Kirsten Green: The Biggest Challenges Scaling Both Teams and AUM | 20VC #912

1. 0:00 – 2:37

   Kirsten's background

   1. HSHarry Stebbings0:00

      (countdown beeping) Three, two, one, zero. You have now arrived at your destination. Kirsten, I'm so excited for this. I can't believe it's been so long since our last episode. But thank you so much for joining me once again.

   2. KGKirsten Green0:15

      Harry, it's a delight to, to see you today and to catch up. And thank you so much for having me on again. And before we started this recording, we did a two minutes of catch-up which started with, I don't know how many years ago, you were kind enough to invite me on your show. But I'm always intimidated to do a podcast, and I was intimidated to do your show back then. But this time, I mean, it's big time. Harry, you've gone big time.

   3. HSHarry Stebbings0:42

      (laughs)

   4. KGKirsten Green0:42

      I mean, you've got, you know, a, a, a, a significant viewership and a lot of, uh, dedicated followers. So, you know, the stakes are high when you get a chance to be on the 20VC Harry Stebbings Show.

   5. HSHarry Stebbings0:56

      I mean, ego inflation will get you everywhere so I thoroughly appreciate that. (laughs)

   6. KGKirsten Green1:00

      (laughs)

   7. HSHarry Stebbings1:00

      Um, I do want to-

   8. KGKirsten Green1:01

      A legendary meat seller.

   9. HSHarry Stebbings1:02

      For- for those who missed our first show, Kirsten, tell me, how did you make your way into venture? How did you found Forerunner? Quick two to three minutes.

   10. KGKirsten Green1:10

       Okay, gonna keep it quick two to three minutes, we move on to other stuff. So, I've been an investor for my career. I spent... I guess it was about de 10 years into it and I, I realized that, like, I needed more for my career and I could get more for my career. And so, I began a personal journey to kind of, you know, uncover what are my true no- motivations and where I think I could really, you know, imagine myself thriving. Um, and that journey was one that I couldn't have planned for, um, but as it unfolded, I, I really kind of grabbed every opportunity to learn. And I'm, I'm glad that I found that, that, that I, that I allowed myself to be satisfied or to lean into that because it really was a journey, um, that, you know, ultimately became clear that early stage investing really offered the things that I valued, which was, um, kind of operating at this intersection of qualitative and quantitative thinking. Um, I, I as a person toggle between both of those for, for energy. Um, I relish the opportunity or the chance to create or see, be part of change and progress. And this business is as much about people and relationships as anything, and I find that to be something worth spending time on.

   11. HSHarry Stebbings2:33

       I mean, I could not agree with you more there. I think relationship's the everything.

2. 2:37 – 4:19

   How does creativity give you an edge in investing?

   1. HSHarry Stebbings2:37

      Speaking of which, I just spoke to Eduardo at, you know, Curated, who's one of your founders, and he said that you are one of the most creative people. Uh, I don't know if I'm allowed to share this, but he even mentioned you sewing your own wedding dress, which I thought was pretty-

   2. KGKirsten Green2:50

      (laughs)

   3. HSHarry Stebbings2:50

      ... awesome and amazing. But his question to you was, "In terms of your creativity, how do you think it gives you an edge or an advantage investing?"

   4. KGKirsten Green3:01

      Oh, that's a good question. Thank you, Eddie. Creativity is pretty closely tied to curiosity. And I think curiosity is one of the most valuable characteristics that has the potential to lead you on fantastic journeys. And I, I like to think I'm a creative- or a curious person, and I think that's a really important characteristic in venture. And I think, you know, it's certainly part of the business that I really appreciate that I think get energy from every day. Every day, getting a chance to meet new people, learn about their motivations, their business ideas, kick tires on that, work with founders that we're engaged with on long-term relationships on topics that come up in the moment as their businesses are evolving and changing. You know, I think that you hope to develop a set of experiences and answers over time, but I find most of, I think, the better engagement, even the better advice sort of comes from that point of being curious, asking questions, probing, and uncovering things over time. And that-

   5. HSHarry Stebbings4:07

      How much-

   6. KGKirsten Green4:07

      ... that, in and of itself is a creative journey.

   7. HSHarry Stebbings4:09

      I totally agree with you on the importance of curiosity in what we do. Y- you mentioned your own, like, you know, curiosity leading you to venture and that kind of personal journey that you went on.

3. 4:19 – 7:49

   What parts of your history are you rebelling from?

   1. HSHarry Stebbings4:19

      Jeremy Liu asked a really good one, which I've never asked before, but I thought it was so good I had to include it, and credit to him. But he said, "We're all a function of our histories. What parts of your history are you rebelling from, and what parts of your history are you running towards?"

   2. KGKirsten Green4:36

      Got to love the good philosophical conversat- or question from Jeremy. (laughs) You know, m- my, my childhood in- really inspired a drive for independence and to create freedom to make choices. And I think that my career journey reflects that. Um, you know, in one part, I value the financial independence that work could offer from the earliest days. But as I navigated my career, I, I appreciated the, the freedom that came from, from learning and from doing things more independently and on my own. Um, there was a time when, you know, I mentioned I spent my first 10 years, uh, investing and working, I worked for a firm, and I, I was, I think, you know, playing by their, by their rules and doing well, or so I was told, and exceeding there, and the company entered into a merger agreement and my position was eliminated. And the firm was good to me and said, "We want to keep you. You can go wherever you want." But I loved the role I had and the job I had. And I thought to myself, "Gosh, I, I did everything I was supposed to do and for no reason in any of my control, that job is no longer available to me." I think I really felt like I didn't want as much as I could for that to not happen again. And, and probably it was as impactful for me because I know how much of myself showed up in the, the time I was spending at work. Um, so I, I think my entrepreneurial bug was kind of rooted in that...... experience of wanting to have more of a role in my own destiny. I know, of course, that, like, most things in life are out of our control. And certainly in venture, the lion's share of things that are out of our control. So, I don't profess to, you know, have, have necessarily been seeking control. But I do think seeking this ability to be independent and flexible is definitely something that, again, was inspired by childhood events. I also, um, I guess on the running tours for my history, when I was, uh, a- a- a teenager, I was sick. I had, I had spinal meningitis, bacterial spinal meningitis, and I was in a coma for six days. And that was, it was an, it was a near-death experience. And I think on the other side of it, I really came out both questioning why I was alive and well, um, and also inspired to make the most of what I was doing here, at least for what my journey needed to look like or could look like. And so I've been paying attention all along the way of, like, how do I continue to grow and evolve as a person and make sure that I'm getting the most out of all of the learning that life has to offer? And that's an experience that I am running toward every day, and probably even more deliberately as I, as I age (laughs) .

