“Just Ask” Is the #1 Career Skill (Pay, Promotions, Power)
43m 56s
Mandy Ginsburg shares her journey from leading Match Group to stepping down as CEO due to a combination of personal crises, including a tornado, health scares, and a growing sense of personal limits. She emphasizes that asking for what you need—like a pay raise—is not just a financial decision but a vital personal and emotional skill, especially for women who often internalize silence as strength. Drawing from her experience at Match, she highlights how gender-based pay disparities were identified and addressed through audits, leading to greater equity and transparency. Mandy underscores the importance of building strong, authentic relationships with colleagues and board members, noting that these connections foster long-term learning and leadership growth. Her time on boards, including Uber and Threadup, reveals how leadership requires shifting from hands-on operation to strategic oversight, with a focus on psychological insight, risk alignment, and team dynamics. She also reflects on how technology, dating apps, and consumer behavior are deeply tied to human psychology, demanding empathy and data-driven decisions. Ultimately, Mandy advocates for women to invest in relationships, speak up early, and leverage their lived experiences to build confidence and resilience—both in career and personal life. These insights form the foundation of her belief that leadership, equity, and self-advocacy are not just corporate goals but essential life skills.
Just ask. The worst that's gonna happen is that we get rejected. But what's the best case scenario? We have to teach our daughters too. Yes. Because, you know, you sort of start to see that girls when they go through puberty, they start to sort of pull back and this is when we need to teach them, like, no, this is actually when we need to speak up. One of the only times I asked for a pay raise was when I saw some of my team members that I had hired and were several levels below me were being compensated more than I was. Who loved you better than you deserve? What? That's so deep. I'm Shari. I'm Jean. I'm Mandy. And where are 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. Many of us have used or at least heard of match.com, Tinder, Hinge, okay, Cupid. What seems simple on the surface is actually a massive ecosystem of love, data, monetization, and human psychology. Mandy Ginsburg helped match group during a pivotal era, scaling from a strong dating brand portfolio into the business behind how millions connect. She's navigated acquisition, culture, growth, and vulnerability in very public ways. Today, we dig into how she played at the intersection of technology, intimacy, growth, and authenticity, and what she's learning now about reinvention. Mandy, welcome to the tiger sisters podcast. So on the tiger sisters podcast, we say that we talk about money, power, and love. And so today we're really excited to dig into our two favorite things, love, and data, and how to use data when it comes to love. So dating is both timeless and ever changing. How did you and your team anticipate cultural or generational shifts before it showed up in the data? I think that the fundamental issue that we are facing is that as young people would sort of go to less bars, meet less in churches, would not meet in college and date, you know, all of a sudden they were in sort of the workforce and people are lonely and trying to figure out how to connect and and this was for the most part match.com in the early days was for second time arounders with a divorce rate that's over 50%. These are people who are like, you have little kids and have busy careers and there's just no way to meet. And so that was really the first big audience that came online probably in the early 2000s and then sort of the rest of history, especially as like young groups came in with Tinder and we are now seeing this huge proliferation of dating. But to your question around like, how did you identify trends and opportunities? At the end of the day, this was like a highly analytical product company. Yeah. It's funny because at one point, we had these daily stand-ups which talked about the metrics of the business and at one point, I'm sort of a marketer at heart, but one of the marketing people said, all we talk about is numbers and we don't really talk about the people. I'm like, well, that's terrible. These are people we're talking about. So if the site goes down, this is like people that might not meet. And so we really tried to make sure that not only do we look at sort of the data and the trends, but not forget the fact that like, these are people who've got their hopes up. Okay. So now, man, do you talking a little bit more about your own experience? So you stepped down as CEO of Match, which was a $20 billion company for health and personal reasons, which was obviously a massive, massive decision you've talked about it before. So what was going through your mind at that point and what did it teach you about sort of like leadership and your personal limits and the combination of all the things that led you to make that decision? Well, it was such a strange time. So I've been at the company for almost 15 years at that point, yeah, by 2019, 2020. And in 2019, at the end of the year, which also we know we, at the time we did not know, but that's when COVID started because COVID was just sort of heating up in early 2020. We didn't really know what was going on back then. So weirdly, I resigned. And then my best friend and successor took the company over during COVID. She's like, I can't believe you leave me and I have to run the business out of my kitchen. So anyway, you're like, I taught you everything I know a lot of changes. Yeah, it was a wild time. But