The Exchanges

Q That is so kind of you to say, and I'm thrilled you like them, but I would love to start with a little bit on you. So tell me, Alexa, how did you make your way into the world of startups and make the transition into the weird, but very wonderful world of venture and also founding inspired?

A So I'll just say it started probably when I was tennis years old. I was the weird kid that rather than like having lemonade stands, I would like take art off the wall, by the way, not fancy art, like just, you know, some, some art off the wall of my parents' house. And I would like sell it on the street and definitely did not make for being a great child, but I think it really early showed me I was an entrepreneur. I went to Harvard undergrad, uh, started my career actually at Insight Venture Partners where I gravitated right there early. And I quickly realized that I was Obsessed with entrepreneurship. I was enamored with it. I was the kid who thought that CEOs were cooler than like pop stars. And I think I quickly in my early twenties realized that that was what I was excited to do. So a good friend of mine, Sam Lassen was starting Dropio. I went over there early and got a full dose of, of what it's like to build a company. And that was 2007 in Dumbo. And then ended up going to Harvard business school, dropped out, had been working on a businessman Plan for LearnVest and did the weird thing of starting a company at the bottom of the recession, and eventually LearnVest got acquired for about three hundred and seventy five million dollars, and through all of that, I realized I was just obsessed with entrepreneurs. I would help them for free nights, weekends, and as I started an…

AI assessment note: “it became clear to me that that's what I wanted to do next”

Q Who is the best board member you've sat on a board with and what made them so special?

A So actually, it's this guy that is relatively unknown. His name is Lee Barba, and he's in his sixties now. He was my board member. He had just sold his business to TD Ameritrade for about a billion dollars, and he is who I hope to be for every board that I sit on, which was he always gave me the toughest advice, and it really was, like, he cared so much. Every board meeting he came to, he was triple prepared, read everything, brought volumes of insights, And then always told me the thing that I did not want to hear because often sadly he was right. He would say, this is going to be a big issue. This is a problem. These two people aren't working well together and one of them has to go. And he always did it with such empathy that he would send me emails at three o'clock in the morning being like, I know you're not sleeping. You're not in this alone. And I think because he had been an incredible CEO himself, like he understood how vital it was for him to push me harder and faster because we were never going to win if that didn't happen. But then on the flip side, he understood the humanity of, I was just human, and I was young, and I was learning, and I was going to make mistakes, and so he did it with such kindness, and I wanted, I, you know, part of one of the reasons why I love Inspired so much is, like, we want to do just that for every one of the companies that we get the pri…

AI assessment note: “His name is Lee Barba, and he's in his sixties now.”

Q That is so kind of you to say, and I'm thrilled you like them, but I would love to start with a little bit on you. So tell me, Alexa, how did you make your way into the world of startups and make the transition into the weird, but very wonderful world of venture and also founding inspired?

A So I'll just say it started probably when I was tennis years old. I was the weird kid that rather than like having lemonade stands, I would like take art off the wall, by the way, not fancy art, like just, you know, some, some art off the wall of my parents' house. And I would like sell it on the street and definitely did not make for being a great child, but I think it really early showed me I was an entrepreneur. I went to Harvard undergrad, uh, started my career actually at Insight Venture Partners where I gravitated right there early. And I quickly realized that I was Obsessed with entrepreneurship. I was enamored with it. I was the kid who thought that CEOs were cooler than like pop stars. And I think I quickly in my early twenties realized that that was what I was excited to do. So a good friend of mine, Sam Lassen was starting Dropio. I went over there early and got a full dose of, of what it's like to build a company. And that was 2007 in Dumbo. And then ended up going to Harvard business school, dropped out, had been working on a businessman Plan for LearnVest and did the weird thing of starting a company at the bottom of the recession, and eventually LearnVest got acquired for about three hundred and seventy five million dollars, and through all of that, I realized I was just obsessed with entrepreneurs. I would help them for free nights, weekends, and as I started an…

AI assessment note: “as I started angel investing, it became clear to me that that's what I wanted”

Q always a nightmare having to write an investment memo for the institutional checks. I do want to touch on the firm itself, and we spoke about the institutionalization there. It's the largest ever female-led VC firm in New York. So starting from a question from one of our mutual friends, Satya at Homebrew, he said, what was your pitch to LPs and why do you think it works so well?

