Tiger Sisters - Lessons From Our Exes: 5 Red Flags We Ignored

Starting point is 00:00:00 Never in a million years did I think I would say this. I am so effing grateful for my ex. You don't get the luxury of a normal breakup when you still share the same Slack channel. I'm not even 33, I'm 30, and I'm imagining one of my 33-year-old friends going on a date or like... With a 20-year-old? I'd be like, excuse me, if one of my guy friends did that, I'd be like, you are no longer my guy friend. Because that's just odd. He played in my face.

Starting point is 00:00:24 That's crazy. And you kind of just went with it. You weren't there for the Japanese bonds conversation. And thank God I wasn't. I would have told you to beat it. These hoes ain't loyal. I'm Cherie. I'm Gene.

Starting point is 00:00:36 And we're the Tiger Sisters. We are your Wall Street and Silicon Valley Big Sisters. And we're a top 10 business podcast bringing late night sister talk meets boardroom strategy. Buckle up, Tiger fam. Today is a juicy episode where we're diving in to the top five lessons that we've learned from our exes. Because today's episode is a little bit different than when we're, we usually talk about on money, power, and career, and we're actually honing in on the love angle of our show. We're diving deep into the mistakes, the red flags we ignored, and the things

Starting point is 00:01:10 that we wish people had told us earlier, because chances are you've been there too, and we want to help you save time and energy and get your love life right. Relationships are one of the biggest forces in a person's life, and they can affect you emotionally, financially, and even professionally. So today, we're combining our own personal lived experience with research and psychology to give you the top five lessons we've learned from our exes. You can think of this episode as a public service announcement to our younger selves. And as Jean said, we don't normally talk strictly about love, but money, power, love, career, these things are all super intertwined because let's be real.

Starting point is 00:01:52 Money is emotional. And love can also be strategic. So these things come together and we're excited to dive in today. And the way you know this is a Tiger Sister special is because for each love lesson, there is also a business lesson. So lesson number one is do not put anyone on a pedestal. This is a lesson that Gene and I have actually both had to learn the hard way. Gene, could you please share a little bit more?

Starting point is 00:02:18 Absolutely. So the first thing I'll say is that once you've decided someone is extraordinary in your brain, you kind of start editing out all the reasons why they're not extraordinary, and you continue to convince yourself that they are extraordinary. So let me tell you guys a little story about this guy who cheated on me. Guys, this is a true candid moment because Gina's actually never told me this before. So I'm hearing it for the first time as you guys are hearing it. So Shereen knows this guy. She's met him, obviously, because he was my boyfriend. But you were really young. I mean, I was in high school. Yeah, so like I wasn't going to tell you this when you were in high school. It wasn't relevant to you. Why not? I wanted to know the T, maybe. No, you had to like study for your SATs. Okay, fair. I couldn't distract you. But okay, so the story is this is a guy that I dated obviously a long time ago and he was my boyfriend. And early on in the relationship, I found out that he when he was younger, he had cancer and he obviously went through a huge ordeal and he beat cancer. So in my mind, that

Starting point is 00:03:22 was kind of the defining fact about him, right? That was like his story. And of course, I didn't realize this at the time, but I immediately put him on a pedestal. In my mind, I was like, oh my God, he is so mature. He knows so much about life because he has beat cancer, right? Like he knows what's important. And I really just like looked up to him as a default. Yeah, once you put someone on a pedestal, it's really hard to see them in a different light no matter what they do. Oh, absolutely. So the fact that he had faced his mortality, it kind of colored every single thing about him. So in reality, he was a very playful, but also incredibly immature guy. And even like he would say things to me.

Starting point is 00:04:05 He literally said to me like, oh, I just always assumed I would die at the age of 24. So that's how I live my life. So like he was kind of a crazy guy. Like he would do all these wild things. But I would just totally ignore it because the prevailing principle or fact about him in my head was that he beat cancer. He's so mature. Like, and everything he did in the face of that that was extremely immature, I would just ignore, you know. And then he did turn out to be, unfortunately, extremely manipulative guy. And he would say all these things to me, like,

Starting point is 00:04:40 I don't think I even told you this, but, you know, once he said to me, you would be perfect at 112 pounds, which was a total, a number he totally pulled out of his ass. That's so weird. He didn't even know how much I weighed. Like, I never even told him. He just made up that number. Weird. Right? Isn't that so weird?

Starting point is 00:04:56 And like all these other things, like he quit his job. And so he was going to work from home. This was before working from home was a thing. So he tried to convince me to also quit my job so that I could work from home with him. Odd. So odd and like very manipulative. And like I mentioned earlier, he cheated on me. So the irony is that this was a guy who while I was dating him, all my friends would be like,

Starting point is 00:05:20 you are so out of his life. league. That's not something that people really say. So when they say it, they mean it. They really mean it. Yeah. But I just could never see it because I'd always put him on this pedestal of like this amazing mature guy who beat cancer. Yeah. That's really, I mean, unfortunate. And I didn't know that he cheated on you, which also adds just like fuel to the fire of all the other red flags that had gone on. Yeah. It was in my face too, because he, the person he cheated on me with was an ex-girlfriend. and I thought they were just friends. So I like didn't.

