From Venture Capital to Women's Sports: Kara Nortman's Defining Career Pivot

Thanks for having me, Jason.

First job. Well, I started probably when I was like 10 or 11 filing and babysitting. Actually, I think I started babysitting when I was eight, which seems...

You and I both know we have three children. Sometimes you do file a baby. And then my first job, you know, kind of I would say in a more formal way was I was a scooper at Ben & Jerry's in high school and took a lot of pride in my career path there actually.

Oh, no. I was like rule follower, but I took it really seriously. You know, we had to memorize every ingredient in every flavor. You know, I would make ice cream cakes and coffee and wash windows. And then eventually I got to become sort of the shift leader and did the financials. And it was actually a really great experience.

Still love...

I love ice cream and I love rainbow sprinkles. So that's still a guilty pleasure.

Yeah. I think what I probably thought my defining strength was early in my career versus maybe even the last year of my career, very different. I honestly thought my defining strength was my work ethic. And I just was always willing to work more, harder, throw hours at it in an unhealthy way, sacrifice sleep. And I always knew I had enough of every other skill. But I just thought it was like the grit and the grind. And there's positives to that, but there's also negatives to that because there are things that I probably am uniquely good at. And then there's things I'm less good at. So, I think there's been a real journey and I often... there's a real journey in particular for women to understand strengths. But I think all of us kind of take for granted the things we're naturally good at. And at least for me, I didn't value them or even see them until really my mid-40s.

How broad do you want to go, Jason?

I'm now in women's sports, but I spent most of my career in tech. You know, I would say I spent probably the first 25 years of my career in tech between investing and operating. So, everything from, you know, working straight out of school at Morgan Stanley and their captive private equity group. Though I was deciding between doing that and going to work for a consumer protection nonprofit. So like very different things were on my mind even graduating from college. Spent a bunch of years in venture at Battery Ventures, Upfront Ventures. I spent close to a decade operating working for Barry Diller and Victor Kaufman at IAC. So ran, which is a public company, to at the time about a hundred different consumer brands. So I ran... I ended up co-heading mergers and acquisitions for them and also operating a number of the business units. So involved with everything from like the early days of Tinder and Vimeo to spinning out Ticketmaster and HSN. But what I do now is women's sports. So I run with my co-founder Jasmine Robinson a $250 million women's sports fund. We're still the only kind of investment platform that is exclusively focused on women's sports. We invest in teams, leagues, and rights and only the most mature parts of the ecosystem. And that really came out of a fun longer story. Where while I was in venture, as my kind of side hustle curiosity, I ended up being one of three co-founders of Angel City Football Club, which was really the first women's sports team to prove out a commercial model and build a real P&L. And I co-founded that with Natalie Portman and Julie Uhrman, having started thinking about it in 2015, and we started that in '19. And that really was a hobby and it led to probably the greatest fit I didn't know I needed.

I mean, it's a lot of moments. I mean, it's one of the reasons we call the firm Monarch. Is sort of like all of the flaps of the butterfly wing, the chaos theory, that if you follow them 10 or 20 times, it might lead you to a completely different place in life. But a couple key moments in 2015, I went to the Women's World Cup finals in Vancouver with my three daughters, my husband, and my parents just to have fun. And we watched this game where the US won 5 to 2. It was the first time the US had won a World Cup in many years. And I mean, even saying it right now, I'm getting the chills. I felt like 12 again. And I just had so much fun. And it was almost like I remembered what fun felt like. I was a working mom in my late 30s and it was almost like I just didn't even know to look for fun anymore. I didn't even know I was missing and it felt really different. I love sports. I played sports but it felt very different than the men's sports events I had gone to. There was like a greater purpose, community. People were face painting, friendly. And so I went to nine stores in Vancouver to find a jersey to buy my girls. Couldn't find any. I think I found one without a name on the back. I then went home and tried to find content for this league I didn't know existed that we now have a team in. Couldn't find it. And ultimately I just started asking people and I became kind of business curious around why would you have some, you know, 90 minutes of something extraordinary that hundreds of millions of people watch and then nothing to do with that enthusiasm and demand, right? It's like having a Nike commercial and then no Nike in the store, you know? And everyone kept telling me, 'No, you're the only one who wants more.' So anyway, that led to a whole wonderful series of events, but the biggest one was when I was asked to be an adviser to the US Women's National Team players union. A woman named Becca Roux asked me to do that and she really became my teacher and mentor. She thought I was doing her a favor. She ended up doing me one of the biggest favors of my life. And I think that is one of the things around, for me at least, how you find fit. So many... I mean, I didn't go into that moment with this idea that I was going to have a complete pivot in my career, but what I found was I went in to help work on pay equity for the team. Visibility. I mean, it's how I pulled, you know, Natalie Portman and other people with bigger Instagram accounts than mine when they expressed an interest. But I also learned licensing and rights and early NIL and group... you know, when one team was starting. So anyway that was the biggest shift and then there's all this wonderful serendipity that led to actually starting Angel City and the way we all came together as co-founders and the way we ended up finding capital which was not easy. All of it. So I can get into it if you want but I'll pause there.

