How to Date a Billionaire (Dear Sugar Mama)

Love is in the air… but so is money drama. This week, I’m answering listener questions on everything from prenups to dating rich men, making more than your partner, and figuring out when you’re chasing love vs. chasing the lifestyle. Get ready for the ultimate Valentine’s Day edition of Dear Sugar Mama — all the tea, no judgment. Financial Tea with Mrs. Dow Jones is a Sony Music Entertainment production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts and follow us at @sonypodcasts To bring your brand to life in this podcast, email [email protected] Pre-Order my upcoming book, FUTURE RICH PERSON, here: https://www.mrsdowjones.com/book Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Haley Sacks?

  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 11:00 PM. 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. Clients can book in seconds too, so there's no login or separate app necessary. So you actually get more appointments.

• 0:43Haley Sacks?

  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. Okay, so I just gave my apartment a major refresh. And hands down, the hardest thing to get right was the rug. I just couldn't find one that fit right. And I really wanted something that pulled the room together because a rug is a big deal. But then I found Ernesta. And Ernesta's amazing, you guys. It makes designer-quality rugs custom-cut to the exact size of your space, so it actually fits instead of almost fits and looks great the first time. Like in the past,

• 1:27Haley Sacks?

  I've just defaulted to stock sizes when buying rugs. And also, when you're in a New York City apartment, that really just doesn't cut it, but they're all weirdly shaped. But with Ernesta, you can send photos and dimension to Ernesta's design team, and they help you get the size exactly right, completely free of charge. Hand-selected by design experts, Ernesta rugs are beautiful, they're durable, and they're made for the way you actually live. Cut, finished, and delivered in as little as two weeks. Visit ernesta.com and order five samples for only $10, and you will get $50 toward any rug of your choice. That is E-R-N-E-S-T-A dot com.

• 2:09Haley Sacks?

  What's up, rich people? It's me, Haley, AKA Mrs. Dow Jones, and this is Financial Tea. What's up, sippers? Welcome back to Financial Tea. This is a very special episode of this podcast because A, we are in our office studio, which I think looks sick. If you're watching on YouTube, you can probably see those fake Andy Warhols behind me. Dupe culture is alive and well. Actually, such a good decorating tip to just like get a picture that you like from Shutterstock or something blown up and have Framebridge and send it to Framebridge. I've done this in so many apartments and now my office, and I feel like it makes your place look rich as hell. But today is a very special episode because it's almost Valentine's Day. And so I thought to

• 2:53Haley Sacks?

  celebrate, we should do a Dear Sugar Mama episode. And just to key you in on what Dear Sugar Mama is, I have a newsletter that you should subscribe to. If you haven't already, just go to mrsdowjones.com. And twice a month, we do these financial advice columns called Dear Sugar Mama, and they are so lit. The tea is so juicy. Like, guys, the submissions that I get are going to absolutely blow your mind. Money drama is crazier than any other kind of drama. I'm not even kidding. But my dream has always been to make Dear Sugar Mama into like a video segment. And so yeah, today we're living our dream. We're doing Dear Sugar Mama Live. And guys, these are crazy submissions, and they're all Valentine's Day themed because it's February and we're feeling

• 3:36Haley Sacks?

  the spirit. But first, public service announcement. If you are looking for a great Valentine's Day gift, flowers die, chocolate just gets eaten, and sometimes it's gross. But if you want a gift that actually appreciates, preorder Future Rich Person, which is my debut book that comes out in May. Okay, Dear Sugar Mama, I feel like a total monster even saying this, but I need a reality check. I've been dating a guy for five months and he is wealthy. We're talking spent New Year's in St. Bart's on a mega yacht wealthy. Wait, what? We were literally at the same party as Alex Earl and Tom Brady. Oh, my gosh, that is the tax bracket I'm currently occupying. But here's the tea, the chemistry is in the basement.

• 4:19Haley Sacks?

  The sex is mid would be an overstatement. He has ED. So most nights, instead of actually being intimate, we just end up in his $15,000 sheets scrolling our phones in total silence. Like, I'm literally there checking my Hinge matches while he's next to me checking his Bloomberg app. I'm not obsessed with him, I'm obsessed with the security and the lifestyle. So am I a financial genius for choosing a soft life over Sparks? Or am I just selling my soul for a private driver? Sincerely, Sugar Baby in denial. Dear Sugar Baby in denial. This is crazy. But honestly, like, if he has ED and you hate the sex, like, you're gonna just hate your life with him. That literally sounds horrible.

• 5:04Haley Sacks?

