

33:32Haley: That's the hardest thing about being in like a service industry. I feel like it's like you can really get caught up with people's drama. I don't have the energy for that. I'm like, I take on a lot of that stuff too. I feel it really heavy in my stomach. and it affects me, so I can't have people like that around me. There's too many good people out there to be working with assholes. That's a really good point. It's like a really good abundance mindset. Observe. The North American Dad. 50s. Great polo collection. He enters his vehicle information on Carvana. An offer appears in minutes. Remarkable.

34:07Haley: He squints, reads it again, smiles, and says, Dang, that's a good offer. The highest form of approval. No haggling. No hassle. No one called him boss. He's still on the couch. Astonishing. Sell your car today on Carvana.com. Pickup fees may apply. This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome? That's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense?

34:45Haley: There's no place like Chrome. Check responses set up required compatibility and availability varies 18 plus. So where do the ultra wealthy like to go? Like what's trending 2026 for travel for them? What do they like to do? Have you noticed changes in how they travel? What they're prioritizing? People always ask me this. I think it's funny for people that, I think it's so obvious, but of course it's not because I'm just so ingrained in this. people are following this Instagram thing. So like three years ago, the Kardashians went to Mallorca. Mallorca is everywhere. It's kind of like Paris fashion and American fashion.

35:19A couple years later, we follow the trend. Same thing. Social media, everybody who's anybody goes out and then it's like St. Bart's. Over the next three years, I think St. Bart's is going to be an absolute nightmare. Even this year, it was a nightmare. There were way too many people there. But of course, because of all the social media blow up, everyone is going to spend every dollar they can to go take a photo in St. Bart's and look like they're a billionaire. So it's just going to get ruined. My people, honestly, there are not as many trends with ultra high net worth individuals. They like what they like.

35:48They go to the same hotels every single time. They take the same vacations with their families. So they're repeating the trips. They repeat their trips. So interesting. Sometimes they'll switch, but if they really like something, especially I work with a ton of families. If they have kids, they don't like to switch it up. If it went great last year, stick with it. It's also really nice to have concierge teams that like know you and you can return back to that and you don't have to build those relationships again. They feel like more trust there.

36:13Haley: 100%. That's how my family traveled growing up. Now, the only outlier there is the new money people. So we work with a lot of crypto people. We accept crypto as payment and they're hilarious. They're so funny. They'll come in, you'll see the market will go up if Bitcoin and any of the coins and we'll just be like, get ready. I want to spend$2 million. Let's go. Let's do it all. They send us crypto. They go off, do this crazy vacation, come back. They'll keep going and then you'll see the crash and then they're dead silent. We don't hear back from them until the market goes back up again. It's really funny.

36:45But they always want the craziest experience. Like, what do you have? What have I not done? How can we get there? So like African safaris. I want to go to Ibiza and do like the craziest nightlife trip for three weeks. I want to go do a boat and somewhere we can barely get a boat into, like just all the things. So those guys are fun, but they want it right away and they want something that they've never done before. So we have to kind of keep a good eye on the client profile to see what they've done so that we don't show up with something that they've already done.

37:11Haley: Do you see your clients sort of performing their wealth in the trips that you book for them? Some yes, some no. Teach their own. I'd be posting like crazy. Now I love social media, so of course my stuff would be everywhere, but some clients would rather die than be on camera. Yeah, I feel like the biggest luxury with the rich is to be private. I hear that. Yeah. I totally hear that. Do you know how exhausting it is to be on camera? And I love my fans. They're amazing. But like some days you want to look like shit and just not talk. We talked about this. I don't want to talk to anybody some days.

37:43Yes. But you lose that privilege when you become famous. Like that's – people always say there's that selling your soul to the devil for fame. I think that that's what it is. It's not selling your soul to the devil. It's selling your ugly. Like you're done. You will never be able to walk down the street looking horrible to go get your morning coffee singing away. Someone's going to take a photo of you and say you're on meth. Like it's gone. It's gone.