Starting point is 00:05:54 I knew it was his ex-girlfriend, but I was like, whatever. I'm like, chill girl. And I'm not really a jealous person naturally. So like I didn't care that they were hanging out. But he like brought her around. I like lent her a dress of mind to wit. I know. That's crazy.

Starting point is 00:06:06 I lent her this really beautiful designer dress to like wear to this formal we all went to. Wait, that's insane. I know. I know. He played in my face. That's crazy. And you kind of just went with it. I know because like I'm a, I'm,

Starting point is 00:06:21 naturally a very trusting person. Yeah. And because I assigned this like really high level of morality to him for kind of not no reason, but a reason of the past. Like something that doesn't have to do with him in the present state. Yeah, exactly. So please guys learn from my mistake. Okay. Also, I know who this person is and I will say about a decade later, I was in San Francisco and I saw this weirdo guy who cheated on Gene. I guess now that I know that he cheated, but this weirdo guy at a club when I'm like, I'm literally, you know, 10 years younger than you, what are you doing at the same club as me? Like, you're weird and old and creepy and I'm like here with my cute friends. And so I'm just like, no, no. So I have that. I have that to share.

Starting point is 00:07:06 So I think the lesson here applied to love is that pedestals are dangerous, putting someone on a pedestal because you fell in love with the story of them, which is what I did. I fell in love with this guy and his kind of hero narrative is something that can totally cloud your judgment for the duration of your relationship. I just think putting people on pedestals is really dangerous in love and also in your career, too, in the professional world, if you have a mentor or a manager, especially if you're very early on in your career. You could be like, this person is so amazing.

Starting point is 00:07:39 I really look up to them. But in reality, they're just a person and they have faults of their own that might come out in the workplace or that might be in their personal lives as well. So like putting people on pedestals sets you up for disappointment, which is sure to come. And I don't even mean that in like a bad way. But like, yeah, you will be disappointed. So just don't put someone on a pedestal and expect them to live out this grand vision you have for them. And the business lesson here is around the decision making lesson.

Starting point is 00:08:05 In the business world, this is called the halo effect. It's when one impressive trait outshines all the other red flags that someone might have. So in Jean's case, it's, you know, her ex who. survived cancer, but also cheated on her and also said all these like extremely manipulative and egregious statements that don't excuse, like it doesn't excuse his behavior. Also, if someone is super charismatic in the workplace, you know, they're great on stage, they have great presence. It's really easy to be charmed by them or really look up to them. But I think just like ground it in reality, like everyone has faults and don't look up to people because they will end up

Starting point is 00:08:46 disappointing you. Yeah, this is truly the Tiger Sister special because you are relating, you're taking my trauma and my love lesson and applying it to business because you're right. This is something that I think people put business people on pedestals all the time, especially in the founder world, right? Like founders of startups, like think about Elizabeth Holmes, right, of Theranos or Adam Newman of WeWork. They were kind of held up as these almost like God and goddess like people who they were like, wow, I can't believe they like came up with this business structure or they came up with this invention and all the other red flags. Think about all the things that were came out afterwards about the way that they acted within their

Starting point is 00:09:28 companies and everyone just ignored them. Well, also the fact that like Elizabeth Holmes like went to Stanford and dropped out following the similar path of like Mark Zuckerberg who dropped out and then Steve Jobs who dropped out. They were like, wait, this is a pattern that. we can recognize, let's ignore all the other red flags. Even I think her documentary, or maybe it wasn't a doc, the movie made about her, the TV show made about her, is called The Dropout. Like, that's what people focused on. Yeah.

Starting point is 00:09:54 And it was this like pedigree that they held so highly. Yeah. When they should have done a lot more diligence on the background. Pattern matching gone wrong. Yeah. Exactly. And so I guess to wrap up this section, be very careful of the pedestal effect and the halo effect and know yourself. Yeah, so I think the takeaway here is that oftentimes when the

Starting point is 00:10:18 story gets too good, people stop doing their diligence, whether it's emotional diligence in a relationship or investor diligence in business. So Shari, how do you think about your checkings and savings account? Because for me, checkings is money that I need to use in the next three to four months and then savings is everything after that, like long term. And because of that, I feel like most of us don't think about the interest that we could be earning on those accounts. Well, the problem is most banks give you next to nothing, like a fraction of a percent, and all the while they're making money off of your deposits. So that's where today's sponsor, SOFI, comes in.