  And I know that we romanticize being with rich guys because it sounds amazing to not have to work anymore. Like, we're all out here grinding girl boss culture. And it's like, no, we just want someone to give us their credit card. But then, once you actually have it, you realize free is the most expensive price tag. Like, nothing is actually free. I think that the culture has done a really good job of romanticizing financial dependency, like, the whole trad wife thing, sugar babies, nepo babies even. We, like, put this on a pedestal because it seems like the ultimate cheat code, that, like, you just are born into or marry into rich, and you don't have to actually earn rich.

• 5:45Haley Sacks?

  But money that you don't earn always comes with a super high interest rate. And it's an emotional interest rate. And that actually ends up being so much more taxing than just putting in the money to support yourself and, like, finding a relationship that actually fulfills you. Look, I think there's a lot of women who wouldn't care about this because their number one value is just being rich. Like, they just wanna be on that yacht, that's all that matters. But you have to figure out what your values are. Like, are you gonna end up depressed because you haven't had a good bone in five years? And, like, at the end of the day, Birkin bags are just bags? Or are you someone who's obsessed with that life and, like, really values that above, like, any other kind of relationship? I know for me, I identify as being a gold digger.

• 6:29Haley Sacks?

  But I think that it's different because I have my own gold. So what I'm saying is like, I don't want to be a nurse or a purse. But I do want someone who like gets the game and is good with their money and can make money. But I always would want to have my own money. Like, I would never want to be fully reliant on someone because I feel like that is definitely the most expensive thing in the world. Also, you have a lot of risk here, too, because you're basically like putting, it sounds like you're putting your career and life and earning potential on hold to travel and like live with this rich guy. But you're not married to him. And so you're basically putting all your eggs in one basket. And for him, who cares? He can get rid of you and he'll have the money and he can find another girl.

• 7:12Haley Sacks?

  But for you, you're gonna have no job, no money, and there's no legal repercussions for him just dumping you if you're not actually married. You're basically one argument away from being homeless, which is crazy, but it's true. He could just kick your ass out. He doesn't owe you anything. One of my favorite authors, Helen Gurley Brown, who was like the founder of Cosmopolitan, had a quote that said, "A woman should always have their own money so that she can look a man in the eyes and tell him to go to hell." That is the ultimate luxury. So basically, I think that like, if you like all the luxury stuff, it's fine to stay with him if that matters more to you than like having a real relationship. But I wouldn't put all my eggs in this basket. I would like try and maintain my earning power and like maybe like keep your own apartment and things like that

• 7:56Haley Sacks?

  until you have legal protection from him, like you get married. And don't give your whole life up just because he's taking you on a yacht. So basically, it's okay to want a billionaire. It's okay to want the yacht, but you have to make sure that you hedge your bets and have your own money so that you can walk off the yacht and walk away from the billionaire if the vibes turn sour. You never want to put all your eggs in a rich man's basket.

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• 9:38Speaker 04

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• 10:10Haley Sacks?

  Dear Sugar Mama, I am six months into my engagement and we've already dropped 150K in non-refundable deposits for our dream wedding at a villa in Lake Como. Okay, chic. But then I landed a massive promotion. We're talking VP level with an equity package that finally makes my bank account look like a future rich person's. Okay, obsessed, love the shout out. At the same time, I'm watching my best friend go through a divorce that is basically a financial horror movie. She's losing her Hampton's house that she put down half the mortgage for and half the RSUs she worked 80-hour weeks to earn. That sucks. So I realized I'd be an idiot not to have a prenup. But when I brought it up, my fiance absolutely spiraled.

• 10:53Haley Sacks?

  He said, it's too late that I'm changing the rules of our relationship. And that if I actually loved him, I wouldn't be planning our divorce before we've even cut the cake. Am I being a cold hearted bridezilla for wanting to protect the empire I'm building? Or is he a walking red flag for thinking my hard earned promotion is our money before we've even said I do? Sincerely, prenupless in Seattle. Okay, I'm very pro prenup. Like, I think that I actually should be hired by big prenup. If that's an industry even to rebrand prenups. Because they have this connotation that if you get a prenup, that you're basically planning for divorce. But I think that we need to reframe that in our minds. And see prenups really as marriage insurance.

• 11:38Haley Sacks?

  So like, you don't get health insurance expecting to get sick. You just get it to have your own back in case something happens. And so a prenup is the same way. It's just insurance in case something happens. But it doesn't mean that you think that you're getting divorced or that you want to get divorced. So I'm very pro prenup. I also think that having that sort of financial transparency before you got married is really important. Because after all, marriage is a business decision. It's basically a merger and you need to know the terms of the contract and the merger before you get into business with this person. The other part of prenups that I need to rebrand is that they're really just for rich people. And like, if you don't have a ton of assets, you don't need one.

