The Exchanges

Q Absolutely. No, that's a very good one. And then the biggest mentor to you, and how did it come about?

A You know, probably Reid Hoffman has been, I've been fortunate that I've, I've had a couple different people who've been mentors for me over, over the arc of my career. I'd say Reid's probably the most influential. I started working with him at, at PayPal, you know, during my time there. And then when he was putting together the founding team for, for LinkedIn, I was one of those folks. And I reported to him as our CEO for, for the early years of LinkedIn. And then even to this day, obviously he's become a VC investor as, as well after, you know, successfully doing a lot of things as an angel. And he continues to provide not just a friendship, but also You know, mentorship and thoughtful guidance for me.

AI assessment note: “I'd say Reid's probably the most influential. I started working with him at, at PayPal”

Q So let's start with your favorite book, and why?

A My favorite book always tends to be the one that I'm reading at that moment in time. Uh, what I happen to be reading at this moment in time is a book called The Globalization Paradox. The author is, I may be mispronouncing this, is Danny Roderick, uh, who's a professor at At, uh, at Harvard. It's an interesting book given sort of the, the global, uh, political and economic climate in that it builds on books that he'd written previously and proposes. Potentially there's a trilemma, an economic trilemma of democracy, hyper-globalization of, of people and, and capital and national sovereignty. I'm still forming my own opinion of whether I agree or disagree with that, but it's been an interesting read thus far. I'm about halfway through.

AI assessment note: “what I happen to be reading at this moment in time is a book called”

Q But before we dive into a quick fire round today, your co-founder Rob told me that you have a particular affinity to VC history. So talk to me, what's behind this love of VC history, and how does it affect and alter the way you approach investing today with NextView?

A I guess it's, it stems from, you know, having studied as an undergraduate engineering in business, and also just having a personal passion for history generally. But I'd like to also think that understanding not just the history of VC, but the history of innovation waves, Has enables me and others who think like this to take the long view of innovation. And what I mean is oftentimes we get caught up in when new and innovative things happen, what's going to happen in the very first phases of the proliferation of a technology or an innovation wave. You know, the classic hype cycle that early days of things people get in many ways over overly optimistic. And then there's a trough of disillusionment, but over time, successful technologies and innovations sort of become pervasive. And so I can draw a direct analogy to my own career and experience as an investor. In 2003, we started LinkedIn at the end of 2002, literally a handful of people working out of Reed's apartment, Reed Hoffman's apartment in Mountain View, and we raised our first capital in 2003, a series A. At that point in time, most people thought the internet and consumer internet was a terrible idea and not an interesting place to invest because we had just been through kind of this huge boom and bust cycle of, of web one point O. Google was a private company at this point in time, if you can think back to this point in…

AI assessment note: “stems from having studied as an undergraduate engineering in business and personal passion for history”

Q Absolutely. No, that's a very good one. And then the biggest mentor to you, and how did it come about?

A You know, probably Reid Hoffman has been, I've been fortunate that I've, I've had a couple different people who've been mentors for me over, over the arc of my career. I'd say Reid's probably the most influential. I started working with him at, at PayPal, you know, during my time there. And then when he was putting together the founding team for, for LinkedIn, I was one of those folks. And I reported to him as our CEO for, for the early years of LinkedIn. And then even to this day, obviously he's become a VC investor as, as well after, you know, successfully doing a lot of things as an angel. And he continues to provide not just a friendship, but also You know, mentorship and thoughtful guidance for me.

AI assessment note: “I'd say Reid's probably the most influential. I started working with him at, at PayPal”

Q What an incredible story, but I do have to ask, then, a natural kind of subsequent question from that is, what did you learn, then, in the subsequent years from working with the various members of the so-called PayPal mafia and how they operated?

A Yeah, you know, it was a really unique group of people to work with, both because, you know, one, it was a pretty young organization. I mean, it was, I was very young. I was, you know, 21, 22 years old. I was right out of college. But if you look at our senior leaders at PayPal, you know, Peter Thiel, who became CEO after Elon, Elon himself, who was CEO for a while at the combined company, David Sachs, who was my first boss, because I started off as a product manager when he was VP of product. Reid Hoffman, who I ended up working on for later on, Max, and on down the line, lots of other folks. The senior leaders of the company were, were in their thirties and still relatively young, by and large. And so, it was a youngish organization, but of, made up of really, really talented and smart people. And ultimately, PayPal became a very entrepreneurial organization, not just in terms of building PayPal itself, but then the different companies that spawned from, from the PayPal mafia, as you, as you highlighted. And, you know, I learned a lot of Things. I learned the kind of passion and energy that goes into entrepreneurship just generally, even though I wasn't a founder of PayPal. I was a, you know, an employee, but, you know, was there in the earliest days and got, got exposure to the founders. You know, the second thing I learned is virtually no startup is a up into the right, you…