   3. HSHarry Stebbings7:46

      Can I ask a weird one? And again, this is where our schedules kind of

4. 7:49 – 10:05

   How do you try to make the most of every moment?

   1. HSHarry Stebbings7:49

      fly out the window. I've been thinking a little bit more now, like, I mean, I'm 26 and I- I will have spent the whole 20s to 30 decade every single weekend in a recording studio on my own.

   2. KGKirsten Green7:59

      (laughs) .

   3. HSHarry Stebbings7:59

      And I think when I'm 50 or 60, will I regret that I spent the best 10 years of my life in my physical body (laughs) in a recording studio on my own every weekend, and will I regret that? And I guess my question to you there is, how do you try and make the most out of every moment, and how do you think about your own relationship to regret?

   4. KGKirsten Green8:19

      Oh, such a good question. Life is a series of choices. There are, you know, a multitude of doors that get opened, and for every, you know, in some ways, for, for every door that gets opened, others get closed. And I think you just have to recognize that you made choices and get the most out of the choices that you make, and appreciate what you got for that.

   5. HSHarry Stebbings8:41

      Mm-hmm.

   6. KGKirsten Green8:42

      You know, in some ways, I look, I look and think, like, I started this venture firm when I was 40. I wish I could have started it at 30. What did I do while I was 30 to 40? You know what I did? I did a lot of journaling, a lot of painting, a lot of therapy, a lot of photography, writing classes. I did some investing too. Uh, you know, but I couldn't take that expe- y- I, I couldn't, I needed that experience to get here. So, like, everything is a building block that contributes to your next journey and your next chapter, and I just think it's important to appreciate what that, what that opportunity that created for you. And sure, there are things you're missing. You're spending every weekend in a s- recording studio, you're missing things for sure. But hopefully you're doing it consciously and you're getting way more out of it than what you're missing. And we can't do everything. I mean, that's just the reality of, of life. It's the reality y- you all make choices, and I'm a big believer in leaning into the choices that you make and trying to make the most of them, and spending less time thinking about the things you didn't do. You can't change it.

   7. HSHarry Stebbings9:48

      I do get paid egregiously for the show these days, which does help. (laughs)

   8. KGKirsten Green9:52

      That does help, that does help, and that will afford you other opportunities later that, you know, who knows how you'll use it? And it wouldn't have been that way if you hadn't done this.

   9. HSHarry Stebbings10:01

      It, it totally does. Uh, we- we've mentioned Eddie, uh, a- a couple of times and,

5. 10:05 – 13:49

   Why do you have a chip on your shoulder?

   1. HSHarry Stebbings10:05

      you know, you mentioned, uh, a little bit your childhood there, you mentioned kind of the financial independence. Eddie said in terms of founders, they have this fanaticism towards working with you. And he said it's 'cause you roll up your sleeves like no other, and add value like no other. Not in the founder friendly bullshit way, but, like, really move the needle for the companies. These were his words. He said that, and I hope this is okay, he, he wondered if it was maybe the insane drive because of a chip on your shoulder. Um, can I ask, do you feel like you have a chip on your shoulder? I know I do.

   2. KGKirsten Green10:38

      (laughs) .

   3. HSHarry Stebbings10:39

      (laughs) .

   4. KGKirsten Green10:39

      I mean, yes, certainly.

   5. HSHarry Stebbings10:42

      Why?

   6. KGKirsten Green10:43

      You know?

   7. HSHarry Stebbings10:43

      And why, also, why now? You've proved so much.

   8. KGKirsten Green10:48

      Well, there's always more to prove, Harry.

   9. HSHarry Stebbings10:50

      This is-

   10. KGKirsten Green10:51

       And there's al- you know, I mean... So, but, um, I, for, you know, for every person that looked at me while I was on this kind of, you know, let's call it my 30s, my, my path of discovery and exploration, which, you know, started to become clearer and clearer that venture was a calling, um, and then it became like, "Okay, what's the right way to pursue venture?" People would tell me I was nuts. I hadn't worked at a venture firm, I hadn't worked at tech. Did I know anybody in this industry? How would I make that happen? And I let that get to me for a while. I looked around for a firm I could work at, or a partner that had the right pedigree or experience. You know, I also don't have an MBA, I don't have an Ivy League education. Like, all those things I thought, "Okay, well, if I don't have them, I need to complement myself to them to be valid for being here." And thank goodness those things didn't come together, because I think it was really important for me to realize that, like, those weren't keys to success. I, those are things I, you know, those are things that are valuable, I'm not discrediting their, their value to people, but they weren't, they weren't the kind of roadblocks that I thought I needed to figure out some way around or to complement myself.

   11. HSHarry Stebbings12:14

       (laughs) .

