Tiger Sisters - Should You Marry For Money? Harvard and Stanford Women Tell All.
Episode Date: October 6, 2025💸 Should you ever date for money? What’s the most ridiculous purchase we’ve made (and don’t regret)? And what’s the single money habit that sets the wealthy apart?Money rules everything, ye...t no one talks about it. In this unfiltered Ask Us Anything episode of Tiger Sisters, we get real about money — answering your top questions on love, power, investing, and what true financial freedom actually looks like.We share:✅ The truth about dating or marrying for money (and the strings attached)✅ Why every woman needs her own money + autonomy✅ Our most “ridiculous” purchases (and why experiences are everything)✅ The wealth habit billionaires swear by (compounding + playing offense)✅ How to lend money to friends & family without losing the relationship✅ The #1 money mistake in your 20s & 30s — and how to avoid it📖 Book mentioned: “I Will Teach You to Be Rich” by Ramit Sethi⚠️ Disclaimer: The views in this episode are our personal experiences and opinions, not financial advice. Please consult a qualified professional for financial guidance.🐯👯♀️ We’re the Tiger Sisters — Your Wall Street & Silicon Valley big sistersDecoding Money • Power • Love✨ New episodes every Monday | Shorts all week ✨🎯 This episode is sponsored by Read AI, a meeting co-pilot that takes notes, analyzes meeting sentiment, and shares smart next steps for you and your team. Try our favorite productivity tool free for 30 days: http://read.ai/tigersisters💌 Want to partner with us? Sponsorships: partnerships@tigersisters.co⏰ Timestamps00:00 Breaking the money taboo01:46 Should you date or marry for money?03:42 Why you should have your own money07:00 The “lakehouse” story & hidden strings07:53 If you do date for money — how to protect yourself08:32 What’s the most ridiculous purchase we’ve ever made?10:56 Angel investing + MBAs as “investments in yourself”14:39 The money habit that separates the wealthy (feat. Fernando DeLeon)18:16 Why you should start investing today19:49 Should you lend money to friends or family?20:54 Sponsor Break: ReadAI22:30 The easiest money mistake in your 20s & 30s26:16 Wrap-up👀 Newsletter: https://cherieluo.substack.com/🎁 Survey: https://forms.gle/rXpQtbpwU3qShHW26Why trust us?▫️ Cherie Brooke Luo – 100M+ views demystifying big tech, finance & MBAs▫️ Jean Luo – ex-Goldman, ex-Snapchat exec, 50+ AI patents, startup investor▫️ Together: 4 Ivy degrees • built billion-dollar products • two startups — decoded for youWhat you’ll get (and keep):▫️ 🚀 Ivy League cheat sheets – no $250K tuition required▫️ Personal finance playbooks – salary jumps, investing, money psychology▫️ Networking scripts – behind $100M+ deals, job offers & VC intros▫️ Real talk with unicorn founders, VCs, and billionaires▫️ Mindset resets – clarity minus the pricey life coach▫️ Fashion, wellness, and productivity hacks that actually work💛 LET’S CONNECT:~ CHERIE ~🤳🏻 Instagram – / cherie.brooke📱 TikTok – / cherie.brooke✍🏻 Substack – cherieluo.substack.com👩🏻💻 LinkedIn – / cherie-luo~ JEAN ~🤳🏻 Instagram – / jeanluo_👩🏻💻 LinkedIn – / jeanluo👉 Hit Subscribe & tap the 🔔, then WRITE A REVIEW and rate us ⭐️⭐️⭐️⭐️⭐️ on Spotify & Apple Podcasts!Share this with someone who deserves to be seen as a leader.🎵 Music: Sammy Signal – https://open.spotify.com/artist/2HsyknHuxhT8RoZfn5rqMS?si=Cn86viQJSveXynv4qhjxE🛍️ Items: 🍵 Sisters Matcha – www.sistersmatcha.com🌀 Everything else – https://amzn.to/3z0dx5b
Transcript
Discussion (0)
Money rules the world, but we treat it like a dirty secret.