in 2019, in Dallas, Texas where I live, there was a tornado that hit a thousand houses in Dallas, which is a little strange. And we got a direct hit on our house about how our house was destroyed. And we were at the house at the time. And I think I had earnings the next week or maybe 10, I think it was the next week. And it was a lot. And then during that time, my doctor had called me about recalling breast implants after mastectomy. And it was associated with breast cancer. And I just didn't see the message and get the message. And I got a terrible email that said, like, we're firing you as a patient. And so I was like, what is that mean? I called and I said, we've been trying to reach you for like months. And you just, you're not responding to our phone calls. You're not responding to our e-bails. I was like, sorry, my life's a little busy. And so the combination, I think of the tornado and the health scare. I was like, maybe I should rethink everything. So and at the time, which is so hard, I think professional athletes think about this too. How do you figure out if you are going to leave when to leave? Like when's the right time? And people always stay too long. And the business was going so well at the time. And the woman who's running the business with me, her name is Shardu Bay. She's a brilliant, brilliant leader. And she and I had been like tag teaming this business forever. In fact, when I became CEO, I asked the board if we could be co-CEOs and they said no. So I'm like, why not? We run it together anyways. And the business was really, I mean, it was in great hands with her. And so I talked to her, of course, and talked to the board at the time. And so she sort of swooped in. And there was just zero transition. So it was the timing was great. I didn't know quite how great it was because a month or maybe six weeks later, the whole world shut down. So that was not planned. And weirdly, that's when things really started ramping up in the dating category because people were stuck at home and lonely. And so there was a lot more activity that was happening. And so as I was transitioning out, the business was weirdly kind of on fire in a good way. And then, you know, there's been more challenges sort of subsequently, but it was, it ended up being a great time. And I think honestly, there was no, none of the investor community knew and thought twice about it because things were going so well. And there was so much continuity in the leadership. Yeah. At that point, was it, like an agonizing hard decision? Or like, this is exactly what I need to do right now. And it was clear to you that there, you had other priorities that were much more important for taking the forefront. You know, I think that I think I had to listen to myself instinctively. I'm like, I think it's time. The other thing too is I really was worried about I've been out of a long time. Am I going to be the person or the team that comes up with that, you know, innovation for the next big growth? And now in retrospect, I have a different view on that. But at the time, I was like, okay, old dog, old tricks. Like, shouldn't we bring in new fresh thinking and innovation into the business? Because ultimately, we saw that we really did disrupt ourselves time and time again. And so, you know, it was like, am I the person's going to do enough disrupting over the next two, three, five, seven years? I think the biggest asset I had in looking back at as a CEO was, and I did play very serious sports. And I loved, so I played serious soccer. I played, I see that. Yeah, I played for, but I loved being part of a team. And I was never the best player. I was never the fastest player, but I love seeing people succeed. And I do, I really do have a genuine curiosity for people. And I like to see people succeed. But building community is actually a real skill. And some people haven't. Some people don't. So you think about your friends. You're like, you're like 10 friends. Who's the one person that can just like plop down anywhere in the world. And they would have like, you know, friends and community in a life within like 30 days. And I don't think I actually knew that I could do that until I did it. Quick pause. If you're enjoying the show, please make sure that you are subscribed. Tiger Sisters is where we break down the forces that are shaping modern life, money, power, and love. The goal is simple. To help you think more clearly about the decisions that matter. New episodes every Monday find us on YouTube, Spotify, and Apple podcasts. Welcome to the Tiger Sisters fam. And now back to the show. I'd love to transition and talk more about your position on boards. What has been the biggest shift from moving from your operating role into more of a board leadership at companies, similar to how you've, how you've been on boards like Uber and threat up. Well, I think is an opera. I mean, at the end of the day, I'm like, I'm an operator. I'm the marketing person. I'm an operator. And I like to get involved in the details. And you think that's what makes you like a strong board member. Well, actually, no, I have to. It's the opposite. So in a really smart board chair, tell me once, you know, the difference between being an operator and board member is that you have to be instead of like fingers in and nose in. You've got to sort of fingers out nose in. And that's a muscle that I hadn't. I mean, first of all, it's so funny because sometimes like, especially for more startups or smaller companies, I just want to be like, no, no, no, actually, I'm not just giving you
