The Exchanges

Q more boutique-y or specialized micro VC funds in the earliest stages of having one or two, because you did amazing work with Hashtag Angels in terms of the gap table, obviously representing the disparities in venture in relation to cap tables themselves. I love the name there. But in terms of your thoughts there, what are the core and most important disparities to highlight in your mind, do you think?

A Yeah, I think some of the biggest disparities are first that we, when we partnered with Carta to measure the gap on the cap table, aka the gap table, we found that only nine percent of equity value goes towards women, and that's looking at over 6000 companies, 15,000 founders, 180,000 employees, and so that is a huge disparity. The second stat that is quite incredulous as well is that less than three percent of funding goes to all female founding teams. And so, in the year, 2020, that's ridiculous. So, and what's also insane is that there was a recent gender gap report that mentioned gender parity won't be attained for almost a hundred years. So, we need to take bigger swings at changing this inequity in the system at ground zero and through the different stages of development.

AI assessment note: “only nine percent of equity value goes towards women”

Q more boutique-y or specialized micro VC funds in the earliest stages of having one or two, because you did amazing work with Hashtag Angels in terms of the gap table, obviously representing the disparities in venture in relation to cap tables themselves. I love the name there. But in terms of your thoughts there, what are the core and most important disparities to highlight in your mind, do you think?

A Yeah, I think some of the biggest disparities are first that we, when we partnered with Carta to measure the gap on the cap table, aka the gap table, we found that only nine percent of equity value goes towards women, and that's looking at over 6000 companies, 15,000 founders, 180,000 employees, and so that is a huge disparity. The second stat that is quite incredulous as well is that less than three percent of funding goes to all female founding teams. And so, in the year, 2020, that's ridiculous. So, and what's also insane is that there was a recent gender gap report that mentioned gender parity won't be attained for almost a hundred years. So, we need to take bigger swings at changing this inequity in the system at ground zero and through the different stages of development.

AI assessment note: “we found that only nine percent of equity value goes towards women”

Q And, uh, it makes the note all the much more challenging when that does come. I do want to ask, you mentioned that the advice from Semel, Samuel, when you reflect on your journey, fundraising, what advice would you then have for fund managers who are contemplating raising their first time fund for emerging fund managers listening? What would you advise them given your experience? Experience raising Moxie Fund One.

A I have a lot of learning. So I think the first one, just build a very long pipeline and just keep building it. And every time you talk to somebody, ask them for three new names, for example. The second is to focus on your allies, the people who know you best, the people who will likely write you that first check or make those first introductions. It's important to get that legitimacy early. The third thing is figuring out what's so special about you and your strategy. Why should an LPK Care about you. Why should they write you that check, and why now? The fourth thing is something that I learned along the way, which was starting the clock early on institutions. Most institutions that have AUMs exceeding, say, two billion dollars are probably unlikely to invest in you early on, but they take a long time to get to know you, so start that clock early. Another learning was just, you know, that determination, and Ray Tanzing of Caffeinated Capital was a great mentor to me along the way, and every time I'd have a tough day, I'd reach out to him and get his advice, and he's just like, keep pushing, keep pushing, and I remember one of my earliest LPs that I talked to that I became emotionally attached to. I really loved them. I thought they were awesome. They rejected me, and I couldn't handle that rejection, so by the time I got to the end of my fundraising, I went back one more time.…

AI assessment note: “I think the first one, just build a very long pipeline and just keep building”

Q other really interesting element to me was, we mentioned the multi-stage firms there. They have very large partnerships. Decision-making is spread between many people, and often you get the benefits of thought sharing across those different people and profiles. How do you think about decision-making as a solo GP, and what are you doing to actively enhance your thinking and decision-making, given that it is just you making the decisions?

A Yeah, it's great to be a solo GP because you can move fast and you can make decisions quickly, but I do rely on a number of people to help me make sure that I'm making the best decisions possible for this portfolio. So I have three secret slash not so secret weapons. The first is that I have an amazing group of LPs, many of whom are operators, entrepreneurs, seasoned investors, and many of whom have expertise in a particular vertical or particular market. And so I lean on them for deal diligence and deal flow. The second is I have a friend of mine that I work with at both Google and Twitter, Alex Redder, who is an incredible leader. He's an engineer. He's a great investor. He's a venture partner from Oxy Ventures and my technical advisor. And so once a company reaches my level of interest, and I've had a number of conversations with the founder, I asked Alex to meet with them and talk to them about the technical challenges and considerations and basically doing that due diligence and helping those companies once they're in our portfolio attract and retain and close great engineers. And then third, I have this amazing group and network with hashtag angels. They're my LPs in Moxie. They're some of my best friends, and they're tremendous individuals and investors, and I share a lot with them to get their feedback because I trust their judgment.

