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Betting $250M on Women’s Sports: How Rejection Became Kara Nortman’s Superpower | E130
01:04:24
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Wow.
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This show is going to be incredible. So buckle up and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast track to leadership land, dream roles, jump to entrepreneurship or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success. So subscribe and download so you never miss it. Plus, it really, really helps me continue to bring amazing guests. Okay, so let's dive in.
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If you are in a place where you can take risk, even if you have a huge expense line and things like this, just look at how long you have to go and then try it.
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Kara Nortman is a managing partner of Mornar Collective and she's the co founder of Angel City Football Club. She also started a raise, a movement to change the landscape of women in venture capital.
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What I discovered in the early days of being curious about women's sports was that I had something to offer that was valued. I wasn't going to be paid for it, but it gave me joy. I think we're in a stage of life where we all just want more, more, more. Something better or something you're missing out on is being marketed to you on social media. And I actually think what we want is.
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I'm sure there's also a journey of rejections and hardship and doubts. What made success?
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My husband said to me last night, he's like, you realize you're in the rejection business. Like, you get so much rejection. And I'm like, you're right. But I love getting rejection around our fund because.
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Our guest today doesn't just talk about change, she just jumps all in and drives it. Kara Nortman is a managing partner of Mollective, the first investment platform exclusively dedicated to investing in women's sports. And she's the co founder of Angel City Football Club, which quickly became the most valuable women's soccer team in the world. She also started All Raise, a movement to change the landscape of women in venture capital. I met Kara when she was a managing partner in Upfront Ventures. I've been following her for years and, you know, at that point, she backed some of the most ambitious entrepreneurs of our time. Kara, thank you for being on the show.
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Thank you for having me, Lana. I'm thrilled to be here.
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Yeah, it's going to be so fun. But first of all, I have to ask women sports like how did you even decide to go for that?
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Yeah, I mean, I'll back it up and say, you know, one of the reasons we. We call it Monarch and I won't go through the whole story. Right. Is following your energy and serendipity. And I very much did that with women's sports. I mean, I was an athlete growing up. People always ask me if I played soccer. I did, but actually my main sport was basketball and then crew. But no. I went to a 2015 Women's World cup game with my three daughters, my husband, my parents, just to have fun. In Vancouver in 2015, I had the time of my life. Sometimes I think I just hadn't had fun in a while. I was a 39 year old working mom of three, and I was like, oh, this is what fun feels like. And so, you know, what do Americans do when they have fun? They want to spend money. So I ran around Vancouver trying to buy jerseys for my daughters at nine stores, couldn't find them. And it was sort of surprising to me that you had this event where you had hundreds of millions of people and now billion people watched the last Women's World cup finals, but there was like nothing to do with that energy when it was done. So the analogy I made, it's like you have a 90 minute Gatorade commercial and then there's no Gatorade in the store. But everyone told me I was the only one. You're the only one who wants Gatorade. And I was like, really? Look at Instagram. So there's a long story in between there and why women's sports. But ultimately what I realized is it was the first place in my life where all the things I cared about on the nonprofit side or just the purpose side, community, joy. Getting different people collaborating together drove different outcomes. And you would, like, build different experiences. And ultimately, women's sports is about gathering community, providing entertainment, providing joy. And so in a lot of ways, it's like the best type of consumer investing you can do, I think. And no one else was doing it, and no one was. We'll talk about building Angel City, but I had had this experience building the team with my two co founders, and I felt that was replicable and that I could both drive a lot of returns and make people a lot of money by doing something first and early that I was passionate about, that very few people actually believed in at the time. Now they do, but when we started, they didn't.
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So take me there to your thought process for a second, Cara, because again, a Lot of people are like, okay, I'm not finding a jersey, and they go home and that's it. And for you, you decide to start this whole journey of raising capital and doing the things and take me there for a second. Especially in the beginning. Like, I'm sure people gave you a lot of hard time. A lot of. Like you said, like, nobody needs this. How did you even start?
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If I were to write a book, you know, or many books, one of them might be the Art of the Side Hustle, or not all your hobbies and passions need to be your job, right? And then if it's meant to be your job, it will magically turn into it. But I think we're all looking for things that bring us joy, right? And that might be mountain biking. It might be acapella singing on the side. It might be having a glass of wine from Bordeaux, where you study Bordeaux. For me, I am really curious and interested in lots of things. Like, I'll get interested in five or 10 different things in a week, and most of them just go away, right? Like, what are you interested in? When you read the newspaper, you go to something and you're like, huh? Why is it that that way? But the things that stick around and you spend time on and for no reason at all. And that was what women's soccer was for me, coming out of that game. I think those are the things to pay attention to, but you don't necessarily need to turn them into a job or something you make money from. Like, you could truly just turn it, like, have an interest. So that's what happened with me, is I just was so intrigued when I realize now, looking at this moment of intrigue, that I've had others like it, and it was like, how do you identify when something you're intrigued by sticks around and you actually put a ton of time into it? So I like to say I was joyfully irritated and, like, deeply curious that I so badly wanted to go watch Tobin Heath and Crystal Dunn and Alex Morgan and Abby Wambach play, but I couldn't. And that I so badly wanted to buy these jerseys and I couldn't, and that everyone was saying I was the only one, but my interest was so deep, so I started what now, in retrospect, looks like market research. And I just started talking to people, and eventually, like, why is this the case? And how do we know? It's like, how do you know that I'm the only one? And then eventually I started being introduced to the players. So they were all starting businesses at the time. And I was a venture capitalist. I'm like free advice over here. And I became friends with a number of them and would help them as they were thinking about starting their clothing line or their community. And there was a lot of joy in just being different kinds of people. I operated in tech and venture capital and they operated in extraordinary virtuosity on the field, but also were like these brilliant women who went to Stanford and UNC and UVA and, you know, had a lot to offer the world off the pitch as well. And then eventually I was introduced to the head of the U.S. women's National Team Players union, a woman named Becca Rue, who I sat next to actually in an Angel City game last night and is like there from day zero for me. And she asked me if I wanted to be an advisor to the union. So anyway, we can get into that. But it ultimately was just something I was really interested in, like the way people get interested in mahjong or EDM music. And when you find joy and interest in it and you're talking about it all the time, which I was, you just follow it. And I created the space to follow it. My kids were finally old enough that I was allowed to have a hobby and it just became, why can't I watch or buy things?
