The Exchanges

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

A One of my earliest investments before I had any success successes that was somewhat high profile ended in just You know, fabulous fashion in terms of just being a big blow up. And I really, really felt like 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, or pointed out to me that I 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 action, like in all of that, like I, I'd had some hard, One lessons, um, and this happened during oh eight, um, and it had to do with how do you, um, lower your burn? How do you reprioritize? How you're going to 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 is, you know, applicable not just today, but But, but very applicable today.

AI assessment note: “I'm so incredibly grateful for that hard earned experience”

Q Um, I, I do want to ask, you mentioned kind of the insecurities and people saying, oh, you can't do something, you can't 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? And I go, I'm a winner, I'm a winner. I, when you question yourself, how do you mind talk yourself?

A 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 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.

AI assessment note: “I try to remind myself that my strength comes from my authenticity”

Q I think when I'm 50 or 60, will I regret that I spent the best 10 years of my life and my physical body 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?

A 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. 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 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, you know, but I couldn't take that, 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 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. You all make choices, and I'm a big believer in leaning into the choices that you make and trying to make the…

AI assessment note: “spending less time thinking about the things you didn't do.”

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

A Well, I get frustrated, Harry, for sure, you know. I mean, come on, yeah. But do I ever lose my shit and just, no, 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. 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 people, and then feedback.

AI assessment note: “do I ever lose my shit and just, no, I don't think so.”

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

A One of my earliest investments before I had any success successes that was somewhat high profile ended in just You know, fabulous fashion in terms of just being a big blow up. And I really, really felt like 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, or pointed out to me that I 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 action, like in all of that, like I, I'd had some hard, One lessons, um, and this happened during oh eight, um, and it had to do with how do you, um, lower your burn? How do you reprioritize? How you're going to 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 is, you know, applicable not just today, but But, but very applicable today.

AI assessment note: “I'm so incredibly grateful for that hard earned experience”

Q you to venture in that kind of personal journey that you went on. 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?

A Gotta love the good philosophical conversation or question from Jeremy. You know, 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, one part I valued the financial independence that work could offer from the earliest days. But as I navigated my career, I, I appreciated 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 love the role I had and the job I had. And I thought to myself, gosh, I, I did everything I was supposed to. 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 time I was spending at work, um, So I, I think my entrepreneurial bug was kind of rooted in that experience of wanting to …

AI assessment note: “my childhood in really inspired a drive for independence and to create freedom”

Q I think when I'm 50 or 60, will I regret that I spent the best 10 years of my life and my physical body 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?

A 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. 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 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, you know, but I couldn't take that, 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 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. You all make choices, and I'm a big believer in leaning into the choices that you make and trying to make the…

AI assessment note: “leaning into the choices that you make and trying to make the most of them”

Q move into the quickfire, I do want to quickly touch on the macro. We've seen many large acquisitions from Dollar Shave Club to Bonobos, both in your portfolio. Massive congratulations for that. But I would love to ask, do you believe that this is a consolidatory environment with the incumbents purchasing the rising stars of commerce, or will there be a next-gen e-commerce company be a twenty billion dollar company?

A I think there will be both happening. I mean, I think what's happening right now is we are still in some early innings of a sector completely reorganizing itself, and a lot of that is being fueled by Amazon. Amazon, having trained a whole generation of consumers, in many ways has opened up more opportunity for new emerging businesses to jump in and delight those consumers with that level of expectation in mind. But it's share shift going on in a massive way right now. And I think you will see more large businesses looking to expand their moats, your word, their moats to say like we are, there's been this word omni-channel retailing, and I think it's been used kind of pretty generically and in its generic form, it's meant I have some stores and I have a website. And that's really not how we think about omni-channel. I think we think about having a very holistic approach to business, Where you've got your technology working in tandem with all of the other touch points and distribution points of your business, and most of the sector is still trying to organize itself towards that, and so that will drive a layer of consolidation and acquisition, and then I think that there are a lot of businesses who are burdened by their infrastructure and might have a very hard time reinventing themselves in an efficient path And they might ultimately lose their place in the market. At the same t…

AI assessment note: “I think there will be both happening.”