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Starting point is 00:11:47 That's sophy.com slash tiger sisters. Sofi checking and savings is offered through SoFi Bank, NA, member FDIC. And now back to the show. To that end, we have a bit of a mini exercise for you guys to ask the right questions. Yes. So if you find yourself in the situation, you're listening to this part of this podcast and you're like, oh, shoot, am I putting stuff? someone on the pedestal. Here are some questions to clarify. So if you're obsessing over someone

Starting point is 00:12:14 who has an amazing job or resume or went to an incredible school, ask yourself, do I actually like this person? What do I like about them aside from their resume values, the things that we can see on the surface? Have they exhibited any other traits outside of the accolades or accomplishments that make me independently like or respect them as a person? Or do I just like the idea of them. So think about why you put them on the pedestal. What is the prevailing reason why you put them on? And then think of counterfactuals based on their actions, right? What are actions that they have done that either support that or go against that? And then you can kind of like, tally them up and be like, are there more actions they've done that support this attribute that I

Starting point is 00:12:59 think is their primary attribute or are there more actions that go against that? I kind of wish I had done that. Okay, guys, lesson number two is mind the age gap. Sheree, kick us off. Okay, so you guys have probably heard of the term cougar or cradle robber. But the thing about age gap relationships is that it's not necessarily about the years itself, but it's about the life stage that you're in. And so I have a personal anecdote about this because I think it's really important to talk about.

Starting point is 00:13:26 It's also when you're much younger in your life and younger than the person in the relationship, it has an outsized impact. So this relates to someone I was dating when I was in college, my sophomore and junior year, and they had already graduated. So they were only four years older than me, which is not that much in terms of age gap. But when you are young in college, that age gap makes a pretty big difference. So this person was already graduated from undergrad. They had their full-time job. We were living in New York City and we matched on a dating app, which is how to be how that happened. But now that I kind of think about it, I'm just like, you're 23 years old or 24 years old and you're dating someone in college. Like now someone had told me that, I'm like,

Starting point is 00:14:12 that's suss. What were you as a junior? I was a sophomore slash junior. So I was 19, 20 years old. And so that's it at that age, the age gap feels massive because we are in such different parts of our life. I was still a student going to classes. And he had a full. time adult job working at a top three consulting firm. So in that way, in that way, you're laughing. But like, when, I mean, yeah, he worked at a really good consulting firm and something that I had, call it by its name. I had always, I had always dreamed of working at this consulting firm. And I really looked up to him. So he was my boyfriend, but also in a very strange way. He was also my mentor. Yeah. So I didn't want to let him down. I would second guess.

Starting point is 00:15:02 or triple guess the things that I said being like, oh my God, did that sound stupid? Also, it didn't help that he graduated from Harvard. And I really looked up to him in that way as well. It was just like, wow, this person is so smart. He's dating me and he's like helping me like, honestly like figure out my course in life and figure out my internships. And he recommended me to go work at McKinsey as an intern. I didn't end up getting it because my GPA wasn't high enough. Well, because you were a computer science major. Yes. Hello.

Starting point is 00:15:33 I was a computer science major with a 36 GPA. Damn. But when you're up against people studying, I don't know, liberal arts and whoever like a 3940, I'm like, it's just different and hard. Sorry. And I'll just say with that. Anyways, back to the age gap. But I would say when you're younger and if you are a woman in the relationship and you

Starting point is 00:15:53 are the younger one, there can be power imbalance, just baked in. Yeah. I also have a story about this that I've never told you. Whoa, she's been holding back on me, guys. She doesn't tell me shit. Yeah. Why don't you share anything? Because you were too young once again.

Starting point is 00:16:11 Okay. So this is, okay, so this is when I was in college. I was a senior in college, which my senior year, I had finished all my course requirements, so I didn't take any classes. But I stayed on campus because it was 2009 and, you know, I didn't want to go out into the workforce. and I had already gotten my job after graduation, which is I was going to work at Goldman. And so what I did on campus was I worked at the Tuck School of Business, and I worked in the

Starting point is 00:16:40 Center for Private Equity and Entrepreneurship. One of the things we did every year was we threw this, this story is a little long-winded, but stick with me, guys. We threw this conference, so this conference for private equity and entrepreneurship. So people would come in from professionals, would come in from, the area and come to this conference at Dartmouth. And so one of the people that came and sat in on the conference with me was this older guy. He was like 33, I think. Oh my God. And he started chatting me up at the conference. And I like told him I was going to work at Goldman. He was like,

Starting point is 00:17:15 oh, I used to work at Goldman. He's like in 1985, 1985. I used to work there. And we were like chatting and like, you know, I said I, I guess he asked me if I liked skiing. I was like, yeah, of course I love skiing. So he asked me out on a date and we went skiing together as a first date. And it was like super, super fun. It was an amazing first date. And, um, but you were 21 or 22? No, I was 20 because I was born in December.

Starting point is 00:17:41 So I'm like a, I'm young for my year. So I wasn't even 21 and he was 33. Oh my God. And he kind of, he had moved to the area because he like started his own hedge fund, blah, blah. And I just thought, obviously I was really curious and like, interested in him because he had done all these things in his career that I thought I wanted to do too, right? Because remember at the time, I thought it was going to be a finance girlie for life.