advice. Just do what I say. People won't do what you say necessarily. They just will listen and hopefully take your advice. So it is different. I will tell you and now that I've been on so many boards over the course of time and you sort of see the pattern recognition of like great board members who can provide real sort of insight and help and direction and also knowing when and how and where to engage at the board level because there's some, you know, board businesses that are doing like great. I was on the board of JC Penney, which seems like normally, but but I'm during a bankruptcy. So that we had to get heavily involved and we had a CEO leave that we had to find a new CEO. So that's where like the boardwork is actually very hands-on. That must have been fascinating. It was fascinating. It's a 100-year-old company. The time I was running match too. So the dynamics between like what we were dealing with a company go through bankruptcy that's 100 years old and a brand that was very Americana and this business that was growing by, you know, two, three, four times. I mean, it was just I was like with Blash going from one board meeting to another. My like nerdy comment is like you lived the case study. Like you actually, there's so many case studies about what happened with JC Penney. You were in it. Yeah, and it was just such a, I mean, not frankly, one of the main reasons is the board members of the time convinced me it was in my backyard. So I didn't have to get out of plane to go, but it was it was fascinating and it was also I learned a lot. Apparently, it was pretty good at going through a bankruptcy. I had firms calling me up and saying we have another company going through bankruptcy. I was like, no, absolutely no way. I know way. I know this is not yeah. But but I will say I never had aspirations to funny enough. I never had aspirations to be a board member. I'm not even sure if I had aspirations to be a CEO. Maybe I should say that out loud for both. I just, I mean, like it, I can't say it just happened because there was a lot of like hard work and a lot of grit and determination, resilience, all the stuff that and I've now dissected and thought a lot about like, how did I get where I got? But but I will tell you from a board standpoint, my first board was a company called Care.com which now is part of interactive corp, which was my old parent company. We were part of IEC match group was. But anyway, I had met the founder at a conference like the one we're at today and she and I stayed friends and I had a board reach out to me, a company reach out to me about being on the board and I asked her advice is no, no, no, just join my board. And that was my first board. And so, which is funny because I've met a lot of people through that board. And now as a result, that was why I'm on another one of my boards, threat up is because the chairwoman was on the board of Care.com with me. So anyway, so all these things like these connections become really important. And I've invested in a lot of these friendships and relationships over the years. But anyway, I thought like I wanted to learn, I wanted to be on one board because I wanted to learn like if I'm going to spend more and more time engaging with the board, then I got to learn what is it like being in a boardroom and presenting to a board. And so that was sort of my first for a. And then over time, frankly, like I thought I'm not going to join any boards. I'm going to go to Florence, eat a lot of pasta for a year, and then probably jump back into operating. And I ended up just more and more opportunities came my way that I had a hard time saying no to which I also establishes a weakness of mine. But they're super interesting boards. And I mean, I don't regret any of them. And I think that there are different stages and different size companies and different sort of consumer offerings. And so it's been fascinating. And as we talked about, it sort of keeps me abreast in learning, especially when it comes to technology innovation, AI, how companies are changing fast. And I think in my context that I see, can I'm a very positive, meaningful impact on user experience? Yeah, one thing that I've heard about boards is that a lot of times, when you look at the composition of board, people try to create a board that has people in specific roles. And I guess like each board member usually has kind of like a super power that they're bringing to the table that is unique to them. Do you feel like boards kind of approach you or ask you to join for a specific set of skills that you bring? Or is it more so just your overall like operating prowess and experience? Like how do you think about that? Well, I mean, at the time, so when I was leaving, well, when I was still at match, Dara, who is the CEO of Uber, reached out and we were at kind of sister companies because he was an Expedia. So, you know, Barry Diller, he went to Barry Diller for a long time. And match group was part of Barry Diller's empire. And so I knew him through that loosely. I didn't know him that well. But he was really at the time looking to evolve the board, because this is he had, you know, I think at the time Travis was still on the board when I was interviewing because I think I overlapped maybe one board meeting with him. But he was really looking for people who were operators, but not there's a lot of great operators on the board at Uber and a lot of CEOs existing in previous CEOs. But there weren't a lot of consumer, you know, digital consumer experience. People who had digital consumer experience had subscription experience, which with Uber one, they've now have a pretty significant footprint when it comes to subscription. And so, so that he sort of said it would be great for me to have, you know, another digital operator on the board who understands customer acquisition, who understands retention, who understands all the dynamics you've been dealing with. And so anyway, that's how I joined that board. And