The Exchanges

Q Absolutely, yeah. And then at Collaborative, you're a partner. Big congratulations on that. Um, and you're very young for the, to be a partner in the industry, so how is that for you, and what challenges do you face as a result of your, your youth in the role?

A That's an interesting question, gosh. I am reasonably young, I just turned 30, and the, are, there are a couple of directions to take this answer, and I'll take a few of them, actually. The first one is What most people don't know about funds, even though you can find it out if you just look for it, is that associated with a, with a fund is, is what's known as a GP commit, which is a, the general partnerships contribution to the fund, and that is effectively skin in the game, and so the limited partners want to know that these general partners aren't just going to take their money and poof, be gone, and or be responsible with it, and so they want to see that these general partners have put their own personal skin in the game. And what that has historically meant is if you're raising a four hundred million dollar fund, it can be hundreds of thousands and even millions of dollars that the general partners need to put up for the sake of demonstrating to the limited partners that they have skin in the game. If you're young, unless you happen to be born into wealth or happen to have had extraordinary financial success early, neither of which is the case for me as an example, then that's actually really hard, and that actually Perhaps counterintuitively makes me more risk averse because the types of hoops and contortions I need to jump through and twist myself around into so as to be…

AI assessment note: “If you're young... that's actually really hard, and that actually Perhaps counterintuitively makes me more risk averse”

Q And despite the difficulty then in determining the output of your actions, how do you find it most effective or most enjoyable for you to market yourself? What strategies have you, you've got a brilliant blog, Is that how you kind of put yourself across, or are there other platforms that you try and utilize?

A You know, the blog is interesting, because there's two pieces of it. One piece is indeed crass. It's just simply marketing, and it's a high leverage marketing tool, and the other piece is somewhat less crass, and fortunately for me, the two of them have, have positively reinforced each other, but the second one is I just like writing, and writing is how I Clarify my ideas to myself, and writing is also how I clarify my ideas by putting them in front of my peers and having my peers challenge them, and so I write for an audience of zero or very few so that I can get smarter, and I think in the course of doing that, I, I write sort of like, like no one's watching, you know, that saying of dance like no one's watching, and so maybe that thereby makes it more interesting to read, and thereby makes it more effective marketing, so there is something like that, I guess going on there, if we're being honest. Uh, and other than that, it's, for me, I'm married, and I'm happily married, and I really like to spend time with my wife. She's in, she's in medical school, and so anytime she's free, I have to make myself free pretty much immediately, and so the intimate dinners with other VCs, and the events, and the summit series, and the conferences, and the stuff that requires either being on a plane, or being outside of my home, I tend to, um, Personally, just limit, or if not limit, be reall…

AI assessment note: “That's why I'm ridiculously active on Twitter, to the point of it being an addiction.”

Q So you said it's not the best way then for you to discover startups. What do you think is then for you at your stage?

A At our stage, if you take a snapshot of where we are right now, I would say it's our existing portfolio companies. So our existing portfolio companies serve as, as a great reference for us. If we want to do an outbound, so we see some company that's just been formed, or some group of ex-Googlers, or you name it, who are leaving to start some company, the first thing I do is go to Facebook, or to LinkedIn, or to Twitter to see if there is somebody within our portfolio who's directly connected to one of them, because if that's true, then what a high High signal introduction and the high signal warm reference that is already, because if somebody is willing to vouch for us as a financial partner, then that sends a really strong signal to the market, and so we rely on that a lot for outbound and for inbound, so entrepreneurs talk to each other, and CEOs treat each other like siblings in the best of ways, and so when they use each other to get access to VCs, we always really welcome that.

AI assessment note: “I would say it's our existing portfolio companies.”

Q And was it tough to leave the security of Stanford then? Obviously, kind of, Stanford, a fantastic school, and, you know, uh, relatively safe and secure path coming out, so was it tough to leave the unknown world of startups, or were you quite sure of your, your future in the tech and startup industry?