AI assessment note: “I do rely on a number of people to help me make sure”

Q there with Hashtag Angels, and now institutionally investing from Moxie. When we had Andy McLaughlin on the show, obviously, he was a very successful angel like yourself, and then made the institutional transition with Soft tech and uncork, but he said he became more conservative when he made that transition. So how do you think about that transition and how do you think your mindset is impacted with the transition?

A Yeah. Similar to Andy, I definitely have become more conservative transitioning from being an angel and now being a full-time investor. And part of that is because I've raised capital from important institutions, from mentors, from friends. And so that bar has been raised quite high. I need to be rigorous and I need to get it right. So that means I spend a ton of time, a lot more time doing diligence. I do a lot of reference checking and I spend time with the teams. I try to talk with customers if that's relevant. And I also have this newer checklist, a checklist item, which is, you know, how would I feel about introducing this founder, this set of founders, this team to my LPs? It's a different bar, something that I didn't really have when I was an angel investor. The other thing is that I'm more willing to walk away from deals because Where they don't fit my criteria. I have a much more narrow set of criteria that I look towards as a fund manager versus being an angel investor. For example, I'm only investing in seed stage deals. I'm looking for valuation caps of less than 10 to fifteen million. I'm requiring a certain allocation level to make sure that it's, you know, time and money well spent. And Arlen Hamilton has this great quote that I heard her talk about recently, which is, you know, I've come for the cake and not the crumbs. And so I think for a lot of fund managers,…

AI assessment note: “I definitely have become more conservative transitioning from being an angel”

Q other really interesting element to me was, we mentioned the multi-stage firms there. They have very large partnerships. Decision-making is spread between many people, and often you get the benefits of thought sharing across those different people and profiles. How do you think about decision-making as a solo GP, and what are you doing to actively enhance your thinking and decision-making, given that it is just you making the decisions?

A Yeah, it's great to be a solo GP because you can move fast and you can make decisions quickly, but I do rely on a number of people to help me make sure that I'm making the best decisions possible for this portfolio. So I have three secret slash not so secret weapons. The first is that I have an amazing group of LPs, many of whom are operators, entrepreneurs, seasoned investors, and many of whom have expertise in a particular vertical or particular market. And so I lean on them for deal diligence and deal flow. The second is I have a friend of mine that I work with at both Google and Twitter, Alex Redder, who is an incredible leader. He's an engineer. He's a great investor. He's a venture partner from Oxy Ventures and my technical advisor. And so once a company reaches my level of interest, and I've had a number of conversations with the founder, I asked Alex to meet with them and talk to them about the technical challenges and considerations and basically doing that due diligence and helping those companies once they're in our portfolio attract and retain and close great engineers. And then third, I have this amazing group and network with hashtag angels. They're my LPs in Moxie. They're some of my best friends, and they're tremendous individuals and investors, and I share a lot with them to get their feedback because I trust their judgment.

AI assessment note: “I do rely on a number of people to help me make sure that I'm making”

Q Totally. No, I do see that. And especially agree with you in terms of getting in there early. Really interesting that you said there about kind of showcasing the founders to your LPs. I do want to talk a little bit about the fundraise. It's a super interesting one. Always a first time fundraise. How was the fundraise for you with Moxie?

A Yeah, it was super interesting until I went through the process myself. I really hadn't given the sources of capital that much thought. I knew VCs had money, but I never really dug into where they got their capital from. So now having gone through that myself, it was a good learning experience. I actually enjoyed the process, and I suppose being an extrovert helps. In terms of stats, I ended up meeting with or contacting 279 potential LPs. So that was a good learning experience. And while I net-net enjoyed it, there were definitely some tough times I try to push myself that if I wasn't getting rejected daily, I wasn't pushing hard enough. And then I realized I was probably pushing myself too hard. There was one day I remember where I had about five rejections and I thought, well, this might be the dumbest idea I've ever had in my career, but I got over it. And I know that process has made me stronger. It has made me more thoughtful. And I think it's also made me a better and more empathetic investor because I feel the pain of founders going through the fundraising process.