Starting point is 00:18:06 And so he was just inherently interesting to me. And I don't know why he was interested in me because I was 20 years old. I mean, now looking back on it, that's creepy as hell. It's kind of fucking creepy. But the thing is, he was like a really nice guy. I mean, the furthest it got was that I think we wanted a day. We went to dinner. We went back to his house. And then I was just like, I shouldn't be here. You're like, mom, can you pick me up? I'm scared. No, I like had a feeling inside. I was like, this is a little bit weird. Like, this is just a little off. I'm like, I feel like I shouldn't be here. Like there's something inherently, I just feel like I'm out of, I'm not in control, right? Like I, there's just a power imbalance here that I can't put my finger on.

Starting point is 00:18:51 And I never would have known to use those words or use those terms back when I was 20, but there was something inside me where I was like, this is not right, as opposed to like, you know, if I went to the house of someone else who was not 12 years older than me or 13 years older than me. Yeah. So I just like beat it. I like got out of Dodge and like went home. Yeah. And nothing ever happened. But I did have that thought where I was like, maybe I should be dating one of the like 4,000 people here who are my own age. Yeah. Instead of this 33 year old man. Yeah. I mean, I'm not even 33. I'm 30. And I'm imagining one of my 33-year-old friends going on a date. With a 20-year-old in college? We'd be like, could you imagine? I'd be like, excuse me. If one of my guy friends did that, I'd be like,

Starting point is 00:19:36 you are weird. I'm like, you are no longer my guy friend because that's just odd. Yeah. So I'm glad that it ended up being like an okay situation. Yeah, it was totally innocuous. And at the time, like, I thought he was so interesting. He was like teaching me all about Japanese bonds and all this. And I'm a fucking nerd, obviously. So I was like, yeah, he really got you to go back to his place with Japanese bonds. He got me with a fucking Japanese bonds. I was like, oh yeah, like Japanese bonds, tell me more. I mean, but honestly, what I see in both of our stories, if I'm going to be a little bit like, we were enamored. Diagnostic. Yeah, like, we were kind of enamored with, now I'm thinking about it. Like, ew, with a hedge fund manager and a consulting guy,

Starting point is 00:20:20 which, you know, like, good for you. But I'm like, that's not something really to be enamored by. I mean, but when we were young, I can see how it's easy to get into that state. Yeah. But that's my- You weren't there for the Japanese bonds conversation. And thank God I wasn't. I would have told you to beat it. But yeah, so mind the age gap.

Starting point is 00:20:40 It's easy to get, I think, like, googly-eyed because they are, like if the person that you're dating is older. But you totally upstaged my story. Sorry. I had a four-year age gap and you're like, hey, wait up. I have a 13-year age gap. for the record, this guy was very good looking. Obviously, otherwise.

Starting point is 00:20:58 Yeah. Yeah. My boyfriend was also good looking too. Yeah. He's very handsome and he's very sweet. But I think the, it was actually not a problem of him at all. Yeah. Like my story is that the guy I dated, my boyfriend, who was older than me, like really

Starting point is 00:21:15 thoughtful, great guy, really wanted to help me and see me succeed. But I was just so in my head because of the age gap that it just didn't. work out at that time. I think at another point in time when we're in the same stage of life, where we were both working adults in the workplace, it could have totally been fine. Or if I was older than like 20, 21 years old, it would have been more normal. Yeah. No, I agree. It was just, yeah. Sorry, I interrupted you. No, it was just, she's upstaging me, interrupting me. My story is just so much better. Yeah, I mean, it kind of is. You went back to his place and then you're like, wait, I shouldn't be here. Yeah. He had like, like,

Starting point is 00:21:54 taxidermy, which I like taxidermy, but I was just like, I didn't, none of my, obviously no one in college had taxidermy in their house. So I was like, hmm. Another reason to leave. But I think actually the thing that I was enamored with was like I wanted to be an adult so badly when I was in college. And this guy had the job. He had, you know, a paycheck, the salary. He had a sexy Manhattan apartment. He had an apartment. He had like really fancy wine glasses. That would, be like, you need to watch these by hand because they'll no break because they're so thin. And I'm just like, ah, you know? Like, that was like what really, I was just like, he's so adult.

Starting point is 00:22:33 Yeah, yeah. But that is something that will get. And like, if you are still really adult and you have a nice place, I'm like, that still is nice to me now. I don't know. It hasn't changed for me. But it's not because you don't have it. Yes.

Starting point is 00:22:42 It's not because you're aspiring to it. It's because like real, recognized real at this point. At this point. Yeah. But what I was going to say was I felt, I think it's the same thing with that guy that I dated is that. But he was a perfectly nice guy. He was really kind.

Starting point is 00:22:58 He never did anything that was like inappropriate. I guess aside from dating a 20 year old when he was 33. Like he never did anything inappropriate. And I think like now that I'm way older, now that I'm 37, like it would be totally fine for me to date him even though he's 12 years, 13 years older. Yes. Right? Because we're we're both adults, right?