A The decision to leave wasn't tough. Once I had left, it was tough, so there is a point of view of, Uh, from a casual observer that being a, uh, startup entrepreneur and being, uh, in the, in the startup grind, uh, has an element of glamour to it, particularly for, for those who are college dropouts, and the reality honestly couldn't be further from it. I dropped out and didn't really care one way or another. I was just sick of school and didn't want to be there, and it wasn't speaking to me perfectly, honestly. But when I got into the startup world, that's actually Where things got tough, and so, uh, income was very hard to come by, and so I was living on credit cards, and it turns out that you need to pay back your credit cards, or else your score is affected, and so, you know, it turns out that there's only certain things you can buy with credit cards, and rent in one of them, and so there's all sorts of tough lessons one learns when going through that experience that I, gosh, had a really hard time with, but I'm glad for now, because I've gotten through, and, and can advise others to stay in

AI assessment note: “The decision to leave wasn't tough. Once I had left, it was tough”

Q And there's a lot of discussion over how effective, um, demo days are, hackathons are, Accelerator days are for VC deal sourcing and deal flow. How effective do you think they are then in terms of kind of making sure that your time is spent most wisely? Do you find them a good source of incoming deal flow?

A That's an interesting question. It depends on the accelerator for one, and I won't cast aspersions and or call out any Particularly, but some, but some communities, you know, some are better than others. That's, that's, that's a fact. But then the other piece is, is that for our style and stage, so we like to be early, and we tend to be in a first institutional round, or even earlier than that, into a company. Uh, when we're meeting them, if we're meeting them for the first time at most of the demo days that one would go to, we're probably meeting them too late. And so, for us, uh, going to a demo day to discover companies, uh, may be a, uh, a decent way of making sure that we've covered our bases, uh, but that's not actually the best way for us to see companies at the stage we really want to see them, because, especially the way that some of the accelerators have started to move up the stack now, and have started to fund companies that are somewhat later in their trajectories, uh, we want to be early, and we like A super high risk and tropic nature of being first money in. And so that's one piece. But the other piece about accelerators, which, which people, you know, well, there's a couple pieces, but one of them is that it's a really great opportunity for me to see all the other VCs and VCs get great deal flow from each other. They learn to trust each other. This is a, an ind…

AI assessment note: “if we're meeting them for the first time at most of the demo days that one would go to, we're probably meeting them too late.”

Q And what would you say was the toughest experience, and why would you advise others to stay in school? That's a very interesting addition to the sentence there.

A Well, the toughest things were, one, the loneliness, honestly, so being very, very young, and the lovely thing about college in particular is that you're around your peers, and there's an element of serendipity, and of density, and Of shared context, which results in being able to make extraordinarily rich friendships, and being able to make really lasting connections with people, and when you're out in the professional world, that disappears, like with the snap of one's fingers, and there are some communities, so to speak, which are, you know, which suffice as replacing that, at least to some degree, but they really don't do as good of a job as college does, and so I was young and just wanted to be around my friends, and that's lonely, and A second piece of that is that people want to do things you understand, and if you're doing something other people don't understand, then that's isolating too, because you don't have people who you can sort of commiserate with, and who you can feel like you're on a journey with, and so the loneliness was hard, and then the truth of the matter also is, if it's not a rocket ship startup, which the vast majority of them are, then it's really hard to justify it to your loved ones, and so my parents thought, what in the world are you doing? Like, why are you, why are you not At school. Like, what are you chasing this stupid thing which is not wor…

AI assessment note: “the toughest things were, one, the loneliness, honestly”

Q Absolutely, yeah. And then at Collaborative, you're a partner. Big congratulations on that. Um, and you're very young for the, to be a partner in the industry, so how is that for you, and what challenges do you face as a result of your, your youth in the role?

A That's an interesting question, gosh. I am reasonably young, I just turned 30, and the, are, there are a couple of directions to take this answer, and I'll take a few of them, actually. The first one is What most people don't know about funds, even though you can find it out if you just look for it, is that associated with a, with a fund is, is what's known as a GP commit, which is a, the general partnerships contribution to the fund, and that is effectively skin in the game, and so the limited partners want to know that these general partners aren't just going to take their money and poof, be gone, and or be responsible with it, and so they want to see that these general partners have put their own personal skin in the game. And what that has historically meant is if you're raising a four hundred million dollar fund, it can be hundreds of thousands and even millions of dollars that the general partners need to put up for the sake of demonstrating to the limited partners that they have skin in the game. If you're young, unless you happen to be born into wealth or happen to have had extraordinary financial success early, neither of which is the case for me as an example, then that's actually really hard, and that actually Perhaps counterintuitively makes me more risk averse because the types of hoops and contortions I need to jump through and twist myself around into so as to be…

AI assessment note: “If you're young, unless you happen to be born into wealth... that's actually really hard”

Q And despite the difficulty then in determining the output of your actions, how do you find it most effective or most enjoyable for you to market yourself? What strategies have you, you've got a brilliant blog, Is that how you kind of put yourself across, or are there other platforms that you try and utilize?

