The Tiger Sisters Get Honest About Money: Going 50/50, Becoming Millionaires & Building Two Businesses

29 Sep 2026 · 49 min · 27 chapters

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In short

The Tiger Sisters (sisters and co-founders) discuss money upbringing, building two businesses together (Tiger Sisters podcast and Sisters Matcha), and how they manage sister + business relationships using a simple 50/50 “operating system,” plus practical personal-finance topics like LLC vs C-Corp/S-Corp and investing basics.

Guests

Cherie and Gina “Tiger Sisters” (older sister Gina and younger sister Cherie). They’re serial entrepreneurs: co-host the top-charting Tiger Sisters podcast and co-founded Sisters Matcha. Backgrounds include immigrant/tiger-parent upbringing focused on education; Cherie worked in finance (mentions Goldman Sachs) and created content during school; Gina worked at Snapchat for ~6.5 years before co-founding.

Key claims

Financial independence was instilled as “freedom from bad situations.” They keep finances aligned via 50/50 rules and one cohesive narrative across podcast + matcha. They’re scrappy/bootstrapped early; they feel “rich” as schedule freedom, not a number. They emphasize intentional money conversations and investing in diversified ETFs.

Notable examples

Sisters Matcha is small-batch first-harvest matcha from a single Kyoto farm (13th-generation; Daiki-san reviving aging farms). They describe corporate-to-founder inflection points (Snap/finance exits) and discuss their entity setup (podcast C-Corp; personal brand LLC; no salary yet for one).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Understanding the Tiger Sisters' Money Background

0:48 to 1:50

The Tiger Sisters share their childhood experiences and lessons learned about money growing up with immigrant parents.

“I'm thrilled for today's conversation because Sisters in Business Together, you guys have built such a successful podcast.”

Financial Independence and Its Importance

1:50 to 3:00

Discussion on the drive for financial independence shaped by their upbringing and how it influenced their career choices.

“Well, so Gina and I are seven years apart.”

The Contrast Between Their Businesses

3:00 to 4:48

Exploration of the differences between their podcast and matcha business, focusing on profitability and scalability.

“We worked really hard in college and getting that job after school.”

The Unique Nature of Sisters Matcha

4:48 to 6:40

The Tiger Sisters explain their matcha company’s premium product focus and limited scalability due to sourcing practices.

“From a financial perspective, I am curious, which of those businesses is more lucrative?”

Heritage and Environmental Impact of Matcha Farming

6:40 to 8:23

Discussion on the cultural significance and environmental challenges faced by matcha farming in Japan.

“because if you look at our podcast business or our media business, Tiger Sisters and Sisters Matcha, they're actually complete opposites.”

Operating System for Sister Dynamics

8:23 to 9:38

The sisters discuss their operating system for managing business and personal relationships, emphasizing communication and equality.

“And we think it's so special and important in the world that we want to bring it to as many people as possible.”

Insights on Shared Business Practices

9:38 to 14:00

The Tiger Sisters and Mary discuss their approach to sharing brand deals and managing finances within their businesses.

“At what point in starting the podcast were you like, oh, we actually might need some written rules, like a little constitution between the two of us?”

Business Structure Insights

14:00 to 15:00

Learn about different business structures like S-Corps and C-Corps.

“It's part of what we're passionate about.”

The Importance of Financial Decisions

15:00 to 16:20

Discussing the financial implications of business structures and their maintenance.

“I get that question all the time, like S-Corp, C-Corp, or LLC.”

Women Discussing Money

16:20 to 17:20

Exploring how women entrepreneurs are increasingly discussing money matters.

“Or even if you are starting to make money on the side, consider an LLC.”
Show all 27 chapters

Bootstrapping and Scrappiness

17:20 to 18:30

Insights on bootstrapping businesses and the scrappy mentality required.

“So up until even today, we are the two only full-time employees of our own company.”

The Drive Behind Their Goals

18:30 to 19:40

Understanding the urgency and purpose driving their entrepreneurial journey.

“And I kind of think about it like if, you know, it's a small company and you're driving the bus and there's no one driving the bus.”

Transitioning from Corporate to Entrepreneurship

19:40 to 21:20

Discussing the fears and motivations behind leaving stable jobs for entrepreneurship.

“And I feel like empowering women to use their expertise and their platforms for good is also what you guys are doing by giving them the tools to build businesses and things like that.”

Creating Financial Stability Before the Leap

21:20 to 24:00

The importance of financial stability before making the leap into entrepreneurship.

“So I'm curious what you guys had set up.”

Reinventing Yourself at Any Age

24:00 to 26:40

How to embrace reinvention and career changes at any stage of life.

“Like we needed to have that high paying job because we didn't have a plan B or anything to fall back on with family or anything.”

Defining Wealth and Happiness

26:40 to 28:00

Exploring the relationship between wealth, happiness, and personal mindset.

“It's great to have a 401k if you can get a job out of college.”

Defining Wealth and Freedom

28:00 to 30:42

Explore the personal definitions of wealth and the freedoms it brings.

“You both became self-made millionaires by the time you were 26.”

Lessons from Ivy League Education

30:42 to 33:19

Discuss the invaluable lessons learned from Ivy League experiences beyond academics.

“Like everyone thinks that being a founder, the burnout culture is very normalized.”

Creating Supportive Conversations About Money

33:19 to 35:00

Learn about the importance of intentional conversations around finance and business.

“that will persist kind of through the rest of your life.”

Stereotypes and Experiences at Ivy League Schools

35:00 to 41:16

Delve into the stereotypes and personal experiences at different Ivy League institutions.

“Yeah, I think it's finding those like-minded people and being intentional about creating the moments where you can spend time together.”

Valuable Lessons from Business School

41:16 to 42:00

Reflect on misconceptions about business school and its true value in careers.

“I thought of one that was actually even before I joined business school.”

The Value of Business School

42:00 to 42:40

Discussing the worth of business school and its impact on their careers.

“I feel like now everyone's saying business school isn't worth it.”

Personal Investment Strategies

42:40 to 43:35

Exploring personal finance choices including ETFs and private investing.

“So we could literally talk for hours, but I ask all of my guests these last two questions.”