AI assessment note: “In terms of stats, I ended up meeting with or contacting 279 potential LPs.”

Q often how I position it. I do want to ask you, because you mentioned some brilliant names there, from Arlen to Breanne, and it's, as you said, a very different crop of seed investors popping up today. I'm interested, in terms of the value-add element, what do you find founders most look for when selecting their VCs, and are there commonalities in where you see founders struggle at this stage?

A Yeah, I think that they're looking for capital they can trust, and they're looking for a specific set of skills. So looking for help going to market, finding product market fit, specific to marketing. Hiring and closing top talent is one of the key things that I get asked as an angel investor to my personal portfolio and something now with my fund portfolio. And sometimes it's just looking for that trusted person to vent. It can be very lonely starting and running a company. And so looking for that partner that they can lean on. And then in terms of where founders are struggling, there are really two things I see. First, valuations. As you know, too, valuations in venture right now are just unjustifiably high. And it's so difficult to invest in a company that is pre-product, pre-revenue, basically zero data, valued between 10 and twenty million dollars. I've seen some seeds in the thirty millions. And I think these are vanity metrics, right? And this may seem really exciting right now, but I do worry for these companies when the market turns. And so I think that's something that some founders are struggling with. And the second is around distribution. So earlier startups used to be able to reach their audiences organically, but now because of distribution consolidations, you see startups that needed to pay for their audiences who are aggregated or consolidated on Facebook or th…

AI assessment note: “they're looking for capital they can trust... in terms of where founders are struggling”

Q there with Hashtag Angels, and now institutionally investing from Moxie. When we had Andy McLaughlin on the show, obviously, he was a very successful angel like yourself, and then made the institutional transition with Soft tech and uncork, but he said he became more conservative when he made that transition. So how do you think about that transition and how do you think your mindset is impacted with the transition?

A Yeah. Similar to Andy, I definitely have become more conservative transitioning from being an angel and now being a full-time investor. And part of that is because I've raised capital from important institutions, from mentors, from friends. And so that bar has been raised quite high. I need to be rigorous and I need to get it right. So that means I spend a ton of time, a lot more time doing diligence. I do a lot of reference checking and I spend time with the teams. I try to talk with customers if that's relevant. And I also have this newer checklist, a checklist item, which is, you know, how would I feel about introducing this founder, this set of founders, this team to my LPs? It's a different bar, something that I didn't really have when I was an angel investor. The other thing is that I'm more willing to walk away from deals because Where they don't fit my criteria. I have a much more narrow set of criteria that I look towards as a fund manager versus being an angel investor. For example, I'm only investing in seed stage deals. I'm looking for valuation caps of less than 10 to fifteen million. I'm requiring a certain allocation level to make sure that it's, you know, time and money well spent. And Arlen Hamilton has this great quote that I heard her talk about recently, which is, you know, I've come for the cake and not the crumbs. And so I think for a lot of fund managers,…

AI assessment note: “I definitely have become more conservative transitioning from being an angel”

Q Before we talk about solutions, like, bluntly, thinking of causation, why is this still happening in twenty-twenty? Is it a pipeline problem, and what's driving this disparity?

A There are a number of things, um, a few theories. So the first, and this is anecdotal, but what I've observed that a lot of female-led startups get valued lower and diluted more. I actually noticed this at YC, and would love to dig into the data a bit, but what I found was that the female-led companies at YC that I met with were valued less than fifteen million. The male-led companies were valued much higher, as high as thirty-seven million. So that's one. The second is that there's less Total capital allocated to women due to some investor and industry bias. The third is that there's an underrepresentation of women and people of color as investors, both DCs and angels, and I'm excited that there are groups like hashtag angels and F seven, and of course, all raised bringing that forward, but we need to do better bringing to the table, more people of color as angels as well. I've also noticed and been guilty of not strong negotiation skills. When I was at Twitter, I managed a very large And I noticed all the men on my team were great at negotiating and less women on my team were great at negotiating. So something I talked about with all the women on my team is just really pushed the teams harder to negotiate. And I think that's something that is a bit pervasive in the industry. And then I'm also seeing too that, you know, women aren't being hired for early engineering and leader…

AI assessment note: “There are a number of things, um, a few theories. So the first”

Q it's pre-product or pre-launch, I hold back, and I say no, but I'm very aware that Bill Gurley said on the show, you know, the secret to winning is to enjoy every last minute of the upside, and If you'd pulled back two years ago, you would have missed out on some great opportunities. How do you think about when to pull back versus when not to on the valuation?