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You know, And I love that. And I do want to go there with you, Kara, because we are big believers in what I call portfolio career. I think that is part of the future anyway. Like, I think gone are the days that you just do this one thing for 40 years and retire with a golden watch in a party. But what I also loved about what you said, Kara, and I want the listeners to absorb that. Volunteering your time is an incredible way to assess if this is something that you love to do more seriously. Like, I think it's just so beautifully that you just said, hey, let me try to help these people and see if this is taking me somewhere.
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I think we are so wired to think about efficiency and transactability. And did I get an ROI on my time or like an idea of what makes us happy? Right. I gotta fit in the run or the push ups. And like, I mean those things do make us happy. You know, my husband, who's been an incredible partner, but also I realized recently, like he, he's an executive coach, but he became that kind of mid career. I realized he'd been coaching me my whole career. He's always encouraged me and our kids to truly understand what intrinsic motivation feels like. He has me do this thing sometimes. Where he's like, just rate your energy after every person you meet, everything you do, your day, truly understand where you're finding subtle pockets of joy or energy and where you're doing things out of obligation. And a lot falls on either side, but a lot falls in between. And so I think this idea of, like, when you actually truly allow yourself just to, like, understand what lights you up and not need it to be anything, it's a hard thing to do as an ambitious American. My youngest daughter at that game, I think was like, three or, no, five. How old was she? She was like, 2015, actually. She was pretty young, but my youngest daughter was old enough that it was like, oh, I could begin having a hobby again. And for a long time, I just was a workaholic. And I always loved what I did. I loved tech and learning tech and working with founders or being a founder. But I finally realized I had the space for something that could just be mine. And people ask me all the time, did you do this for your kids? And it's been a powerful thing for them to see something that they understand and that I think inspires them. But, no, I did it for me. I really was curious, and I loved it, and I love this community. So I think it's just like, letting things sneak up on you, but then bringing the awareness to, like, oh, how do I get serious about really wanting to spend time on this thing? Otherwise we're so busy. We don't make time for things that don't make money or drive success in other people's eyes. And I think we're all looking for community. And so I think we're in a stage of life where we all just want more and more and more, and it impacts all of us, right? This gluttonous stage of development that we're in as a world possibly right now, where it's always like, something better or something you're missing out on is being marketed to you on social media. And I actually think what we want is real relationships. People we can call up last minute and say, do you want to go on a walk? And one out of every two times, they may say, yes, and do it. And then I think being in service and being in service around things that we have something unique to offer, where we feel valued and where we can partner around the things that we're not as good at and not feel shame around it. And so that is really what I discovered in the early days of being curious about women's soccer and then women's sports was that I had something to offer that was valued. I wasn't gonna be paid for it, but it gave me joy. You know, I could bring these players in the union into understanding kind of my world a little bit. And you can do that as like a parent, as a friend, as in anything. And I think we're all pretty lonely and not doing enough of just that.
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I think we are living in a world that there's just endless possibilities and there's this constant game between. I'm gonna look at it from the 30,000 foot view of what else is possible and what do I want to say yes to? But then you also want to focus, and at the end of the day, just start like, okay, do I want to make this real or not? And so you're helping the union. Before we go back in time to your career, I want to kind of close a little on this. Like, because you created something incredible that nobody was there, nobody almost cared about, and you brought it to a whole different level. Take me to that journey for a second.
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Yeah. And maybe I'll try to line it up to your sort of portfolio career. I think it's like a portfolio of just interest, too, and having the right sense of urgency around each one in your portfolio. So I have a deep sense of urgency around my job. Right. And then my kids. And it's sort of like I'm always balancing that and my husband, you know, But I had sort of like a moderate sense of urgency around women's soccer. And there were other things I was just as interested in at the time. And so if I think about it, it's like the interest began in 2015. I don't think I met Becca for a few years, you know, and so at that point in time, I just was, like, thinking about it. I remember I couldn't get a jersey. I finally got a jersey from a friend of mine who worked at wme, which is one of the big agencies here. And it was Carli Lloyd's jersey. I was trying to get actually Megan Klingenberg's jersey. Carly scores a lot of goals. Megan stops a lot of goals at the time. Or I'd be at an event or dinner or somewhere. You know, I talked to a friend of mine who ended up on our board at Angel City being like, why doesn't women's sports get put on traditional media distribution? He's like, because, you know, you can't get sponsors. And by the way, that wasn't right. Right for women's sports. So there were a lot of people who thought Things that were, like, not first principle thinking that were kind of. And we can get into that if you want to, but I think it's a portfolio of interests and just being ready for serendipity to show up. Right. Like, I got introduced to Becca Rue by a woman named Heidi Patel. She runs the biggest impact fund maybe in the world, at least in the U.S. rethink impact. And she's like, cut. My friend Kara, and she calls me something else. I have a lot of nicknames. They're all pg. But she's always talking about women's soccer as this example of X, Y, and Z. And I'm gonna introduce her to Becca. She spoke at an event we threw, and she was amazing. And that happened years later. And then Becca was like, you know, and we had these constant little butterfly effects, you know? Julie, my co founder at Angel City, who's the CEO of Angel City, I played basketball against her in high school. We had a pickup women in tech basketball game. And literally was at that game, I was like, hey, Julie, I'm working on this soccer thing. Do you want to come hear about it? Go to a game with me on the men's side. She's like, sure, I'll watch any sport once. So anyway, there's all these little things that showed up, but they didn't show up immediately. Versus, like, I think about COVID and I think Covid played a role in all of this. I think a lot of things played a role in all of this. But Covid was the first time in my career I wasn't traveling a ton. I had a time to slow down and really, like, think about what lit me up. But I picked up a lot of things during COVID I mean, I became a downhill mountain biker during COVID So I picked up, like, women's sports in an even bigger. I mean, we were already off and running with Angel City, but it is when I started thinking about, like, how does it scale even beyond a team? And so I think it's just, like, presence to know when things hit you, to realize what people may be important, to, like, allow things to marinate and go away, but also to allow them to come back. And then when you. For me, it's about people. Like, I'm inspired by, like, having accountability with people who kind of begin to see what I see. And I do see certain things earlier than others, you know, where it's real. And then it's sort of like if I find an accountability partner and I'm working with someone who gives me energy and Sometimes this is like somebody who just makes me want to write and it's a friend, but other times, like, you know, Natalie Portman and then Julie Ehrman finding the two of them, I was like, oh, these women see the world the way I see the world. And then it was like a one plus one plus one equality, 35,000, you know, but it marinated for a while before I got there.