Exciting Ventures in Private Investing

43:35 to 44:29

Highlighting promising startups and their innovative business models.

“One of them, actually you may know, do you know Cooper?”

Finding Balance in Business and Life

44:29 to 45:56

Struggling to balance personal hobbies with the demands of business.

“Y 'all are both so mission driven, which is exciting.”

Integrating Personal Interests into Business

45:56 to 47:29

Discussing how personal passions can enhance their business.

“Honestly, this is so lame, but I really love what we do.”

Future Plans for Tiger Sisters and Growth

47:29 to 48:26

Discussing the long-term vision and plans for their business ventures.

“And I'm sure a lot of people at the Ivy's like are interested in art.”
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Transcript

Automatic transcript. May contain errors.

0:00The following podcast is a Dear Media production. Hey, y 'all. Welcome to Growing Interest. Today, I'm sitting down with the Tiger Sisters, two serial entrepreneurs with the top of the charts podcast and a sister matcha brand. But what fascinates me most is that they're sisters. As you know, I have three sisters myself, and we're starting to build businesses together and build a brand together. And so going into this episode, my intention is pretty much that, to figure out how they are dealing with interpersonal financial relationships. We all know money is hard to talk about, and we all know that sometimes family dynamics are hard to deal with.

0:36So I'm really going into this eyes wide open to figure out how they have structured their sister relationship, how they separate that from their business relationship, and where the money fits into it all. All right, let's get into it, y 'all. Let's grow.

0:54Welcome to the show, Tiger Sisters. Thank you. We're so excited to be here. Oh my gosh. I'm thrilled for today's conversation because Sisters in Business Together, you guys have built such a successful podcast. Thank you. So exciting. And now you're building or you launched Sisters Macho, which is y 'all's business together. So I'm excited to see how the interpersonal relationship works with building a business. Obviously, I have three sisters. and we work together, also live together, also do everything together. So it's insane. You guys get it. Yeah. But I want to start with a question that I ask a lot of my guests, which is your money story, kind of where you came from, how you grew up with money.

1:34And you guys grew up with first generation tiger parenting, hence the name Tiger Sisters, which is so clever. But I'm curious what messaging you absorbed around money specifically and which ones you had to unlearn, you know, as you entered business together. So much to unlearn. Well, so Gina and I are seven years apart. I'm the younger sister and she's the older sister. So she left for college when I was 10, like when I was in fifth grade. And so there has been a part of our life where we've, you know, had that relationship growing up and she was my babysitter. But then a lot of my childhood too was like kind of like an only child.

2:12But I would say a similarity between us is that growing up with immigrant parents and also a tiger mom, so much of what we learned was based around prioritizing our education, which is why I think the tiger mom, tiger sisters really make sense for us, where it's education or going to good school, getting good grades, getting the job out of graduation was just like, that is the way to succeed and grow in socioeconomic mobility. And so that was where we started from. We had to go to a good school. We didn't really have any backup plan or anything to fall back on. So it came from a place of like, you must do this or figure it out, which I think really served us.

3:00We worked really hard in college and getting that job after school. But I think going into adulthood And especially as you're a new grad, figuring out things on your own, like so much to unpack and unlearn when we become adults on our own and we get to choose how we want to spend and live our lives and have financial stability and financial independence. Yeah. And I think that was a really big thing that we learned growing up with a single mom, just kind of observing that and living with that every single day. I think something we really embodied almost subconsciously was building financial stability for yourself and being financially independent because that was what allowed our mom to change her life in a positive way, right?

3:45For her to leave her a bad situation. And so for us, that's something that we've always, always sort of lived our lives by and really prioritized. So even for, you know, our first jobs out of school, that was something that we knew we have to optimize for something that isn't just interesting to us, but something where we can financially support ourselves. No, like, because like, I was like, I need a high paying job out of school to like pay my loans. Like, it's literally not an option. I have like no other choice. And like, I really loved my first job out of school, but I felt like that was totally a constraint for me.

4:22Whereas I could only find or go through these certain industries where I could have my own check in that way. I mean, that's the only reason I entered finance. Let's be real. I was like the highest paying check. And financial independence equals freedom from bad situations that was instilled in you from a very young age. Flash forward now, you have two huge major businesses, Macho Company, top business podcast. From a financial perspective, I am curious, which of those businesses is more lucrative? Absolutely, the podcast. It's been in biz for a while. And the backstory around the matcha business where Gina and I started our podcast around two years ago, and then the matcha business is about a year and a half old, but it came from very, very different origins.

5:10So we have a matcha company together called Sisters Matcha. And I interned on a Japanese matcha farm when I was a student between my first and second year. So like I lived on the farm, like literally it's in the middle of nowhere, an hour and a half outside of Kyoto, like the most beautiful place where like the neighbors are like 80 years old and don't speak any English. And I've been like, you know, 13th generation tea farmers. It's like a really beautiful like heritage. And I became so, so deeply ingrained in that matcha world. And Jean and I wanted to bring it to life with Sisters Matcha. That being said, it is so, I mean, it's a very premium product because there's like different types.

5:54Let me nerd out for one second. Please nerd out on the matcha. Different types of matcha because there's more commercial farming where all the land is like very flat and you can have these like giant tractors and you can get large grade, large amounts of matcha, whereas the farm that I lived on is in like the mountainside hills of Kyoto. And so there's no industrial farming there. It's all handpicked and very, very small batch. So in that way, our matcha company has a very limited, has a constraint on how much we can have. So we say our matcha is small batch, it's premium, it's first harvest. And so it's really something we feel very, very passionately about, but we know in our heart of hearts, there's not really a scale to it.

6:37There's a limit to how much it can scale. I mean, I actually think it's funny because if you look at our podcast business or our media business, Tiger Sisters and Sisters Matcha, they're actually complete opposites. And the fact that we designed and strategize and built Tiger Sisters so that it would be a huge scale, right? We talk about our goal is to empower and uplift 1 billion women. So to do that, you need to get to a pretty big scale versus Sisters Matcha is by design, we only source from that one family farm that we worked and lived on. And so unless we really change the sort of values of the Sisters Matcha company, it's never meant to scale.