• 12:18Haley Sacks?

  I also think that's not true because I think that a prenup just shows that like, you're serious about the future that you're building. And that you want financial transparency with your partner. You would be shocked at how many people get married without having ever talked about money with their significant other. And then money becomes the reason that they divorce. So I do think that this is a red flag of your fiance. I sort of want to know like, how you phrased it to him. Like, I feel like maybe part of the issue is like, did you just spring it on him? Like, some people carry their money traumas from when they're seven years old. Like, that's when we all form our relationships with money. And so like, you might Have triggered seven year old him who like hates talking about money or like something happened with his parents and like

• 13:02Haley Sacks?

  this just he's not a bad person. It just like brought him back to a place that felt bad. So we're going to give him the benefit of the doubt. I think that you need to sit him down in a calm way. Make it seem like the prenup is for both of you, not just to protect your money, to protect him too. And then let's see how he reacts. Um, and I know that there's this added pressure of like the big deposit that you put down in Lake Como, but like, girl, so many people want to get married in Lake Como. There's this app that lets you buy non-refundable vacations from people who like can't go on them anymore. I'm sure there's the same thing for wedding venues that people have put deposits down on and then like can't use anymore.

• 13:45Haley Sacks?

  Like I guarantee there's a way to recoup some of the 150K. You can sell it to someone at a discount, whatever. But whatever the financial loss is that you take from walking away from the wedding, if he does have still a weird reaction when you bring it up again, is going to be so much less than the amount of money and emotion and energy that you're going to have to put in to divorce this man without a prenup down the road. Because if you're fighting about money now before you're married, I guarantee you're going to keep fighting about it when you're married. And it's just always going to be a weird sore subject. But also just weigh your options. Like you could marry him without a prenup, so you don't have to walk away from the deposit. But then you're like probably

• 14:30Haley Sacks?

  gonna get divorced and that's going to be so much more expensive than if you just like walked away from the 150K wedding deposit.

• 14:41Haley Sacks?

  Right? It's gonna suck. It's gonna be a little bit like, maybe you're gonna have shame about it. But I actually think it's sort of chic to be like, I had a broken engagement. I have a friend Samantha who had a broken engagement and like, I think it's one of the most interesting things about her. And now she, by the way, remarried to an amazing guy who's very financially fit. He was reading the new Ray Dalio book when I saw him at their wedding this summer in Italy. So the grass is going to only Get greener if you walk away from what's not meant for you, which is broke loser guys who don't want prenups and towards your beautiful future, which is your cool ass promotion, fun life and like new dating pool of people who are down to like build empire with you instead of trying to stick their grubby paws in your empire and take it for themselves.

• 15:27Haley Sacks?

  Dear sugar mama, I'm a senior project manager in tech and my income just doubled into the mid six figures. Okay. Today's theme is like women in STEM who are getting peed a lot. My boyfriend of two years still coasting. What? I refuse to live a budget life. Same. So I'm currently running a girl fit. What? So I'm currently running a girlfriend scholarship program, paying for our $400 sushi omakase's VIP Coachella seats and a mom stays. I don't mind being the breadwinner, but I mind that he's a total passenger who doesn't even handle the mental load of booking the trips I pay for. No. When I asked him to step up, he called me

• 16:08Haley Sacks?

  transactional and said I'm making money a competition. Am I being unfair or am I just subsidized? Or am I just subsidizing a lifestyle for a guy who's happy to let me coast? Sincerely, reluctant breadwinner. Okay. Dear reluctant breadwinner. I get why you're reluctant. This man has an amazing life. Like I want to go to the Aman with you and he's out here like he can't even book the trip. Are you kidding? No, he needs to have like a folio. He needs to have like, he needs to have an itinerary. Even me, like I'm single and I go on trips with my girlfriends and I'm always like, girl, I'll pay for the nicer hotel if you just like book everything and if you just book everything and plan the itinerary and it's like done deal because relationships

• 16:53Haley Sacks?

  should be reciprocal, not transactional. And I think in general, we need to rethink this idea that relationships, like the financial split should be 50 50 because there is always someone who's making more money. It's like so rare for a couple to make the exact same amount of money. But so I think that things should be split reciprocally, not transactionally. If your income split with this guy is 80 20, then like his efforts need to reflect that. If he's putting 20% of the money in to support the lifestyle, he needs to be putting in 80% of the energy to be like creating the lifestyle. When I best friends, Joanne is like the biggest girl boss, like literally I should have her on the show. She's iconic, makes a ton of money. And so she retired her husband because she was like, why are you working?

• 17:38Haley Sacks?