A Well, first I'll just say we've got a lot of work to do. I really do think that we have 20 years ahead of us of exceptionally hard, focused work, and so it worked well in that we got into business very quickly, which is wonderful, but I really do feel like we're just getting started, and I think what resonated was one, our team, so the group of people behind Inspired Capital, We've known each other for maximum 20 years, minimum a decade, and I think that that just really makes a really different chemistry in terms of the group of people. So Penny Pritzker, who was Secretary of Commerce, has, you know, six, uh, companies that she's helped build and scale and sell behind her belt. Mark Batsian, who I've worked with for a decade, he and I were the deal team behind LearnVast. We were running Northwestern Mutual Ventures together after our acquisition. And then Lucy Deland, who was a co-founder of Paperless Post, Who literally was my best friend, undergrad at Harvard. We both were building companies at the bottom of the recession, her at Paperless, me at LearnVest, and she also worked at Insight Venture Partners. And so I think the DNA of our team there was one highly, highly tightly knit team of, we're quite different people, but exceptionally committed to excellence in entrepreneurship. We all started on the investing side and then migrated to the entrepreneurship side and then we…

AI assessment note: “what resonated was one, our team, so the group of people behind Inspired Capital”

Q I mean, that portfolio construction element is actually, as you probably know from listening to the show, one of my favorite topics to discuss. How do you think about that with a hundred and seventy-five million then? What does that look like in terms of diversification, in terms of initial to reserves? How do you break that down in terms of the core mechanics?

A Yeah. So our fund is two hundred million. So for a two hundred million dollar fund, you know, we really do think about it as saving a sizable chunk, 50% for reserves, 50% for initial deployment. We almost then break that up into three smaller funds inside our own fund. We think about them very formally and very separately. And I think that, again, is more about our process and our decision-making rigor. And then we essentially think of it as we have an Early stage seed funds where we think about big, big, big, contrarian, wild ideas with founders we're really passionate about and take the time to get to know. And in that portion, we'll bet on an entrepreneur with an early napkin idea to a true kind of seed deal. And then the majority of our capital really goes into that second bucket, which is that I'm going to call it a series A, but I almost think we need to get rid of the names because I think in this environment, some series A's look like B's, some series A's look like seed extensions, some series A's are real series A's of the decade ago when I was building LearnVest, and I think of it more in terms of progress of the company, de-risking of the asset on that spectrum, so series A. And then our third kind of portfolio, if you will, is really our follow-on, and that has its own rules and operations of how we think about it coming back to committee. So that's a bit how we act…

AI assessment note: “50% for reserves, 50% for initial deployment. We almost then break that up into three smaller funds”

Q Who is the best board member you've sat on a board with and what made them so special?

A So actually, it's this guy that is relatively unknown. His name is Lee Barba, and he's in his sixties now. He was my board member. He had just sold his business to TD Ameritrade for about a billion dollars, and he is who I hope to be for every board that I sit on, which was he always gave me the toughest advice, and it really was, like, he cared so much. Every board meeting he came to, he was triple prepared, read everything, brought volumes of insights, And then always told me the thing that I did not want to hear because often sadly he was right. He would say, this is going to be a big issue. This is a problem. These two people aren't working well together and one of them has to go. And he always did it with such empathy that he would send me emails at three o'clock in the morning being like, I know you're not sleeping. You're not in this alone. And I think because he had been an incredible CEO himself, like he understood how vital it was for him to push me harder and faster because we were never going to win if that didn't happen. But then on the flip side, he understood the humanity of, I was just human, and I was young, and I was learning, and I was going to make mistakes, and so he did it with such kindness, and I wanted, I, you know, part of one of the reasons why I love Inspired so much is, like, we want to do just that for every one of the companies that we get the pri…

AI assessment note: “His name is Lee Barba, and he's in his sixties now.”