AI assessment note: “I learned a lot of Things. I learned the kind of passion and energy”

Q No, absolutely. I, I recently had Mika Rosenblum on the show from, or Micah Rosenblum from Founder Collective, and he stated, uh, his annoyance that the requirement for startups now to be unicorns, and that 102 hundred million dollar exits were still a victory for VC funds. To what extent do you think you agree with that in terms of exit expectations and then kind of fund returning economics?

A Yeah, so as a seed fund, we think very similar. In fact, we, Micah and the folks at Founder Collective, we collaborate a lot with and have a lot of respect for. For us, we think about the world in the same way, right? If you're an entrepreneur and you raise a modest amount of capital and you build a very good business that exits for a 102 103 hundred million dollars, that's a win for, for most folks. And as a seed stage investor, we can win with that as well. Our funds are, you know, sort of sub a hundred million dollar funds by and large, not, not all seed funds, but by and large. And so if you own You know, rough math. If you own 10% of a company that exits for a hundred, hundred fifty billion dollars with a 40, 50, 60, seventy-five million dollar fund, you can still return a meaningful portion of that fund with a, you know, a 102 hundred million dollar exit. Obviously, the math is very different if you're a multi-stage investor investing out of a half billion or billion dollar pool of capital where that exit really does not move the needle. I think, though, that I wouldn't want to put words in Micah's mouth or Founder Collective's, you know, mouth, but certainly the way we think about it here at NextView is an exit of the 102 hundred million dollar scale Can be impactful for our fund, but that doesn't mean that we, that's all that we look for. That's, you know, sort of the s…

AI assessment note: “as a seed fund, we think very similar.”

Q But before we dive into a quick fire round today, your co-founder Rob told me that you have a particular affinity to VC history. So talk to me, what's behind this love of VC history, and how does it affect and alter the way you approach investing today with NextView?

A I guess it's, it stems from, you know, having studied as an undergraduate engineering in business, and also just having a personal passion for history generally. But I'd like to also think that understanding not just the history of VC, but the history of innovation waves, Has enables me and others who think like this to take the long view of innovation. And what I mean is oftentimes we get caught up in when new and innovative things happen, what's going to happen in the very first phases of the proliferation of a technology or an innovation wave. You know, the classic hype cycle that early days of things people get in many ways over overly optimistic. And then there's a trough of disillusionment, but over time, successful technologies and innovations sort of become pervasive. And so I can draw a direct analogy to my own career and experience as an investor. In 2003, we started LinkedIn at the end of 2002, literally a handful of people working out of Reed's apartment, Reed Hoffman's apartment in Mountain View, and we raised our first capital in 2003, a series A. At that point in time, most people thought the internet and consumer internet was a terrible idea and not an interesting place to invest because we had just been through kind of this huge boom and bust cycle of, of web one point O. Google was a private company at this point in time, if you can think back to this point in…

AI assessment note: “enables me and others who think like this to take the long view of innovation”

Q So let's start with your favorite book, and why?

A My favorite book always tends to be the one that I'm reading at that moment in time. Uh, what I happen to be reading at this moment in time is a book called The Globalization Paradox. The author is, I may be mispronouncing this, is Danny Roderick, uh, who's a professor at At, uh, at Harvard. It's an interesting book given sort of the, the global, uh, political and economic climate in that it builds on books that he'd written previously and proposes. Potentially there's a trilemma, an economic trilemma of democracy, hyper-globalization of, of people and, and capital and national sovereignty. I'm still forming my own opinion of whether I agree or disagree with that, but it's been an interesting read thus far. I'm about halfway through.

AI assessment note: “what I happen to be reading at this moment in time is a book called”

Q Okay, this is a really hard question for me to ask. What innovative new products or technologies do you think are calling the hype cycle, and what are sustaining and durable? So an example might be sustaining and durable is artificial intelligence and machine learning integrated into technology, and not sustaining might be virtual reality.