Q move into the quickfire, I do want to quickly touch on the macro. We've seen many large acquisitions from Dollar Shave Club to Bonobos, both in your portfolio. Massive congratulations for that. But I would love to ask, do you believe that this is a consolidatory environment with the incumbents purchasing the rising stars of commerce, or will there be a next-gen e-commerce company be a twenty billion dollar company?

A I think there will be both happening. I mean, I think what's happening right now is we are still in some early innings of a sector completely reorganizing itself, and a lot of that is being fueled by Amazon. Amazon, having trained a whole generation of consumers, in many ways has opened up more opportunity for new emerging businesses to jump in and delight those consumers with that level of expectation in mind. But it's share shift going on in a massive way right now. And I think you will see more large businesses looking to expand their moats, your word, their moats to say like we are, there's been this word omni-channel retailing, and I think it's been used kind of pretty generically and in its generic form, it's meant I have some stores and I have a website. And that's really not how we think about omni-channel. I think we think about having a very holistic approach to business, Where you've got your technology working in tandem with all of the other touch points and distribution points of your business, and most of the sector is still trying to organize itself towards that, and so that will drive a layer of consolidation and acquisition, and then I think that there are a lot of businesses who are burdened by their infrastructure and might have a very hard time reinventing themselves in an efficient path And they might ultimately lose their place in the market. At the same t…

AI assessment note: “I think there will be both happening.”

Q 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 going to 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?

A I don't know, Harry, that we, I ever, you know, we, I ever said we're only doing consumer investing. 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 demographics 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, while I don't know if it's one third or two, you know, 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 B to B business, you're still serving another business that ultimately is serving someone else at somewhere in there, there's a consumer. So in some ways, the consumer is kind of, you know, …

AI assessment note: “I don't know, Harry, that... I ever said we're only doing consumer investing.”

Q you to venture in that kind of personal journey that you went on. 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?

A Gotta love the good philosophical conversation or question from Jeremy. You know, 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, one part I valued the financial independence that work could offer from the earliest days. But as I navigated my career, I, I appreciated 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 love the role I had and the job I had. And I thought to myself, gosh, I, I did everything I was supposed to. 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 time I was spending at work, um, So I, I think my entrepreneurial bug was kind of rooted in that experience of wanting to …

AI assessment note: “my entrepreneurial bug was kind of rooted in that experience of wanting to have more”

Q Um, I, I do want to ask, you mentioned kind of the insecurities and people saying, oh, you can't do something, you can't 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? And I go, I'm a winner, I'm a winner. I, when you question yourself, how do you mind talk yourself?

A 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 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.

AI assessment note: “I try to remind myself that my strength comes from my authenticity”

Q Why? Why also, why now you've proved so much?

A Well, there's always more to prove, Harry. And there's all, you know, I mean, so, but, um, for, you know, for every person that looked at me while I was on this kind of, you know, let's call it my thirties, 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 compliment 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 compliment myself. Um, and so that was a chip on my shoulder in early days. You know, I think venture…

AI assessment note: “Well, there's always more to prove, Harry.”

Q Why? Why also, why now you've proved so much?

A Well, there's always more to prove, Harry. And there's all, you know, I mean, so, but, um, for, you know, for every person that looked at me while I was on this kind of, you know, let's call it my thirties, 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 compliment 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 compliment myself. Um, and so that was a chip on my shoulder in early days. You know, I think venture…

AI assessment note: “Well, there's always more to prove, Harry.”

Q So, um, can I ask with, can I ask with firm scaling, what gets easier over time and what gets harder?

A 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 Forerunner is humble. So we don't assume that we, that we know everything or that we're the reason for everything, 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.

AI assessment note: “So what gets easier over time is you have the benefit of experience”

Q I mean, ego inflation will get you everywhere, so I thoroughly appreciate that. Um, I do. For those that missed our first show, Carson, tell me, how did you make your way into Venture? How did you found For Honor? Quick two to three minutes.