7:19Right. So every single time we source from them, we sell out because there's just not that much matcha available from that one farm. And that's by design. It's more of a passion of you guys, It's like a passion project. Like, are you guys making money off of it? We make money off of it, but that's really not the goal of it, to be honest. It's more so that we love the story. We love the heritage. There's so much that they're doing at the farm, which is they're reinvigorating the farming culture of that area. Because a lot of those farms, like Sheree said, they're 13th generation farms. Right. That at this point, the people, you know, the children who are our age, they don't want to live in the countryside anymore.

8:00They don't want to run a farm. They want to move to the city and have corporate jobs. So a lot of those farms are becoming almost abandoned and they're losing that entire culture. And so the farmer that we work with, he's coming in and he's sort of helping to revive those farms. So it's just something that we've had the privilege of being exposed to and being really close to. And we think it's so special and important in the world that we want to bring it to as many people as possible. yeah there's this huge problem of an aging population in japan okay where so many like jean said of these farmers they're like 80 years old and no one will take over their farm and so um the farmer that we work with daiki san and he's like an entrepreneur in his own right he is um expanding his farm and making sure that um it's done in a way that really honors the people who owned it before okay oh my gosh i didn't know all of this history about it there's so much geographic like nerdy component to it i'm like so so passionate about okay wait last question about the matcha because I'm just so hooked.

9:01When is the best season? Just so we know. It's first harvest, which is spring. And first harvest is when the leaves are the most supple and have the most nutrients. They're the most nutrient dense. And what happens is when they harvest it, they shave it off and they collect it. And that is the first harvest matcha. Is y 'all's podcast popular in Tokyo? Like, does it reach that far? Actually, yeah. It is popular in Japan. Well, that would be cool to do like a live show on the farm. Wait. Wait a second. not to pun it but we love a pun no that would be sick and like give everyone your matcha combine the two brands oh my gosh okay i could talk about the matcha the whole time but we'll get back to what i'm supposed to ask you guys have talked about having an operating system between the two of you and this is where we get into like the sister dynamics yeah which is basically an agreed upon set of money rules that you abide by if a conflict does happen so i'm curious if you guys only created that because you entered business together?

9:56At what point in starting the podcast were you like, oh, we actually might need some written rules, like a little constitution between the two of us? And have you tried to implement, like, has it worked in implementation? Yeah. I love that you asked about it because I do think an operating system is something that is so important and everyone can have in pretty much all of their business relationships and even beyond because we have a business relationship and obviously a sister relationship. And it's very funny because as Sheree mentioned, we live together, we work together, and we pretty much do everything together.

10:32We vacation together, we go to the gym together, we willingly hang out with each other every time. It's like everything is combined. Which is interesting because now we're in our 30s, and the last time we lived together, she was 10 years old, and I was 16 or 17, and I went off to college. So it's very funny to come together again. And for me, at least, see Cherie as an adult and not only an adult, but a highly, highly competent adult. Right. I'm highly functioning. She's not 10 anymore. She's not 10 anymore. She's so amazing at what she does. Yeah. And for us, our, I guess, operating system honors that.

11:08It honors the fact that we are now both adults and we see each other as equals and as equal business partners. So for us, it's very simple. We're honestly just 50-50. So we've kept it really simple. But it's more so to say that for everyone who is going through building a business, it's more so the exercise of thinking about it and being intentional and saying what works for us versus what doesn't work for us. For us, it was keeping it simple. And being just overly communicative, like at the very beginning, whether it's a business partner or a family member. So if someone brings a brand deal, let's say 50-50, the person who brings it It doesn't get more.

11:47It's 50-50. And I would say that like we also we have Tiger Sisters and we also have our personal like Instagram accounts and TikTok accounts. Right. But it all is kind of just like one big bucket to us where we do 50-50 because I do more brand deals on my like Instagram account. But I would say like throughout my like content creation career, which has been over the last five years, Jean has brought so much value even in the behind the scenes. like when I'm writing like a script or something for like an ad read like I'll always ask Jean for help on it right and in that way like yes I am the person who is in front of the camera like doing an ad read for my Instagram or some sort of brand deal but like she brings so much more value that isn't on screen but is off screen and I think that deserves 50 50.

12:33Yeah I mean the Nader sisters are a little different because Brooks my older sister. I'm so curious. Yeah wait tell us. I'm really curious. I am really curious. How do other sisters do it? Our older sister, Brooks, kind of put us on the map. You know, she'd kill me if I didn't say that. She did put us on the map for real. And so she has obviously like millions of followers and it has much more celebrity than any of us. She is an EP on our show. So she kind of like spearheaded it. And we get so many, like most of my brand deals as it stands. Hopefully that's changing because I'm starting to be my own person on social media.

13:06But as it stands, most of my brand deals are sister deals. So it's like one brand will do a campaign with all of us. And usually Brooks gets much more than us, which is assumed. And then the younger three split it three ways, which sometimes is a point of contention because like we all have different engagement, different amount of followers and like different audiences. So I think that in season two, people will see also that like we're trying to find our own deals and our own identities. With four sisters, it's definitely a little bit bigger. That's why the operating system, I think, is so fascinating.

13:40It sounds like you guys, your values are so aligned. Does it come into one combined bank account for businesses or is it separate business bank accounts for Sisters Matcha and Tiger Sisters? It's all on pop because we see Sisters Matcha as a broader part of our narrative of Tiger Sisters, right? So it's kind of all part of the same story. It's part of our offering. It's part of what we're passionate about. And it's just the two of us, too. We don't have any outside investors or investment in either Tiger Sisters or Sisters Matcha. And so to us, they really feel like the same sort of cohesive storyline in that way.

14:17That makes sense. And so Giuga, I assume it's like an S-corp. that you guys pay yourself a salary out of. Okay. Love it. Is that what you're doing? I have outside investors for Mary and Pip. All of that is completely separate. I actually don't pay myself a salary yet because I'm making money on brand deals and stuff. So I just obviously don't want to dip into company money. We've only raised, you know, our friends and family we're raising again right now. So that's a C-Corp. So that's a C-Corp. Yep, exactly. Because there's equity involved. And then my LLC for my personal brand deals is actually still an LLC.