38:03Haley: And that's like the sell your soul. Totally. Unless you can tell us where to go, like a secret island where you can just like be looking like a meth hat. I mean, you can rent out Necker Island anytime you want, but you got to have some money to do that. So your, one thing I think is really interesting about your work is like how intimately aware you are of your client's life. And I'm sure with this, you're able to learn not just about how they travel, but how they handle money. Like it's clear they really love value. They don't want to get ripped off. That makes sense. But what have you learned from working with the ultra rich that you apply to your own finances?

38:37Get somebody who knows how to do it to do it. Yeah. My wealth managers are fantastic. And I also am starting to understand deeper into the saying like the rich just keep getting richer. You just have access to more things. You really can't deny that. I even like two years ago would never have known about like pre-IPOs and all these incredible, and I'm just not a finance girl, but now I have these amazing people that are calling me and are educating me on what this is. This could be risky. This could not be risky and just helping me really diversify my portfolio. But I think just having connections and being in these circles, unfortunately for the everyday man is, is growing my wealth for me.

39:16So I know that's a a hard thing for everybody to say, well, I want to do it too. But just being able to get educated by this level of people is like put so many new things into my head and it's quite incredible.

39:27Haley: Yeah, it's so true. The access really is crazy. Everything. Yeah, it really is. To get those deals where you're going to get those beyond average returns. Yeah. So I think a lot of people listening are definitely fascinated by all your stories. I know that I am, but we're not operating on the same wavelength as your clients. We can't afford the million dollar trip. Me either. So like what tips do you give to people traveling on a budget? Do you have, I know that's not your specialty, but, or like, where do you go? Obviously you're saying, okay, St. Bart's is cooked, you know, all these Instagram places, not worth it.

40:03Haley: But like, do you see any up and coming locations that we like, okay, for example, I go to Greece every summer, but it's always, is there's a hot new island in Greece and I'm like, I got to avoid it. So like last year I went to Sipnos and Fologondros. This year everyone is in Sipnos. And so I'm going to Amorgos, which is, you know, there's a new hotel there that I'm going to go do. That's like going to be great, but it's not quite in the zeitgeist yet. So like, do you have those cusp places? I have a couple, but I already hear it. Like I've made a couple of videos and I've gotten messages. I actually, I won't even say the name again because I'm stopping to advertise this spot, but there's a island in Hawaii that I used to talk about constantly.

40:38And I actually had like five or six local people message me and they're like, we are so overwhelmed. Please stop advertising our island. And I haven't talked about it since. So I try, I always feel bad talking about the underrated places because they're going to blow up. It's going to happen. Montenegro is my like, I think it's going to absolutely explode. Everybody's slowly starting to whisper about it. That's where we're starting to send people. The one and only there is spectacular. There's a lot of good spots over there. So I would say Montenegro. Obviously, if you can afford it, just get on a boat because it's never going to be overcrowded there.

41:12Is that really like the peak travel? That is in my opinion. Because you have like a full staff, you can go wherever you want. I don't think you can beat luxury yachting. It's phenomenal. You can stay in your bubble. You don't have to talk to anybody, but you still have access to all the best restaurants and you can go to the best hotels and go hang out there and get drinks. It is like the elite of elite traveling in my mind, but it's very expensive. So I would say best hack is try, and this is tough because you don't want to travel not on peak season. Of course, everybody wants to go to the same parts during your season, but if you can, I call it shoulder season, but people don't know what that means.

41:47So if you can travel not on peak season, that is ideal. And you can just Google that, like Google when is it the best in Costa Rica and then go when it's not the best. Unfortunately, you might have a lot more rain than you might on peak season, but you're going to save so much money by traveling. And also just please, for the love of God, stop booking your trips three weeks before you go. That's such a good tip. You can't book hotels longer than a year away, but if you can start at eight, nine months, you are going to save thousands of dollars. So please just go in advance. Everybody works. You know when you're going to have time off.