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I think we're also impatient creatures. Right. Like we want everything yesterday and it should be big and famous.
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Right.
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And I think there's like, it's interesting to see, like how do you balance between the venture capital, operations, tech operations hat that you have, which probably was a lot of go, go, go, go, go. And then on the other hand, the patience who just kind of simmer in this and, and give it a shot.
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Yeah. No, you're actually really. Because there's certain things in my life right now that I'm not taking my own advice on. I'm not feeling particularly patient around, you know, and it's like, oh, I want this outcome now. And if it's not happening, just the idea that I could sit in the gray and let it be, knowing hopefully I have another 50 to 70 years to live or another day, none of us knows. So I think the things we really want and need to happen that are a core part of our identity or like our day to day happiness, whether it's work, relationships, whatever, it's really hard to take this advice. So I'm going to try to take my own advice.
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If you're feeling stuck, underpaid or unappreciated, or you're simply ready to take your career and life to the next level, I have the perfect solution for you. We have a program that helps you fast track and leap your reputation and career, become the best version of yourself, get the dream role you deserve, move up to leadership, jump to entrepreneurship, or even build a portfolio career. This program helps hundreds a year and it will help you gain the income, influence and impact that will transform the second part of your life. Watch our free training today@leapacademy.com free training. The link is in the show notes. Now back to the show. I want you to talk to me for a second. From the moment that you're saying, you know what, let me, you know, I simmered in this. I met these people, I know I can add some value. What makes you say, okay, this is what we're doing and now you're starting to create this partnership and raising capital. Like, take me for a second on that journey, because I'm sure there's also a journey of rejections and hardship and doubt. So take me on that journey.
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My husband said to me last night, he's like, you realize you're in the rejection business. Like, you say you don't love rejection, but you get so much rejection. And I'm like, you're right. But I still don't like it in certain contexts. In other contexts, I'm like, reject me. Listen, it was this confluence of things that happened and always played a really big role in it. So I have this interest in soccer, trying to think what else I was interested at the time. I'm always interested in personal development and self improvement. So I got really interested in how do I be better, how do we build great cultures. But I came across it very scientifically. And during this time, I also was getting really interested in. In things that my family of origin would consider. Woo, woo. You know, personality profiling, enneagrams, astrology. How do you construct teams in a way where you really understood people's energy and motivation and core vice and not just kind of their tactical skills? So I'm always curious about, like, a whole lot of things. Right now I'm reading about Margaret Thatcher and the coal mines and the. I'm going to just sound really smart here for a second. I'm sort of being forced to read it because I'm doing a fellowship at the Aspen Institute. But I'm also really enjoying it. Like, I feel like I'm back in college, so I have a portfolio of things. What really got me serious, though, about what led to Angel City was, I think, finding, like, purpose in creating kind of the nonprofit I was involved in starting in the beginning, always. And then the friendships that came out of that and realizing I was making, like, real friendships, not like, how do we do deals and who's gonna send me what, but real friendships with women at my stage of career, Female partners in venture capital firms, because we had a joint project to work on. So to make that concrete, things got, I think, pretty serious around the time that we were starting all raise, and there were 15 of us. Right now, it's like the whole industry, and it's been built 10 times over by extraordinary, extraordinary people. Page CEO is incredible. Eileen Lee and Jess Lee, who got it going. But there were 15 of us in the beginning who were just like, hey, there's a bunch of weird stuff going on in tech and a bunch of things that were just really upsetting to us. And I was one of two people from la, who flew up to the Bay Area and just started working on how do we help female founders and women in venture firms. And we launched a bunch of projects, Female Founder Office Hours, a data project, to look at the percentage of women in venture funds and gps, a bunch of things around that. And I kind of like, was responsible for business development with other organizations because there was a number starting at the same time and then running a Female Founders Office Hours event in la. And so I just started working with a lot of the women, Jess Lee, Eva Ho, Kirsten Green, and we all became friends. And through that, I realized I ended up getting to know a lot of the women in Hollywood involved in Time's up and other things like that. And then eventually we had. I mean, this is actually a fun part of the story, so I'll get crystallized here. We had an event where kind of women from different parts of the business industry, from Hollywood to tech to finance to media, got together to just sort of collaborate on how do we get to know each other and how do we bring. How do we just help more women get into senior roles and underrepresented people. And they asked me to speak on stage to represent tech. And at the end of that time, it was a small room. It was 150 people. I said a bunch of things like, let's make the room bigger. How do we bring men in? How do we bring more women in? But I said, while we're here, go make a new friend. In an industry where you probably are never gonna do work and just make a new friend, get their number, go out to a meal and see if they're weird. Block em, but maybe you'll make a new friend. And the person who came up to me and gave me her number was Natalie Portman. And we went and had a meal and we talked about everything in the world. In the last 10 minutes. I told her about my work with the US Women's National Team Players Union. She said, how can I help? And then I brought her in. I mean, she has many more Instagram followers than anyone else I knew who had asked that. And we threw an event together to bring her actress friends. I brought my tech friends in the lead up to the 2019 Women's World Cup. You can still find the picture of her in Eva Longoria, Benizo Budeau and Jessica Chastain. And I brought my tech friends, you know, Ali Rosenthal and Claire Hughes Johnson from Stripe. And I don't know, there's just a ton of people down there. Layla Sturdy and like Everyone loved meeting each other and sort of like new friendships were emerging. And then eventually Natalie looked at me and was like, why don't we start a team? The idea had never crossed my mind, and I went to the men's teams and said, like, how can I help you start a team for free? I just wanted it to exist and so I can go from there. But ultimately, I would say no one really believed in it. And I said to Natalie, are you crazy? I think you need to be a billionaire much later in life. And she said, no, I think we could do it. Don't you know how to do that? And I'm like, well, I know how to build teams and raise capital, but I don't have a stadium in my back pocket. But so I went to the men's teams and then I realized, well, we have a bunch of stadiums in la, and ultimately I was doing a lot of work to try to get other people to say yes and own all of it, but I was doing a lot of work on it, and Natalie was doing a lot of work on it. And she said, is this how it works in your industry? Right, And I'm a venture capitalist at the time, you do all the work or we do all the work and somebody else owns it? And I was like, huh? No, there's something called founder equity. And so we just kind of completely switched our mindset and we're like. I was like, oh, I'm in the business of building things, but also pricing risk. What would be the risk of me and Natalie and then Julie starting this like you would a tech company and owning 100% of it as founders, not having a license to operate in la, not having a stadium, but having, like, a real plan as to how we would do that. And then we ended up raising just shy of a million dollars after a long process and many people being like, you guys are nuts. But three weeks before COVID at, you know, a $6 million valuation, we gave away 10, 15% of the company, but we owned 85% of it. Right. And then Covid came, and then you're like, oh, my God, we got to figure this out. So anyway, that's how Angel City started. And I would say it was as someone who's, like, grown up in business and in this world, it was very organic. We started angel city in 2019, but I started thinking about this in 2015, and it was a four year journey of just not having an agenda and just following my interest and getting to know the players and the union and everything else.