Starting point is 00:23:17 Like we've both experienced enough of life and been through life experiences and like had full careers. You have confidence and there's no way it can be used to manipulate you or something. Like either consciously or subconsciously. Yes, exactly. It's like even if he's not intending to use his experience and the fact that he's like older as a way to manipulate you, it's kind of like you almost subconsciously do it to yourself. Sure. And I would say the business application here too is also, you know, at the,

Starting point is 00:23:53 workplace, if someone is much older, I think that can be reverse ageism in a way where we give deference and credibility to people who are older in the workforce just because they're older, not because they've proven it in a way that you're like, okay, they're super legit. So I think that's a little bit different depending on the industry that you work in. But if there is an engineer on your team who is a lot older, you're like, oh my God, I totally look up to this person or the like MD on your team. team. You're like, oh, just because they're older, they know better. Not necessarily true. Like, stick to your own guns and know yourself and work on yourself to gain the confidence so that you

Starting point is 00:24:31 guys can honestly be peers. Okay, I didn't really think I was going to tell that story, but I did, guys, for you. And so just to put, just to tie a bow on it, I would say that if you are in an age gap relationship and you're the younger person and you are in different stages of life, just know that the older person is going to inherently have more financial power. more life experience, more emotional leverage, and that gives them sort of more power and leverage in the relationship, whether or not they actually exert it. That's always going to be the status quo of your relationship. Yeah, and we're not saying that age gap relationships can never work. They can, but I think the biggest asterisk here is that the timing really matters more than the

Starting point is 00:25:17 actual number itself. So age gap relationships tend to work better when both people are fully formed adults, both people have financial independence and both people have strong boundaries that they can uphold. Hit them with the financial independence. Yeah, right? I feel like that's really important, so you don't feel like you are relying on someone else, especially when you're in a very vulnerable state. And that's because you never want to feel like you owe them something in relation to the financial things that they provide for you. Quick pause. One thing we've been hearing more and more is that Tiger Sisters is the group chat that you always wish you had. Yeah, it's the group chat where someone's talking about venture capital, another person is talking about attachment issues,

Starting point is 00:25:58 and then another person comes in and gives you the framework that completely changes how you think about your career. Sounds like a great group chat. So subscribe wherever you get your podcasts, Spotify, Apple Podcasts, or YouTube. And big news, we have a Tiger Sisters newsletter dropping soon. So sign up to get more group chat energy. The link is in the description. Now back to the show. All right, lesson number three is don't date for money, date for track record. So Shari, can you share your thoughts on this? Yeah. So a question we get a lot from our Tiger fam is should you date for money?

Starting point is 00:26:31 And it's a very icky, sticky subject. And you're like, ugh, how do I even approach this? But the way that Jean and I think about that is like, yes, money is nice because it affords you to have a nice life with your partner and you guys can go on nice experiences and everything. But it's not about the money, right? It's about the person and their resilience, their ambition. and if they were able to make a lot of money, that's fabulous.

Starting point is 00:26:54 But if they lost that money, would you still date them? Because then they have a way inherently to make it back and they have new ideas and they're going to figure out a way to grind and get back to where they were. When it comes to looking for a life partner, you want someone with the resilience and grit who can build the wealth with you and not just someone who just has it. Exactly. You want to look for trajectory, not just current status. And of course, this is Tiger Sisters, so we have research to back this up.

Starting point is 00:27:23 So last year in June 2025, the National Library of Medicine published this really interesting study where they looked at 3,700 households. And they really wanted to understand how people cope with financial hardships. So what they found is that financial resilience, meaning someone's ability to adapt and recover from financial shocks, actually buffers the negative effects of economic setbacks. So in other words, people who are better at managing setbacks tend to stay happier and mentally healthier even during financial adversity. And so that's the type of person that you want standing behind you whenever the next recession comes because it will. Right? Like we're living

Starting point is 00:28:03 very long lives these days. And I feel like every 10 years something happens where it's like, this has never happened before in history. And so you want to pick someone who can weather the storm with you, not just someone who happens to have a lot of money because that is not necessarily a measure of character. Yeah. Yeah. Honestly, if we're going to go off on this train of thought, just because they have a lot of money, I'm like, if they are inheriting money, did they do anything to earn it? And a lot of times everyone knows there's a bunch of like children of billionaires who've gone off the deep end, much love to you.

Starting point is 00:28:43 but like they are having a lot of trouble with money because they haven't had to have the grind and the challenges and the hardship to earn that money. So some could argue that's like not even good to have a lot of money unless you've earned it in a way that has shaped your character. No, but seriously, it's not just like I know you're saying billionaires because that's what's in the headlines. But even like multi-millionaires. No, seriously. Because a lot of these people I've encountered personally, what you realize is that they've built their life on being so dependent on that sort of money that they know is going to come to them. But it always comes with stipulations, right? It's never totally free. No money is ever free. If someone tells you that, they're lying to you, honestly. And so even money that's coming from family has rules and stipulations around it. Conditions. And conditions. And conditions. And it can. shape a person's life in a way that initially is not visible to you, but like once you get into a relationship with them and that you dig into it, you start to see, oh, the reason they're