A I think not sustaining, there's a lot of emphasis on Sort of chatbots and messaging AI happening at a messaging layer. I think that's actually going to be critical in many, many ways to a broader array of applications, but I think undue emphasis has probably been placed on it within the past year in terms of how many companies are going to be built solely based on an innovation that happens in, you know, chatbots or message AI. Things that will endure and persevere, I'm biased because one of the most recent investments I led was in an autonomous vehicle company, but You know, I think we're in the very early days of the impact AI, computer vision, and a confluence of technologies are going to have in changing transportation and mobility. The future always takes longer than, than you think to get here, and so I happen to be of the opinion that we're not going to have self-driving autonomous vehicles everywhere in a very, you know, in the next two years or three years, but I do believe that there's a massive opportunity in transforming transportation, which is a huge Huge piece of the global economy that's going to play out over the next decade, and maybe more than a decade, and so I'm quite bullish on that.

AI assessment note: “I think not sustaining, there's a lot of emphasis on Sort of chatbots”

Q And then what's your advice to a junior starting out in the VC industry?

A I think two things. The first is, which I think others have provided this guidance, is develop a point of view and a perspective that is unique. That might be around a particular sector or investment theme. It might be around a particular stage or geography. But if you become known, even as an associate or principal level VC investor, for having a unique point of view about something, entrepreneurs will seek you out. Other VCs, both junior and, you know, partner level will seek you out. And Even though, and it won't be constraining in the sense that you can always develop expertise in other things. And the second thing is never express more than, than who you are, right? Um, I think people respect, you know, junior VCs who never try to let on that they're going to lead an investment if that's not really the capacity that they're in within their firm. But when they become, be high signal to noise and, and, and be who you are, um, I think that's critical.

AI assessment note: “I think two things. The first is, which I think others have provided this guidance”

Q Can I ask, how would you respond to people that say opportunistic is another word for lacking strategy?

A I would say that we as VCs can be extremely thoughtful about markets and innovation waves based on both our activities as investors and sometimes our experience as entrepreneurs or operators before becoming investors, and so I think it's entirely possible for VCs to think and develop very thoughtful themes about investing. That being said, there are literally thousands and thousands of very thoughtful and talented entrepreneurs out there who are thinking about new market opportunities A 110% of their time. I might like to think that, you know, based on my experience at PayPal, I'm a thoughtful FinTech investor, and I have invested in a number of FinTech companies, you know, here at NextView. But there are undoubtedly countless talented, thoughtful entrepreneurs thinking about a narrow market, a 110% of their time, or a newly developing market, a 110% of their time. And so, I believe that by being open to learning about new markets and learning about new themes from people who are Deeply thoughtful and frankly spending more of their time thinking just about that than I am. I think that's a good thing. I don't think that's a crutch in, in, in our investment strategy because at the end of the day, investment strategy is not purely on based on theme or investment sector. It also includes stage. It also includes what's the nature of the teams that you like to back. It also includes …

AI assessment note: “an investment strategy is not synonymous with an investment theme or a sector.”

Q No, absolutely. I, I recently had Mika Rosenblum on the show from, or Micah Rosenblum from Founder Collective, and he stated, uh, his annoyance that the requirement for startups now to be unicorns, and that 102 hundred million dollar exits were still a victory for VC funds. To what extent do you think you agree with that in terms of exit expectations and then kind of fund returning economics?

A Yeah, so as a seed fund, we think very similar. In fact, we, Micah and the folks at Founder Collective, we collaborate a lot with and have a lot of respect for. For us, we think about the world in the same way, right? If you're an entrepreneur and you raise a modest amount of capital and you build a very good business that exits for a 102 103 hundred million dollars, that's a win for, for most folks. And as a seed stage investor, we can win with that as well. Our funds are, you know, sort of sub a hundred million dollar funds by and large, not, not all seed funds, but by and large. And so if you own You know, rough math. If you own 10% of a company that exits for a hundred, hundred fifty billion dollars with a 40, 50, 60, seventy-five million dollar fund, you can still return a meaningful portion of that fund with a, you know, a 102 hundred million dollar exit. Obviously, the math is very different if you're a multi-stage investor investing out of a half billion or billion dollar pool of capital where that exit really does not move the needle. I think, though, that I wouldn't want to put words in Micah's mouth or Founder Collective's, you know, mouth, but certainly the way we think about it here at NextView is an exit of the 102 hundred million dollar scale Can be impactful for our fund, but that doesn't mean that we, that's all that we look for. That's, you know, sort of the s…

AI assessment note: “as a seed stage investor, we can win with that as well.”

Q Can I ask, how would you respond to people that say opportunistic is another word for lacking strategy?