Q I mean, that portfolio construction element is actually, as you probably know from listening to the show, one of my favorite topics to discuss. How do you think about that with a hundred and seventy-five million then? What does that look like in terms of diversification, in terms of initial to reserves? How do you break that down in terms of the core mechanics?

A Yeah. So our fund is two hundred million. So for a two hundred million dollar fund, you know, we really do think about it as saving a sizable chunk, 50% for reserves, 50% for initial deployment. We almost then break that up into three smaller funds inside our own fund. We think about them very formally and very separately. And I think that, again, is more about our process and our decision-making rigor. And then we essentially think of it as we have an Early stage seed funds where we think about big, big, big, contrarian, wild ideas with founders we're really passionate about and take the time to get to know. And in that portion, we'll bet on an entrepreneur with an early napkin idea to a true kind of seed deal. And then the majority of our capital really goes into that second bucket, which is that I'm going to call it a series A, but I almost think we need to get rid of the names because I think in this environment, some series A's look like B's, some series A's look like seed extensions, some series A's are real series A's of the decade ago when I was building LearnVest, and I think of it more in terms of progress of the company, de-risking of the asset on that spectrum, so series A. And then our third kind of portfolio, if you will, is really our follow-on, and that has its own rules and operations of how we think about it coming back to committee. So that's a bit how we act…

AI assessment note: “saving a sizable chunk, 50% for reserves, 50% for initial deployment.”

Q For you, is it difficult, having been a founder and being such an innate founder, when there is that moment of, well, I'm an investor now, and I'm a shareholder, and it's not optimal for me to give them that price? I'd like to cram it down to this price because that's optimal in terms of my ownership. Is it difficult switching hats and having those sometimes moments of misalignment?

A No, I actually, and I don't even think that, and maybe this is too optimistic of me, but I don't even think that those are moments of misalignment. And let me be clear, venture returns are not made on like a few million dollars evaluation. That in the end, it's about picking the breakout companies that are the category creating businesses of the next And making sure that you are at the table in a handful of those. I think in those moments of like, I actually feel deeply aligned to the entrepreneur. And again, maybe this is just my vantage point, but one thing I often say to the entrepreneurs is, Hey, listen, in the end, often it's founders, you know, sole founder, double founders, whatever it may be. I say only one thing truly matters here. And it's you in a decade. And I often say it's a decade because start to finish for learn best. It was really about seven and a half years. Most of the times it's about a decade. And I say to them in a decade, we want to have the biggest exit that we humanly can. And that's how I approach it. And I say, one thing matters is the W at the end of this. And we want to every day come to work and make great decisions. And so it's about every decision being a little bit up and to the right. And so again, if a founder is in that position, I'm like, I'm not looking to get the squeeze of the absolute best valuation and they shouldn't either, right? It…

AI assessment note: “No, I actually, and I don't even think that... those are moments of misalignment.”

Q guy. And then the third is, you mentioned the angel investing there, and it's a really interesting one for me, and one that I'm actually navigating the transition to now with our new fund is, how do you think your mindset changed angel investing compared to institutional investing? It was actually Josh Koppelman and Andy McLaughlin that said they became more conservative. How did your mindset change, do you think?

A Yeah, I mean, to think about it, when you're angel investing, you're a steward of your own capital, and That may mean you really like somebody, you give them some money, the return profile may be two X, five X, maybe lower. When you're running your own fund, you are stewards of someone's capital. I take my fiduciary responsibility extremely seriously. My, as I ran LearnVest, I ran a regulated company, a registered investment advisor. I became a certified financial planner and I take the fiduciary piece so seriously. And so I think how it changes is you then think about what are my goals with this Capital, and if your goals are to perform a powerful top decile fund, it changes, right? And as an angel investor, you may say, oh, I love this entrepreneur. They're onto something, but here's the 25 K versus I'm here, and this is my full-time job, and it just sharpens the investing pencils, I think, quite a lot.

AI assessment note: “it just sharpens the investing pencils, I think, quite a lot.”