Families hide it. Couples fight over it. And friends pretend that it doesn't matter.
But today, we're breaking the silence and we're answering your questions about money.
So let's strip away this taboo and get into it.
Since we started Tiger's Sisters a year ago, the number one questions we always get are all about money.
Do you have issues with money? Does money scare you? I mean, money is the number one reason for divorces and relationship problems, but it can also mean freedom.
And so we decided to do this episode to demystify money and answer your top questions.
In this episode, we're going to be sharing how we approach money, personal finance, and how it's a tool for you to use.
I'm Sherey.
I'm Gene.
And we're the Tiger Sisters.
We are your Wall Street and Silicon Valley Big Sisters.
And we're a top 10 business podcast on Spotify, where we talk about money, power, and love.
I was actually talking to a listener of hours and she said that she loves her podcast because on our
episodes where we talk about money and personal finance, it's not a topic that was ever spoken
about in her home.
So like she didn't learn anything from her parents, if anything.
Money was like a very taboo topic.
Yeah.
And so she felt super excited and just like happy to listen to our episodes because she could
learn more about it from us and in like a very friendly and approachable way because we want to
be there for you and with you on the same.
money journey. Yeah, I think that's really common actually, that money is a taboo topic in a lot of
households growing up. Yeah, I think culturally it can be. Okay, so the first question that we got is,
should you ever date or marry for money? Juicy, right off the bat. This is a super juicy question,
and I love it because it combines money and love. And power, actually. Yeah, all three of the things that we
talk about. Because there's a lot of power dynamics surrounding money. Who has it, who doesn't have it,
who's kind of controlling it. Yeah. Yeah. Yeah.
I think it's a pretty unromantic thing to say that, like, you are marrying someone for money.
And I don't think people should do that.
But if you are going into a partnership where the number one most important financial decision of your life is who you marry, you have to think about how that will impact your own life.
So, like, who you marry or who you decide to be with for the rest of your life, you're like having all your meals together.
You're maybe buying a house together, raising kids together.
Those are all pretty big financial decisions.
And while I don't think you should be marrying for money, I think it just goes so much more to show their drive, their ambition, their motivation and who they are as a person rather than like how much money they actually have saved up.
Yeah, I see what you're saying. You're using it kind of as an indicator of how they want to live their life and their personality.
And like it's a way to sort of see how your life together would be.
Yeah.
It's not always one to one, but I see what you're saying.
I think it's a good measure of lifestyle as well, because if you have a certain lifestyle and they have a certain lifestyle, like, when you guys come together as a pair and start living together and building a life together, like, it is important to consider how those two will come together. And I think we'd be lying to ourselves if we said money was not part of the equation.
Yeah. And I think like some people can be more flexible about their lifestyle or live many different types of lifestyle. But especially as you get older, you kind of get used to a certain way of special.
and living your life.
And that can be something that ends up being a non-negotiable.
Like I am a firm believer that even in any relationship that you're in as a woman,
like you should have your own money.
You should have your own career, your own ambitions,
and definitely your own money.
Because I've heard of like horrible stories where, you know,
women are contributing so much to a relationship,
but they don't have the financial backing to show that.
And if the relationship goes south,
they don't really have anything left for themselves.
I think that is the scariest thing,
which is why I don't feel comfortable myself,
completely depending financially on another person.
It's like money can be used as power over someone else,
like control over someone else, control over spending.
And I never want to be in that point in my life,
which is why I feel like, I mean, one, I love my career,
and I don't think I'll ever stop because I like what I'm doing,
but that's why I think it's also so important to have my own finance.
is in order. Yeah, I will say on that point, it's not just in romantic relationships. I have personally
seen it in familial relationships where people who are... With me? No, not with you. I'm just kidding.
I'm like, between us? No, I'm saying like with people who are full grown adults, like in their late 30s,
and they cannot make their own life decisions because they feel indebted to their parents,
but like literally, like they're depending on their parents for a certain lifestyle that they've led
their entire lives, and they cannot just live their own life, like their own true values,
because they are controlled.