A You know, the blog is interesting, because there's two pieces of it. One piece is indeed crass. It's just simply marketing, and it's a high leverage marketing tool, and the other piece is somewhat less crass, and fortunately for me, the two of them have, have positively reinforced each other, but the second one is I just like writing, and writing is how I Clarify my ideas to myself, and writing is also how I clarify my ideas by putting them in front of my peers and having my peers challenge them, and so I write for an audience of zero or very few so that I can get smarter, and I think in the course of doing that, I, I write sort of like, like no one's watching, you know, that saying of dance like no one's watching, and so maybe that thereby makes it more interesting to read, and thereby makes it more effective marketing, so there is something like that, I guess going on there, if we're being honest. Uh, and other than that, it's, for me, I'm married, and I'm happily married, and I really like to spend time with my wife. She's in, she's in medical school, and so anytime she's free, I have to make myself free pretty much immediately, and so the intimate dinners with other VCs, and the events, and the summit series, and the conferences, and the stuff that requires either being on a plane, or being outside of my home, I tend to, um, Personally, just limit, or if not limit, be reall…

AI assessment note: “That's why I'm ridiculously active on Twitter, to the point of it being an addiction.”

Q So you said it's not the best way then for you to discover startups. What do you think is then for you at your stage?

A At our stage, if you take a snapshot of where we are right now, I would say it's our existing portfolio companies. So our existing portfolio companies serve as, as a great reference for us. If we want to do an outbound, so we see some company that's just been formed, or some group of ex-Googlers, or you name it, who are leaving to start some company, the first thing I do is go to Facebook, or to LinkedIn, or to Twitter to see if there is somebody within our portfolio who's directly connected to one of them, because if that's true, then what a high High signal introduction and the high signal warm reference that is already, because if somebody is willing to vouch for us as a financial partner, then that sends a really strong signal to the market, and so we rely on that a lot for outbound and for inbound, so entrepreneurs talk to each other, and CEOs treat each other like siblings in the best of ways, and so when they use each other to get access to VCs, we always really welcome that.

AI assessment note: “I would say it's our existing portfolio companies.”

Q And was it tough to leave the security of Stanford then? Obviously, kind of, Stanford, a fantastic school, and, you know, uh, relatively safe and secure path coming out, so was it tough to leave the unknown world of startups, or were you quite sure of your, your future in the tech and startup industry?

A The decision to leave wasn't tough. Once I had left, it was tough, so there is a point of view of, Uh, from a casual observer that being a, uh, startup entrepreneur and being, uh, in the, in the startup grind, uh, has an element of glamour to it, particularly for, for those who are college dropouts, and the reality honestly couldn't be further from it. I dropped out and didn't really care one way or another. I was just sick of school and didn't want to be there, and it wasn't speaking to me perfectly, honestly. But when I got into the startup world, that's actually Where things got tough, and so, uh, income was very hard to come by, and so I was living on credit cards, and it turns out that you need to pay back your credit cards, or else your score is affected, and so, you know, it turns out that there's only certain things you can buy with credit cards, and rent in one of them, and so there's all sorts of tough lessons one learns when going through that experience that I, gosh, had a really hard time with, but I'm glad for now, because I've gotten through, and, and can advise others to stay in

AI assessment note: “The decision to leave wasn't tough. Once I had left, it was tough”

Q And there's a lot of discussion over how effective, um, demo days are, hackathons are, Accelerator days are for VC deal sourcing and deal flow. How effective do you think they are then in terms of kind of making sure that your time is spent most wisely? Do you find them a good source of incoming deal flow?