Q guy. And then the third is, you mentioned the angel investing there, and it's a really interesting one for me, and one that I'm actually navigating the transition to now with our new fund is, how do you think your mindset changed angel investing compared to institutional investing? It was actually Josh Koppelman and Andy McLaughlin that said they became more conservative. How did your mindset change, do you think?

A Yeah, I mean, to think about it, when you're angel investing, you're a steward of your own capital, and That may mean you really like somebody, you give them some money, the return profile may be two X, five X, maybe lower. When you're running your own fund, you are stewards of someone's capital. I take my fiduciary responsibility extremely seriously. My, as I ran LearnVest, I ran a regulated company, a registered investment advisor. I became a certified financial planner and I take the fiduciary piece so seriously. And so I think how it changes is you then think about what are my goals with this Capital, and if your goals are to perform a powerful top decile fund, it changes, right? And as an angel investor, you may say, oh, I love this entrepreneur. They're onto something, but here's the 25 K versus I'm here, and this is my full-time job, and it just sharpens the investing pencils, I think, quite a lot.

AI assessment note: “when you're angel investing, you're a steward of your own capital”

Q one other way to do it is also really approach the advice element from mentors. And we did chat before about mentors and you said about the importance of having mentors of All ages. Now, I love this because I'm a strong believer in the mentorship model, but what did you mean by the mentors of all ages, and why do you believe so strongly in this structure of support?

A So a few things. As I was 21, developing my career now over a decade ago, I didn't know much, right? I grew up in Jacksonville, Florida. My family's in medicine, so doctors, nurses, etc. I'm like the total black sheep in the business world, and I quickly learned that I don't need to know everything. I shouldn't expect to know everything, and that I should Constantly surround myself with people that will broaden my perspective, add to the contours of my own thinking. And so the way that I just approached this was over time, and I almost just, the word mentor, I think of it as just friendships, like real genuine friendships. So I had a great guy named Anson Beard, who was the chairman of Morgan Stanley Securities when I worked at Morgan Stanley, who became my friend. And he taught me two key things, pick up the phone and call people when there's a When there's something that you know should not be an email or a text, pick up the phone and use your actual voice. You'll always respect yourself more for doing it. And the other thing is he was like, show up on time, like just be on time. And those two things have stuck with me for a really long time. Some of my old investors were incredible people of different decades, different generations. So in their sixties, and they talked to me a lot about how do I develop the ability to lean in a But I also, I have a family, and I have three l…

AI assessment note: “investors were incredible people of different decades, different generations.”

Q saying no. So either don't Terrible. I know. And that's really an area for improvement. Or I don't give a very specific reason because I find then people just argue back with the reason and it's not productive. You're an entrepreneur turned investor. You have that mindset, as we said, innately within you. What's the right way? And how would you advise me on the right way to say no?

A Yeah. So I will just share that I fully get it, Harry. And having had lots of people say no to me and actually just like intimately knowing how much that that would hurt is That part of my, I'm a very empathetic person, as you probably can even just tell from this interview. Yeah, it sucks, and what I have learned is that the nicest thing you can do to somebody is say no early, say no honestly, and with real, real care, and sometimes I only know the way that I know how to do it, which is to say, I hate having to say no to you because I like you so much, but this isn't a good fit, and here are the three ways that I think I can help you otherwise, and it takes more time, and so I think Again, so much of our process is we only get closer to companies where there's a true and genuine chance of saying yes. Even then you still have to say no lots and lots of times more often than not that all the odds are towards saying no. And in fact, this is a job of saying no. So just developing a real muscle. And I, and as I always recommend to people, you got to figure out your authentic way to do it so that you can do it yourself. And Harry, you're never going to hate it less ever. You just have to get good at it because it is the part of the job. It is a core part of the job.

AI assessment note: “the nicest thing you can do to somebody is say no early, say no honestly”

Q always a nightmare having to write an investment memo for the institutional checks. I do want to touch on the firm itself, and we spoke about the institutionalization there. It's the largest ever female-led VC firm in New York. So starting from a question from one of our mutual friends, Satya at Homebrew, he said, what was your pitch to LPs and why do you think it works so well?