for universal music group, which has been wild, just like, you know, nothing about the music industry. Yeah. But I know a lot about subscription. And they, you know, they like arm's dealer, they have all the incredible music and relationships with the artist through the record labels and they work with Spotify, which is a subscription business. And so again, I think that that experience has been really helpful because, you know, for 15 years, I spent a lot of time understanding consumer, consumer subscription. And then the other thing too is over time, which, you know, when you're on boards, and you're on different committees, there's expertise to develop. And I've spent a lot of time thinking about equity compensation, executive compensation. Okay. So I spend quite a bit of time on the governance side. Yeah. And on thinking about, and frankly, it's more of that it's not just best and best in class and sort of best practices with it comes to compensation. There's a lot of psychology that is involved when it comes to executive compensation. And so I'm not a psychologist, but there is a lot like a truly understanding people and what motivates and drives them and makes them tick is an important part of that process, I think. Wait, can we share a little bit more? How do you think about like what are the different components that are important and what are the different like driving psychological factors that you have to take into account? Well, I mean, this is a really good example, you know, risk tolerance is so individual specific. And so, and I've seen the course of my career, people that are big risk takers that want to sort of shoot high for like high risk high returns. And there's other people that are like, I don't want the risk. And so one of the things that we introduced at match at the time and now it's changed, but we gave people that this is a while ago, but we gave people the choice between an option and RSU. With an option, there's like higher risk, higher reward, potentially with a restricted stock unit. There's less risk, but it's a little bit more, it feels a little bit more cash like. And so, but we gave people a choice. And so, and it was really interesting because then people could make their own decisions and they can manage their own risk. And so these are things that we've now introduced at other companies too. It's just tools to help people make decisions based on where their own sort of psychology and relationship with money is. I love that. It's giving people more options and more, I guess, autonomy to like make a decision that's right for them in their life. Yeah. And frankly, most humans are not big risk takers. So I mean, it's given the choice, most people will choose less risky, yeah, less risky outcomes. And then when it comes to executive compensation, is it more so like someone who opts in to a bigger equity package versus like a larger upfront like cash pay? Is that kind of the the trial? I think like with all, I mean, look, it's with all boards and it's with all investors, it's all around just making sure that you're aligned to performance. And so, you can give people huge pay packages, but it has to be aligned to huge value creation. And so I think that, you know, I've seen, I've seen people who are incredible and drive the most impact to a company not make as much money as they should. And I've seen people make a ton of money that are not that valuable. Or as valuable is money that they made. And so getting compensation right is is never going to be perfect. You have to sort of try to get it mostly right. But I do think that, you know, really figuring out how to align people with ultimately shareholder return, yeah, our investor return. Well, and then now that I think of it,
this is something that you've been on the forefront of and sort of like driving this your entire career because you led the sort of pay equity, what do you call it? Like program at match? - We did it on it, which was. - You know, it was so interesting. I went to, I think it was like a women's fortune conference and there was, I think it was like sales force, did a pay audit and I think they were the first company in like the B2B SaaS world to ever talk about pay audits. I mean, this is probably 13, 14 years ago. It was so long ago. And you know, compensation was something I thought a lot about. What we're talking about is like executive compensation, how to structure it, but like I wanted to make sure that within the organization at match, and you have to understand when I first started it, match group, I started out running a tiny little business as a $25 million business called chemistry.com. And so there's 25 people, there's 25 people at chemistry and then I was asked to take over the match.com business. It was about 250 million revenue at the time. And it's tiny business. I think our internal value of the business was like 600 million. I mean, it was just, it was small relative to what it ultimately became. But I realized that the reason I thought a lot about it, 'cause there was one woman on our team, she was amazing. She was a PM. She was an immigrant, her parents came from Asia and one of the most talented product marketing people I'd known, extremely diligent, very analytical. But she often would underestimate herself and would certainly never ask for money. Just not. It wasn't in her personal DNA. It wasn't in her like cultural DNA, which she, she and I talked about like over time. And so I, Sharon, I, who's the woman I talked to you guys about, this partner I worked with for a long time who became the CEO after me, she and I spent a lot of time making sure that just because, and we saw often that men would ask for money and pound their fist on the table more than women. And so I grew up with a mother