Because they're controlled, because the power of their life is sitting with their parents.
Their parents have certain types of expectations, values that maybe don't align with them,
and they're forced to live the life that their parents set out for them.
And I think that's really, really deeply sad.
Yeah.
The idea behind that, whether it's in like a family relationship,
or romantic relationship, a lot of it is generosity and trust.
Because even if you are dating for money and you're with someone who has a lot of money,
if they're not generous with their money or with their time and they don't trust you,
then that's not really for you to enjoy.
Or it's the same thing with your family.
If your family isn't generous or doesn't allow you to make your own decisions,
like that is not, what is the point of dating for money or being in a space with money
if it's not for you to have autonomy over your own decisions.
Yes, there are expectations and like strings and requirements attached to that money.
So one of my girlfriends, she was dating this guy for a really long time and she kind of like
thought like, oh, this is it.
Like she's from like a very comfortable background, but he was from like an ultra wealthy
background.
And his parents, ultra comfortable.
Ultra comfortable.
And he, you know, had this like trust fund like money that he was supposed to come into.
But part of the requirement was that he had to move back to where his parents lived and where he grew up in order to get like, you know, the lake house and the house and like all of the things that were in that trust that were supposed to, that he had expected his whole life.
And so like she would have had to uproot her entire life to like live the life that was wanted by his parents.
Right.
And so ultimately that was a really big part of the reason why they separated.
Right.
which is so interesting because I can imagine some people just watching this podcast and being like,
that sounds really nice.
Like we can have a lake house.
We can live together.
And like I think on the surface, what you're saying is like it does sound really nice.
But the scary thing is like the strings attached.
Like I think feminism not to go there.
But feminism is having autonomy and controlling your own decisions, whether it be money or with your body or with your time.
Like that is the ultimate Maslow's hierarchy, right?
is like having control over your own destiny and in this situation like yeah maybe you end up with
a lakehouse but then you may be a prisoner inside the lakehouse yeah i mean i think it's not just
feminism i think you expand it's humanism humanism humanism is having autonomy part of having autonomy
is having the means to make decisions that you want to make so in that way like money is really
important so for the people who are watching and we can't convince them otherwise and they do want to
date for money. Do you have any advice or thoughts for them? I think everyone should make their own
decisions. Sometimes it is important to you and it's the best path for you to date for money.
I would say in that case, I would also take the opportunity while you're dating for money to
invest in yourself. So like use that as an opportunity to build up your skills, to build up your
relationships, like to build up maybe some sort of like business of your own or enterprise of
your own so that you can kind of start to get yourself to the place where you don't have to
date for money. Okay, the next question is, what is the most ridiculous purchase that you've ever made?
So I was thinking about this question and I was like going back on my past purchases over the last
year and I'm like, I don't really spend on anything like big that's like very material.
But then I went back and I was like, oh, this is probably my biggest expense and it's the category of
experiences. And this includes travel, international travel, domestic travel. It includes going to nice
restaurants. And of course, that's like food and dining, but also like because I go to like nice
sushi restaurants and like enjoying that experience, I, I guess see it more as an investment in
myself to expand like my aperture and worldview. So an example of this is that like when I go
travel, I'm usually not just like sitting by the pool and just like reading because I get bored.
and I have like me to do something all the time.
But I really invest in seeing new things, trying new things, eating new things, because
that is just the joy I find in life.
So like, for example, like if we go to Hawaii, like I'll be like, let's go on, you know,
a kayaking thing.
Let's do a surfing lesson.
Let's make sure we go to like a luau or a cookout.
Like I'm always, you know, finding like zip line.
Like I really enjoy doing those things and I never regret it because I feel like, one,
it's really fun for me.