I mean, it felt really exciting and really scary. You know, I have a wonderful partnership in my marriage and I did have a big job. My husband made a lot of changes in his life and career to support mine. So, I was also responsible for earning money for the family. I had just become managing partner at the firm I was at. That's where I thought I'd be forever. And as you know the way venture works, it's long-term vests and equity and all that sort of stuff. And so, leaving right as you're moving into a role like that comes with a lot of changes financially. And so, I don't know that a lot of people would have done it. And I'm not even sure I'm here to encourage a lot of people to do it. But I will say that I couldn't imagine... you know me pretty well. I'm a pretty happy, joyful person. I really have enjoyed just about every job I've had. And I was often the person they would cart out to like sell people on why working 100 hours a week building Excel models was going to be amazing. But so I think in some ways even harder because I was always kind of happy where I was. It wasn't like I was looking for something new, but it was almost like having this feeling of like, oh, this is what true alignment feels like. And I didn't know it could feel this way to have such a drive, a purpose around what I'm doing and feel like my skill set was so uniquely suited to it. And it didn't necessarily feel as suited to venture anymore. Like I don't know if I would have admitted that to myself. Because the industry had changed so much while I was in it. So it felt really exciting, really scary. And I mean I had also a great husband who happens to now be an executive coach alongside of me and he would like make me decks and he was really encouraging me to take that risk. But it was a journey. I mean it was definitely a journey and I got a lot of coaching externally and internally to be able to do that and I left about a little over three years ago to start Monarch starting at a zero salary and being told that the strategy we were raising capital against was exotic because Angel City never paid me a salary. We just... Natalie, Julie and I owned 100% of the team when we started. It's actually a C corp. And so, the equity piece of it was meaningful obviously, but it was not like kind of paying the bills. You know, as a working mom of three.

Yes. And it's forever work to create the container to find it. Like I don't think that flow is just consistently there for you. I would say all the like getting the ingredients right make it... it's almost like I'm always looking for step functions and sometimes you just kind of have to realize like you might just take a step back and be like wow okay like my daughters are good my marriage is good I'm sleeping I'm traveling like a crazy person but slow release melatonin on occasion really is helpful. But I do think I still... I mean I'm a self-improver. I sort of practice what I preach. I'm always sort of trying new things to bring consciousness and the right kinds of collaboration into my own life for myself with my team. I do unique things with my partner to actually onboard our team which we could go into. But I do... I think I feel flow like these days I feel it a ton. But it also wasn't just like a leaving one thing for another. It was actually doing a lot of work on like fundamental personality patterns and I had worked for other people and candidly for men my whole career. Which is great. I had wonderful mentors but like actually... and I kind of... I was coaching a venture capitalist the other day. It's almost like practice while you're doing what you're doing in your firm to come into who you are and flow and like the more you can find where you are versus thinking something on the inside is going to solve it. So for me, I feel like I've actually just come into it in the last couple months in a way that's really consistent and where I constantly am looking at my husband and being like, 'Wow.' You know, and this is kind of year six or seven years after founding Angel City and almost three years after I founded Monarch with Jasmine. So I think it's a journey.

I mean, I write these crazy morning pages still, you know? It's like will this pattern ever change? Is this pattern good or bad? Right? But like I think the awareness and habits that you build once you have the ingredients in the environment and your marriage and like those are the things that create flow. And for me it's writing and talking and running and music but for other people it may be other things but I do think habit building has been probably one of the most productive things I've done really in the last six months to get more consistently into flow.

I don't think there's anything I did that was the wrong thing for me to do because I think one of the things I probably do naturally that I don't know that a lot of people do is like pull out and like hear hard feedback from others or just myself acknowledge and everything that was bad or hard or put me into this period of time is something that made me who I am today. And I kind of think we're all on a hero's journey to truly understand how to surround ourselves with the right people, understand what we're great at, not have shame around what we're not great at, and partner around that. But I can give you anecdotes like where I felt that way. And they were important, right? Like some of them were anecdotes where I was like, 'Oh, you know, I did something else to like put an ointment on it, even if it wasn't like a full-fledged skin graft.' Good things came out of it. Like one of them actually has a connection to a class you and I maybe took back in the day called Paths to Power. Did you take that class?

Yeah. Did it have an impact on you?