A Yeah, I'm with you. You know, I am price sensitive now that I'm managing a fund, and I'm trying to be consistent with what I have, you know, talked to my LPs about, but I also am mindful that sometimes the best deals are the priciest deals, and bottom line, like, if you have conviction on the team, you should write the check, and you should right-size it for your fund, not necessarily your ownership target. And, you know, ultimately, the price may not matter in the long run if it plays out, and I would be so mad at myself if I missed the next Stripe or Glossier or Google because I thought it was priced too high at Seed. So it's really tricky. So I think, you know, ultimately, it's a balance between having some, you know, criteria, but also when you have high levels of conviction to just go for it.

AI assessment note: “if you have conviction on the team, you should write the check”

Q And, uh, it makes the note all the much more challenging when that does come. I do want to ask, you mentioned that the advice from Semel, Samuel, when you reflect on your journey, fundraising, what advice would you then have for fund managers who are contemplating raising their first time fund for emerging fund managers listening? What would you advise them given your experience? Experience raising Moxie Fund One.

A I have a lot of learning. So I think the first one, just build a very long pipeline and just keep building it. And every time you talk to somebody, ask them for three new names, for example. The second is to focus on your allies, the people who know you best, the people who will likely write you that first check or make those first introductions. It's important to get that legitimacy early. The third thing is figuring out what's so special about you and your strategy. Why should an LPK Care about you. Why should they write you that check, and why now? The fourth thing is something that I learned along the way, which was starting the clock early on institutions. Most institutions that have AUMs exceeding, say, two billion dollars are probably unlikely to invest in you early on, but they take a long time to get to know you, so start that clock early. Another learning was just, you know, that determination, and Ray Tanzing of Caffeinated Capital was a great mentor to me along the way, and every time I'd have a tough day, I'd reach out to him and get his advice, and he's just like, keep pushing, keep pushing, and I remember one of my earliest LPs that I talked to that I became emotionally attached to. I really loved them. I thought they were awesome. They rejected me, and I couldn't handle that rejection, so by the time I got to the end of my fundraising, I went back one more time.…

AI assessment note: “the first one, just build a very long pipeline and just keep building it.”

Q Before we talk about solutions, like, bluntly, thinking of causation, why is this still happening in twenty-twenty? Is it a pipeline problem, and what's driving this disparity?

A There are a number of things, um, a few theories. So the first, and this is anecdotal, but what I've observed that a lot of female-led startups get valued lower and diluted more. I actually noticed this at YC, and would love to dig into the data a bit, but what I found was that the female-led companies at YC that I met with were valued less than fifteen million. The male-led companies were valued much higher, as high as thirty-seven million. So that's one. The second is that there's less Total capital allocated to women due to some investor and industry bias. The third is that there's an underrepresentation of women and people of color as investors, both DCs and angels, and I'm excited that there are groups like hashtag angels and F seven, and of course, all raised bringing that forward, but we need to do better bringing to the table, more people of color as angels as well. I've also noticed and been guilty of not strong negotiation skills. When I was at Twitter, I managed a very large And I noticed all the men on my team were great at negotiating and less women on my team were great at negotiating. So something I talked about with all the women on my team is just really pushed the teams harder to negotiate. And I think that's something that is a bit pervasive in the industry. And then I'm also seeing too that, you know, women aren't being hired for early engineering and leader…

AI assessment note: “There are a number of things, um, a few theories.”

Q often how I position it. I do want to ask you, because you mentioned some brilliant names there, from Arlen to Breanne, and it's, as you said, a very different crop of seed investors popping up today. I'm interested, in terms of the value-add element, what do you find founders most look for when selecting their VCs, and are there commonalities in where you see founders struggle at this stage?