  Like, I'm good. Like, take care of the kids, go do Taekwondo, like, love you. But just make sure that the house is taken care of. And so that woman, I don't think she has put gas in her car in 30 years. She has not been to a grocery store. She doesn't see a bill. Like, he is in charge of the household and gives so much back to her in that way. And they have an amazing equal relationship because they have balance. Like, she's bringing home the bacon, but he's also bringing home the bacon in different ways, doing things that she wouldn't want to do, but also like really earning his keep. And I think that's how it should work. I don't think that it, that they, I don't think that you need to split money 50 50. I think that you can split things proportionally to how much you're earning.

• 18:21Haley Sacks?

  So I think that you need to either talk to him and restructure things, or you need to leave him. Like, and let's not forget, like, he's your boyfriend. He's not even your husband. This man is living a good ass life. Like, he's got it figured out. If he can't like add a little bit to the relationship with his efforts, you gotta kick him to the curb. Being single is so much better than being with these deadbeat men. Like, I don't know why people stay in these relationships with these guys who just sound like absolute drains. You're gonna feel so much happier if you just release him and you don't have this resentment anymore. I mean, of course, give him the chance to change, but if he won't, you gotta keep going, girl. Your life is too good to let him drag you down. And just a reminder, if you want to submit a question for Dear Sugar Mama,

• 19:04Haley Sacks?

  email [email protected]. That's [email protected] with your submission. These are always anonymous and always super juicy.

• 19:16Haley Sacks?

  Okay, now we're gonna do a little portfolio audit. I'm going to open the books on the crazy DMs that I've gotten from you about money and relationships. Okay, first one, brags about his income, but needs an immediate Venmo for a $14 cocktail. I'm gonna call it, he's insolvent. If you need to invoice for a margarita when you've invited someone there for a margarita, you aren't rich. Tips like it's 2004. Ooh, cheap is tough. I'm gonna say walk away from that too. Has 30K in a checking account and thinks it's a flex. I'm gonna say it, he's an inflation risk. That money is losing value and so is he. Ex-husband who won't set the kids up for success despite having the funds. Damn. Zero ROI, glad that he's your ex-husband.

• 20:00Haley Sacks?

  Hoarding wealth at the expense of his own legacy. That is some fucked up shit. Pardon my French. Won't take me on dates because it's expensive, but orders Uber Eats every night. Damn, that is, that would be, that would be so grating to me. Like, I would be so annoyed at him. That is the most passive aggressive man in the world. I'm gonna have to say, like, walk away as well. I hope we get some where, like, the guy's not so bad. Okay, I will say, a lot of the theme of this episode is sunk cost fallacy, which is like, when you feel like you're too deep in something to walk away. But like, you can always restart your life. I just wanna remind you that. Like, if you're in a relationship with someone who is disrespecting you financially and you're not down with how they treat money, you can leave. Like, it doesn't matter if you've been there for eight years.

• 20:44Haley Sacks?

  It doesn't matter if you have a kid with him. It doesn't matter if, like, you, if you put a deposit down on a late Como wedding. Like, if it ain't right, you gotta go. And that's why having your own money is so important, because that gives you the power to walk away. I promise, it's easier to restart than to try and make it work with someone who's not right for you.

• 21:06Haley Sacks?

  I do have to run, though. Tell me if this is crazy. I guess this is my own submission to Dear Sugar Mama, but this man sent me a DM with a screenshot of his $13 million investment portfolio. And this is like, a super fan. Like, he's always being so positive on my posts, which, like, we love to see. And he's like, I really wanna take you out. I'm gonna fly in. I wanna take you to dinner. Blah, blah, blah. And so I was like, fuck it, you know? 2026, let's say yes. And I know that it's sus that he sent me that screenshot and I actually found out something else sus about him, which is that he is in a lawsuit for giving bad investment advice. But I'm sort of just like going on the date anyways to see what

• 21:45Haley Sacks?

  happens. Maybe there's two sides of the story. Maybe it will just be a story for me. But I will report back. So I have to go get ready for that, even though, you know, I gotta blow out for this just for you guys. So I'm sort of ready already. But yeah, see you next Thursday. Don't forget to read and subscribe, follow for more and stay rich.

• 22:10Haley Sacks?

  This is a Mrs. Dow Jones production for Sony Music Podcasts.

• 22:16Speaker 03

  This episode is brought to you by State Farm. Football has a play for just about everything. You can go deep, keep it on the ground, or draw up something nobody sees coming. And whether you want to run a flea flicker or the tush push, you need a plan to fit your unique situation. That's why State Farm takes the time to get to know you so they can help personalize coverage for your life and budget. Now that's a solid game plan. Like a good neighbor, State Farm is there.