14:50I'm only just this year crossing that threshold of like making enough to make the extra paperwork and the extra tax accounting worth it to pay myself a salary and get those tax incentives. Yay! I know! Thanks, guys! Proud of you! I officially crossed the threshold. Proud of you. I get that question all the time, like S-Corp, C-Corp, or LLC. And I think a lot of people jump right in and they're like, oh, if I have an S-Corp, I can have all these tax incentives. But an individual who's making under, let's say, 200K, like does not need to worry themselves with an S-Corp. Yeah. It's so funny. I was just having this conversation with two of my girlfriends on a, we did a girls trip in Portugal.

15:28And we had this exact conversation, like one of my girlfriends was grilling the other one about, should I do an S-Corp? Do I need to do this? And she was, I was like, I should film this. The reason to do an S-Corp is because you can basically pay yourself. if I paid myself$100 ,000 salary and I was making$500 ,000 this year, I would only be taxed on $400 ,000 of it. Like you basically lower your tax bill by paying yourself a salary. And the negatives are it's a little bit more to upkeep. It costs a little bit more to maintain. And you really do need kind of a tax accountant to be helping you run that payroll.

16:05You have to run payroll on yourself. So it's a way like, you know, cost benefit analysis like anything else. But I always say like, unless you're making bank, you know, an LLC should be just fine. Yeah. Well, it's a good place to start. Yeah. I also love that we're talking about it now and that you brought up that you talked about it with your girlfriends in Portugal on your trip because like it's the conversation that like women founders, entrepreneurs and like business owners are having probably in private because you like talk, you have a girls chat or like you're talking to your other friends who are founders.

16:34It's good because we're talking about it, but now we're making it more public that like even if people aren't going to start a business in the next year or so, at least it's like in the back of their mind, it's percolating that like when I do start a business, I should look into that. Yeah. Or even if you are starting to make money on the side, consider an LLC. Just separate your finances so you can write stuff off. Yeah, I agree. I mean, that's the whole point of this podcast, right? Like just normalize money conversations. Wait, you did say something. Y 'all haven't raised any money. So that's called bootstrapping for those listening, when you just use all of your own money.

17:08Can you, I don't know if you guys know this off the top of your head, but how much money have you guys invested into the podcast or Sisters Matcha? I mean, a good amount. Luckily, the two of us are just by nature similar to you. We're really scrappy. Yeah. So up until even today, we are the two only full-time employees of our own company. Edit, you do it all. Well, so up until the beginning of this year, Sheree edited every single episode. Shut up. Sheree. It was a lot. I'm so impressed. Thank you. I wish I could clone you. And she was making short form. And we were filming the episodes and we were writing all the episodes.

17:45Like it was crazy. So now we've started to work with a part-time producer and now we've started to work with a part-time editor. So we have built up some of these systems. Yeah. But I think the reason why we have built up a really good machine is because we did everything ourselves at the beginning. Even though I was really probably only like 25 % as good as editing as Cherie was, I was still doing it. I was still editing some episodes so that we could both learn the craft and know what good looks like basically or have an opinion ourselves of what we think good looks like. Yeah. In your taste.

18:19And I think when you're being like super scrappy too, and you're like, this is my own money on the line, like it kind of puts you in a mindset where you're like, I have to, it's like kind of do or die. It's just like, it's the two of us. And I kind of think about it like if, you know, it's a small company and you're driving the bus and there's no one driving the bus. If Jean doesn't do it, I got to do it. If I'm not going to do it, she's going to do it. Or it's just not going to happen. Yeah. Yeah. Like, whereas like if you're working at a big company, it's like I think about it like you're on a boat and like everyone's rowing.

18:48And if you're like taking a break, the boat still moves forward. Right. But when it's like scrappy, the two of us and your own money, it's just like, wow, kind of everything is on the line and it makes it way more exciting and way more scary. Yeah. Do you guys work better that way with the pressure? I don't know. I think I'm just used to it. I've always I've always worked that way. So we just put so much pressure on ourselves, sometimes unnecessarily so. But I think we are just really used to that. And we also feel, honestly, a lot of urgency. Right. We feel like we have this huge goal of uplifting, empowering a billion women.

19:22And we just want to run at that with as much energy as we can. I'm like, if I have got to do this, I have these hours in the day. And it is like my voice and like my videos that are helping people make more informed decisions or, you know choose whether or not they want to study computer science versus something else or whatever it is I'm just like this is like kind of the greatest goal of my lifetime and what an honor it is to be like a part of someone's journey in that way even if it is a very small part that I feel very called to do this whereas like I could go back and work my corporate job but would I be working this hard and this like insanely hell no yeah like it's not the same I mean what you guys both just said there is like y 'all have a purpose why like having that tangible we want to make an impact on 1 billion women and then having the sense of purpose of like, I have this platform.

20:14I was given this platform for a reason. I built it myself for a reason. I'm going to use it for good. And I feel like empowering women to use their expertise and their platforms for good is also what you guys are doing by giving them the tools to build businesses and things like that. So it's truly inspiring. I want to talk about y 'all's inflection point because I too left a prestigious job to enter this grind and a half of building a business and, you know, having much more of a purpose, but coming with a lot more responsibility. You both left very prestigious, you know, high ranking jobs, Snap, Goldman Sachs, LinkedIn, for something that was super uncertain.

20:50When I left Deutsche Bank, I had a bit of a cushion. I think I had 20 grand in my high yield savings account. And then I had, I think like, you know, whatever it was in my 401k from work, but it wasn't a huge cushion at all. You know, I was talking to a friend who's now leaving. She's looking to leave her Wall Street job. And she's like, I have 100K in savings. Is that good? I'm like, that's way too much. Put it to work. What are you doing? But yeah, invest that money. But it is really, really scary. And I resonate with her. I was super scared leaving the stability of a paycheck. So I'm curious what you guys had set up.

21:24What time did you realize like, oh my gosh, it's time for me to go out on my own. Was one of you more scared than the other before you made the jump? I want to get into all of it. Yeah. I came at it from a different point. It was less like me leaving a job because I had just graduated from business school. That's right. So that was already like a transition point for me to be like, okay, I'm in exploration mode. Like the world is my oyster. Like you go to like Stanford's business school and like, you know, these professors are in your ear. Like, what are you going to do to change the world? Like every single day.