Starting point is 00:29:50 making this life decision is because of the money. So that is something that if you're dating someone who has inherited wealth or expects to have inherited wealth, that is something I would really, really dig into and truly examine. Yeah. And I think, you know, we're putting all these anecdotes and research and stories in front of you, I think it's up to you to dive in deeper if you're having some questions in a relationship or you are dating someone, who you're putting on a pedestal, or maybe there's an age gap, or, you know, if they do have money. Like, it's up to you to ask yourself these questions and also observe. Like, you can only learn more about another person's character when you are put into

Starting point is 00:30:35 perhaps like a uncomfortable challenging situation where you have to bring something up with them or ask them further in questions so you can understand how they would approach something. So it's up to you. You're collecting data points. That's kind of how I think about it. It's just like if you can zoom out of like your own body in your head and you're like, okay, I'm a scientist and like, why did that person do this or why did they do that? Like you're collecting data points to better understand how you react to it and if it's

Starting point is 00:31:02 something that you are okay with because it's all, honestly, it's all about you. And in a way that's like, how do you make decisions that make you happy? I love that approach. Okay, so to wrap up here, Shari, what attributes should we look for in a partner if not just their bank account? So there's a couple that Gene and I wrote down. So the first one is resilience. Second is discipline. Also related to that is work ethic. The third is long-term thinking. Are they thinking past tomorrow? past a month are they thinking for the next years ahead? And the last one is the ability to rebuild after setbacks, which is similar to resilience and I would say discipline. So these are traits that you can only observe over time after being with someone and really putting, I don't know,

Starting point is 00:31:50 a different hat on where you're like, how do I feel about this after you've seen their behavior? And I want to add just three more quickly. I want to say also loyalty, integrity, and character. Well, I guess my response to loyalty is, these hoes ain't loyal. And also my other response is that might be your learning from the person who cheated on you. Yes, but I think it's a learning that can apply to people who have even never been cheated on, right? You want someone who's going to be loyal to you. Yes. But you've learned that after you were cheated on. I guess that's, you're right, there is a presumption there. The presumption is that you yourself are a loyal person. So if that's not an attribute that you consider to be super important, then it doesn't apply to you.

Starting point is 00:32:38 But if you're kind of more similar to me, then it applies to you. Okay, lesson number four is don't shit where you eat. So Sheree, can you tee us off? Okay, so this lesson is a tough one because it is a personal lesson from both Jean and me. Don't shit where you eat. That saying exists for a reason because unfortunately we've both had to learn it the hard way. And workplace relationships can feel very convenient. You see that person every single day.

Starting point is 00:33:06 You're potentially in a working environment together in meetings or whatever. It can feel fun until it's not. So you probably know what we're talking about because a third of U.S. workers have dated a coworker at some point. That's what the Society for Human Resource Management says. And honestly, it might feel like a small intimate bubble when you're dating someone at work. but breakups, they don't stay inside a bubble. So what we've learned is that workplace relationships introduce three major risks.

Starting point is 00:33:36 Power imbalance, reputation consequences, and emotional fallout affecting your job. And not to mention, workplace relationships are one of the top sources of complaints for HR. According to a 2024 SHRM survey, 68% of HR professionals identified perceptions of favoritism or unfair treatment surrounding work. place romances as a primary concern, while 61% cited potential conflicts of interest as a key issue. So I have a personal anecdote about a workplace relationship. This was my first job out of school. It's someone who worked at the same company as me. And we weren't part of the same team. We actually worked on two very different projects and different organizations in the company and had

Starting point is 00:34:23 different roles, but I would see this person in common areas. So like the cafe or even the lobby, like I would see this person and we were dating. And so when things weren't going so well in our relationship, it was kind of awkward because I would have to see them at the workplace where I wanted to like focus on doing well in my career. But then I also had a second, you know, a second thing that was distracting where it was like, this person is here. Oh my gosh, are they at the cafe at the same time I am? Are they grabbing lunch the same time I am? Are we getting lunch? It was just a, a whole host of like secondary and tertiary thoughts when I really felt like my focus at the time should have been and wanted to be on building my career. So it was a very confusing time. And which is why

Starting point is 00:35:08 I think especially because I was pretty young in my career. It was my first job. It was their first job. It was very confusing. And I don't think it was handled in the best way because we were so young. And so I just warn against shitting where you eat at the workplace. It can be very distracting, especially if it's a very deep and personal relationship. And do you really want to be that distracted when you're at a place to build your career? So a callback to the age gap lesson is that timing really matters. I think if you are more further along in your career and more mature, like the both of you guys are and you're working at the same place, it can work and you can discuss what will happen if you guys do break up. In a way, it's kind of like a pre-nup when you're

Starting point is 00:35:53 getting into a workplace relationship. But if you are on the younger side, things can get just messy and dramatic and you're at the workplace and you don't really have a space for that. So the flip side of this love lesson is that when applying it to business, one thing you need to think about is that it may seem like an amazing idea at the time, but you don't necessarily want to always work with someone that you're already friends with. So sure, Can you give us some examples of this? Yeah. I think both in the personal love aspect and then also like the professional work aspect, the main

Starting point is 00:36:27 lesson here is that you have to be prepared for the consequences if these relationships or friendships don't work out. So I know even with a lot of co-founders, you think it's a really good idea to start working with your best friend because you guys are super close and you have perhaps a shorthand or a lot of harmony when you're working together. Yes, I think there's a lot of benefits. but then you also have to think about the downside too because if it doesn't work out, we've seen time and time again a lot of friendship breakups over starting a company.