A Well, first I'll just say we've got a lot of work to do. I really do think that we have 20 years ahead of us of exceptionally hard, focused work, and so it worked well in that we got into business very quickly, which is wonderful, but I really do feel like we're just getting started, and I think what resonated was one, our team, so the group of people behind Inspired Capital, We've known each other for maximum 20 years, minimum a decade, and I think that that just really makes a really different chemistry in terms of the group of people. So Penny Pritzker, who was Secretary of Commerce, has, you know, six, uh, companies that she's helped build and scale and sell behind her belt. Mark Batsian, who I've worked with for a decade, he and I were the deal team behind LearnVast. We were running Northwestern Mutual Ventures together after our acquisition. And then Lucy Deland, who was a co-founder of Paperless Post, Who literally was my best friend, undergrad at Harvard. We both were building companies at the bottom of the recession, her at Paperless, me at LearnVest, and she also worked at Insight Venture Partners. And so I think the DNA of our team there was one highly, highly tightly knit team of, we're quite different people, but exceptionally committed to excellence in entrepreneurship. We all started on the investing side and then migrated to the entrepreneurship side and then we…

AI assessment note: “what resonated was one, our team, so the group of people behind Inspired Capital”

Q one other way to do it is also really approach the advice element from mentors. And we did chat before about mentors and you said about the importance of having mentors of All ages. Now, I love this because I'm a strong believer in the mentorship model, but what did you mean by the mentors of all ages, and why do you believe so strongly in this structure of support?

A So a few things. As I was 21, developing my career now over a decade ago, I didn't know much, right? I grew up in Jacksonville, Florida. My family's in medicine, so doctors, nurses, etc. I'm like the total black sheep in the business world, and I quickly learned that I don't need to know everything. I shouldn't expect to know everything, and that I should Constantly surround myself with people that will broaden my perspective, add to the contours of my own thinking. And so the way that I just approached this was over time, and I almost just, the word mentor, I think of it as just friendships, like real genuine friendships. So I had a great guy named Anson Beard, who was the chairman of Morgan Stanley Securities when I worked at Morgan Stanley, who became my friend. And he taught me two key things, pick up the phone and call people when there's a When there's something that you know should not be an email or a text, pick up the phone and use your actual voice. You'll always respect yourself more for doing it. And the other thing is he was like, show up on time, like just be on time. And those two things have stuck with me for a really long time. Some of my old investors were incredible people of different decades, different generations. So in their sixties, and they talked to me a lot about how do I develop the ability to lean in a But I also, I have a family, and I have three l…

AI assessment note: “surround myself with people that will broaden my perspective, add to the contours of my own thinking”

Q So that's what worked well in terms of the fundraise. If you're kind of maybe more self-reflective and critical of yourself, maybe, what do you think that maybe you didn't do so well? And what elements would you really like to improve about the pitch or the process of fund two?

A Well, I think just, and I don't know that I changed this. So my last day, as I transitioned off the management team at Northwestern Mutual, the firm, literally the last day that I left Northwestern Mutual and launched Inspired, it was the same day. And on that day, we closed about a hundred and twenty-five million. So it happened instantly. And then I had my baby, my, my baby girl, Rosie, she was born right after we launched and I couldn't fly. So I like couldn't run a proper fundraise Because I literally couldn't get on planes. And so we kind of took a minute break, and we kind of put our pencils down for 90 days just so that I could get organized. The full team was coming together. We got our back office set up. We got all of the logistics and the infrastructure set up. And then we finished the final seventy-five million over the summer, 90 days. And I'll just say, I couldn't change what was going on in my personal life. And so we fundraised in the middle of the summer, which I think probably any smart human would tell you don't do it. But it was just for us, our reality, and so we did it, and it ended up going really well, and you know, we got everything wrapped up, but I would just say in general, like fundraising, do it in the beginning of the year when people are super focused, do it in the fall when people are super focused, but we did it in the summer, and I think that …

AI assessment note: “we fundraised in the middle of the summer, which I think probably any smart human would tell you don't”

Q saying no. So either don't Terrible. I know. And that's really an area for improvement. Or I don't give a very specific reason because I find then people just argue back with the reason and it's not productive. You're an entrepreneur turned investor. You have that mindset, as we said, innately within you. What's the right way? And how would you advise me on the right way to say no?