A 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 10 years into it, and I, I realized that, like, I needed more from my career and I could get more from my career. And so I began a personal journey to kind of, you know, uncover what are my true north 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.

AI assessment note: “ultimately became clear that early stage investing really offered the things that I valued”

Q you know, Curated, who's one of your founders, and he said that you are one of the most creative people. 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 awesome and amazing. But his question, she was, in terms of your creativity, how do you think it gives you an edge or an advantage investing?

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

AI assessment note: “Creativity is pretty closely tied to curiosity. And I think curiosity is one of the most”

Q with fund management. That I think people don't see. Um, I do want to ask, you know, 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? Because I'm sure this one has done with experience and scale.

A 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 Forerunner, I strive every day for Forerunner 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 that. 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, and 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 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. Um, so I think, you …

AI assessment note: “My leadership style, I would say, is I, I believe and I hope that I empower”

Q you know, Curated, who's one of your founders, and he said that you are one of the most creative people. 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 awesome and amazing. But his question, she was, in terms of your creativity, how do you think it gives you an edge or an advantage investing?

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

AI assessment note: “Creativity is pretty closely tied to curiosity... really important characteristic in venture.”

Q 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 going to 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?

A I don't know, Harry, that we, I ever, you know, we, I ever said we're only doing consumer investing. 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 demographics 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, while I don't know if it's one third or two, you know, 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 B to B business, you're still serving another business that ultimately is serving someone else at somewhere in there, there's a consumer. So in some ways, the consumer is kind of, you know, …

AI assessment note: “All of it has a tie to the consumer because every business is in service”

Q I 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? This is open for advice. I basically use the show as my own counseling session. How do you retain quality and scale all of those things? How does, what have been your lessons on what can be done to do that?

A 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, 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 want to have The best in class people feeling like they have an opportunity to shine here. You know, it really, it really Demands you to be focused on the process, the org development, you know, what are those areas where people…

AI assessment note: “Demands you to be focused on the process, the org development”

Q with fund management. That I think people don't see. Um, I do want to ask, you know, 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? Because I'm sure this one has done with experience and scale.

A 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 Forerunner, I strive every day for Forerunner 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 that. 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, and 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 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. Um, so I think, you …

AI assessment note: “My leadership style, I would say, is I, I believe and I hope that I empower the people”

Q on digital commerce set out its portfolio construction in terms of Say entry points, valuations, and reserves, given the fact that it takes a fair amount of time for a brand company to develop and establish that traction, in addition to the commerce companies not receiving the same valuation multiples that traditional enterprise companies might. So how do you think about that? First, let's start with from a valuation perspective.

A Okay. Well, I think just generally stepping back before we get into details, holistically speaking, I'm not sure we think terribly differently about portfolio diversification or portfolio strategy than another VC firm. I think it comes down to So specifically on, on the valuation question, I think one of the things about the commerce ecosystem and businesses that have business models that are tied to transactions with consumers, the good and the bad is oftentimes there's a very evident business model and there are enough components of the business model to enable you to identify values around customer lifetime value, around customer acquisition costs, the cost You know, certain components, and you can really understand, like, what it takes to build that business, so that's the good side. The other reality is, is that it's grounded in reality, but it's grounded in kind of the size of the market and, and what you can expect in terms of market share take in that context, and the valuations are reflective of that, and you have to be mindful of that while you're investing, and think about, give some thought to ultimately what Could this business be at its full potential? How will, at that point, the public markets, for instance, look at it and start to walk back to wherever you might be at a stage of a company and, and think about the valuation with that in mind.

AI assessment note: “specifically on, on the valuation question, I think one of the things about the commerce ecosystem”

Q on digital commerce set out its portfolio construction in terms of Say entry points, valuations, and reserves, given the fact that it takes a fair amount of time for a brand company to develop and establish that traction, in addition to the commerce companies not receiving the same valuation multiples that traditional enterprise companies might. So how do you think about that? First, let's start with from a valuation perspective.