Yeah. It's such a great example. And I will answer your question, but it brings up like there's a few frameworks that have been really powerful for me. One is victim, villain, hero framework. And I did a lot of coaching with Conscious Leadership Group where if you're in... you know, yes, you can be a victim of things that are terrible in the world that you have no control over. But if you're sort of a knowledge worker, etc., and you're in just... or even in a marriage, right? Like I do think they're similar. I think one is addressed by therapy and one is addressed by coaching, but actually like the people I've worked with kind of work on the whole person because you can kind of show up in both in the same way. And I think it's strange to take like a segment of a person. Becoming better in work made me better as a mom and a wife, right? And vice versa. But so the victim, you know, you can actually roleplay this like what do you... when you're in the victim mode or the hero mode or the villain mode and when you're pointing fingers. And it really is a helpful thing around like facts and stories and how you choose to digest them. So that's one thing that's been really powerful. And then I think the other is truly understanding those situations like the mail room. People do have natural personality profiles or trends, right? And this I got very into the Enneagram as a personality profiling tool and these days I'm like down the human design rabbit hole. So I pick a new one every 12 to 24 months. But we do an Enneagram test everyone who comes into the firm. And I think it is really helpful to like hold this stuff loosely but understand that there may... like there isn't a kind of an aha and epiphany of like oh I see this person acting in this way but they love taking on authority and challenging them right in an Enneagram 8 versus like oh my gosh I'm sort of addicted to positive reinforcement and achievement and so I'm so thinking about image that I'm not actually going and asking for something that would make my life much better when the worst thing that could happen is a no. Right? So I do think having that lens can help people also take a step back and do things differently. But I'll go to the example. So this Paths to Power class I always think about Henry Kissinger taking over like a defunct global conference and turning it into a must-do conference or Lyndon Johnson did the same thing with mock congress before they moved into their power. Or Keith Ferrazzi who was deciding between two consulting firms and went with I think Deloitte or E&Y instead of McKinsey and said but hey will the CEO meet with me twice a year. So a lot of this is around like what are things in the margin that people aren't doing that they don't value that you can take and make your own that you have natural energy for. And I did one of those things at Battery Ventures straight out of business school when I was feeling like not fully comfortable in my skin, even though I was a pretty good associate. I was a great associate for them before business school, which was I started writing a blog. They needed someone to write a blog in 2004 and I was like in Silicon Valley doing venture capital for the first time. Facebook was coming out and this and that. It's like why would anyone want to talk to Kara Nortman, you know? And so I became like a journalist. I always have written, loved writing, kept a journal since I was in seventh or eighth grade. Took it really seriously. I'd publish two, three times a week. I had like an ethics policy. I wouldn't write on our portfolio, which is sort of ridiculous now that you think about it. But it became this extraordinary way when people weren't doing it, right? It seems obvious now, but this was over 20 years ago. And where I wasn't like excited about the companies I was bringing in to like do something unique that was good for like getting Battery's reputation out there but my brain out there in a way where people who wanted that level of feedback or substance would find me and that actually led to my job at IAC which I got at a very young age right I became sort of a senior person in their M&A group and then co-headed it I think at 30 and it was because my blog was sent to the vice chairman. And he said I'd never seen one of those before. And he was notorious for like being one of the toughest guys out there. And he gave me the easiest interview because he said, 'I know how you think. I read your blog.' And then of course they made me shut it down because it was a public company and blogs are weird. But that's an example of like... and I have another really good one when I was at IAC and running a falling knife that ultimately led to the incubation of Tinder. But like both of them were in painful moments where I was like just butting my head against the wall. And in this case it was CitySearch and we just could not figure out how to get its data uncorrupted and it was reporting into an ad network. And so I joined the mobile incubator board and recruited in a guy named Sean Rad and oh my gosh we incubated Tinder, you know, like while I was pregnant with my third child and it's so like those things that like when you're frustrated, you're hitting a wall, you're doing... I was doing empirically a bad job. I could not turn around CitySearch. I could not figure it out because the data set was corrupt beyond those advertising. So those moments were like, you know, out of frustration, I just look for a creative outlet outside. Or something that just like the blog felt like a lot of work to take on, but I was like, okay, I'm going to do it. And then it gave me a lot of gratification for doing it.

That's a really good question. I shouldn't say this on your podcast. But I'm actually thinking again about joining a board outside of Monarch. Like I was on 10 or 12 boards before I left my last role at Upfront and a nonprofit board that is aligned with something I care about deeply. We're an impact-oriented fund, but very non-concessionary. And there's just great things happening in sports and women's sports and adjacent things in entertainment like and so I'm spending time with a lot of people around that's moving my thinking around Monarch. I also kind of want to start a secret not so secret society I even have a working name for to gather people to kind of like build friendships but then transact like new forms of karatus where the idea would be like if you show up in London or Seattle or LA you're like okay here are 10 people who care about the same stuff on the personal development side do really cool things in the world and I'll just enjoy having a meal with but with an intentionality around like what are we putting in here to transact against like that I've been sitting with for a long long while and I think there are ways different kinds of people can come together to create impact wealth culturally relevant moments you know stuff like that.

And people are deeply lonely. People are deeply lonely but I would say I've been really really focused I haven't had a side hustle in a while I did realize the other day that I miss a little bit of like this creative outlet.