A Yeah. So I will just share that I fully get it, Harry. And having had lots of people say no to me and actually just like intimately knowing how much that that would hurt is That part of my, I'm a very empathetic person, as you probably can even just tell from this interview. Yeah, it sucks, and what I have learned is that the nicest thing you can do to somebody is say no early, say no honestly, and with real, real care, and sometimes I only know the way that I know how to do it, which is to say, I hate having to say no to you because I like you so much, but this isn't a good fit, and here are the three ways that I think I can help you otherwise, and it takes more time, and so I think Again, so much of our process is we only get closer to companies where there's a true and genuine chance of saying yes. Even then you still have to say no lots and lots of times more often than not that all the odds are towards saying no. And in fact, this is a job of saying no. So just developing a real muscle. And I, and as I always recommend to people, you got to figure out your authentic way to do it so that you can do it yourself. And Harry, you're never going to hate it less ever. You just have to get good at it because it is the part of the job. It is a core part of the job.

AI assessment note: “nicest thing you can do to somebody is say no early, say no honestly”

Q No, totally you didn't. I mean, incredible time there in terms of productivity in such a short time span. In terms of the actual management of it itself, We mentioned Satya earlier, and he also asked, as a first-time fund manager, what's been the most surprising element of fund management for you?

A You know, as I said in the past, starting on the investing side, and then I was responsible for Northwest Mutual's venture fund, and so nothing has surprised me because we were doing this prior. I think the one thing that we just think so much about really is that portfolio construction and being incredibly thoughtful about how we think about the math around the portfolio, and I think That's really critical on our Monday agenda. It's literally at the top, front, and center. We have like a full model that matches our pacing and where we are, and not because we need to follow it exactly, but it's more to just really make sure that it stays front of mind. I think that's one thing that I think a lot about and our team thinks a lot about. So yeah, I would say that's probably the thing that, you know, you think about it from afar. It's about ideas in the future and ideation and thesis building, but it's also really about I call it the Venn diagram between the market, the founder, and the deal. You need all three to come together, and you need that tiny triangle between the three to be your bullseye when you actually decide to deploy capital into something.

AI assessment note: “nothing has surprised me because we were doing this prior.”

Q No, totally you didn't. I mean, incredible time there in terms of productivity in such a short time span. In terms of the actual management of it itself, We mentioned Satya earlier, and he also asked, as a first-time fund manager, what's been the most surprising element of fund management for you?

A You know, as I said in the past, starting on the investing side, and then I was responsible for Northwest Mutual's venture fund, and so nothing has surprised me because we were doing this prior. I think the one thing that we just think so much about really is that portfolio construction and being incredibly thoughtful about how we think about the math around the portfolio, and I think That's really critical on our Monday agenda. It's literally at the top, front, and center. We have like a full model that matches our pacing and where we are, and not because we need to follow it exactly, but it's more to just really make sure that it stays front of mind. I think that's one thing that I think a lot about and our team thinks a lot about. So yeah, I would say that's probably the thing that, you know, you think about it from afar. It's about ideas in the future and ideation and thesis building, but it's also really about I call it the Venn diagram between the market, the founder, and the deal. You need all three to come together, and you need that tiny triangle between the three to be your bullseye when you actually decide to deploy capital into something.

AI assessment note: “nothing has surprised me because we were doing this prior”

Q So that's what worked well in terms of the fundraise. If you're kind of maybe more self-reflective and critical of yourself, maybe, what do you think that maybe you didn't do so well? And what elements would you really like to improve about the pitch or the process of fund two?