that said, open up your mouth and ask if you want something. And so I, I did, I got that sort of constant training just like, open up your mouth and ask. And so, and I was fine hearing no, 'cause my mom would often say no. And so, but I knew that most people didn't like money and asking for money comes with a lot of anxiety for some people. And so we spent a lot of time making sure that as we look at pay bans and looked at people that we were really paying people based on the contributions of the business. And so we did that kind of from the beginning. And so I inherently knew that we had every year compensation, we had taken that to account and taken into account the male female dynamic that we were seeing and we did it, there's a lot of women at the top because, you know, I hired them. And so we, you know, it was sort of in our DNA. And so we did the audit, I made them run it twice because there was real packity based on bans between males and females and I didn't believe it. But it was right. And then we actually did find an anomaly weirdly, I think in the accounting department at the time because the women were paid lower than the males. I was like, how did that happen? And what had happened is women had been there a very, very long time and then new people coming in happened to be men. And so, when you often come in from the outside versus to their long time, it's just that the compensation gets out of whack. So we had just sort of a just side of our time. But it was constantly on my mind. And so that was something that, and we talked about it a lot at the company. - Yeah, I mean, that's something, one thing I've shared before on our podcast is that even, you know, 10 years after you did this audit, like one of the only times I asked for a pay raise was when I saw on my team, some of my team members that I had hired and worked for me and were, you know, several levels below me were being compensated more than I was. So that was when I was finally like, okay, I can't avoid this anymore. Like the numbers are right in front of me. I need to, I need to, you know, speak up for myself and say something to make it like a fair sort of pay situation. So that was, it was very hard for me to do that. Kind of like you were alluding to. - Yeah, and look, I mean, I will say that I hate this fact, but often you have to clearly not you, but people have to clearly great value, but squeaky wheels do get paid more. And so, and the thing is, I think it's really important, which I tell women is like, look, even if you don't get it, ask, because it puts something in sort of your manager's head that it matters to you and you care. And over time, you'll figure it out, whether it's like this job or the future jobs, but you've always got to ask and be okay hearing now. - Yeah, it's really a muscle that you need to train and especially if it's not something that you grew up doing or, you know, asking for things, whether it's in relationships at work or anyway, it's really hard to get into that mindset. And so I really admire that you came from it. To me, it lands that it is a protective measure in the sense where there are employees who are doing great work, but they are unable or like they don't know how to speak up for themselves. - Yeah, I think that's true. And also, we have to teach our daughters too. - Yes. - Because you sort of start to see that girls, when they go for puberty, they start to sort of pull back. And this is when we need to teach them like, no, this is actually when you need to speak up. - Yeah. - Just ask. The worst that can happen is that like you get, no, you get rejected, but what's the best case scenario? - Right. And you actually have to learn to ask, I think it's an important muscle, not just to learn to ask for money, but just to learn to ask for things in general in relationships and you know, for promotions, for like, you know, from your family members. And so that is a, I think it's important. And also like, sometimes if you manifest it, you say it out loud, it also makes it feel really real. - Yeah. That's something that we've really gotten into where I've been, I've been doing this thing called the artist's way where a big part of his journaling every day and like writing down, just getting all your thoughts out. And it's crazy how the, the thoughts that you have if you just write them down, they just happen. - Yeah. - I don't know how else to explain it. - Yeah. - Yeah, they become more real. - Yeah. - Yeah. - You're like putting the energy out into the world from just your brain, you're putting it in the physical world in some way. And that helps you sort of actualize it. - I think. - I agree. It's advocating for yourself. And also when you put it down on paper or you tell someone or tell yourself, say it to yourself in the mirror, it's making it more real. - Mm-hmm. - Yeah. - Yeah. - Cool. - So we have a lot of women who are watching Tiger Sisters podcast and following. And one question that we get a lot is about serving on boards. So what would your advice be for women who are interested in serving on boards? 'Cause it seems like for you a lot of it happened like quite organically. And it's like one happened after the other. So yeah, what would your advice be? - Look, when it comes, so I wanted to donate between private boards and public boards because I do think that there is generally, it's hard to be asked to be on a public board. 