21:53And so, you know, I come in with that attitude. But I would say like because I was in that transition point and I had been creating content before that, I already had it like growing in my mind that I'm like, I want to do something in the creator world. I wasn't sure whether or not like I wanted to build a startup for creators or help creators in some way. But at that point that I was graduating, Jean was also going through her own inflection point because she worked at Snapchat for six years. And I'll let you talk about that. But like, we really wanted to come together and do something. And so I think it's probably a lot scarier for Jean.

22:25I think I had a more similar experience to you where I had come straight from corporate and now you were in corporate for five years, right? Yes. So I had been in corporate for 15 years. Wow. So if you can imagine, I catch myself, I'm like, oh, I'm so corporate pilled. Yeah. Because I'm like doing something. I'm like, oh, that's so corporate. Like, why am I still doing that now? But she's like, hope you are well. Yeah. Okay, but actually, side note, it is very good to be professional. Yeah. Which like I will honor our experience and say that these days, it's so valuable to have that experience to fall back on.

22:59And I think a lot of people don't have that and it really helps you stand apart. Yeah. When you're entering. You can kind of tell when someone hasn't spent any time in corporate like at all. So you were leaving Snap. Yes. So I had been at Snap at that point for six and a half years, which in tech is like 10 lifetimes. Right. And I had just, I was just really at that point ready to try something new. I'd been in tech for a really long time. And I felt like I had had so many opportunities through that. And I'd done so many things that I didn't even imagine I would ever do. And Sheree had always said to me that she wanted to start a business together.

23:37And it was always me that was like, no, like the time's not right. The time's not right. Like I'm doing great at Snap. Like I don't want to leave. and it just so happened that it kind of all came together where she was graduating and I was ready to try something new. 15 years you probably had a healthy cushion. Yes. And you were working while you were in business school so you had you been making money or no? Well creating content and doing brand deals while I was a student but I was working for five years before going to business school and I would say that's like in addition to like having that professional background I would say like creating that cushion for yourself, like kind of how we started the conversation.

24:15Like we needed to have that high paying job because we didn't have a plan B or anything to fall back on with family or anything. And also like to pay off student loans. But then like unwittingly, like we created a cushion for ourselves so that 15 years after kind of like slaving away in a corporate job, she could kind of like do whatever she wants. I think a lot of the times too, like when people are in their career for five, 10, 15 years, I see a lot of my peers who take sabbaticals now they take like year long or micro retirement right kind of to kind of like explore like okay this chapter of my life this is what i learned what do i want to do for the next chapter of my life and life is so long so like a lot of my friends now are like living in europe for like months like figuring it out which they have the luxury to do that because they set themselves up with this job that they grinded away at for a while the tables have turned since our even our parents like we're growing up.

25:08But I feel like now the workforce is so dynamic. It's changing so fast. I mean, in 10 years, the job you're doing now very well might not exist. And you need to be OK with that. And in order to be comfortable with that, it goes back to the beginning. Financial stability and security is how you're going to feel calm in this chaos of the world that's changing around us so fast. If you have a cushion and a relationship with money that can withstand change, then I think you're set and you can take micro retirement because life is long and it's short if you slave away in corporate America for 50 years and then all of a sudden it's over.

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25:45But it's so long. If you think about it in phases, you don't have to be married to your career that you have when you graduate college. I mean, we're eight, we're 21 years old, for God's sakes, when we graduate, like no one knows what they want to do. I mean, yeah, when I graduated and I went to work at Goldman Sachs, I thought that this was my career for the rest of my life. Like I was like, I am a finance girly through and through. My life's dream was to become a partner at Goldman Sachs. And then two years later, I'm working in mobile gaming on Farmville, which is something that didn't even exist five years ago.

26:18Literally, mobile gaming did not even exist. So crazy. So I mean, that's something that we talk about all the time on Tiger Sisters, which is, yes, you need to have your financial grounding, but also the concept that you can reinvent yourself at any time. And you're such a good example of this because you've now reinvented yourself and you're a multi-hyphenate. But a lot of it is also based on your first career. That's where you get the credibility. Exactly. Yeah. And the experience and the cushion. It's great to have a 401k if you can get a job out of college. It's great to get that match. There's so many lessons.

26:53And I think it's really easy for young people to be like, I just want to start living my life because they're so focused on other people on Instagram, just being entrepreneurs. And it seems like everyone has a business and everyone's a millionaire and everyone's doing this. We have a lot of ambassadors at Mary and Pip, and I encourage them, like, if you getting a job out of college is a good thing. You can pivot when I pivoted when I was 26. And that's still really young. I could have stayed five years. I was I was thrown around five years on Wall Street and someone, one of my investors or something was like, maybe don't flex that.

27:23Like, that's not that long. They were like, I mean, you have experience, but like five years is like, you're not geriatric. You don't have all this wisdom. I was like, oh yeah, maybe you're right. But my whole point is five years is better than nothing. I'm so proud to say that. Well, anyway, for your audience, like for me, I was 35 when I left Snapchat and started Tiger Sisters with Cherie. And I left my company and I ended my engagement at the same time. And so like, it was like a whole, there were a lot of things changing. A lot of things were happening. I moved into her house. Yeah. And so I guess it's, it's just all to say back to the idea of you can reinvent yourself at any time and don't be afraid no matter what age you are.

28:02You both became self-made millionaires by the time you were 26. I want to know at what point, because everyone always says like, does money buy happiness? At what point do you actually feel rich? Was there a point, an inflection point where you were like, oh my gosh, like we've made it? Was it being able to spend without looking at your credit card bill or without your stomach dropping? Or I'm curious what that moment felt like. I would say I don't know if that moment has come yet. And I don't mean to say that as like a bad thing. I think it's just so much of the mindset that I've grown up with to be like super frugal and to save a lot.