A Okay. Well, I think just generally stepping back before we get into details, holistically speaking, I'm not sure we think terribly differently about portfolio diversification or portfolio strategy than another VC firm. I think it comes down to So specifically on, on the valuation question, I think one of the things about the commerce ecosystem and businesses that have business models that are tied to transactions with consumers, the good and the bad is oftentimes there's a very evident business model and there are enough components of the business model to enable you to identify values around customer lifetime value, around customer acquisition costs, the cost You know, certain components, and you can really understand, like, what it takes to build that business, so that's the good side. The other reality is, is that it's grounded in reality, but it's grounded in kind of the size of the market and, and what you can expect in terms of market share take in that context, and the valuations are reflective of that, and you have to be mindful of that while you're investing, and think about, give some thought to ultimately what Could this business be at its full potential? How will, at that point, the public markets, for instance, look at it and start to walk back to wherever you might be at a stage of a company and, and think about the valuation with that in mind.

AI assessment note: “start to walk back to wherever you might be at a stage of a company”

Q So, um, can I ask with, can I ask with firm scaling, what gets easier over time and what gets harder?

A 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 Forerunner is humble. So we don't assume that we, that we know everything or that we're the reason for everything, 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.

AI assessment note: “So what gets easier over time is you have the benefit of experience”

Q No, absolutely. I mean, given the kind of vast landscape of opportunity inherent within that bracket, uh, David also asks, do you think your fund size is big enough to accommodate this and attain meaningful ownership with dilution and subsequent rounds?

A That's a really good question, and it's one that we're talking through internally all the time and one that we're discussing with our LPs. I think, in general, our belief is that we can create advantages as investors and for our partners if we have With this thematic focus and really leaning on that and with the aim to invest in the best, most ambitious endeavors to reshape commerce. And that's more of a sector orientation than it is a stage orientation. That being said, we've spent a lot of time developing a skill set to partner with entrepreneurs early on and to, to hopefully be helpful then. And we're pretty excited about the impact and quite frankly, the fun of doing that too. But I think over time, we do have an eye towards Broadening our entry point and broadening how we can continue to help founders build companies. So that's a nod to say that Forerunner went to market as a thematically dedicated investment fund as opposed to a stage-specific investment fund, and I think we're going to continue to kind of explore how that translates over to our fund size and how the firm develops.

AI assessment note: “explore how that translates over to our fund size and how the firm develops.”

Q I 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? This is open for advice. I basically use the show as my own counseling session. How do you retain quality and scale all of those things? How does, what have been your lessons on what can be done to do that?

A 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, 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 want to have The best in class people feeling like they have an opportunity to shine here. You know, it really, it really Demands you to be focused on the process, the org development, you know, what are those areas where people…

AI assessment note: “Demands you to be focused on the process, the org development”

Q No, absolutely. I mean, given the kind of vast landscape of opportunity inherent within that bracket, uh, David also asks, do you think your fund size is big enough to accommodate this and attain meaningful ownership with dilution and subsequent rounds?

A That's a really good question, and it's one that we're talking through internally all the time and one that we're discussing with our LPs. I think, in general, our belief is that we can create advantages as investors and for our partners if we have With this thematic focus and really leaning on that and with the aim to invest in the best, most ambitious endeavors to reshape commerce. And that's more of a sector orientation than it is a stage orientation. That being said, we've spent a lot of time developing a skill set to partner with entrepreneurs early on and to, to hopefully be helpful then. And we're pretty excited about the impact and quite frankly, the fun of doing that too. But I think over time, we do have an eye towards Broadening our entry point and broadening how we can continue to help founders build companies. So that's a nod to say that Forerunner went to market as a thematically dedicated investment fund as opposed to a stage-specific investment fund, and I think we're going to continue to kind of explore how that translates over to our fund size and how the firm develops.

AI assessment note: “we're going to continue to kind of explore how that translates over to our fund size”