A I would say that we as VCs can be extremely thoughtful about markets and innovation waves based on both our activities as investors and sometimes our experience as entrepreneurs or operators before becoming investors, and so I think it's entirely possible for VCs to think and develop very thoughtful themes about investing. That being said, there are literally thousands and thousands of very thoughtful and talented entrepreneurs out there who are thinking about new market opportunities A 110% of their time. I might like to think that, you know, based on my experience at PayPal, I'm a thoughtful FinTech investor, and I have invested in a number of FinTech companies, you know, here at NextView. But there are undoubtedly countless talented, thoughtful entrepreneurs thinking about a narrow market, a 110% of their time, or a newly developing market, a 110% of their time. And so, I believe that by being open to learning about new markets and learning about new themes from people who are Deeply thoughtful and frankly spending more of their time thinking just about that than I am. I think that's a good thing. I don't think that's a crutch in, in, in our investment strategy because at the end of the day, investment strategy is not purely on based on theme or investment sector. It also includes stage. It also includes what's the nature of the teams that you like to back. It also includes …

AI assessment note: “investment strategy is not synonymous with an investment theme or a sector.”

Q Okay, this is a really hard question for me to ask. What innovative new products or technologies do you think are calling the hype cycle, and what are sustaining and durable? So an example might be sustaining and durable is artificial intelligence and machine learning integrated into technology, and not sustaining might be virtual reality.

A I think not sustaining, there's a lot of emphasis on Sort of chatbots and messaging AI happening at a messaging layer. I think that's actually going to be critical in many, many ways to a broader array of applications, but I think undue emphasis has probably been placed on it within the past year in terms of how many companies are going to be built solely based on an innovation that happens in, you know, chatbots or message AI. Things that will endure and persevere, I'm biased because one of the most recent investments I led was in an autonomous vehicle company, but You know, I think we're in the very early days of the impact AI, computer vision, and a confluence of technologies are going to have in changing transportation and mobility. The future always takes longer than, than you think to get here, and so I happen to be of the opinion that we're not going to have self-driving autonomous vehicles everywhere in a very, you know, in the next two years or three years, but I do believe that there's a massive opportunity in transforming transportation, which is a huge Huge piece of the global economy that's going to play out over the next decade, and maybe more than a decade, and so I'm quite bullish on that.

AI assessment note: “I think not sustaining, there's a lot of emphasis on Sort of chatbots”

Q Now, I'd love to get started today with slightly before the move into VC for you, and a question from Rob. So Rob asks, how did you get the job at PayPal first, and what's the literal story?

A Yeah, so it's a fun story for me. I was fortunate to join PayPal as one of the early employees, literally my first job out of undergrad. And I don't know how much you know about the genesis of PayPal, but there were originally two separate companies in the early days. There was one half started by Elon Musk called X.com. It was backed by Sequoia Capital. That's the part of the company that I joined. The other half was called Confinity, which was started by Max Lovechin and Peter Thiel, backed by the old Nokia, now Blu-ray Ventures. And the two companies sort of started off independently and were working on their own thing, but both ended up focusing on online payments, and particularly in the early days of eBay, sort of electronic transactions for eBay buys and sellers. So The two companies ended up merging a fifty-fifty merger of equals in the spring of 2000. So I joined originally the x.com side, and the way I got my job was Elon Musk. I went to the University of Pennsylvania at UPenn as an undergraduate and did a program there that combined an engineering degree and an award in business degree. And Elon is a panel alum a few years older than me, and so he came back, gave a guest lecture. This was after he had sold his first business, which was called Zip Two. This is back in the sort of late nineties, kind of Internet one, one dot O company, uh, which was also backed by Sequ…

AI assessment note: “the way I got my job was Elon Musk. I went to the University of Pennsylvania”

Q Work-life balance. What are your tips for me?

A I'm a believer, uh, I think, uh, Brad Freld and others have kind of promulgated this idea of work-life harmony. What I think there is, it's less about a balance of, it's an equal ratio of time and energy at any moment in time, because, you know, there are times where aspects of your personal life certainly come to the fore and take precedence, and there's times where your professional life, certain things might take precedent at that particular moment. So, I believe in harmony.balance, and for me, what works, I'm not sure that this works for everybody, for me, what works is a, is a fairly, You know, bright delineation of my, my work life and my personal life. I try not to mix the two too much, and I find that that helps me keep the two things in harmony. And a small tip for me that happens to have worked in that regard is when I get home at night, plug my phone in and in the kitchen, and I can hear it. It's available if there's something urgent I need to deal with, but I don't walk around my house with my smartphone so I can be, you know, genuinely with my wife and small daughter and spend time together.

AI assessment note: “when I get home at night, plug my phone in and in the kitchen”

Q What an incredible story, but I do have to ask, then, a natural kind of subsequent question from that is, what did you learn, then, in the subsequent years from working with the various members of the so-called PayPal mafia and how they operated?