   12. KGKirsten Green12:15

       Um, and so that was a chip on my shoulder in early days.You know, I think venture is, it's a collaborative industry and I really appreciate that about it. It's also a competitive industry, and I really appreciate that about it. It fires me up. You know, I look around today and I think venture has gotten even more dynamic. It's a, it's a mature industry that is still innovating and thriving. That's what we should be doing because that's what we're investing in. And there are more ways to do venture today than there ever have been before. There's firms of all different sizes, there's partnerships of all different sizes, there's accelerators, there's incubators, there's people doing, you know, full s- various stage investing, stage specific. There's all these different ways to, to do things. And, you know, I, I think that there's a lot of people that are successful that I look up to that I'm, you know, constantly kind of trying to say like, "How can we challenge ourselves to be competitive in that situation, better in that situation?" And I mean, I, I guess that's just, like, a lifelong orientation (laughs) that continues that I'm actually, like, happy to have, so I continue to cultivate it or accept it.

   13. HSHarry Stebbings13:29

       You me- you mentioned the competition there. It's funny, I spoke to Alfred Lim before the show and he said he's never met anyone who competes at such high level, with such, uh, brilliance as you, but also does it with such elegance and grace. (laughs) Uh, and I thought that was a great compliment.

   14. KGKirsten Green13:44

       Oh, yeah.

   15. HSHarry Stebbings13:45

       Um, I, I do wanna-

   16. KGKirsten Green13:46

       Yeah.

   17. HSHarry Stebbings13:46

       ... ask you. You mentioned kind of the insecurities and people saying, "Oh, you can't do something, you can't

6. 13:49 – 16:36

   What do you tell yourself when you're questioning yourself?

   1. HSHarry Stebbings13:49

      do something," what do you tell yourself now when you question yourself? Like, I say to myself, "There's winners and there's losers. Which one are you, Harry?" (laughs) And I go, "I'm a winner, I'm a winner." I- when you question yourself, w- how do you mind-talk yourself?

   2. KGKirsten Green14:04

      I really try to go back to a place of being, like, authentic. I, I, I think that, um, every time I have tried to say, "People in the room behave like this. I'll get more respect if I behave that way," I mess it up. You know, because I'm, I'm overthinking it or I'm getting nervous as my words are unfolding because they're not coming from a place of real power. Um, and so, I try to remind myself that my strength comes from my authenticity and that sometimes that might expose that I don't have the answer to something (laughs) or I don't know something, and that's okay. Who knows everything? You know? I mean, again, back to the curiosity. If you're a curious person, you're continually learning, so you always know less than what you aspire to know. And I think that, um, just, you know, kind of tapping into that power that comes from being real and being able to be vulnerable and saying, "Some people will judge you for that, but the right people won't," and I don't need to attract everybody. I just need to be in line with people and things and ideas that I feel, um ...

   3. HSHarry Stebbings15:40

      Represent you. It's, it's, it's like-

   4. KGKirsten Green15:42

      Yeah.

   5. HSHarry Stebbings15:42

      ... for me in the early days. I probably fucked up because I tried to be an investor that I wasn't. I tried to be analytical and numbers based, and I, you know, I can't count, Kirsten, and so that was a completely futile exercise. So, I, I totally agree with you there on finding, like, the time.

   6. KGKirsten Green15:56

      Right. And I think then, you know, you, there's... One of the things about venture and it being a, um, kind of an ecosystem-driven business and being a founder and thinking about the various investors that you bring along around the way is you can get, like, a council of experts. And the best ones have people who shine in different areas and complement each other. And the way to do that is to stand for something, is to be known for something, to have some way to contribute where people are like, "Oh, I would like Harry in the room with me because Harry's the one that always offers X, Y, and Z." And, um, that makes the conversation, the discussion richer, and particularly when I have this other person who

7. 16:36 – 18:30

   What is "high performance" to you?

   1. KGKirsten Green16:36

      knows A, B, and C.

   2. HSHarry Stebbings16:38

      Can I ask, in terms of, like, performance and high performance, I think a fascinating question is, like, what does high performance mean to you? If, if I say those words to you, what do you immediately think of and what resonates with you when I say high performance?

   3. KGKirsten Green16:56

      Quality. So, showing, and to me quality is showing critical and thorough thinking in the work and the approach. And then results. So, knowing what excellence is and delivering that.

   4. HSHarry Stebbings17:10

      Can I ask has that changed over time for you?

   5. KGKirsten Green17:13

      No.

   6. HSHarry Stebbings17:15

      (laughs)

   7. KGKirsten Green17:18

      (laughs) No.

   8. HSHarry Stebbings17:18

      No, I've always known it. (laughs) No, I, uh, I, I like that one.

   9. KGKirsten Green17:21

      And in part because, Harry, both of those, while quality and results, you know, just on face value are simple concepts, if you really think about what they mean, and that's what I was kind of articulating a little bit, like, thorough work, showing critical thinking, and, you know, kind of being holistic in how you're approaching something, that i- requires different depth and different scenarios and different situations. So, it's not always operating the same way. It's just having, like, the right approach for the particular challenge or opportunity that you're meeting. Same with results. Results as an investor could mean I wanna be in the top 5% of performance in my peer group for funds. That's one way to evaluate results. And the other way is, I wanna be, um, the most effective person in the boardroom. I wanna be somebody who c-can contribute to making the conversation richer and the decision process better.... those are, you know, different areas require very different ways of measuring results, but they both have a goal and an idea of what excellence is in mind.

   10. HSHarry Stebbings18:25

       A couple of things I have to di- dig in on. You said about kind of quality there. The thing that I think, I

8. 18:30 – 21:08

   How to retain quality while scaling AUM?