Like that's where I find like a lot of.
of enjoyment rather than having like a material thing like like designer clothes or bags which I think
are is nice but it doesn't fulfill me the same way as like experiences do and like of course experiences
can be free like you can go camping but like the experiences I'm talking about like they cost a lot
camping is not free camping is not free but you know once you buy the expensive equipment it can be
more cost effective but yeah so I just love travel
and I don't think that's an area where I would like limit my spending.
Like that's where I see a lot of my guilt-free spending is like when I am on vacation
and I am here.
I want to make the most of it and do the most.
And I think the thing that's really interesting is like the ROI on investing in experiences.
It feels like it's investing in myself because I gain a new perspective.
I see new things.
I see new cooking techniques that I can use at home.
But like these are things that I will take with me until like I'm 80 years old.
look fondly, very fondly back on in my life.
For me, the most ridiculous purchases that I don't regret at all, it also has an element
of that like education and investing in myself because my answer is probably some of the
angel investments that I've done.
Because my approach when it comes to angel investments is that you kind of have to just
expect that it'll go to zero.
Like maybe it'll turn into a $100 billion company, but in all reality, it's not.
not something that you can have any expectation around.
So one, diversify.
But two, make sure that it's money that you can afford to lose.
And I kind of think of it as more of like, I'm investing in myself when I invest in this
startup.
And it's more so investing in the experience of like learning and having the opportunity to
like be on the inside of this company and have more of like an ownership mindset and
learn more about the industry and, you know, connect more with other people who are also angel
investors. And it's kind of just like opening yourself up to this whole new world that you
weren't really privy to or you wouldn't be a part of were you not on the cap table.
Yeah. I think in that same vein, too, like investing in yourself, whether it's through
angel investing or like even like getting our MBAs, like education is like a huge part of our
lives and part of our stories. But it's like a way that like you can invest in yourself.
And if things go to shit, like you lose your job and you can't figure things out.
But like you always have your education to fall back on.
They can never take that away from you.
They can never take your education away from you.
I don't know who they is, but they can never take it away from you.
The powers that be can never take your education away from you.
Because it's hard and you get a degree and it's something that you earn and it's tough.
And I don't know, it's something that you can always use and reuse as well, even if you go back to school.
Yeah.
And I think it's like kind of back.
to what you're saying. It's education and also your experiences. Yeah. Like that can never be taken
away from you. Going back to the first question about should you date or marry for love, I guess like
in this second for money. Sorry, for money. Where's my head at? Yes. Should you date or marry for
money? Through this question that we're answering now, the second question, like we're basically saying like
build yourself up. Like use money as a tool to invest in yourself. Invest in your experiences so that like if you do date
for money or don't. Like, I don't know. Like, you just have yourself. You have a sense of self
so that you don't have to rely on someone else. Yeah. Wow. We're so like Dwight D. Eisenhower.
I don't know. Like, pull yourself up by your own bootstraps. Was that him or FDR? I forgot now.
Yeah. I don't know. I just feel, I just like don't want to have such a big part of my life rely on someone.
I think there are a lot of stories about people who have done that, especially.
women and where things go south for them or they can't leave a situation they don't want to be in
anymore. Oh, that's the saddest part. That's a really good thing to bring up. Yeah.
If they feel stuck in a situation that they can't leave. Yeah. That's all too common.
It's like heartbreaking. Yeah. I mean, I don't know if it's like scarcity mindset, but like I don't
want to ever be in that situation. I will, I will, you will never find me in that situation.
Yeah. Like I'd rather, I don't know, work 90 hours a week, which I've already done,
then do that.
So I guess I have lived out my morals.
Yeah.
And I guess I sense that a lot of people watching this,
like don't want to feel stuck either in a relationship
or in a power dynamic where they can't see a way out.
Okay, Gene, so the next question is,
what is one money habit that separates the wealthy from everyone else?
I think we have some good answers around this
because between the two of us,
We've interviewed multiple billionaires, 100 millionaires who've, like, given us advice.
Yeah.
And the Tiger Sisters family advice about this.
Yeah.
One answer that really sticks out to me is the idea around playing offense, not defense,
with your money and like not just thinking about it as a resource, but like as a tool that you can deploy.