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I'm sure. First of all, there's a ton of rejections on that $1 million. Is there a moment where you're saying, am I kidding me? Like, what on earth am I doing?
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Natalie and I met, I don't know, 2018, maybe 2009, early 19. Getting Julie involved was like, you know, a major milestone in retrospect, right. And Natalie and I took her to an LAFC game, August of 2019. And that's when we really, like, working, like, two in the morning on this. And Julie and I were sending decks back and forth, and Natalie would give us feedback and really trying to refine the model. How much revenue could we drive and just get ready to. Okay, we got the team. We can do this together. Who are we going to go to lease the stadium? All this stuff? And we got a lot of people close to yes. And then they would pass in the last moment. It was like, what kind of investor are we bringing in? And actually, at the game last night, someone was reminding me about one investor I really wanted. He ran a very big private equity firm. A bunch of my friends had worked for him at one of the big banks. Kind of all the things like, great investor, great operator, great human, had really supported all different kinds of people rising in his organization. And I remember he called me, I think it was January, and said, I'm going to pass. And I still remember why. And I was just like, on the floor, like, God, I thought this was it. And so I'm a pretty, like, if I believe in something, I'll keep going. But I also always gave founders the advice, like, eventually you have to take the signal and your time is valuable, and maybe you're wrong, you know, like at some point or you figure out how to do it without needing capital. But Julie would pull me up and the same thing, like, when she had those moments, I'd pull her up. So a lot of what I think made this work ultimately was Julie and I were never down at the same moment. We kind of gave ourselves April as the deadline, and we got the capital kind of closed in February. But I remember January being really low, really low. Wow. Wow. I didn't know if I was raising $50 million or 500,000. I knew ultimately it was probably gonna take 50 million. And in venture, you'd raise like, a $4 million seed. And then you're whatever crazy Series A's are now your $10 million, $20 million Series A, and you just go, here. It was like, we did it in a way that was, like, different to My knowledge, I think we're the only C corp in sports, you know, and it was a kind of a founder driven thing. Every other team has the concept of a control owner, which we ultimately had and we brought in an investor to be that. But you know, I mean a couple investors to be that at different stages. But it was like I didn't know initially I went out looking for someone who was going to own 90% of it. Maybe we'd get an equity pool as founders and be our control owner and backstop everything and be ready to put in 50 million. So there was a lot of learnings around like you know, to go to Cedar Series A investors. If you're starting a tech company, I'm like going to family offices and some funds and then our friends, some of whom happen to be famous and. And so it was very confusing. How much are you raising? How do you price it? Are you doing rounds? Is this more venture like or is this more sports like? And we ended up more venture like and then more sports like. But it was like a real journey of what is our product market fit even in finding the right funding for US Capital.
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B
Yeah, that's incredible. I mean especially because you did come from again, you have a ton of tech. We'll talk about it in a second. And a ton of investment venture capital. And still just hearing your story I think is really, really important because I, I literally wrote this quote. You are in the rejection business. Like I think every single person that is driven and wants more from their career, from their life, will eventually push their limits to be in the rejection business. And I think the bigger you're trying to aim, the more rejections you're gonna face.
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A
Yeah, I mean it's a takeaway from talking to you today. It's almost like you can like segment rejection. There's some rejection is comfortable for me taking. There's other rejection that hurts every time I get it, you know, and it's like the ones where you think it's gonna happen and then it doesn't in the last minute or like you don't feel seen by someone that you have like a deep relationship with versus like, you know, this just isn't for me. And up front, now that I raise capital for a fund, right. I run with my partner, Jasmine Robinson, Monarch Collective, where $250 million women's sports fund and we raised that fund also. When like another one doesn't exist, more will come. But there's some real first mover advantages where I love getting rejection around our fund because it's just like those people often become my friends because, like, it's what we do is really different. We're gonna really differentiate in how we make people money. We're in this risk asymmetry that no one else is in the most mature parts of the women's sports ecosystem. And there's a whole lot of people who are like, well, this isn't for my university. And by the way, like, a lot of university endowments are like, this very much is for my university. It's uncorrelated, it's culturally impactful, it's differentiated, all that stuff. But if you then stop and are like, okay, I'm not gonna get this order for the thing. I know some of those people have become my really close friends. And then they come back to me, they're like, why aren't you pitching me? I'm like, cause I thought we were friends. And so it's almost like segment rejection. And where is it hard for you and where is it easy? And then what are the other things in life behind that rejection that could be positive on the personal relationship front? My husband rejecting me and like, hey, I want to go to this festival. We can't go to that festival. Wait, why not? Because I always want to do more than he does. So anyway, I think it's interesting to segment rejection, understand where it's easy and where it's hard. Because I think as human beings, we're all in the rejection business. If we're trying to find purpose in work, passion, in love and in relationship, and we're looking for plans. How often do you invite yourself to someone's house? If you did it more often, you'd probably have more of the plans you want. And if people could just say no, you might be having more of the plans you want to have.