   1. HSHarry Stebbings18:30

      think about a lot as I scale my investing practice is like, how do I retain quality with scaling of AUM, scaling of team, scaling of portfolio size? Uh, this is open for advice, so basically use the show as my own counseling session. How do you retain-

   2. KGKirsten Green18:47

      (laughs)

   3. HSHarry Stebbings18:47

      ... quality and scale all of those things? How does... What have been your lessons on what can be done to do that?

   4. KGKirsten Green18:56

      (inhales deeply) So, it's a great, it's a great question and it's a topic that I, in many ways am obsessed over. Um, you know, Forerunner is still a relatively small, tightly-knit team. That's intentional. Um, our culture is, is very team-oriented and it's very much kind of based in, in another, um, operating model I really value (laughs) which is to think about how you get, you know, something exponential, so how do you do one plus one and get something more than two? I think we approach our business like a startup in that our ambition is bigger than our resources generally, and so we need to think about being, you know, really deliberate in everything we do, both in terms of focus and, and in terms of impact. And if I can do something and have it accomplish more than one thing, that is likely something worth leaning into versus another thing, um, and it takes a team to execute that. So, you really do win together. But realistically, ambitious people, they, they need to be able to flex their own individuality and have room for their own wins. And so, you know, when you think about having the desire to build a healthy team, um, and you, you want to have a team approach but you wanna have the best in class people feeling like they have a opportunity to shine here, you know, really, it really demands you to be focused on the process, the org development, you know, what are those areas where people can flex their strength? And in so many ways, that is an entirely, you know, second job, um, to being an investor, um, and it does... It is one that gets more dynamic as the team grows and, you know, our approach to that, you know, has, has been, um, to recognize that, to plan around that, and to be bringing people on in a way that we can layer them in, in honor of that.

   5. HSHarry Stebbings20:55

      (laughs)

   6. KGKirsten Green20:55

      And so it isn't going and hiring, you know, 30 people in one year and trying to figure out how to navigate that.

   7. HSHarry Stebbings21:01

      I- y-

   8. KGKirsten Green21:01

      I'm always in awe of the companies we work with in hiring hundreds of people a year and thinking about how to accomplish all of that inside an

9. 21:08 – 27:15

   Why did you decide start investing in enterprise businesses?

   1. KGKirsten Green21:08

      org.

   2. HSHarry Stebbings21:08

      You said, you said about the importance of focus there, and my word, I do switch topics from insecurities to investing focus. (laughs) Uh, but in terms-

   3. KGKirsten Green21:15

      Yeah.

   4. HSHarry Stebbings21:15

      ... of focus, I have to ask, and I, I, I hope it's not too blunt. You had the most dominant brand in consumer. You owned it, you were one of the first there. I mean, stellar. Stellar, stellar, stellar. And every consumer brand that I spoke to and consumer company wanted Forerunner. And, and then with the recent funds you also said, "Hey, we're not only doing consumer, we're also gonna do enterprise." And I just would love to understand, like, why did you decide that? What was the decision-making process for doing it, and why did you think it was better to widen the aperture rather than stay very focused on consumer?

   5. KGKirsten Green21:52

      I don't know, Harry, that we e- I ever, you know, we, I ever said, "We're only doing consumer investing."

   6. HSHarry Stebbings22:00

      (laughs)

   7. KGKirsten Green22:02

      So, what, what was true in the earliest days of Forerunner and is still true today is that the consumer is our North Star. It's where we seek our inspiration and it's our starting point for idea exploration, opportunity exploration. We think about what's going on with people, how are their lives changing, their preferences, their needs, their wants, their expectations, um, their patterns, their behaviors, how the demographic's changing, what's going on with the different age ranges, and then we think about how is that evolution that we're witnessing likely to impact business? And where are the areas of business that are either vulnerable because big change is coming that's fueled by the consumer, or what are the areas of newness that arise, because there's going to be a demand for it or a need for it? And, you know, a- while, I don't know if it's one-third or two- you know, s- some percentage of the, of the economy is built off of consumer businesses and some of it is built off of business-to-business. All of it has a tie to the consumer because every business is in service of a user. So, if you're a B2B business, you're still serving another business that ultimately is serving someone else, and somewhere in there, there's a consumer. So, in some ways, the consumer is kind of, you know, like, the core of all of it, and so we use that as our starting point, and then we start, you know, thinking about, again, like, where are the opportunities in business and, and follow, follow that evolution? And we can do that from various different segments and we can do that within a segment. So for example, like back to the earliest days, we did some companies, you know, uh, have been called D2C companies now but we think of them really more as just branded companies that y- that leverage D2C as their go-to-market strategy as much as anything. But those were businesses that were reshaping the way that business traditionally was done, that were challenging the fundamentals of retail and wholesale models, and in the rise of those companies came a whole new set of needs and demands from a business tooling perspective...Um, and so, as we were partnering with those businesses and seeing what their opportunity set was and where they were being served and not served, we looked over and say, "Okay, the underserved parts of it, where is technology? Um, you know, where is newness being developed and innovation being delivered to service those needs?" And then we invested in those companies. We've always had a mix of B2B and B2C companies in our portfolios. The, the mix shift has changed over time, so our earliest funds were at that cycle of w- were... I mean, we can spend a minute backtracking on the, on the firm history to, to tie this together, but the earliest fund had more of a focus on the consumer companies, in large part because it was me and Yuri, and there's only so much two people can do, and I'm a big believer in the power of doing fewer things better, so we stayed focused. But as we've grown as a team, we've been able to dedicate time and attention to learn about other areas, and that's taken us on this journey that continues to evolve. And our most recent fund that we just finished investing, I need to find the stat, actually, 'cause, uh, we were referencing it internally the other day, but I want to say somewhere around 70% of the dollars went to B2B companies. But there's no change in how we develop an investment thesis, where the start of it is, and what our process is as a team. So, getting back to, like, the firm thing, um, I think about... I don't really usually say this around entrepreneurs because I like to leave them with the glory of being the entrepreneur, but, but let's pretend for a minute Forriner is my, or let's just say for a minute Forriner is my own entrepreneurial journey. And-