A Yeah, I think that they're looking for capital they can trust, and they're looking for a specific set of skills. So looking for help going to market, finding product market fit, specific to marketing. Hiring and closing top talent is one of the key things that I get asked as an angel investor to my personal portfolio and something now with my fund portfolio. And sometimes it's just looking for that trusted person to vent. It can be very lonely starting and running a company. And so looking for that partner that they can lean on. And then in terms of where founders are struggling, there are really two things I see. First, valuations. As you know, too, valuations in venture right now are just unjustifiably high. And it's so difficult to invest in a company that is pre-product, pre-revenue, basically zero data, valued between 10 and twenty million dollars. I've seen some seeds in the thirty millions. And I think these are vanity metrics, right? And this may seem really exciting right now, but I do worry for these companies when the market turns. And so I think that's something that some founders are struggling with. And the second is around distribution. So earlier startups used to be able to reach their audiences organically, but now because of distribution consolidations, you see startups that needed to pay for their audiences who are aggregated or consolidated on Facebook or th…

AI assessment note: “in terms of where founders are struggling, there are really two things I see”

Q and I totally agree with you there in terms of the elements of causation. So say you had a magic wand here, Katie, what would you do? What solutions would you suggest and really actively advocate for in the coming years that can really reduce this disparity, not in a hundred years, but in the next Three to five years that we can really see and enjoy the benefits of.

A Yeah. I mean, the first is data. And as you know, we say in Silicon Valley, you can't manage what you can't measure. And really give props to Henry Ward, the CEO and co-founder of Carta, who partnered with us at Hashtag Angels to measure that gap. And so, and Carta did a really good job of updating the data earlier this year. So we need to keep pushing for the data to be open, transparent, and talked about. The second thing is ownership. So I think for founders, being intentional and fair and mindful about how allocations of equity are being made for founders, for early employees, for women investors, for executives, for angels, and so forth. So just being, again, more intentional. And then also for VCs and for founders, also being thoughtful about those valuations, how they're being said. Is this something, you know, that is fair? Is this reasonable? Especially in this hyper crazy market, but being thoughtful too about if this were an all male team, would this get the same valuation? If this were a more diverse team, what is the right and fair thing to do?

AI assessment note: “The first is data. And as you know... The second thing is ownership.”

Q Totally. No, I do see that. And especially agree with you in terms of getting in there early. Really interesting that you said there about kind of showcasing the founders to your LPs. I do want to talk a little bit about the fundraise. It's a super interesting one. Always a first time fundraise. How was the fundraise for you with Moxie?

A Yeah, it was super interesting until I went through the process myself. I really hadn't given the sources of capital that much thought. I knew VCs had money, but I never really dug into where they got their capital from. So now having gone through that myself, it was a good learning experience. I actually enjoyed the process, and I suppose being an extrovert helps. In terms of stats, I ended up meeting with or contacting 279 potential LPs. So that was a good learning experience. And while I net-net enjoyed it, there were definitely some tough times I try to push myself that if I wasn't getting rejected daily, I wasn't pushing hard enough. And then I realized I was probably pushing myself too hard. There was one day I remember where I had about five rejections and I thought, well, this might be the dumbest idea I've ever had in my career, but I got over it. And I know that process has made me stronger. It has made me more thoughtful. And I think it's also made me a better and more empathetic investor because I feel the pain of founders going through the fundraising process.

AI assessment note: “it was a good learning experience. I actually enjoyed the process”

Q and I totally agree with you there in terms of the elements of causation. So say you had a magic wand here, Katie, what would you do? What solutions would you suggest and really actively advocate for in the coming years that can really reduce this disparity, not in a hundred years, but in the next Three to five years that we can really see and enjoy the benefits of.

A Yeah. I mean, the first is data. And as you know, we say in Silicon Valley, you can't manage what you can't measure. And really give props to Henry Ward, the CEO and co-founder of Carta, who partnered with us at Hashtag Angels to measure that gap. And so, and Carta did a really good job of updating the data earlier this year. So we need to keep pushing for the data to be open, transparent, and talked about. The second thing is ownership. So I think for founders, being intentional and fair and mindful about how allocations of equity are being made for founders, for early employees, for women investors, for executives, for angels, and so forth. So just being, again, more intentional. And then also for VCs and for founders, also being thoughtful about those valuations, how they're being said. Is this something, you know, that is fair? Is this reasonable? Especially in this hyper crazy market, but being thoughtful too about if this were an all male team, would this get the same valuation? If this were a more diverse team, what is the right and fair thing to do?

AI assessment note: “I mean, the first is data... The second thing is ownership.”

Q it's pre-product or pre-launch, I hold back, and I say no, but I'm very aware that Bill Gurley said on the show, you know, the secret to winning is to enjoy every last minute of the upside, and If you'd pulled back two years ago, you would have missed out on some great opportunities. How do you think about when to pull back versus when not to on the valuation?