- [31:51]
B
So with this in mind and with how you look at rejections and pitching people and not being afraid, and I'm hearing a lot of things about also, like looking at a big, huge, humongous project and instilling it into smaller projects. But let me take you back in time for a second to how did you even get into the venture world in the first place? Like again, there was like Morgan Stanley and Battery Ventures. Take me for a second to like a little bit back in time. How do you even get into this pretty crowded, male dominated area? Like, how did you even get in?
- [32:27]
A
I grew up in the San Fernando Valley in la. I did my undergrad at Princeton. I studied politics and did a side of a lot of other things. Economics, et cetera. But honestly, I didn't really have a background in finance. And then coming out of school, I was deciding between working at Morgan Stanley in their captive private equity firm, which was very quantitative, very specific, you know, sit around, build big models all day and night, or going to work for a consumer protection nonprofit. Unfortunately, you can't do that anymore. But those were, like, my two interests. And in a way, what I'm doing now, it's like bringing those two together, combining. And honestly, I mean, I actually ran into one of the guys who convinced me to go work at Morgan Stanley this week at this, like, event where I was talking to university endowments and pensions, and I was like, God, would I even be in this room if it wasn't for this guy who had taken me to a meal? And what he said to me was, kara, if you come to Morgan Stanley and you do well and learn finance, you can do all your other save the world stuff. You're going to have a skill set to go save the world. So go get a skill that scales across both. And so it's a little bit of the life advice that, okay, yeah, you should follow your passions. But also, what do I tell my daughters now? In a world of AI, what are the skills to have? What are the skills that could really span across a lot of different things? And so that was good advice. And then, honestly, you would interview with different groups at Morgan Stanley. You take the job, and then you didn't know what group you were in. And I just ended up in one of the maybe two or three there. That was the most quantitative hardest. I'd never used Excel. I'd never taken a finance course. And I'm like, I'll go do the hardest one. But I was scared. I mean, it was scary. And I was wearing nylons and suits, but I did it, and I did pretty well. But I also realized the things even then that made me feel different, and they weren't things I necessarily felt good about. I think sometimes I say it took starting a professional women's soccer team in my 40s with two other women to have confidence in myself and understand where what I saw differently was a positive. And everyone says they want cognitive diversity in their firms and. But I think the hard thing is when you think differently in a firm and if you've actually spent the time to, like, gain credibility and learn how that firm works and learn how that industry works, like, you can't come in at day one and be like, here are all my ideas, and they're better than yours. But if you've done that, it's very hard to not feel like these are bad or wrong or I must not be getting it right. I think that's disproportionately female, but it could be male as well. Like, you know, if you come from a different socioeconomic background, different races know you, different kind of family. And so I guess what I would say is one of the things that was different about me at Morgan Stanley was like I seem to want to become the expert on back in the day DSL or cable modems or unbundling local loops, which was what tech was in the 1997 when I was there. And then I was reading books like Electrical engineering for non electrical engineers and being asked to send a conferences. And then once I cold called a company that I thought we should look at and I'm working on leverage buyouts right in healthcare and chemicals and they're like, you can't do that. You can't call companies. You just model quietly and sit in the room. And I just got really passionate about tech and I was actually I did sit in a room of a board of this telecom company with Rick Frisbee, who was the founder of Battery Ventures. And he took a liking to me. We had a meal and he was like, why don't you come work for us? And I mean it wasn't that easy. But I interviewed to work for them along with a lot of private equity firms and hedge funds. And I took a 50% pay cut. I remember my dad, who's a doctor being like, why is everyone else you're working with going and making more money and you're taking a pay cut to go work at Battery Ventures. But it just felt like the gold rush to me. I love learning about like the protocols and OSI stacks and super nerdy stuff. And I just found that a lot more interesting than manure business. You know, a buyout on a manure business. And I love the innovation. So that's how I ended up at Battery. And then it's a whole story from there. But I learned to cold call and source and I loved it. And it turns out like wedding those two skill sets of learning tech, being able to go out and generate business and sell things you believed in and then being able to work on what you. It's like what is it? You eat what you kill? I guess. So I do the due diligence and then eventually I would even get the board rolls. So I was given my first couple board roles battery in my mid-20s and I was learning from Tom Crotty, Rick Frisbee, Todd Diggers, all these guys who were like, went on to either start other firms or like, build one of the best firms around in battery ventures.
- [37:11]
B
And I think one of the things that I literally just talked about with somebody, I was like, one of the best pieces of sitting on a board is that you, yes, obviously you get to help and, you know, et cetera, and with your, you know, and share knowledge, et cetera. But the biggest thing is you sit with really smart people and you learn from each other. It's like, it's pretty amazing. But then you went into the tech.
- [37:33]
A
By the way, one other quick thing I'd say too is like, it was a different time in venture in a lot of ways. I make the analogy to the way it is in women's sports now, where it's like, there are not very many firms looking at and doing what we're doing. But yet, like, when we invest in the Boston expansion franchise and they buy in at $50 million and the last franchise went to Denver at 100 and whatever it is, 20 million, like, we are there as Boston's partner, we're working every day with them on stadium financing, building, the executive team, and we're doing it at a much lower valuation than just the right to operate in another market. So your downside's protected, right. And your upside is venture like. But we were the only ones working on it. And it requires like, stakeholder relationships and operating skills. And coming out of Angel City, my partner came out of the 49ers. Venture wasn't that different back then. There were five firms in Boston, five firms in the Bay Area. Now there's thousands. It's an efficient market, but it was inefficient back then. And so I also, like, you could price things reasonably, you could exit reasonably and generate 5-10x funds because the market was behaving more responsibly, you know, and it was much more fragmented. And so it is one of the things, like I learned being not just at battery, like, these were like really high integrity, hardworking, low ego guys just like, hustle harder, do the right thing, never sit on more than six boards at the time and work so kind of a similar model right now in women's sports. And so I've thought a lot about that as well and the analogies there and how different venture is now. Where it's so much of it is marketing and it's such an efficient market.