A Yeah, you know, it was a really unique group of people to work with, both because, you know, one, it was a pretty young organization. I mean, it was, I was very young. I was, you know, 21, 22 years old. I was right out of college. But if you look at our senior leaders at PayPal, you know, Peter Thiel, who became CEO after Elon, Elon himself, who was CEO for a while at the combined company, David Sachs, who was my first boss, because I started off as a product manager when he was VP of product. Reid Hoffman, who I ended up working on for later on, Max, and on down the line, lots of other folks. The senior leaders of the company were, were in their thirties and still relatively young, by and large. And so, it was a youngish organization, but of, made up of really, really talented and smart people. And ultimately, PayPal became a very entrepreneurial organization, not just in terms of building PayPal itself, but then the different companies that spawned from, from the PayPal mafia, as you, as you highlighted. And, you know, I learned a lot of Things. I learned the kind of passion and energy that goes into entrepreneurship just generally, even though I wasn't a founder of PayPal. I was a, you know, an employee, but, you know, was there in the earliest days and got, got exposure to the founders. You know, the second thing I learned is virtually no startup is a up into the right, you…

AI assessment note: “I learned the kind of passion and energy that goes into entrepreneurship just generally”

Q Now, I'd love to get started today with slightly before the move into VC for you, and a question from Rob. So Rob asks, how did you get the job at PayPal first, and what's the literal story?

A Yeah, so it's a fun story for me. I was fortunate to join PayPal as one of the early employees, literally my first job out of undergrad. And I don't know how much you know about the genesis of PayPal, but there were originally two separate companies in the early days. There was one half started by Elon Musk called X.com. It was backed by Sequoia Capital. That's the part of the company that I joined. The other half was called Confinity, which was started by Max Lovechin and Peter Thiel, backed by the old Nokia, now Blu-ray Ventures. And the two companies sort of started off independently and were working on their own thing, but both ended up focusing on online payments, and particularly in the early days of eBay, sort of electronic transactions for eBay buys and sellers. So The two companies ended up merging a fifty-fifty merger of equals in the spring of 2000. So I joined originally the x.com side, and the way I got my job was Elon Musk. I went to the University of Pennsylvania at UPenn as an undergraduate and did a program there that combined an engineering degree and an award in business degree. And Elon is a panel alum a few years older than me, and so he came back, gave a guest lecture. This was after he had sold his first business, which was called Zip Two. This is back in the sort of late nineties, kind of Internet one, one dot O company, uh, which was also backed by Sequ…

AI assessment note: “the way I got my job was Elon Musk. I went to the University of Pennsylvania”

Q How do you view, then, the current landscape? What do you make of it? And I'm intrigued, particularly, how do you look to gain headspace in the mind of the entrepreneur in such a proliferated market?

A It's a, it's a great question. And, candidly, one that we think about and evaluate, you know, here at NextView on a, on a daily basis. Rob, David, and myself started the firm in, which is not that long ago, but it feels like ages ago in the seed stage landscape. We certainly weren't The first, you know, seed VC fund here in the U.S., you know, folks like First Round and SoftTech and Floodgate and others kind of pioneered the way in sort of the 2006, seven, eight timeframe. But when we started in 2010, there were really still not that many seed VC funds in the U.S. And, you know, we here at Next View Wave Offices in Boston and New York, we're pretty active in both ecosystems, and we invest throughout the United States. So we've got a portion of our portfolio on the West Coast and a portion here on the East Coast.

AI assessment note: “Rob, David, and myself started the firm in, which is not that long ago”

Q How do you view, then, the current landscape? What do you make of it? And I'm intrigued, particularly, how do you look to gain headspace in the mind of the entrepreneur in such a proliferated market?

A It's a, it's a great question. And, candidly, one that we think about and evaluate, you know, here at NextView on a, on a daily basis. Rob, David, and myself started the firm in, which is not that long ago, but it feels like ages ago in the seed stage landscape. We certainly weren't The first, you know, seed VC fund here in the U.S., you know, folks like First Round and SoftTech and Floodgate and others kind of pioneered the way in sort of the 2006, seven, eight timeframe. But when we started in 2010, there were really still not that many seed VC funds in the U.S. And, you know, we here at Next View Wave Offices in Boston and New York, we're pretty active in both ecosystems, and we invest throughout the United States. So we've got a portion of our portfolio on the West Coast and a portion here on the East Coast.

AI assessment note: “Rob, David, and myself started the firm in, which is not that long ago”