A Well, I think just, and I don't know that I changed this. So my last day, as I transitioned off the management team at Northwestern Mutual, the firm, literally the last day that I left Northwestern Mutual and launched Inspired, it was the same day. And on that day, we closed about a hundred and twenty-five million. So it happened instantly. And then I had my baby, my, my baby girl, Rosie, she was born right after we launched and I couldn't fly. So I like couldn't run a proper fundraise Because I literally couldn't get on planes. And so we kind of took a minute break, and we kind of put our pencils down for 90 days just so that I could get organized. The full team was coming together. We got our back office set up. We got all of the logistics and the infrastructure set up. And then we finished the final seventy-five million over the summer, 90 days. And I'll just say, I couldn't change what was going on in my personal life. And so we fundraised in the middle of the summer, which I think probably any smart human would tell you don't do it. But it was just for us, our reality, and so we did it, and it ended up going really well, and you know, we got everything wrapped up, but I would just say in general, like fundraising, do it in the beginning of the year when people are super focused, do it in the fall when people are super focused, but we did it in the summer, and I think that …

AI assessment note: “fundraising in the middle of the summer, which I think probably any smart human would tell you don't do it”

Q For you, is it difficult, having been a founder and being such an innate founder, when there is that moment of, well, I'm an investor now, and I'm a shareholder, and it's not optimal for me to give them that price? I'd like to cram it down to this price because that's optimal in terms of my ownership. Is it difficult switching hats and having those sometimes moments of misalignment?

A No, I actually, and I don't even think that, and maybe this is too optimistic of me, but I don't even think that those are moments of misalignment. And let me be clear, venture returns are not made on like a few million dollars evaluation. That in the end, it's about picking the breakout companies that are the category creating businesses of the next And making sure that you are at the table in a handful of those. I think in those moments of like, I actually feel deeply aligned to the entrepreneur. And again, maybe this is just my vantage point, but one thing I often say to the entrepreneurs is, Hey, listen, in the end, often it's founders, you know, sole founder, double founders, whatever it may be. I say only one thing truly matters here. And it's you in a decade. And I often say it's a decade because start to finish for learn best. It was really about seven and a half years. Most of the times it's about a decade. And I say to them in a decade, we want to have the biggest exit that we humanly can. And that's how I approach it. And I say, one thing matters is the W at the end of this. And we want to every day come to work and make great decisions. And so it's about every decision being a little bit up and to the right. And so again, if a founder is in that position, I'm like, I'm not looking to get the squeeze of the absolute best valuation and they shouldn't either, right? It…

AI assessment note: “No, I actually, and I don't even think that those are moments of misalignment.”

Q a different element that you said there, and you said about kind of differentiator and capital not being a differentiator anymore, and I spoke to our mutual friend Rebecca at USV before the show, and she said, you know, you've got to speak to Alexa about how she thinks about personal brand. How do you think about personal brand today in quite a marketing-driven VC world that we have today?

A First of all, I think probably personal brand exists everywhere, and I think as we all have these abilities to have our personal brand out there and build them in Pretty much every platform that exists is a micro way to build your own personal brand. I almost think of it more as just reputation. None of us are perfect in my own career. I think I've learned lots and lots of lessons, but I really do believe reputation is everything. And you build your reputation one day at a time, one decision at a time. And in the same way that I think what I really do believe LPs and our investors buy is our judgment and they buy it every day. Our full judgment is Going to work, making one hour at a time, our best decisions that we can. And I really do believe in the inverse for an entrepreneur. What you buy is someone's track record of their trust, worthiness of their reputation, of their following through and showing up. And I think that's honestly like, forget the rest of it. It's noise. It really is underneath it all. Are you an incredibly good human? Who's going to make the best decision who in the face of major adversity, because that will happen in all of our And I'm sure I will face major dark days and hard decisions that I have to make. Are you going to be fair and trustworthy? And are you going to take the high road? That's what I care about. And I care about that even beyond like my …

AI assessment note: “I almost think of it more as just reputation... reputation is everything.”

Q there. And I can just, as I said, you can tell you're an innate entrepreneur just from listening to you. Do you find it tough today? Cause I find this tough with such excess capital funding rounds is so much Faster moving than in my eyes they ever have been. Do you find it tough to really build that family relationship in such compressed timelines, and does that worry you?