'Cause generally people want people who've had experience running a public board. And so what's the best way to become a public board member is be a public CEO. So that's not always easy. That said, I mean, there's a lot of private boards that will ultimately go public where people are looking for important skill sets. For example, if you've got a very complex and diverse workforce, then having a person who does sort of talent management or HR, they need those kind of skills. And so if you're a CFO and they have a whole for audit committee and finance, then I think that that's an interesting path. What I will say, which is like more of a macro statement because it's funny, I went to Morton Business School and they have a women and boards course that we teach, a handful of us who are on board, so we teach. - Oh, wow. - And then we get the same question all the time, like how did you get on the board, you're on? But I found on the boards that I am on, I will often hear men talk about the golf games that they have how with each other or the university boards that they serve on together. And a lot of the women are not talking about that, because we are taking care of our children and our parents and we take a much more active role in other parts of our lives that oftentimes the men that I serve on boards don't do. And so I actually reached out to a couple of the board members from Uber and I said, hey, we're doing this strategy session. Do you guys wanna come in a night before and have dinner together? And the women who I ask, they're like, yeah, no one's ever asked us to do this. So we don't have time to play golf, nor do we play golf, but we caught up over dinner and we built a relationship over time by trying to catch up the three of us, the women on the board. And the only reason I bring that up is a story is that I think about the relationship I had with Patricia Nakash, who's the chairwoman of Threadup, one of the boards I'm on. She was on the board of very early VCs, she's incredible. She was on the board of care.com. And she and I, because I just think she's incredible. She and I have kept up through the years and every four to six months.
We'll reach out, we'll try to have coffee or we'll catch up over Zoom. And so the whole moral of my story here is invest in the relationships, not because you need a network, but because, you know, these people make you happy. You learn something from them. They're interesting because those are the relationships that over time really will have a big impact in your life, and especially we started off the conversation you guys were telling me you've had incredible careers, but like you were PM at a fast growing company and there's probably so many interesting people that were in your network, but then as we have kids and are busy and are running around, we just don't have time to foster those relationships and women are the worst at it. More than men, most conference that you go to, at least that I go to, it's like 90. I never have to wait in that women's bathroom because there's no women, but we just don't have the time because you're like, it's, that seems like an inefficient use of my time. But these relationships, well, they will really bear fruit over time. And so that's what, think about the people right among your list and put the people down that like, I really want to, what are they doing in a year from now, six months from now, 10 years from now? And those are the ones that over time, you'll be surprised at how much opportunity you'll have to learn to potentially serve on boards to advise your name and to invest. So it's investing in the relationships with people that you admire, you respect that you enjoy working with, that you sort of have like a natural relationship with and affinity towards. Yeah. And look, networks are, I mean, I, I have a lot of friends from business school. It's been so fun connecting to all these people over the course of their careers. I'd say like, think about it from your very first job, all the way to where you are today. There's so many people you're going to come across that you're like, I would love to spend more time with them. Yeah, that's one thing that I have really enjoyed about the two of us starting our company together is that now that we have our own company, we get to like pick who we work with. We get to decide who we spend our time with and who we invest in and who we build with. And it's just been so much fun to just get to work with your friends who you like really admire and you, you know, think the world of and so talented. Yeah. Wow. We actually get to work with them. Yeah. I talked about this woman, Sharr, a lot, I mean, who it was very lucky I got to run a business with my best friend. I mean, she wasn't when she started, but we became such close confidants and friends over time. And when she left Match Group as the CEO a few years after I did, she said, well, the thing, well, I told her, the thing I miss most is working with her because we had so much fun together. And she's also brilliant. We are a very symbiotic part, we had a symbiotic partnership. And we ended up saying, okay, well, let's figure out if we want to work with private equity or with the venture capitalists together, but let's try to do it as a team because we know as a team, we are probably better than individually. And also it's so much more fun. And we know that people like working with us as a team as well. So we ended up joining private equity firm as operating partners, but together. So we were like a package deal. So it just goes to show, yeah. So people are like, you, we have to hire you together and like, yes, yes, you do. And if you don't want to, we don't care, but so that's the kind of the relationship we just talked about. Sometimes those are, you'll look back and like, wow, this is the best thing that ever happened to me in my career aside from building a great business, which we did. I just think you're so cool. You create your own reality. You're just defining and just doing things. You're like, hire the two of us together. That would never be as she's asking. Yeah. Exactly. That would be most