   8. HSHarry Stebbings26:04

      I think it absolutely is. I think it absolutely is. A fund is a startup if you-

   9. KGKirsten Green26:06

      ... thought about it that way, and have thought about it with, we have a vision for what opportunity we want to seize, and it might be really big, but we got to start somewhere today, like every startup does. And so, where do you start to do a proof of concept? Where do you start to de-risk your model? Where do you start to show some of that early, you know, traction, the early KPIs, the early metrics that prove that you're onto something? And then, as you do that, like, what other opportunity can you unlock, and how do you set up a new set of standards or metrics for that and evolve it? And so, you know, that's what we've been doing. We went from having a really, you know, again, like, the big picture being consumer North Star, but saying, "Okay, we're gonna do this one segment, we're gonna do the evolution of e-commerce, and then we're gonna expand it into the B2B tools that serve that." And then when the early e-commerce on discretionary has sort of played... Early winners have been identified, we're gonna move into, like, how that same trend is impacting financial products or healthcare products. And then once we do that, we'll see another

10. 27:15 – 29:16

    When scaling, what gets easier and what gets harder?

    1. KGKirsten Green27:15

       set of tools, et cetera, so.

    2. HSHarry Stebbings27:17

       (laughs)

    3. KGKirsten Green27:17

       Um-

    4. HSHarry Stebbings27:17

       Can I ask, with Fir-

    5. KGKirsten Green27:18

       ... e-

    6. HSHarry Stebbings27:18

       Can I ask, with firm scaling, what gets easier over time and what gets harder?

    7. KGKirsten Green27:24

       So, what gets easier over time is you have the benefit of experience, um, and that can be leveraged. And I would say in general, like, while, um, by nature, our culture at Forriner is humble, so we don't assume that we, that we know everything or that we're the reason for every- anything working, right? But we do think that, like, experience can help us build confidence and conviction in both the investments that we're making and the conversations that we're engaging in around, you know, strategic decisions. And as you grow and you have more of those experiences, you have more people on your team collecting those experiences, you definitely have a wider base of examples to draw from.

    8. HSHarry Stebbings28:05

       Yep.

    9. KGKirsten Green28:06

       So, I do think that that, if harnessed right, becomes a really, a big advantage, um, both, you know, tactically and, again, like, in terms of the confidence and conviction it, it allows you to act with. Um, on the what gets harder-

    10. HSHarry Stebbings28:24

        Yeah.

    11. KGKirsten Green28:24

        ... I think I'd probably double down a little bit on, um, on what I was sharing earlier about, um, t- team, you know? So, like, this, this culture being t- team-oriented and winning together, but the more people you have, the more you're kind of also serving for those ambitious people and their own needs to be recognized and to have successes and wins. And you just... It requires you to be, I think, thoughtful and deliberate around your work development and how you create that opportunity for people while maintaining a tight-knit culture. Um, and that obviously gets more dynamic as the team grows, so, so that gets harder.

    12. HSHarry Stebbings29:02

        I to-

    13. KGKirsten Green29:03

        It's another job that keeps growing.

    14. HSHarry Stebbings29:05

        I, I totally agree with you. I think, like, bluntly, being an ambassador and being a fund manager is, is totally different, and people often conflate the two, and there is so much that comes with fund management that I think people don't

11. 29:16 – 31:28

    How would you describe your leadership style?

    1. HSHarry Stebbings29:16

       see. Um, I do want to ask you, though, you mentioned it being your startup, which it totally is. How would you describe your leadership style? You mentioned the team multiple times. You mentioned the culture. How would you describe your leadership style today? And actually, has it changed over time? 'Cause I'm sure this one has done with experience and scale.

    2. KGKirsten Green29:35

       My leadership style, I would say, is I, I believe and I hope that I empower the people that I work with. I would love for Forriner, I strive every day for Forriner to be a place where people can do their best work and feel that they're acknowledged and appreciated for it, and that part of doing your best work is, is being able to, to have some clear, you know, contributions that you make to the team and some clear ways that you support your partners and your teammates. And I celebrate th- I encourage those and we celebrate those, and so I think that's an important part of leadership. I try to lead by example. Um, you know, I really love the work that I do, um-... I, I don't think I could show up with as much energy and enthusiasm if I didn't authentically. I, um, I think that that leadership style probably attracts people that feel similarly. Um, I, I, I think I, you know, I demand a lot of myself, um, and I really do want to always feel like I'm putting my best foot forward, and I want the team to be putting their best foot forward. And so, um, you know, I think that I empower people to do things on their own. I am not a micromanager. You can double-check that with my, with my teammates. But I do have clear ideas (laughs) and preferences for, like, what a quality work product is or what our reputation should be in the market and how we should stand up against it.

    3. HSHarry Stebbings31:18

       Okay.

    4. KGKirsten Green31:19

       Um, so I think, you know, being, being clear about those things and, and hopefully demonstrating them myself at all times is, is a leadership

12. 31:28 – 32:48

    How to give negative feedback

    1. KGKirsten Green31:28

       trait that I, I hope I put forward.

    2. HSHarry Stebbings31:30

       In, in terms of that communication, I spoke to Annie, uh, at YC before this, and she said you're on the FAIR Board together and said you are one of the best she's ever worked with in terms of giving great and constructive feedback the right way. And that's sometimes hard to give. I'm really actually not very good at giving feedback. I'm British, and so we kind of, uh, don't really say much and just kind of bumble along. Uh, uh, how do you think and advise me on what it takes to give hard feedback well and elegantly?