- [39:10]
B
So then you decide to become an operator Right. I mean there's like IAC and Urban Spoon and you're in those executive level roles. What do you feel are some of the maybe hard lessons that you learned when you switch from venture to actually an operator? Because I'm sure it's very different experiences as well, which I'm sure you're also bringing in today.
- [39:32]
A
Yeah, I mean, to the extent people who listen to this are thinking about like, am I an operator and am I an investor? I think a lot of people go through that journey and I always say am I well suited to both or ill suited to both. But I think ultimately what I've realized over the course of my life and career is I'm a very operationally oriented investor and you can kind of hit either side of it. But knowing how to structure, be disciplined, be intellectually honest and walk or Chase and price risk is a real skill set. Right. And I learned that at Morgan Stanley and Private Equity, at Battery Ventures, at Upfront Ventures and at IAC where I started an M and A and ended up co heading the M and A group. And there we were, very creative structure. I worked for Victor Kaufman who was Barry Diller's right hand and is still a mentor to me. And it was really about how do you generate EBITDA or what they called oiba. But every structure was different and in a lot of ways, actually that's what I now really my partner Jasmine Robinson and I do at Monarch. Every deal is structured differently, but the risk outcome is the same. But the operational side I always really valued because I think there are two kinds of investors who emerge over time. There are those who are portfolio managers and sort of generally know how to price risk, manage a big portfolio and are more passive. And then there are those that are really operational, hands on. And your portfolio size is an indicator. You may say you're operational and hands on, but if you haven't scaled a huge operating team to go alongside a big portfolio, it's hard to do that. And so I'd always wanted to be an operator. I'd worked for my summer between my two years at business school at Microsoft. I'd always been placed in Corp Dev. Nobody wanted me to be an operator. And so IAC was this opportunity to come into M and A, do something I knew how to do and if I did a good job, IAC had a reputation for taking senior executives in corporate and giving them a chance to operate. And it was one of my most fun, most intellectually honest. I loved the job and also a meritocracy you know, like, there were two women in corporate, me and Shanna Fisher. But it was a really, like, much more cognitively diverse group. And, you know, like, we were, in a way, really disciplined. But we'd come in and be like, how do we get something in front of Barry that moves his brain? And then how do we, like, beat each other up in the nicest way possible to find out? Is this something IAC should do? And so while I was there, we spun out Ticketmaster, HSN, LendingTree. We also incubated Vimeo out of college humor. And then I moved into these operating roles where I ran a bunch of businesses. Some were falling knives, some were high growth. So Urban Spoon, super high growth. We took it from 1 million to 30 million users. First iPhone product I was part of led the team. We were building out a salesforce, rolled out a competitive product to OpenTable, ended up selling it to OpenTable, but also City Search, which was like, going like this when I was given to it. I ended up playing a key role in incubating what became Tinder while I was pregnant with my third child and recruited Sean Radden. And just that was incubated out of LA for a mobile incubator, where this became, I think, the main thing that generated returns and is obviously the heart and soul of a dating business now. So there was a lot of diversity there. And so what I would say is I love building things. Right now, what I'm loving building is Monarch as a firm. So we're built. We have an investment product, but we are building a company at Monarch. Many of the people we hire come out of operating roles at the MLS or, you know, the NFL or a big team in England, and we train them to be investors, and then we have excellent investors who are great at structuring. But we're building it much more like a company than a firm. And so what I'm doing now is the best of both worlds. I think a lot of the journey is just knowing what you personally love and then honestly finding a great partner who compliments you. And I've really found that at Monarch, and I really found that at Angel City with Julie and Natalie, which is.
- [43:30]
B
Incredible because that's also one of the hardest pieces. I think where I started hearing about you and we talked a little bit about it is in Upfront Ventures. And was it your first partner role in a, you know, pretty prominent. You're next to Mark Suster, who is very vocal, like his seal, you know, at least at that point was like, I don't Know, like, we saw him all over. What was that like?
- [43:59]
A
I mean, everyone I've worked with and for in my career has been extraordinary at something. And I think this in general is a thing to get in touch with. Like, we all have spiky superpowers and like Mark, for example, it was just incredible how he would see talent and bring it in and really understand sort of how to build a fund in the LP side and all the other things. But I think for each, it's something I think about is like, where does everybody spike? I was actually writing up, I'm going through, thinking through our next fund right now because pipeline's really good and, you know, and we have, you know, a lot of interest coming in and the like. And I. But I, you know, I know that this word used to irritate me, but now I love it. I was going back to first principles. I'm like, what is really different about us? What is our differentiated product before we invest, after we invest, what? You know, how has Monarch become this brand? And then like, why do we have the right to win? And then why do people want to work here, you know, and work with us? And, you know, there's a lot of things in there, first mover, our operational value add product, et cetera. But one of them was like, we really have 10xers in terms of people and they all spike on something. And then I have gone above and beyond to figure out with my partner Jasmine, how do we be collaborative internally, how do we pass the baton back and forth and when do we double up on things, which we do a lot where somebody's strong at one thing and somebody else is strong at another thing. And so I think being at upfront and all the firms that came before that, it's like each one of them, I took something away that, I mean, I started monarch in my mid-40s and I wasn't necessarily, you know, a lot of things I've done that people now know me. For Angel City, which, for those who don't know Angel City, it was the first majority female owned, female led professional sports team in the country. We went from 0 to 30 million in revenue our first year and had more season ticket holders than two professional teams in la. And we really proved out the commercial model for a women's sports team was viable. We built the first P and L and then a lot of the other teams. There were a lot of people who've been doing work for a long time, but everyone said a professional sports team in LA wouldn't work another one, like, essentially an old 12th one. And so I think we showed that if you build an incredible experience, butts and seats, and you have a product on the field that people just don't get, but is as fun, if not more fun than anything else out there, it can work. And we exceeded our initial forecast in our first year live by 4.2x. How often does that happen in ventures? So I just want to mention that.
- [46:27]
B
What happened, what made it a success for Angel City?