28:40And I just even remember having to unlearn as like a new grad. I was like, okay like public transit for like right I didn't even have a car until like two years ago where I bought my first car on my own my god which was like late late 20s like I've been taking public transit I've been living in cities and so that definitely helped and I didn't need a car in that way but I just feel like I've grown up in a very frugal mindset and so when I think about money and like feeling rich I guess like it's not really like a money number but more that like now Jean and I work together and live together and we're on our own schedule, we can kind of control our own day to day.

29:21I think that feels more rich to me than like a number. I'm also like not someone who spends a lot of money on like clothes. I do spend a lot of money on experiences and trips, which I love. But I would say like the material things, like I drive a Toyota. Toyota Hybrid. Come on, put some respect on her. We are eco-friendly over here. cross hybrid Pacific Pearl. That's her car's name. Pacific Pearl. How cute on the PCH. I can see Pearl whipping it. So like it's not really a number in that way. But I just I think the richest thing is that like we I can wake up at like 9 a.m. and then go to a gym class and then start working and control my own schedule and still work really hard, but then not be forced to jump on like a 7 a.m.

30:05meeting. Yes, it's the freedom. After 15 years in corporate, I can say It is 100 % the freedom to be able to schedule a facial in the middle of the day, in the middle of the week. Or if there's a class I want to go to, like a gym class, going in the middle of the day and not worrying about having to be on Slack, like having to check your messages, having to being worried about getting back to someone because we are our own bosses. And to me, that is the ultimate freedom. Can't pay for it. Oh, my God. It is. I completely agree. It's the best feeling in the entire world. It is the best feeling. It's awesome.

30:41And I was talking about this with someone else. Like everyone thinks that being a founder, the burnout culture is very normalized. And you can work 24-7. But to your point, I can wake up at 10. And if I need to stay up a little later, then like I'm going to wake up at 10. You know what I mean? Or if going to a party is good for business, then like I'm going to go. It's work. It's work. It's all work. Skipping into the habits and lessons you guys have learned from your Ivy League degrees. So there is four degrees between the two of you, Ivy League degrees between the two of you, which is so impressive.

31:13You've said that you've spent a combined$500 ,000 on those degrees, which I assume is money very well spent. So what is one thing that the Ivies have taught you guys, each of you, that money that you can't learn outside of outside of those Ivy Leagues? Basically, assuming the money was worth it. Yeah. What's one thing each of you have learned that you probably couldn't have learned in the real world if you didn't go? I mean, I think one of the main reasons why people go to business school is not for the courses or the classwork. Because in the first year, you're taking finance 101 or accounting 101, which you can go to YouTube and actually take that same coursework.

31:55It's really not that. It's so much more of the experience of the people that you meet and the relationships that you build, which are kind of priceless because you don't know where that's going to lead. It could be you meet your founder or your co-founder for your company, or you meet someone who invests in your company, who's in your class. I think just the caliber of people who are smart, ambitious, but also really kind in my program, I don't think you could kind of find that in a different environment in such a compact way. Right. That makes sense. Yeah. I think the experience really opens the aperture of what you understand both about people and understand about the world because you get to know people who are so different from you and you get to know them really well in a very intimate way that only comes from, you know, sitting next to the same person every single day for a year in class or going on a trip together to Morocco and taking a road trip through Morocco, which as four, it was like five women.

32:58I don't know if it's, it may have been a little ill-advised, but it's those kinds of experiences that I think are, it's kind of like investing early on. And then later on, you're like, wow, I didn't realize that all of these, all this time that I thought was just socializing was actually building these really strong relationships that will persist kind of through the rest of your life. Yeah. And I would say like you're starting the friendship off with your classmates in like a very like we get to know each other and it's all fun kind of way. But then you really learn about their character and what they're interested in.

33:37And then like five years later, you don't know how. But like, okay, now we're like business partners or we're talking about something. and S-Core, like LLC, like those things come up. And it just is a very natural conversation where you flow through all those different parts of like the things that we're interested in, but it doesn't feel transactional. I love that. And it seems like, because obviously, you know, not everyone can get into these schools or pay for these schools, but it seems like one of the biggest value adds of these schools is those conversations about business, about money. You're learning how to talk about these things in rooms with people who presumably had parents who talked about these things or are in an environment with professors who are encouraging conversations about these things, which was what you guys are doing with Tiger Sisters.

34:20What I'm trying to do with this and with Mary and Pip is just for anyone out there listening who's like, oh, well, I'll never be able to go to an Ivy League. It's like, we'll go to a live, like talk to anyone at work about these things and just start bringing up these hard. If you don't know what an S-Corp is, ask someone and it's likely they don't know either. And like you guys can figure it out together. And I think that that is what's so exciting about having access to some of this education online is like you can take that and then go bring it to your friends and have like a girl's night with wine and be like, let's talk about money and like talk about how we're managing it or how to start a business.

34:57Like, let's look it up together before and figure it out, which is so exciting. Yeah, I think it's finding those like-minded people and being intentional about creating the moments where you can spend time together. So for me, I think going to business school can be a sort of a shortcut for that. Because for me, I have this group of women that I went to HBS with. And every year we do a retreat. We call it Harvard Beach Club. Love. Chic. I make all the merch for it. I was about to say, there better be merch. I'll just buy it. The merch is actually really good. I'll show it to you later. Please.

35:29But yeah, every year we get together. It's about 20 of us. And we have these really honest conversations that even amongst us, we're always like, wow, I never have these conversations with anyone else. But we create that space for ourselves where we'll even assign one or two people to be the moderators. I love it. We'll be like, okay, this is the finance conversation. Kick it off. And they start asking us, what do you do with your money? Who's doing trusts? Who's doing prenups? Who's doing postnups? And it's a very candid conversation. I think you have to just be intentional and sort of put yourself out there.

36:03to seek that. And if it's not coming to you, maybe you're the one that creates it. Exactly. Yeah. You host the book club or host the dinner or, you know, it's just being vulnerable with yourself and your own, like being able to say, I don't, I didn't know this or I don't know this and it's okay to not know. I think that puts people's guard down and it's like, okay, we can actually, you know, talk about this. I'm going to have like some fun and play a little game. It's not really a game, but let's pretend that we're in the mean girls like lunchroom. Okay. I'm sure there's got to be stereotypes for each Ivy League, right?