rewarding for you. Yeah. I mean, but I'm also old. And I got, I fortunately had enough success that I earned the ability to do that. I probably wouldn't have that when I was in my late 20s or 30s, though, but I, I was, I slogged it out for a long time, though, but it's fun. And by the way, thank you for saying I'm cool because my kids would not say so. I really appreciate that. Okay. We have a fun little segment. Yes. The last part. We have these fortune cookies that are, they have questions inside them. We have mild and wild. Okay. And so you'll take one of each. Okay. And I can't wait. Yeah. And it was so funny, guys, because I filled out your questions. I think for your newsletter. Yeah. And did you guys look at my answer? We did look at them. Yeah. We're saving them. Okay. You can say them. I won't mention them. But it was very funny. Are they wild? No, I was just laughing because it was like, what sure are you watching now? But I was like, I'm just going to say it. So I was like, well, I am more obsessed with the summer I term pretty more than my daughter. Oh my god. So she's like, I know. It's embarrassing. But you watch this stuff. I was like, I can't help it. I'm just, I can't, I'm team Conrad. Yeah. Hey, I just can't help it. Well, do you know there's like so much literary analysis about the show? Well, yes. Of course. Yes. Because I like, I bond TikTok all the time. You win the show. Okay. We have the exact same outfit. I guess. Yes. I'm happily married. But I'm in love with Conrad. Yes. Oh my god. Me too. That's because he was written by a woman. Yes. Exactly. Yeah. Yeah. That's a whole conversation. Yes. I have the wild. I have the mild. I have the mild. Okay. Maybe we start with you. Yeah. Okay. Okay. Okay. So this is the mild. This is so fun. I know. What is it? Okay. This is funny. I mean, I can't wait to see what the wild is. What types of people do you tend to attract? Yeah. That's a good question. So it's so funny. So I'll just use my husband. Yeah. So I think that, you know, that I definitely, at some point, you know, got him intrigued enough to want to ask me out. I tend to, well, I tell you there's a different stream work and non-work. And my personal life, I definitely, people who are a little bit more introverted and less big personalities. My husband is a very contemplative, wise, introvert, so that is probably who has attracted to me. And then in work, it's so interesting because I am a very instinctive decision maker and probably more of a creative at heart. And I'm pretty good when it comes to consumer instincts. But I generally hire people who are way more analytical, focused in decision makers. And so when we did assessments on team dynamics at MATCH, it was shocking to see how many people were not like me than like me. So. But I love that. It means that you're hiring just a diverse group of people that balance you out. Yeah. Well, maybe they just balance me out. They're all very similar. But yes. And I think that that was, okay, I can't wait to see what Wild West. Okay. These are random. We don't know what you're going to have. We don't even know. We have no idea. Okay. This is our first time trying this out. Oh, really? Yeah. Okay. So, who loved you better than you deserved? Oh, my god. Oh, my god. What? That's so deep. It is so deep. Did we approve that one? I don't know. I might need to get another one. I thought I was going to be like sexy. Kind of like hard. Well, it's so funny to talk about about my husband again, but I do feel like that he is the kindest human I've ever met, and sometimes I feel like I got lucky. I don't deserve him. That's beautiful. And he's so lovely. He's a wonderful guy, so I do put up with a lot of women in his life, so he and my daughters. Yeah. Okay. I think I might need one more like wild one, just because that didn't seem very wild. Okay. We'll see if we can. Let me just. Many ones. One that's just about sex. Straight up. I'm going to ask a lot about it. Over the years. Okay. Oh my god. Oh my god. What is it? What is it? What is it? These are not. Like, these are, who in your life are you secretly competing with? Oh my god. Do they even know it? Oh my god. That's pretty juicy. I mean, maybe Belly, since we just talked about, so we just talked about Conrad, I will say, which is like, I don't mean to be a pivot, but I compete a lot more with myself and others. No. And so, and I do know that. Classic. Yeah. That's felt. Yeah. I would agree with that. Yeah. Thank you for sharing. Yeah. This is so fun. We're so glad to have you. Yeah. Yeah. Thank you. And good luck, you guys. Thank you. I've seen you're a podcast, and then when you guys asked me, I went back and watched a bunch more. Oh. Thank you. I had seen you guys beforehand through like friends sharing, and then, and then I, so I knew, I knew about Tiger Sisters, and then I, I mean, I'd heard about it, and I'd seen maybe a podcast, and then when I got the note from Imran and you guys, I, I went and watched a few more. Oh my god. Amazing. We're so flattered. We're so happy to have you. Thank you. You guys have good energy. Thanks. So do you. A quick note, so I know a lot of people think that podcasts are just about talking off the cuff, but I think what you don't see is that for Tiger Sisters podcast behind the scenes, there is so much research and cultural curation that goes into every single episode. Yeah. And I feel like you can kind of feel it, because I know that you guys, I know that you guys
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Podcast Summary
Key Points:
Mandy Ginsburg transitioned from CEO of Match Group due to personal health concerns, a tornado disaster in Dallas, and a breast implant health scare, highlighting the importance of listening to one’s instincts and personal limits.