And really also just being strategic and like creating opportunities for yourself and thinking about it.
as the idea of the abundance mindset and thinking of the world as your oyster and being like,
there are so many ways.
This is what Fernando de Leon used to say.
There are so many opportunities out there in the world to make money if that is what you care
about and that is your goal.
And like you just have to be a little bit creative and put some like elbow grease into it
in order to create these opportunities for yourself.
A lot of wealthy people that we've talked to sort of have that same approach.
Also, I love this interview that we did with Fernando.
because he is on the Forbes billionaires list.
Yeah.
And like they rank the billionaires or I guess they like rate them like one to 10 of like how
self-made are you.
And like one is basically like you're the type of billionaire that's inherited a lot of stuff.
Fernando is literally like a 10 out of 10 billionaire, which means he like literally,
he started from nothing.
He grew up poor and really built himself up and his family up.
And so that's why like your like lesson or takeaway from Fernando is just.
like make something out of nothing because like nothing comes for free. And I really love that
episode with Fernando because he talks about some of his like mindset around money. If you don't have
anything, how do you get something? So I highly recommend listening to that episode with Fernando.
I would say my answer for this in talking to a lot of billionaires and 100 millionaires
and interviewing them, the thing that they tell us, like you don't get rich overnight. It's the
power of compounding. And what that basically means is that like if you invest today, like where
that money will be, it'll grow over the next like 20, 30 years. But like the power of compounding
works when you start now. And there have been times in the past, the mistake I've been made in terms
of investing is like, oh my God, maybe I should time the market or like maybe it'll be down.
Like you can never guess like if you're trying to invest in ETFs or the stock market. Like there's
not really a good time. There's no better time to invest than like right now is what people say,
because you can never guess when it'll go up or when it'll go down. And timing the market is
really hard. I'm not a genius. I don't know how to do it. There's many companies that try to do it
or claim they know how. But I think for people like you and me, it's just the best thing you can do
is start today. That's exactly what Ryan, my financial advisor, says. We had him actually on an earlier
episode. Whenever you like exit an individual position, like let's say you have a bunch of shares in
one company and you sell them, you should actually just put all that money directly into like
S&P 500 or like a diversified mutual fund or ETF or something like that. Instead of trying to
time the market, you're just taking the money that you have that was in one stock and diversifying
it and putting it back into the market today. And he's like, no matter what, that's better than
than just leaving it there and trying to find the right time. Like, or you can,
can like leg into it a little bit, but in general, that that is what he says. Yeah. Yeah. If you don't start
today, look at all the money that you're missing out on. There's a stat that we had where people in
general, if you don't invest now or you delay investing, you can miss out on half a million
dollars throughout your entire career. That's like money lost. That's like that you can invest into
like a down payment for a house. That's like real substantial money. I would say the power of
compounding is one of the core principles that I hear, like wealthy individuals make not like
those people who are like, get rich overnight, which I have never experienced. I don't have any friends
who do that. Like, that's not what we do in our circles. It's much more investing in yourself
and investing in things that will grow slowly and assuredly over time. It sounds like it's not
just the power of compounding, but it's also the value of taking action today. Yes. Or as soon as you
can. Have you heard that like the most successful investment,
investors are dead people.
Yeah, yeah, because they like forget about their portfolio that they started in like 1929.
And yeah, they just left it there and it just kept getting like reinvested.
I mean, it sounds grim, but it's like true.
It's just like if you just invest and like kind of forget about it and you're not like moving
things around like, I mean, obviously this is extreme, but like you're not day trading every
day.
Like who knows what's happening there.
Also, like I'm not someone who like wants to make a.
quick buck. You know what I mean? Like, I don't want it. Like, those things are so risky because,
like, of course, there's upside, but there's massive downside. And that's not the long game that
Gene and I talk about on this podcast. This next question is really interesting. I did not expect it.
Kind of like came out of nowhere, but the more I think about it, the more important I think it is.