- [46:31]
A
I would say, like, there. It really was, a unique dynamic between me, Julie, and Natalie. I mean, so first of all, like, I do think the market timing was right for something like us to emerge. But it was hard. I mean, it was the hardest six years of work in my life until we brought Bob Iger and Willow Bay in as our control owners. And we're all still very involved and have equity stakes, and Julie's the CEO, but it was like, I mean, did we create the market or was the market ready? I guess we could have that debate. I think it really was like, Natalie had this sort of very. Like, we were all mission oriented, but she really held it, like, what does it mean to have representation? I remember we had certain conversations around stadiums where we're gonna have room for rooms where people could nurse, and how are we going to create an environment that really stood for our values? Julie just ran through walls, and so did I, in a way. Julie and I had similar skill sets, but we both could sit in the complimentary nature of them and, like, fundraising, building a team, getting sponsors on board, building community. I'd say one thing, like, Julie was out at every community event. We did 300 community events, and we pioneered a new sponsorship model. We donated 10% of every sponsor contract into a community cause. So doordash, we broke records. They were a $10 million contract for our Chronic kit, which is unheard of. And we hadn't sold a single season ticket or had a single player. But we'd go to dinner with these people and we'd tell them the vision. And I think we inspired people to believe it was possible. And that changed things. And then now it kind of blows my mind, you know, like, when I go to games even. Last night, I got a note from my friend who was in from the Bay Area, my friend Michael, who said, I get it now. This is a community. And I'm randomly bumping into someone I grew up with or my teacher from preschool. It's so. And I, you know, I've the. I grew up in la. I know these People. But that's the case for everyone. Like, I'll meet. I'll just meet different groups of people who are like, have a whole group of friends that they meet there and they love. So that was Angel City. And I think it was like, honestly, we just killed ourselves working on it. At some point, I realized this was my life's work and it wasn't to be managing partner of a traditional venture capital firm. And I had to recognize that that was a big change for me because I loved upfront. It was where I thought I would spend, like, I thought I'd be in venture the rest of my career. I got this job I thought I wanted, and so one might call that a midlife awakening. But I listened to it, and it was scary because there wasn't the concept of Monarch out there. And I didn't know if I was gonna ever make money again. Right. And I have three kids and live in la, so I think it is really finding that thing and when it speaks to you, and it may speak to you in your 20s, your 30s, your for your 50s. Arianna Huffington didn't start her first business until her 50s. So I think it's just being ready for that when it shows up and then finding people that you can walk with who inspire you, and knowing when to run through walls and take risk.
- [49:27]
B
We are big believers, especially now that we see people leaping again and again, that the pace of change is ripe, that you're gonna change anyway every year or two. Right. And it might be in the same place, but then in the same place, you'll change functions, you'll change responsibilities, you'll change whatever. And it might be in different industries or it might be a portfolio. It might be another venture that you're after. So I think you will find those. Like, you're just gonna need to leap again, again and adapt. But now, you know, let's go with Monarch, because, again, like, at some point, you decided to leave this incredible venture that you were part of. And that must be scary.
- [50:10]
A
Yeah, it was really scary. And by the way, one quick thing, just on what you said, so we wrote a case study for a business school on Angel City, and there was a fair amount of interest in doing that. And one thing I realized that was important to me was that we put it in a class that was not a sports class, even though we love the sports classes and we've done cases in sports classes. But how we built Angel City, I really wanted it to be in a class where many people who think they know what they're doing, which I thought I knew what I was doing when I was 28 and graduating from business school. Could think about, like, you think you know what your application is, but actually, like, finding the thing that's uniquely yours to do may come at different times and it may be an area that you're very insecure about, you're nervous about, the world doesn't see. So I wanted to inspire people to do that. And so Julie and Natalie and I wrote the Case with Harvard. And it's in their kind of like second year elective with Jeffrey Rayport Scaling Ventures. And it's, it's everyone. Because I think these things pop up sometimes when you least expect it. And the story of that, to me transcends sports. Right. And so monarch similar thing. Honestly, I had a spiritual moment in a cathedral in Spain. As ridiculous as that sounds. It does. I was in a cathedral in Seville with my husband and daughters and I had this moment where I was like, it takes hundreds of years to build these cathedrals. And when we go to Europe, we visit cathedrals, we visit the Coliseum, we visit palaces. Again, one of the reasons we call it monarch, building new kinds of monarchies that can stand the test of time. The yin and the yang, the black, brown and white, the male and female. But I was in this cathedral and I'm like, I'm laying the brick in the middle of a cathedral that there's a lot of them, you know, and it was a really good one. But like, I see something and feel something in women's sports, which is really just consumer or community. Right. Like, if you think about women's sports or sports, the men, like the whole ecosystem is probably a half a trillion dollar total addressable market. The women's side is a couple billion, and it was like 100 million when we started. So it's a venture market growing quickly. It's a fraction of the men's side. But if you think about it, these are like monopolistic consumer IP platforms. There's no reason why this can't be trillions of dollars and it's a half a trillion now. But the women's side is teeny. But like that segment, if you do things a certain way, like Angel City or like the New York Liberty or like teams we're looking at now in Europe, and you build the cap table in a certain way, you get the best talent in and you drive financial outcomes. You can also drive cultural outcomes. You can get a different fan base in. You're going to get different sponsor partners and activate Them in different ways. So if you go to a Liberty game now, and I was there last week with a bunch of our LPs after a wonderful industry event we threw where we explained to everyone how the market works. You know, they have their Fenty cam, and it's like. Was Fenty. And it's great. It's like a kiss cam, but with women and their makeup or men and their makeup. And, you know, you look at all the sponsors that are coming into teams like Angel City, Liberty, you know, Boston Unity, which is another one of our investments. San Diego Wave, another one of them. It's a whole category of, like, brands that are getting that have never advertised in sports, period. Like, there's no reason the women's side couldn't be bigger. But I think, like, Monarch started for me there. I wrote this little Jerry Maguire memo, and I'm like, I gotta go do this. I gotta build something where we can help more teams, leagues and rights. But, like, teams be more like Angel City, where we can come in as a large shareholder, work alongside family offices. In some cases, we help them bid and understand the market entirely. In other cases, we come in later, side by side, and we'll bring, like, we bring talent, we bring brand sponsors, we bring our brains, we bring. You know, and so I wrote this memo, and then I went looking for a partner, and Jasmine and I just really hit it off. She has this extraordinary background at Bain and then the 49ers. She was in every operational role, you know, more or less. You know, it's just a star. When they moved from Candlestick to Levi's, and we shared a similar vision when, honestly, many others didn't. Now, a lot of people do, but when we came together a handful of years ago, this was exotic. And we set out to raise 100. We ultimately realized the right fund size was 250, and that was our hard cap, which is a nice thing to say as a fund manager, but we have a very disciplined strategy where we're only focusing on the most premium brands, teams, leagues and rights that can have cultural impact and drive. Can drive financial returns in a way that are unique. So that's how it started with a memo and a partner who was a great compliment to me.