Starting point is 00:36:58 And one of my best friends has told me that she will not hire one of her friends or best friends to work with her just because there's so much risk and she values that friendship so much. She would never want business or professional stuff to get in between them. And I think also just in pop culture too, we've seen a lot of friendship breakups too because between two co-founders when they're super tight and everything is going great. But when things aren't going well, how do they work out things and will it work out in their friendship?

Starting point is 00:37:27 Maybe not. And so I think it's a really good lesson that like don't shit where you eat. Business gets messy. Business gets, you know, hard. Yeah. And I think that some of the reasons why your friendship can be so strong can be the exact reasons why you shouldn't necessarily work together. Because I think like what Cherie said about like when you are best.

Starting point is 00:37:48 friends or when you are friends at all, you have like a short of a sort of shorthand or you have some inherent level of trust. A lot of times that can sort of be applied to business and you can impute or assume that you're on the same level of understanding about something. And that can lead you to have much sort of looser contracts or just be like, oh, we're on the same page because we're always on the same page about everything. So I'm sure they're going to do this project the same way that I would do this project. So then you're kind of like lulled into. to this default of maybe not defining things as clearly as you would with someone who you don't know professionally, right, or who you don't know at all. And if you think about the phrase, it's not

Starting point is 00:38:29 personal, it's business. When it's your friend, it can never be true, right? It'll always be personal, even when you're bringing them into business. So dating a coworker can work or working with a friend can work, but you just have to be prepared for the consequences because this is what Tiger sisters is all about. It's like we say finances are emotional. Love can be strategic. Work and professional stuff can be messy. So you just have to be prepared for whatever outcome might be. Okay. So our final lesson is something you might have seen before. Maybe experience yourself. If so, I'm sorry, but it's something that I have personal experience with and Jean does too. And that is love bombing. All right, beware the love bomber guys. They are running rampant through the streets.

Starting point is 00:39:13 Sometimes you can tell who they are. Sometimes you can. I have a story to share with you guys. All right, guys. So this was after I had gotten out of a very long-term relationship, eight plus years, as you guys, most people know. And I met this guy. He was super charming, so fun, so playful, really hot. And he was courting me.

Starting point is 00:39:34 And it was a super fun experience. And I would say everything kind of about our experience of getting to know each other felt really heightened. And I think his personality also was that he very much like wore his heart on his sleeve. And he is just kind of a very grandiose and expressive person in the first place. And so I am very much a person that reciprocates like kind of like what I get. And so I remember, I think the first week that we started dating, I think we went on a date on Sunday. And it lasted like eight hours or something.

Starting point is 00:40:12 It was like a super long date. And then a few days later, he texted me and he was like, hey, like, I'm in your area. Like, I just finished basketball practice. Like, can I come over and say hi or like, blah, blah, blah. And I was like, okay, like, I guess. And I think for me, it was because I had just come out of a long-term relationship. So I was so used to having like a ton of points of contact, right? Like I used to live with my ex-fiancee, obviously.

Starting point is 00:40:39 So I was used to seeing him every single day. So I didn't clock that it was like a little bit weird to go on a first date with someone and then have them be like, hey, like I'm here. Like I'm right near your house like a couple days later and be like let's hang out again like just to kind of like drop in. And so that was kind of like how the whole thing kicked off. And that really set the tenor for the entire relationship. But it was this like super full on like truly like love bombing situation. and I don't think it was even meant to be like manipulative on his end. I think that's kind of just people's personalities sometimes.

Starting point is 00:41:17 And it's kind of up to you to define your own boundaries and to actually be aware of it. I think I was just totally unaware of it because, well, I guess also I was so new to dating. Like I hadn't dated in like a decade or something. Yeah. Also, I feel like doing a multi-assie. our date as like the first or second date is a love bombing red flag. Yeah. See, I also wasn't aware that that was not normal because I was so used to like hanging out with my ex all the time. And when we went on a date, it would be 24 hours long, you know, because that's what happens

Starting point is 00:41:56 when you live with someone. Yeah. I think when you're first getting to know someone, it's the moments of like apartness or the moments of pause where your guys are not together. that you can kind of back off and then be able to evaluate how you feel about someone. I think the other thing I would add to my story for context is that this person that I was dating, I think he's just also very much naturally a salesperson, right? Like that is his personality. And one thing he told me is that he's like, I'm a people pleaser. Like I want other people to be happy.

Starting point is 00:42:30 And so I think like those two aspects combined and just like his personality, he just drove the relationship in a way that was like very intense from the very beginning. And it was intense the entire time. I only learned that fact later on as I saw him interact with more people who are not me. So as he met some of my friends or like I met some of his friends and I brought him to parties and I saw him interacting with other people. I was like, oh, he is just a natural salesperson. He is just an extremely charismatic guy.