A Yeah, I'm with you. You know, I am price sensitive now that I'm managing a fund, and I'm trying to be consistent with what I have, you know, talked to my LPs about, but I also am mindful that sometimes the best deals are the priciest deals, and bottom line, like, if you have conviction on the team, you should write the check, and you should right-size it for your fund, not necessarily your ownership target. And, you know, ultimately, the price may not matter in the long run if it plays out, and I would be so mad at myself if I missed the next Stripe or Glossier or Google because I thought it was priced too high at Seed. So it's really tricky. So I think, you know, ultimately, it's a balance between having some, you know, criteria, but also when you have high levels of conviction to just go for it.

AI assessment note: “if you have conviction on the team, you should write the check”

Q How did that lead to the founding of Moxie?

A Yeah, so, um, while I was at Google, I felt like I was surrounded by these Exceptional entrepreneurs. And it gave me my first two opportunities to invest. The first was in a fund. Second was in a company. And in both of those cases, they were exceptional people with a ton of guts to start something new. So with a fund, it was Chris Saka, who told me he was creating this new fund called lowercase capital. The first time I was exposed to a venture fund. And I said, well, what does that mean? He's like, well, you give me money and I Spend it on other companies. Like, well, that seems weird, but okay. Like, you're really smart. You've got a lot of hustle, and I believed in Chris. And then the second person was Summit Agarwal, who was creating Shape Security, and they're, too, another exceptional founder with a tremendous background who understood this intersection of defense, cybersecurity, and products, and I invested in Summit. And I got, you know, very lucky with both of those two investments. Lowercase Capital became one of the, if not the top-performing fund of all time, And then Shape Security was just acquired about a week and a half ago, actually, in mid-December for a billion dollars. And so at that time, I really didn't know that much about angel investing. I got very busy with my day job raising three kids, and so I didn't have much time for other things. But then this r…

AI assessment note: “then this really interesting turning point happened about five years ago”

Q the industry there, so to speak. And so if we talk about one that's particularly really interesting for me at the moment, and Samuel Shah, actually, who you mentioned, said on the show that founders are voting with their feet in taking multi-stage money at seed, end quote from Samuel. I'm interested. Would you agree with this? And how do you think about the multi-stage approach to seed investing today?

A Yeah, I agree with Semmel, and I think there's something really interesting happening at a super high level, and Jim Marshall at Silicon Valley Bank frames this pretty well. So he talks about there are four waves of venture, and this first wave was the original giant, and it was kind of the old boys club of Silicon Valley. Capital was scarce, and there were families looking for some high yield return potential, and so we saw these iconic firms of Sequoia and Kleiner. And nothing changed for a while, but then we had this boom in 2000, and we saw this second wave, a venture as a service, and we saw some great firms emerge, Andreessen, First Round, True Ventures, and we saw more of this service business, and capital started to get commoditized. And then we had this democratization of VC. We saw this micro VC boom, and we saw, you know, new companies at C-level and firms who could raise these new funds and funding Web And that's where we saw lowercase and uncork and felices start to emerge. But now there's this really interesting fourth wave, which you and I are a part of. So there's differentiation, there's diversity. This isn't just a Silicon Valley story. This is something that is starting to become geographically spread. You're in London. I'm in Silicon Valley. Um, there are people who come from different backgrounds who didn't go to Stanford, but they have a really strong netw…

AI assessment note: “Yeah, I agree with Semmel, and I think there's something really interesting happening”

Q I think it just shows how old that I'm getting. I feel like Benjamin Button right now, but I would love to start a little bit on you. So hugely respected figure in the industry, operator and experienced angel. But for those that maybe don't know, how did you make your way into the world of tech, but also how did that lead to your founding of Moxie very recently?

A Yes. So my path to tech was a little bit random. I was working in New York as a banker and was pretty miserable in my job. And this was in the late nineties. And I thought to myself, like, I need to get out of this. It's not what I intended to do. And I remember using Yahoo, one of the earliest iterations of Yahoo. And I thought, well, that's interesting. How fun would it be to work at a company like Yahoo? And at the time they just launched a version of Yahoo finance. And I realized that was my opportunity. That was this intersection of this financial background that I had and bringing that content to more people and convinced a friend of a friend of a friend to offer me this role at Yahoo and Got a job, moved out west, and that became my path in tech. So that was in 99. I worked at Yahoo for three years. After Yahoo, I thought, wow, you can really love your job. What could possibly be better than Yahoo? And was lucky enough to get this role at Google. Um, so worked at Google for six years. So between Yahoo, Google, and Twitter and Color, that became my pathway in technology.