- [54:54]
B
Ah, this is so beautiful. So right now, I think you. Are you guys raising again or are you gals raising again?
- [55:03]
A
We're not raising right now, but we're always meeting. We're always meeting like, mind. I mean, we also care about impact. We're an impact fund, so we really look for Values alignment in every part of our ecosystem. And if you come to our LP meetings, it's like some of the top family offices and institutions in the world and they're the most fun, right? And so it's like deep intellect and deep joy and we say no to people on occasion and keeping that alignment is important, but we're always, always, always meeting new LPs and the like and we try to spend time getting to know each other far in advance because it is a real two way relationship. And so anyway, but yeah, we, I'd say Pipeline is really exciting and strong. We do a lot of thesis based work so we try to like we'll have theses we're running that we won't invest in for two to five years, but where we're mapping stakeholders in a new sport or a new country. So we invest between the U.S. and Europe. Soccer, basketball, golf, tennis, we spend time in volleyball, hockey, cricket, rugby. But we spend the most time in those first four sports where media revenue is up and to the right and where we can get the core business to break even or better. So it's really like a venture like market with a growth equity kind of risk profile. And it's fun and we help people learn and a lot of those people go on to buy their own teams. Like sometimes they don't become investors in Monarch, but like side by side partners or just friends in the ecosystem because we're all operating together in these leagues and hopefully we can help a lot of people learn. Like why would you invest in women's sports versus men's? What's the right president profile for a women's team versus men or a chief revenue officer? Or like how would you build a season ticket holder base and challenge your assumptions? Because for many of the best teams, the overlap with the men's team in that market is like less than 10%. So where do you kind of look at doing things the same but what you do differently is maybe the most important to build Real Madrid or the Cowboys or the Lakers or Dodgers, because that's where you are in women's sports. We don't know who all those teams are going to be. They're being built right now and they may be worth many billions of dollars over the course of the next couple decades.
- [57:03]
B
And that's so exciting because it is changing everything in the ecosystem. So I'm inspired by this conversation, Kara, and what you guys are doing.
- [57:12]
A
And I mean, maybe last thing, we have an all female firm we look to hire though, like in an open way. And so we put every job spec out on LinkedIn. It's been incredible to see the response just from that, you know, even we just made our first hire over in Europe, in London, to see the amount of people with interest, you know, over there. But I think we, we really do try to think about how to build a firm that can look at every investment in an intellectually honest way, you know, and just. And so I think I'm personally passionate about just sort of how do you build financial institutions too in a way that it's not just different to be different, but that we're culture skills because I think people enjoying their jobs is how you be 10x in the thing you're excellent around. So thanks for the opportunity to talk about it. It's sitting next to Becca Rue who runs the national team players union. Last night she said if you look back at the last seven or eight years and everything, you're like, maybe. And it's just I don't get to do it as often. But it's hard work. But I have a lot of gratitude for being able to be on podcasts like this occasionally and talk about it. So thanks for having me.
- [58:18]
B
Oh, it was so fun. So maybe summarize that. If you would look at yourself 10, 20 years back, what would you want to know?
- [58:29]
A
Oh God.
- [58:30]
B
What would you tell yourself?
- [58:31]
A
I got the chills when you asked me that question. You know, I think operate out of abundance and not fear. And when you're feeling the fear, you just can't make it go away. But like sit in the pain and the fear and it's, you know, I have a good life. I'm really grateful for it and I've learned a lot of things, you know, over the years. I've been to like, I did a lot of executive coaching and a lot of things to like make this change, you know, and feel responsible for earning income for my family. And I have a really good life and you know, went to the Hoffman Institute. Anyone has some self improvement questions, I'm your woman. But I would say lean in. I guess I'd say like when you're feeling the pain, personal pain, professional pain, know that don't run away from something, sit in it. It's always better to run to something and know what you're running to and you know, like figure out ways to actually figure out ultimately, you know, I have this executive coach that was life changing. Her name's Diana Chapman. She's started Conscious Leadership Group. She changed my life probably more than anyone other than my Parents, my husband and my husband and my kids. And she talks about aliveness and just how you find it and then just how you just keep getting curious and not defensive. And I think I would say gratitude. Look for the joy. And then if you are in a place where you can take risk, even if you have a huge expense line and things like this, just look at how long you have to go and then try it and then know when you're gonna stop and it's gonna be okay. Like it's gonna be okay. As my husband always said to me, and I married well, we can always sell our house and go live in this area and earn money this way or that way. And I didn't always believe him. He has more of that mindset than me. But I think pick your partner well. If you can, pick your partner well. People who help you move through the low moments and anxiety, one foot in front of the other. Some days, like when it's hard and you're not feeling the inspiration, just wake up and put one foot in front of the other and wait for the magic to show up. And when it does, grab it.
- [60:43]
B
That's so good. Kira, thank you. Thank you for coming to the show. Thank you for sharing all of this. Thank you for what you're doing and this is just beautiful. Thank you.
- [60:55]
A
Ilana, thank you for having me on. This was fun.
- [61:10]
B
I hope you enjoyed this as much as I did. If you did, please share it with friends now. Also, if you're feeling stuck or simply want more from your own career, watch this 30 minute free training@leapacademy.com training. That's leapacademy.com training. See you in the next episode of the Leap Academy with Ilana Golan Show.