A Yeah, but I think it's a little bit of our approach of how we think about it, which is, and again, maybe this is, like, incredibly stupid how I think about it, but the absolute truth is, I signed up to do this job for the rest of my career, and I am a complete, I, you know, I love to work. I kind of come to terms with, like, I don't have hobbies, like, this is my life, it's my hobby, it's everything, outside of my family and friends, and I really have Approach building relationships with entrepreneurs as just like everyday community building. I plan to live in this ecosystem in New York for a really, really, really long time. And so we often go for fun to like go meet people pre-thinking through ideas. I once a month have a dinner where people come over to my apartment and we just totally with zero agenda talk about categories we're interested in. And, and again, it's probably stupid because a lot of time goes into just like getting to know people. Truly with no agenda on the table. And I'm sure at some point over the next decade out of that, like a great entrepreneur will surface and it'll be someone that I got to know and I, and I've had a longer relationship with, you know, I think in this world where an entrepreneur pops up and they're getting a deal done in seven seconds and you've never met them. Yeah. Those are the ones where so much of this is you're betting on a single…

AI assessment note: “I really have Approach building relationships with entrepreneurs as just like everyday community building.”

Q there. And I can just, as I said, you can tell you're an innate entrepreneur just from listening to you. Do you find it tough today? Cause I find this tough with such excess capital funding rounds is so much Faster moving than in my eyes they ever have been. Do you find it tough to really build that family relationship in such compressed timelines, and does that worry you?

A Yeah, but I think it's a little bit of our approach of how we think about it, which is, and again, maybe this is, like, incredibly stupid how I think about it, but the absolute truth is, I signed up to do this job for the rest of my career, and I am a complete, I, you know, I love to work. I kind of come to terms with, like, I don't have hobbies, like, this is my life, it's my hobby, it's everything, outside of my family and friends, and I really have Approach building relationships with entrepreneurs as just like everyday community building. I plan to live in this ecosystem in New York for a really, really, really long time. And so we often go for fun to like go meet people pre-thinking through ideas. I once a month have a dinner where people come over to my apartment and we just totally with zero agenda talk about categories we're interested in. And, and again, it's probably stupid because a lot of time goes into just like getting to know people. Truly with no agenda on the table. And I'm sure at some point over the next decade out of that, like a great entrepreneur will surface and it'll be someone that I got to know and I, and I've had a longer relationship with, you know, I think in this world where an entrepreneur pops up and they're getting a deal done in seven seconds and you've never met them. Yeah. Those are the ones where so much of this is you're betting on a single…

AI assessment note: “I really have Approach building relationships with entrepreneurs as just like everyday community building.”

Q a different element that you said there, and you said about kind of differentiator and capital not being a differentiator anymore, and I spoke to our mutual friend Rebecca at USV before the show, and she said, you know, you've got to speak to Alexa about how she thinks about personal brand. How do you think about personal brand today in quite a marketing-driven VC world that we have today?

A First of all, I think probably personal brand exists everywhere, and I think as we all have these abilities to have our personal brand out there and build them in Pretty much every platform that exists is a micro way to build your own personal brand. I almost think of it more as just reputation. None of us are perfect in my own career. I think I've learned lots and lots of lessons, but I really do believe reputation is everything. And you build your reputation one day at a time, one decision at a time. And in the same way that I think what I really do believe LPs and our investors buy is our judgment and they buy it every day. Our full judgment is Going to work, making one hour at a time, our best decisions that we can. And I really do believe in the inverse for an entrepreneur. What you buy is someone's track record of their trust, worthiness of their reputation, of their following through and showing up. And I think that's honestly like, forget the rest of it. It's noise. It really is underneath it all. Are you an incredibly good human? Who's going to make the best decision who in the face of major adversity, because that will happen in all of our And I'm sure I will face major dark days and hard decisions that I have to make. Are you going to be fair and trustworthy? And are you going to take the high road? That's what I care about. And I care about that even beyond like my …

AI assessment note: “I almost think of it more as just reputation.”