36:36Like types of majors, jobs, whatever it is. Between the four, rattle off the four really quick. But then between the four, what is kind of like the stereotypical amongst the Ivy League crew of types of students at each school? Okay. I'll kick it off. As someone who went to Harvard herself, I can for sure say that at least 50 % of people who go to Harvard are insufferable. Like kind of in the best way. Right. But also in the worst way. In the best and the worst way. So some of them really mean well, and they just really want to learn everything and know everything. But a side effect of that is maybe the other half of those people are just total know-it-alls.

37:13Oh my gosh. And are not really looking to understand anything about you. Well, also like I feel like there's a stereotype too, if like people have gone to Harvard, they're like, they don't say they've gone to Harvard. They're like, I went to a school outside of Boston. And I'm like, where? On the East Coast. On the East Coast. I'm like, MIT. And they're like, no, I'm like, Boston University. I'm like, no. I'm like, okay, so Harvard. I'm like, just say Harvard. Just say it. It's like so weird. At this point. Right? So I would agree with that. That is funny. And then I went to Barnard, which is part of Columbia University for undergrad.

37:43And I would say being in New York City, it was like very Gossip Girl-esque. Or like a lot of people who wanted it to be like Gossip Girl. I think it's kind of hard going to school in the city. Like it seems very glamorous, but you're also like in the middle of Manhattan and you're like, I'm 18. What am I supposed to do by myself here? It's kind of crazy. So expensive. Yeah. So expensive. And I think like there were a lot of sharp elbows, as you can imagine. Like you're going to school in Manhattan. There's like only limited amount of internships. Everyone thinks they're like the next Wall Street, like bro or girl.

38:11And I'm like, there's a lot of sharp elbows. So I would say it was like very cutthroat competition in not the healthiest way. Yeah. That's toxic a little bit. I would say so. But it was so funny, like, seeing her college experience through my eyes. Like, I would see her and her girlfriends would be going out to dinner at, like, Budokan or, like, Nobu or, like, all these, like, really fancy restaurants. And I was like, how are you guys doing this? I was also struggling because, like, all my friends, like, had money to, like, pay for these dinners. And I was just like, what do I do? Yeah. No, that's, like, one of the biggest stressors in college.

38:45I had no money. And I was literally, like, writing essays for extra checks. I was like, I have people to work. No, literally. I was like doing anything to make a buck. Nannying, babysitting, just so I could go on spring break. Yeah. So I can't imagine New York City. I would be so overwhelmed. My little sister went to Fordham and I don't know how she did it. She was modeling on the side. I feel like you have to just double hustle. You have to have a job. Well, Jean had like a zillion jobs when she was an undergrad. I had eight jobs at Dartmouth. Oh my gosh. Eight? Yes. Okay, you win. Throughout the four years.

39:17Dartmouth. What was Dartmouth like? Any stereotypes there? It was amazing. Okay. I loved it. The stereotype is that it is extremely crunchy, which is true. It's in the middle of nowhere in New Hampshire. Granola, IV. So granola. It's basically white. Everyone's wearing tevas. There's no bars and it's all Greek life. So basically, and it's the middle of nowhere. So you just really, really bond and it's a pretty small school. So you get to know each other really, really well. Yeah. Sounds like camp. yeah oh my gosh and ironic because we have this thing called sophomore summer where the summer between your sophomore and junior years all the sophomores stay on campus and it's just you guys and you become like everyone becomes like the president of your for uh sorority or fraternity or your clubs and you like run the campus it's it's so fun it really needs to be a show or movie about sophomore like darkness we all should maybe that's your next ventures like producing and write a little show.

40:19Mindy Kaling writes it. Yes. Only Mindy. That's the only one. She was my sorority sister. No way. Oh my gosh. I don't know if she knows that. Mindy. FYI. Now she knows it. We were sorority sisters. Stop. Literally what sororities were y 'all in? Mine was Sigma Dell, which is a local sorority at Dartmouth, which is okay. I'm like obsessed with Dartmouth. So now you've gotten me started. I love, but it's basically, it's basically a local sorority means you're not affiliated with any national. So you could do whatever you want. So we would actually hold campus-wide parties. So we were basically a fraternity, which is pros and cons.

40:58I mean, but fraternity without the hazing. It's like, I'll take it. Because then you left your Ivies, you worked at prestigious jobs between Silicon Valley and these Ivies. Was there any like misconception or misconstrued financial advice that you guys received that when you left and started doing it on your own, you were like, oh, it's actually not that way? I thought of one that was actually even before I joined business school. When I got into HBS, I was working in Silicon Valley. I was working at Zynga, which makes Farmville. And I remember most of the people that I worked with were like, why are you going to business school?

41:37That's a waste of your time. That's a waste of money. You are already a product manager in Silicon Valley. It's 2013 or what was it? I guess it was 2014 at the time. They're like, if you take any time away from this, you are losing out on your career and you're already on the fast track. So luckily I didn't follow that advice. But for me, going from Silicon Valley to business school was actually very counter, counterculture. Yeah. I feel like now everyone's saying business school isn't worth it. Would you disagree? I would disagree. I would disagree. Well, I think also the programs that we went to, because it's super strong in its network of alumni and also like our classmates, our peers and professors, I would say because of that, it was worth it for us.

42:22Right. It is a huge burden of debt that you do have to take on if you don't go to one of those schools. So I would definitely investigate and think very deeply. Yeah. It's a trade off for sure. your cushion, get a good rate, interest rate on the loan. Yes. Things like that. So interesting. Okay. So we could literally talk for hours, but I ask all of my guests these last two questions. So the first is what are each of you investing in? And this is more on the personal finance side. I would say mine is pretty boring. Like it's nothing like crazy or sexy. I think there's beauty in the simplicity and the boring when it comes to investing.