And the question is, should you lend money to friends or family? Or is that the fastest way to lose
them. If your friend or family is in need and they need help, I think you can lend them money,
but there are certain parameters around what this actually means, parameters and expectations
with them and with yourself. And I think a really good rule of thumb here is don't lend money
that you cannot afford to lose. Because if there's any risk of you feeling resentful or like
angry at this person around the money that you are giving them, it's really not worth it.
Yeah, if it's money that you can't afford to lose and you actually are needing it back in a certain timeline or expecting it back for your own lifestyle, you're really putting that relationship at risk.
Think of it that way. Are you willing to put your relationship at risk if it's money that you can't afford to lose?
And we'll get to our next question right after this break.
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Okay, so the next question is, what is the easiest money mistake that people don't realize
that they're making in their 20s and 30s?
Okay, so I have a bit of a controversial answer that I think most people would not expect,
which is that I think young people, especially women, should take more risks in their
sort of like approach to money and building out their investment portfolio earlier on.
You don't have to be so serious when it comes to investing and almost think of it.
as a way to like explore your interests, right? So like if you're looking at building out a stock portfolio,
like what are things that you're interested in? And then kind of you can express that naturally in the way
that you invest. And I think that's a way, a good way to like approach investing so that it doesn't
feel so scary. And it almost feels like more of like a hobby or an interest or something that
you can participate in and have fun in and like build like a really positive relationship with
investing and money for the rest of your life. And I'm not saying like do really experimental
investments with like all of your money. I'm saying take a small portion of your money and think
of it as like your play money and it's your like learning account. I mean when I think back to
my own 20s, I feel like I've definitely made some really big money mistakes. It was more so like
my mindset and my sort of almost like emotion driven approach when it came to money. And I think a lot of
it was around the fact that like I felt like I didn't know enough to make the right decision sometimes
or like I felt like I had to learn more, like figure out the exact right thing to do. And like because
I didn't know the exact right thing to do the default for me was to do nothing, which ultimately
was the worst possible decision. So I think like that's a really big thing where a lot of people in
their 20s feel like they need to be in the perfect position or have the exact right answer of like
what to do when honestly the best thing you can do in those instances is to just make some sort
of decision and actually just act as opposed to waiting. Not making a decision is a decision.
Tell me about it. Yeah. And like I remember you and I talked a while ago about Rameet Sathie's book.
I will teach you how to be rich. And that was a light bulb moment for the both of us in different time periods.
Yeah. Because I think you and I struggled with the same.
issue, but like a couple years apart because, I mean, you're older and you're facing these issues
first. And you read that book and it was like kind of enlightening. Yeah. And it was like your first,
like if you don't know anything, get educated type of experience. And I can speak for myself. Like when I
read that book as a new grad, you recommended it to me. It was a moment where I was like, oh,
there's like these really tangible tips that you can do. And my biggest takeaway was like the guilt-free
spending. I was scared to spend money because I felt like I had none and that's because I didn't do
my own internal audit. But now I'm like, if I can put this money aside, I can enjoy my money,
I can go on the travel and the trips and do those things that I really like and feel good about it.
I can imagine that a lot of people who are watching us right now might be naturally like perfectionists.
You might be naturally someone who is always trying to like optimize or make things as good as they
possibly can be. And so you're waiting for that perfect opportunity or that perfect timing in the
market to like make these decisions and make them happen when in reality, I think a lot of times
when it comes to money, just being like 80% there, like having 80% of the information and then
just making a decision is the best actual outcome over the long term. Thank you guys so much
for tuning in to this episode of the Tiger Sisters. We hope you enjoyed our AMA.
where we addressed money, personal finance, all the things that people don't like talking about.
But honestly, money is such a big topic in relationships, in friendships, in family.
It's something that we should be talking about more.
And so if you enjoyed this conversation and you want to continue to talk about money with us,
please like, comment and subscribe, most importantly subscribe, so that you can get notifications
about our upcoming episodes.
Thank you guys.
We'll see you next time.
Bye.