Starting point is 00:43:01 Like he wants everyone to love him and everyone does love him. And so once I was able to see that context of how he exists in the world, then I had more information to apply to my own interactions with him so that I could be like, oh, this is kind of his like default in life. Yeah. I feel like a lot of it is observing and gathering information and going into the situation very eyes wide open. Okay. So Sheree, what are some methods if you find yourself to be in a love bombing situation. Yeah. Look, it can be really hard because I think once you are in it, in the thick of it, and you are being love bombed, it can feel really good in the moment. It feels amazing. You're like, wow, this person is devoting so much time and energy and effort

Starting point is 00:43:49 into courting me. Like, it feels so good. You're like, I'm the best person in the world. Right. Which is why I think it's really important in taking a pause and having that time apart. So you can like, you know, get on out of it and take a breath and be like, okay, what the heck is actually going on here? So if you do feel like you are being love bombed, the most important thing is knowing your own boundaries and having boundaries, whether it's physical boundaries or time boundaries or like scheduling boundaries, mental, emotional boundaries. Like, no, I will not talk about this topic right now because I just don't feel like we are there yet emotionally. Yeah. And so having very strong boundaries around what you will and will not engage in. Because I think a lot of people are very charming. They can be salespeople like you mentioned. And that part, I'm like very susceptible to that. I'm like, oh, you love me. Like, okay, that's great. You're obsessed with me. I love this. You're like as you should. As you should. And so and like I, I know myself like I seek a lot of validation externally or I have for many reasons that we will not get into having to do with traumatic. immigrant parents growing up. But anyways, like I think since I know that about myself, I need to go into a relationship or a friendship or any sort of partnership knowing myself and knowing my boundaries first.

Starting point is 00:45:11 Otherwise, if you don't have that, you can kind of be thrown into love bombing and you can go whichever way the other person is leading the relationship. I think that's such smart advice because applying that and diagnosing my own relationship that I just told you guys about. I think the crux behind my mistake in the relationship is that I went into the relationship with miscalibrated boundaries, right? Like I applied boundaries that were relevant to the last relationship I was in, which was an eight year long relationship where I was engaged to the person. So I applied those sort of boundaries to this new person that I had never met before and was

Starting point is 00:45:49 newly dating for the first time. And I was giving the sort of like leeway and like way more lax boundaries. that require five, six, seven, eight years of trust to build up and like eight years of understanding to get to that level. But I kind of like gave him those boundaries or like lack of boundaries from the very beginning. Yeah. So that's a lesson for me from me. Yeah. To you guys. It's kind of like people, I've seen like a funny TikTok or Instagram meme where it's just like, you just haven't unlocked this level of my personality yet. You are on level one. you haven't gotten to level two, you haven't earned or shown, you know, your loyalty,

Starting point is 00:46:32 you're a trustworthy person, you are, you know, ambitious, resilient and you will back me up. Like you haven't earned or unlocked like level two, three, four, or five yet. And so I think having very clear boundaries helps you avoid the love bomber. I like that phrase too, that phrase of using levels. And it's kind of an interesting way if you wanted to really do a mini exercise or like like think through it, be like what are the different levels? Like think through it yourself ahead of time and like preset. Like what are the levels of boundaries or like behavior that I think is acceptable for someone that I'm going on a first date with? For someone that I've dated, gone on seven dates with

Starting point is 00:47:13 for six months in, et cetera. So that could be something that's really helpful to do ahead of time. So in the business or professional world, if someone is overselling or overhyping something, we would just normally be pretty suspicious. We'd be like, okay, you're making all these promises about a product, prove it or show me, or where's the free trial here? So why don't we apply that to our romantic or our love lives? Why aren't we more discerning with our time, our emotions, our bodies, and everything else? Because once we're love bombed in our romantic lives, I think a lot of the critical thinking

Starting point is 00:47:52 and prefrontal cortex goes out the window, but we need to be more thoughtful and discerning there. So remember Tiger Fam, in business and in love, charisma is not the same thing as credibility. The people that you want to trust are the ones that build slowly and consistently over time. So how are we feeling Tiger Fam? After this episode, are you triggered?

Starting point is 00:48:12 Are you excited? Are you questioning the relationship you're in? I don't know. Well, just remember that every relationship that you have is just more data points for you. It's data points on where your boundaries are, when you'll speak up, and there are lessons that you can apply to the next relationship or business relationship that you're in.

Starting point is 00:48:33 So if today's episode saves even one person from repeating our mistakes, then we can finally say, I'm so fucking grateful for my ex. So thanks for watching, guys. And let us know if there's any lessons that we did not cover that you think should have made it into the top five that you guys have learned, because all of this is based on our personal experience and our personal traumas.

Starting point is 00:48:55 But I know you guys have tons of experience out there and it's really worth us learning from you guys as well. So please, please, please, please comment. Also, please, please, please subscribe. And we will see you soon. Alrighty, guys. We'll see you next time. Bye.

Tiger Sisters - Lessons From Our Exes: 5 Red Flags We Ignored

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