42:59So it's a lot of ETFs, which makes it very diversified. So I'm not just choosing one stock. I'm of the mind if you choose a stock, it's really easy to choose it wrong. Totally. And I'm not very risk-taking in that way. So I would say just broad-based ETFs based on the S &P. Amazing. I agree completely. This is not financial advice. This is not financial advice. I agree. It's just what I do. We have a whole disclaimer at the end. Don't worry. Yeah. I would say the same. And then also, I have done some dabbling in private investing in some startups and precede some angel investing but also the other thing sometimes people ask about this even if you don't have the money you can invest your time and you can invest and be brought on as a advisor and get a little equity in the company and just dedicate your knowledge and your time that is so true I mean all of my advisors have like 25 basis points of equity that's incredible any companies you want to shout out that you've private invested that you're excited about?

43:58Okay. One of them, actually you may know, do you know Cooper? Yes. Yes. So it started by these two amazing women, AG and Caroline. And I met with them at this point many years ago and they were like, yeah, we're building this. It's basically a retail platform for emerging fashion designers and they just have incredible taste and they're really uplifting all these designers that would never normally be discovered by people in North America. So it's just something that I love fashion. She's so into fashion. I'm really into fashion. So it's something that really spoke to me. Y 'all are both so mission driven, which is exciting.

44:33You don't enjoy the private investing as much. You're more broad-based ETFs. Just broad-based ETFs. Yeah. Okay. The last question is any growing interest outside of investing, outside of the business? Oh my gosh. So many for her. Too many to share. I mean, I think something that I've been trying to figure out with starting a business, which is 24-7, it feels like, is like, what is the balance I bring into my life? And when can I shit off my brain, if at all? Because I love thinking about Tiger Sisters and our business. And so I really have to try and tune that out or else my brain will just go there automatically.

45:06And not really in a stressful way, but just in a way that's all-encompassing. I'm like, okay, these are the things I need to do today, tomorrow, next week, et cetera. And I'm very excited about Tiger Sisters. So I've been investing in more hobbies for me. I don't know. Like, I love cooking. I love skiing. I love tennis. I love golf. It's just like trying to figure out where to slot into my life. And also how much time to dedicate to each of them. Gina's swimming. She does a lot of plants. Oh, my gosh. I don't know. What is it? Gardening? But it's only indoors. It's like indoor plants. Indoor plants.

45:39Propagating my pothos. There's just like a lot for me. Wait, what was that one? Propagating my what? My pothos. What does that mean? It's just like a green plant. Oh, your pothos. My pothos plant. Got it. Your plant. Prothicating my pothos. I mean, I love it. I love it. Jean, what is your growing interest? What do I? Honestly, this is so lame, but I really love what we do. And I think so many things that I'm interested in are either directly a part of Tiger Sisters or adjacent to Tiger Sisters. Or we make it a part of Tiger Sisters. We kind of do. If we love it, we kind of figure out a way to incorporate it.

46:17The beauty of podcasts. Talk about whatever you want. I mean, even for me, I love art. I love fashion. I love going to art galleries or museums. And that's something that we've somehow now incorporated into our content. And Sheree made a bunch of TikToks or reels about. Yeah, like carousels about how. Well, like we love art. That's a shared interest of ours. And like recently when we were in Paris, we went to Musée du Lingerie. and like so much of it is like enjoying art in person and having these experiences with each other and with the artist all of that but like in the age of like ai how do we grow our attention span and also like be more in person and enjoy some things that are more classic in that way yeah and i think it actually lends itself really well to our podcast because we say tiger sisters we talk about money power and love and love as part of love there's self-love there's self-development right?

47:12And so we really are trying to bring our whole selves to the podcast and bring even things that we're interested in that we think are a big part of developing yourself as a person, as a human, as someone who is a broader part of the culture. Yeah. So that's awesome. I will say art is like a very rich interest, like rich people. And I'm sure a lot of people at the Ivy's like are interested in art. So if you want to be interested in something that rich people are interested in, like art is one of them, I will say. Yeah. Art, wine, golf, skiing, like all of these, they're like a, they're cultural touch points, but also having the language.

47:47I took two semesters of art history. I studied computer science because I needed the bag, but I like love art history, you know? And I think that is also part of being a well-rounded human. Right. I haven't started collecting, but I would love to collect even just like small pieces of art. I mean, that's part of your net worth. Like you can lend against art. We had art lending at DB all the time. Sounds like you guys have no plans to sell the business. Tiger said like this is a lifelong mission. I think so. And same with Sisters Matcha. Hopefully we expand to different farms. I will be attending the live show on the farm, by the way.

48:21In Japan. Yeah, in Japan. It will be my first trip. Live from Mazooka. Live from Mazooka. You guys got to tune in. But thank you guys so much for coming on. This was so much fun. We'll have to hang again. This was great. Thank you. Yay. Hey, everyone. I hope you enjoyed today's conversation. If I leave you with one takeaway, it's this. Structure creates clarity. Jean and Cherie didn't leave their equity split, their spending decisions, or any other boundaries when it comes to money up to whatever felt right in the moment. They decided those things beforehand. So this week, challenge yourself to write down at least one money rule with someone who you share your finances with.

49:02It doesn't have to be perfect. It just has to exist. It's going to save you a lot of headache down the line. All right, y 'all. See you next week.

From the publisher

What happens when your sister is also your roommate, business partner—and the person you split the money with?

Jean and Cherie Luo, better known as the Tiger Sisters, walked away from careers at Goldman Sachs, Snap, and LinkedIn to bet on themselves. Since then, they’ve built one of the biggest business podcasts on Spotify, launched Sisters Matcha, and say they became self-made millionaires before turning 26.

But Mary Holland wants to know what happens behind the numbers.

Jean and Cherie get candid about: 

- how they actually split money and equity as sisters

- whether everything is really 50/50

- putting their own money into their businesses

- what happens when one sister brings in a deal. 

They also break down the very different goals of starting their media company versus matcha business,  whether four Ivy League degrees were worth the price tag, and the moment they actually started to feel rich.

Keep Up With Mary Holland

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Produced by ⁠Dear Media⁠

DISCLOSURE: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. All investing involves risk, including loss of principal. Guests and the host may own securities discussed on this show, and nothing said here is a recommendation to buy or sell any security. Always do your own research and consult a licensed financial advisor before making financial decisions. This podcast is not produced, reviewed, or endorsed by Mary & Pip Investments LLC, a registered investment advisor, nor its affiliates. Nothing said here reflects the views, advice, or services of that firm.
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