    3. KGKirsten Green31:59

       When I'm in a position of giving hard feedback, I, um, try to be really thoughtful in advance and plan my words relatively carefully. So for instance, the other day, I had to send a note to give somebody some feedback which also included, like, an answer to a question that they didn't want, (laughs) you know? And I think I thought a lot about, "How do I create the right setup in this conversation for them to ex- hear what I'm saying and to start to be able to accept it if they can't all the way accept it in that moment?" And so, it's about, uh, uh, it's about being direct but being respectful all the time. Um, and I think it's using your words wisely and not trying

13. 32:48 – 34:06

    Do you ever lose your temper?

    1. KGKirsten Green32:48

       to say too much in one conversation.

    2. HSHarry Stebbings32:50

       Do you ever lose your... W- in the UK, we'd say shit, but do you ever lose your temper? Do you ever get very angry? You, you have this incredible kind of calmness. (laughs) Do you ever lose your shit, and how does that come out?

    3. KGKirsten Green33:06

       Well, I get frustrated, Harry, for sure.

    4. HSHarry Stebbings33:09

       (laughs)

    5. KGKirsten Green33:09

       You know? I mean, come on, yeah. But do I ever l- l- lose my shit and just... No, n- I don't think so. I mean, I'm pretty good at holding multiple feelings at once. It's something I've worked hard to cultivate, like, throughout my personal life, which is, you know, being able to say, "I'm really angry at this person. I'm really frustrated with how they're not showing up or how they're not hearing, but at the same time, I know that they're doing their best. And at the same time, I know that if they could grasp it, they would." (laughs)

    6. HSHarry Stebbings33:49

       (laughs)

    7. KGKirsten Green33:50

       So, I think that that empathy, um, creates, creates room for you to not have the crazy flare-up but to be able to be more balanced in your approach to

14. 34:06 – 38:00

    Do relationships detract from ability to work hard?

    1. KGKirsten Green34:06

       people and then feedback.

    2. HSHarry Stebbings34:08

       Uh, w- when we spoke before, you know, uh, you just mentioned that you have kind of high expectations on yourself. I have very high expectations for myself too, and I have this quite binary view of relationships, that relationships always detract from your work ability. And actually, you can always spend more time working, and that is kind of the view that I've held. When we chatted before, you gave a different view, which kind of made me change my mind (laughs) in a way that I haven't changed my mind on for many years. (laughs) S- how do you resp-

    3. KGKirsten Green34:39

       (laughs)

    4. HSHarry Stebbings34:39

       ... how do you respond to my statement there of, like, relationships detract, and do they or do they not actually?

    5. KGKirsten Green34:48

       So, m- there are positive constructive relationships in the world that not only, um, add, but enable or even make possible things that you want, that you wanna do as a person. And I wanna talk about that in a minute, but I also wanna say that there are also unhealthy, not-good relationships that do detract. So, part of it is understanding, like, what does a constructive relationship versus a destructive relationship look like for you and in your life? And knowing how to prioritize the constructive ones and surround yourself with those types of relationships and cultivate those types of relationships. But the example I was giving you was really specific, which was I, you know, I would've liked to... If I could draw up my perfect path, I would've liked to have, like, you know, gone down to college, had a job or two, and then found venture early and started my venture firm at, you know, I don't know, 30, and you know, have success by the, in, in the first 10 years, and then be able to, like, reap it for the next 10 years and then be able to have room for a whole nother career afterwards. But you don't just... You know, life doesn't work out that way. I think you have to be open to the journey. You have to kind of embrace, like, what's unfolding in front of you and grab the opportunities as they come t- make the most of them. For me, my path was, um, you know, not, not planned at all, and I didn't come into venture until I was...... 40, and it was shortly after the birth of my first child, which in so many ways was like the most inopportune time. I'd been, in my 30s I'd had, you know, relatively minimal responsibilities and I was doing painting and photography and thinking about like the meaning of life (laughs) and what I wanted to do. Um, and then, you know, I, for a lot of reasons, the timing, it became clear that the timing was right for Forerunner, um, you know, around the time I launched it, and that also, again, coincided with having a baby. And I wanted to... I, you know, I, I, it had not been easy to get pregnant and stay pregnant. I was really thrilled with the opportunity to be a mother. I'd already been married for 12 years by the time I had this baby, and I didn't wanna shortchange that experience. Um, but I also had worked so hard to find, like, my right career path, and it was right here to have. And my husband who'd been my, you know, partner for a long time already and knew me well, was able to come say, "I'm here to support this." Like, "I've been on, you know, prioritized my career for X amount of years. Like, you go do what you need to do. Like, I understand it's gonna mean less of this or less of that. I can carry weight here." And I just... If I hadn't had a partner that had stepped up that way and had known what it meant to me and the value of that, I could not have, I could not have been a good mother and started something that had potential to be successful at the same time. And that relationship really enabled that.

    6. HSHarry Stebbings37:56

       Aww, I, I love that, and as I said, like, that really (laughs) changed

15. 38:00 – 40:49

    How did becoming a parent change how you think about investing?

    1. HSHarry Stebbings38:00

       what was quite a static mindset around it. Can I ask, on, on the final one before we do a quickfire, y- obviously, uh, parenting is such a crucial role in anyone's life, the most important job you'll ever have. How did becoming a parent change how you think about investing and operating?

    2. KGKirsten Green38:19

       Honestly, I will say, I think for me, it was really an unlock.

    3. HSHarry Stebbings38:22

       Hmm.