AI assessment note: “between Yahoo, Google, and Twitter and Color, that became my pathway in technology.”

Q I think it just shows how old that I'm getting. I feel like Benjamin Button right now, but I would love to start a little bit on you. So hugely respected figure in the industry, operator and experienced angel. But for those that maybe don't know, how did you make your way into the world of tech, but also how did that lead to your founding of Moxie very recently?

A Yes. So my path to tech was a little bit random. I was working in New York as a banker and was pretty miserable in my job. And this was in the late nineties. And I thought to myself, like, I need to get out of this. It's not what I intended to do. And I remember using Yahoo, one of the earliest iterations of Yahoo. And I thought, well, that's interesting. How fun would it be to work at a company like Yahoo? And at the time they just launched a version of Yahoo finance. And I realized that was my opportunity. That was this intersection of this financial background that I had and bringing that content to more people and convinced a friend of a friend of a friend to offer me this role at Yahoo and Got a job, moved out west, and that became my path in tech. So that was in 99. I worked at Yahoo for three years. After Yahoo, I thought, wow, you can really love your job. What could possibly be better than Yahoo? And was lucky enough to get this role at Google. Um, so worked at Google for six years. So between Yahoo, Google, and Twitter and Color, that became my pathway in technology.

AI assessment note: “between Yahoo, Google, and Twitter and Color, that became my pathway in technology.”

Q the industry there, so to speak. And so if we talk about one that's particularly really interesting for me at the moment, and Samuel Shah, actually, who you mentioned, said on the show that founders are voting with their feet in taking multi-stage money at seed, end quote from Samuel. I'm interested. Would you agree with this? And how do you think about the multi-stage approach to seed investing today?

A Yeah, I agree with Semmel, and I think there's something really interesting happening at a super high level, and Jim Marshall at Silicon Valley Bank frames this pretty well. So he talks about there are four waves of venture, and this first wave was the original giant, and it was kind of the old boys club of Silicon Valley. Capital was scarce, and there were families looking for some high yield return potential, and so we saw these iconic firms of Sequoia and Kleiner. And nothing changed for a while, but then we had this boom in 2000, and we saw this second wave, a venture as a service, and we saw some great firms emerge, Andreessen, First Round, True Ventures, and we saw more of this service business, and capital started to get commoditized. And then we had this democratization of VC. We saw this micro VC boom, and we saw, you know, new companies at C-level and firms who could raise these new funds and funding Web And that's where we saw lowercase and uncork and felices start to emerge. But now there's this really interesting fourth wave, which you and I are a part of. So there's differentiation, there's diversity. This isn't just a Silicon Valley story. This is something that is starting to become geographically spread. You're in London. I'm in Silicon Valley. Um, there are people who come from different backgrounds who didn't go to Stanford, but they have a really strong netw…

AI assessment note: “Yeah, I agree with Semmel, and I think there's something really interesting happening”

Q How did that lead to the founding of Moxie?

A Yeah, so, um, while I was at Google, I felt like I was surrounded by these Exceptional entrepreneurs. And it gave me my first two opportunities to invest. The first was in a fund. Second was in a company. And in both of those cases, they were exceptional people with a ton of guts to start something new. So with a fund, it was Chris Saka, who told me he was creating this new fund called lowercase capital. The first time I was exposed to a venture fund. And I said, well, what does that mean? He's like, well, you give me money and I Spend it on other companies. Like, well, that seems weird, but okay. Like, you're really smart. You've got a lot of hustle, and I believed in Chris. And then the second person was Summit Agarwal, who was creating Shape Security, and they're, too, another exceptional founder with a tremendous background who understood this intersection of defense, cybersecurity, and products, and I invested in Summit. And I got, you know, very lucky with both of those two investments. Lowercase Capital became one of the, if not the top-performing fund of all time, And then Shape Security was just acquired about a week and a half ago, actually, in mid-December for a billion dollars. And so at that time, I really didn't know that much about angel investing. I got very busy with my day job raising three kids, and so I didn't have much time for other things. But then this r…

AI assessment note: “this really interesting turning point happened about five years ago.”