42:20Book the Christmas vacation after Christmas this year. Go week after. Just book it. There's going to be great discounts, great deals. It's like that is the way to go. Book early. Go off peak season.

42:30Haley: Those are really good hacks. Thank you. What are your non-negotiables when traveling? I am a carry-on freak. No, you need to – I need your help. What are we doing? It's so serious. And what flavor carry-on are you – what brand is it? Like we need to know. So I'm trying to look cuter at the airport because I look kind of like I just crawled off the street. Usually when I get on a flight, I'm like full of track pants, giant sloppy duffel bag. I usually I have I just bought a Todd's like leather bag that just will allow me to beat the crap out of it and look good I love that bag so I got like a big purse that I'm liking but also usually they have a bays black carry-on that's like a laptop bag that one's great to pack if you get a long flight that's like that's the must go um hydration sheet masks non-negotiable for me I always bring an extra strength melatonin because I think not sleeping on a flight especially if you have a time change horrendous um and then like you need of course good headphones always a must go what else do I bring hand cream usually I get really really dry while I'm on there um oh and electrolytes I was gonna say electrolytes for sure have to have electrolytes and I feel like throughout the interview every question that I gave you you'd be like oh I haven't heard that before or you'd be like people always ask me that so I'm wondering besides about cocaine what are they?

43:49People try and ask and normally I'm like let's just not talk about this but it's a real thing of course people do drugs that is a real thing we just don't handle it.

43:56Haley: Yeah rich kids love to just snort a few lines but are there any other things that you wish that people would ask you and you haven't had the chance to answer like that you feel like people like don't know about what you're doing that you're like oh this is good? I don't know I you know I'm it's really cool when I get to talk about just like life as a human. I am not accustomed to this and I'm getting to see so many things. You work with your fiance. Yeah. What is that like? It's beautiful. It's so nice. Of course, we literally try and kill each other once a week, but in like the nicest fun way.

44:29We are, you know, we'll yip at each other when we're working sometimes because we will disagree on something. But the second that it's over, we're just like, we're so in love. We're so happy right now. And just like, even like I show up last night after such a long day of shooting and there's a massive bouquet of flowers and a martini waiting for me and this like beautiful handwritten note. Like he's always just celebrating me and so congratulatory and like won't stop bragging. It's so embarrassing when we go out anywhere. He's just so proud to be my partner and to have that in a business. And we're also insane.

44:58Like both of us work 22 hours a day, so we don't sleep and you can't have a partner that's not on the same level as you. So I just feel very blessed to like have that connection in life. It's been very cool. I love that.

45:08Haley: Did you have like toxic relationships in the past where it wasn't like that? Horrendous. Horrendous. I've dated just horrible people before Troy. I think I learned my lesson and then came back. I just always believe the best in people from the get-go and it's bitten me in the butt a couple of times. Okay. My last question for you is you – like you're saying, okay, you got – like you are saying with your fiance, he gave you sort of a luxury experience when you got to the hotel. like martini, huge bouquet waiting, whatever. So what luxury experiences do you really love? I'm an F1 girl, A till I die.

45:40I think F1 Vegas is the coolest event I have ever been to. If you have not been, you need to put it on your bucket list. I think it's the coolest thing ever. Even if you don't like F1, the parties, the people, networking wise, young women, get over there. Get over there. You don't have to go to a great club. You don't have to do all the things, but go hang out at the Wynn and meet people. It's just celebrities and business moguls everywhere. Okay, that's fantastic. The room where it happens. The room where it happens. This is F1.

46:04Haley: Okay, well, thank you so much, Olivia, for being here. This was so good. Of course. Thank you for having me. And stay rich. Stay rich.

46:19Haley: When you spend enough time around great companies, you notice that the best ones treat trust as a growth strategy, not a box to check. Vanta helps companies build and prove trust from day one. Its agentic trust platform connects compliance, risk, and trust at enterprise scale. Vanta delivers a 526 % return on investment over three years and pays for itself in just three months. Learn why over 16 ,000 of the fastest growing companies use Vanta at Vanta.com.