    4. KGKirsten Green38:22

       It really, um... You know, we're all, we're all a, a tapestry of different strengths and experiences that come together, um, so it's not just one thing. But for me, like, when I had my child, I really was motivated into making the most of every moment. Recognizing that I had X amount of time with him, X amount of time for work, X amount of time for my marriage, for myself, you know, et cetera, and, like, I really needed to be present and to make the most of the time I had, and to try hard to not... We're always multitasking. I'm also multitasking in the context of Forerunner, I think this job is a juggling act e- every day. But, when I'm at work, I'm at work. I try really hard to be there and make sure that I'm, uh, being deliberate with my time and moving the ball up the field in a way that, you know, matters. And when I'm home with my kids, I try to really, like, get down on the ground and play with them and, and be engaged. And I think that, like, that motivation that stemmed from Reese becoming part of my life w- was something that has made every experience richer, is being present.

    5. HSHarry Stebbings39:31

       What was the biggest surprise about parenting?

    6. KGKirsten Green39:36

       (laughs) Hmm. Well, parenting is a journey.

    7. HSHarry Stebbings39:43

       (laughs)

    8. KGKirsten Green39:44

       You know? I mean, the kid at 12 is very different than the baby at six months. And the, you know, um-

    9. HSHarry Stebbings39:51

       Which one, which one do-

    10. KGKirsten Green39:52

        ... and one child-

    11. HSHarry Stebbings39:52

        ... which one do you-

    12. KGKirsten Green39:53

        I have a son and a daughter.

    13. HSHarry Stebbings39:54

        Which one do you pr-

    14. KGKirsten Green39:55

        I have a son and a daughter. They're very, they have so many similarities and they are also very different. And so, parenting is, you know, challenging with respect to one in a different way than it is with respect to another. Um, so maybe, like, maybe a little bit like what we've been talking about, that's been a, a bit of a theme in this conversation, it's, it's, i- i- it's dynamic and it's unique and, and, um, and it changes and evolves, and I think you have to be open to that journey, you know? I, I, m- parenting a baby is very different than parenting a twin.

    15. HSHarry Stebbings40:30

        I, I'm, I'm sure. I'm, I'm speaking from a complete lack of experience, but I think we've actually got a podcast for parents coming off the back of this with Kirsten and Harry. This is a great side gig that we could do.

    16. KGKirsten Green40:41

        (laughs)

    17. HSHarry Stebbings40:43

        Uh, (laughs) but, uh, I, I wanna move into my favorite, Kirsten, which is a quickfire. So, I say a short statement and you give me your immediate thoughts. Does that sound

16. 40:49 – 42:00

    Kirsten's biggest strength/weakness

    1. HSHarry Stebbings40:49

       okay? (laughs)

    2. KGKirsten Green40:50

       Okay, let's do it.

    3. HSHarry Stebbings40:51

       So, what's your biggest strength and what's your biggest weakness?

    4. KGKirsten Green40:56

       My biggest strength is, um, I'm, I'm an optimizer, and I, I think I'm a pretty good strategic optimizer. Um, my biggest weakness, my biggest weakness is, um... Well, i- this is... Listen. I, m- I, I care so much, and that's not a weakness, that's a strength in life. But, you have to make hard decisions every day, and I think that, like, I am a person who likes to say yes, who likes to roll up their sleeves and helps, who aspires to have a way to support somebody, and ironically I'm in the business of saying no. I'm literally in the business of saying no. Like, how many times... Like, s- 5,000 deals last year, and, you know, eight or 10 investments.

    5. HSHarry Stebbings41:50

       Right.

    6. KGKirsten Green41:50

       And so, I think that, like, that, you know, I've gotten over that, but, like, a lot of times, like, having to give the hard feedback or having to give the hard answers weighs on me.

    7. HSHarry Stebbings41:59

       What's

17. 42:00 – 43:37

    Most painful lesson Kirsten learned (but doesn't regret)

    1. HSHarry Stebbings42:00

       the most painful lesson you've learned, that you're also super glad to have learned?

    2. KGKirsten Green42:09

       One of my earliest investments, before I had any success- successes, that was somewhat high-profile, ended in just, you know-

    3. HSHarry Stebbings42:18

       Mm-hmm.

    4. KGKirsten Green42:18

       ... fabulous fashion in terms of just being a big blow-up, and I really, really felt, like at my deepest core, that, like, my career was over before it had started. Um-... but shortly thereafter, after some deep reflective thinking, someone that I respected reminded me or, uh, or pointed out to me that I'd gained, like, real experience through that. That, you know, kind of watching that unfold, being part of how that unfolded, um, taking action or not taking act- like, in all of that, like, I'd, I'd had some hard-won lessons. Um, and this happened during '08, um, and it had to do with how do you, um, lower your burn? How do you reprioritize how you're gonna show progress? You know, things that I think are on a lot of people's minds right now. And I'm so incredibly grateful for that hard-earned experience, uh, that's... is, you know, applicable not just today, but, but, but very applicable today.

    5. HSHarry Stebbings43:24

       You can take one luxury to a desert island. What do you take, Kirsten?

    6. KGKirsten Green43:30

       Hm. Harry, these rapid fire questions are always the hardest for me. One luxury... Well, so this depends on what we consider to be a luxury,

18. 43:37 – 44:27

    So you're stranded on a desert island..

    1. KGKirsten Green43:37

       right?

    2. HSHarry Stebbings43:38

       (laughs)

    3. KGKirsten Green43:38

       But, um... sunscreen? (laughs)

    4. HSHarry Stebbings43:44

       Sunscreen? You are- you're giving me sunscreen?

    5. KGKirsten Green43:47

       (laughs)

    6. HSHarry Stebbings43:47

       I want, like, a Chanel G12 watch, and you're giving me sunscreen? That is pathetic.