She emphasizes that asking for what you deserve—especially in pay or career advancement—is a critical skill for women, with the best outcome being personal empowerment, not rejection.
Mandy led early pay equity initiatives at Match, identifying gender-based compensation gaps and advocating for transparency, which she believes is vital for fairness and long-term organizational health.
Her experience shows that board roles often emerge organically through trusted relationships and shared values, with personal connections and consistent engagement being more impactful than formal networking.
She stresses the importance of building community and emotional intelligence, noting that women often withdraw during puberty and need guidance to speak up for themselves in personal and professional settings.
Mandy reflects on leadership as a team-based effort, exemplified by her partnership with Shari, who co-led Match Group and demonstrated the value of symbiotic, trust-based collaboration.
She highlights how data and human psychology intersect in dating apps, showing how companies must balance technology, user needs, and emotional well-being.
Her board experience teaches that executive compensation must align with performance and reflect individual risk tolerance, with psychological insights being essential for fair and effective structures.
Summary:
Mandy Ginsburg shares her journey from leading Match Group to stepping down as CEO due to a combination of personal crises, including a tornado, health scares, and a growing sense of personal limits. She emphasizes that asking for what you need—like a pay raise—is not just a financial decision but a vital personal and emotional skill, especially for women who often internalize silence as strength. Drawing from her experience at Match, she highlights how gender-based pay disparities were identified and addressed through audits, leading to greater equity and transparency.
Mandy underscores the importance of building strong, authentic relationships with colleagues and board members, noting that these connections foster long-term learning and leadership growth. Her time on boards, including Uber and Threadup, reveals how leadership requires shifting from hands-on operation to strategic oversight, with a focus on psychological insight, risk alignment, and team dynamics. She also reflects on how technology, dating apps, and consumer behavior are deeply tied to human psychology, demanding empathy and data-driven decisions.
Ultimately, Mandy advocates for women to invest in relationships, speak up early, and leverage their lived experiences to build confidence and resilience—both in career and personal life. These insights form the foundation of her belief that leadership, equity, and self-advocacy are not just corporate goals but essential life skills.
FAQs
Mandy stepped down due to a combination of personal health concerns, including a breast cancer-related health scare, and a devastating tornado that destroyed her home. These events prompted her to reassess her life priorities and personal limits.
Mandy believes dating apps are deeply rooted in data, human psychology, and consumer behavior. She emphasizes that while data reveals trends, it's equally important to remember that these platforms connect real people with hopes and emotions.
Mandy stresses that asking for more is a necessary skill—especially for women. She says the worst that can happen is rejection, but the best outcome is learning to advocate for oneself, which builds confidence and fairness in the workplace.
Mandy shifted from being an operator to a board member by learning to step back and focus on strategic insight rather than day-to-day details. She believes effective board members must 'fingers out, nose in'—engaging with advice, not just decisions.
Mandy brings deep experience in consumer subscription models, customer acquisition, retention, and executive compensation. She also has a strong understanding of psychological factors influencing employee and executive behavior.
She advises women to invest in meaningful relationships with professionals they admire, even outside of formal networks. These relationships help build trust, open doors, and create long-term opportunities for board service.
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