    7. KGKirsten Green43:52

       Well, it depends on what you consider a luxury. Like, are we starting out with, like, you know, mini- like, cup, like covering, and food? Or what are we starting out with?

    8. HSHarry Stebbings44:00

       Um, I think-

    9. KGKirsten Green44:00

       Like, a luxury? Uh, I, I would like my, um... I would like my iPhone. I would like my iPhone.

    10. HSHarry Stebbings44:06

        O- okay, I'll, I'll take that. I mean, you've got 12 hours of usage before it runs out and then you're (laughs) screwed, but yeah, sure, you can have it.

    11. KGKirsten Green44:13

        No, that's bad. You're right.

    12. HSHarry Stebbings44:14

        You didn't- (laughs)

    13. KGKirsten Green44:14

        I didn't think that far ahead.

    14. HSHarry Stebbings44:15

        ... didn't get it sorted. (laughs)

    15. KGKirsten Green44:16

        Harry, that's good. A journal.

    16. HSHarry Stebbings44:17

        Uh-huh?

    17. KGKirsten Green44:17

        A journal, but you said... a journal's not luxury, but if you're there, you have more time to think than you ever have in any other time. I'd like to write it down.

    18. HSHarry Stebbings44:24

        (laughs) Uh, tell me, what three

19. 44:27 – 44:42

    What three traits would you most like your children to adopt?

    1. HSHarry Stebbings44:27

       traits would you most like your children to adopt?

    2. KGKirsten Green44:32

       Um, I would like my children to find resilience, curiosity, and empathy.

    3. HSHarry Stebbings44:41

       What do

20. 44:42 – 45:37

    What do you know that you wish you'd known when you started Forerunner?

    1. HSHarry Stebbings44:42

       you know now that you wish you'd known at the start of Forerunner?

    2. KGKirsten Green44:50

       Well, remember, I started Forerunner a little later after a lot of thought and deliberation, so it's not like I haven't had things, uh, pop up along the way that I had no idea about. But in some ways, I'd, I'd, I'd thought through it a lot before I started, and I knew how much work I was getting into. But, you know, it's really a long haul. It's, it's, you know, a... it is a, um... every fund is a 10-year commitment at least, and I think really understanding that that is stacking up over time, (laughs) and, um, you know, what that commitment all entails.

    3. HSHarry Stebbings45:30

       Penultimate one, and I- I'm interested by this one. Alexis Ohanian asked this on Twitter when I tweeted about you coming on. He

21. 45:37 – 47:10

    What would a man in VC take for granted that you've had to adapt to in starting Forerunner?

    1. HSHarry Stebbings45:37

       said, "What would a man in VC take for granted that you've had to adapt to in order to build Forerunner into a top firm?"

    2. KGKirsten Green45:47

       Wow, that's a good question.

    3. HSHarry Stebbings45:49

       I thought so too.

    4. KGKirsten Green45:49

       Um, what would a man in VC take for granted that I had to adapt to to start Forerunner, build Forerunner? Well, I don't know. We're making, we're making gender generalizations, and I really don't like to make general- gender generalizations. I appreciate the question though, certainly. Um, you know, I think that paying attention to how you're building your team is paramount. And I think this isn't just about hiring, you know, smart people or people who are willing to do what you tell them to do or whatever, whatever, but it, it is about really understanding that in the best case scenario, you're attracting ambitious people who are being thoughtful about their career and want to leverage what you started or what you built for that end, and how do you do that in a way that balances the benefit of the firm and for them too? And I think some people do not appreciate the importance of that or the weight of that.

    5. HSHarry Stebbings47:05

       I think it's a good one. Um, final one for you. Uh, next five years for you

22. 47:10 – 48:59

    Where will you be in five years?

    1. HSHarry Stebbings47:10

       and for Forerunner. If we do this in 2027, where will we be then, Kirsten?

    2. KGKirsten Green47:19

       I like 2022 better than I liked '21. I think what's happening right now... I know, look at that surprise look.

    3. HSHarry Stebbings47:26

       Oh my god, I don't. I'm like-

    4. KGKirsten Green47:27

       I think what's happening right now is people are having really important conversations that really require them to understand their businesses-

    5. HSHarry Stebbings47:36

       Mm-hmm.

    6. KGKirsten Green47:36

       ... and to understand the, the levers of their business, what it's gonna take to really prove that they're on a path to something that has potential, that they are successful. And I believe, and... that we're gonna, you know, that that is gonna inspire better business building. And so, you know, I think we're in for some hard times given the economic backdrop, um, that we're gonna be operating in here for the near term foreseeable future. But I think looking out, you know, past that, I think the upside is huge, and I couldn't be more excited to have a really motivated team and a new fund and kind of the benefit of 10 years of experience. But the drive to take 10 years more, like, you know, that feels like wind in our sails. So, five years, I think we're gonna be talking about incredible companies that were built.

    7. HSHarry Stebbings48:32

       Kirsten, this has absolutely made my week. Seriously, uh, it's shows like this where we can have authentic discussions like at the beginning, move to investing, talk about parenting. This is why I love what I do. Frank-

    8. KGKirsten Green48:43

       (laughs)

    9. HSHarry Stebbings48:43

       ... uh, no, honestly, it really is. So, thank you.

    10. KGKirsten Green48:45

        That's why you're good at what you do, Harry. You inspire a good, uh, authentic conversation.

    11. HSHarry Stebbings48:51

        But thank, but thank you for joining me.

    12. KGKirsten Green48:52

        So hopefully y- you're right and your editors are magical and they can make that sound good 'cause

    13. NANarrator48:56

        (laughs)

    14. HSHarry Stebbings48:56

        But thank you so much for joining me. I loved it.

Episode duration: 48:59