A That's an interesting question. It depends on the accelerator for one, and I won't cast aspersions and or call out any Particularly, but some, but some communities, you know, some are better than others. That's, that's, that's a fact. But then the other piece is, is that for our style and stage, so we like to be early, and we tend to be in a first institutional round, or even earlier than that, into a company. Uh, when we're meeting them, if we're meeting them for the first time at most of the demo days that one would go to, we're probably meeting them too late. And so, for us, uh, going to a demo day to discover companies, uh, may be a, uh, a decent way of making sure that we've covered our bases, uh, but that's not actually the best way for us to see companies at the stage we really want to see them, because, especially the way that some of the accelerators have started to move up the stack now, and have started to fund companies that are somewhat later in their trajectories, uh, we want to be early, and we like A super high risk and tropic nature of being first money in. And so that's one piece. But the other piece about accelerators, which, which people, you know, well, there's a couple pieces, but one of them is that it's a really great opportunity for me to see all the other VCs and VCs get great deal flow from each other. They learn to trust each other. This is a, an ind…

AI assessment note: “that's not actually the best way for us to see companies”

Q And what would you say was the toughest experience, and why would you advise others to stay in school? That's a very interesting addition to the sentence there.

A Well, the toughest things were, one, the loneliness, honestly, so being very, very young, and the lovely thing about college in particular is that you're around your peers, and there's an element of serendipity, and of density, and Of shared context, which results in being able to make extraordinarily rich friendships, and being able to make really lasting connections with people, and when you're out in the professional world, that disappears, like with the snap of one's fingers, and there are some communities, so to speak, which are, you know, which suffice as replacing that, at least to some degree, but they really don't do as good of a job as college does, and so I was young and just wanted to be around my friends, and that's lonely, and A second piece of that is that people want to do things you understand, and if you're doing something other people don't understand, then that's isolating too, because you don't have people who you can sort of commiserate with, and who you can feel like you're on a journey with, and so the loneliness was hard, and then the truth of the matter also is, if it's not a rocket ship startup, which the vast majority of them are, then it's really hard to justify it to your loved ones, and so my parents thought, what in the world are you doing? Like, why are you, why are you not At school. Like, what are you chasing this stupid thing which is not wor…

AI assessment note: “Well, the toughest things were, one, the loneliness, honestly”

Q And do you think then that this theme specialization results in the higher returns for the fund overall? Do you think that's, that's the kind of secret sauce, or do you think stage specialization is there's often this kind of divergence between, ah, we, we don't have, we're theme agnostic, but we're only series A. Which one do you think is kind of more effective to be?

A That's a good question. I think that any theme being Fully candid is used as a way to be efficient with one's time. And so, at the end of the day, somebody, somebody in the venture community said to me, you don't have to do every good deal. You just have to only do good deals. And so, I'm going to pass on plenty of really excellent companies. In fact, the best investors of all time have passed on 10 to more companies multiple times over each of them. And so, There's this world in which I need to figure out a best way to be efficient with my time. I need to figure out a way to look at companies in a way that I can fundamentally process. Sam Altman tweeted something a couple of weeks ago saying that he estimated there were between four and 6000 seed stage companies looking for funding every year, which means more than 10 a day every single day, and there's no way you can do that. So you need some sort of a heuristic or some sort of a tool whereby you can decide on a point of view and say, I noticed stuff outside of that point of view, and just hope your point of view is more right than wrong, and that you can find the winners within it. And I think that's true about stage, and I think that's true about theme. And so that can go for both. It's just a matter of, can you find enough of a way to constrain your sample set, and then within that sample set, optimize for getting lucky, b…

AI assessment note: “I think that's true about stage, and I think that's true about theme.”

Q How did you get over those hard times then of loneliness and of, you know, credit card debt at a young age? I mean, was there a kind of vision in your mind that drove you on?

A There, there wasn't, it was the way that I, you know what it actually was, was I didn't feel like I had that much of a choice, so I felt like this is the path that I had chosen, this is the path I was on, and all I really had the opportunity to do at that point was to see it through to the best of my abilities, and to, to turn, to turn lemons into lemonade, and so one of those things, too, that a lot of people often think about is that it's, it's the actual purity of one's vision, and the And the real promise of this great dream of success that drives people when sometimes it could be, I don't really know what else I could do. I don't really know what else I would do. I'm doing this, so I got to keep at it at least until I can finish it so that I can do something else. And so it was in some ways less of a sort of a glamorous and a really easy to tell story than I didn't think of anything else really.

AI assessment note: “There, there wasn't... was I didn't feel like I had that much of a choice”

Q Mm-hmm. And, and, and now you're at Collaborative, as you mentioned there, so can you give us a little background on the fund, your investment thesis, the stage that you like to go in on, and, and any preferred themes?

A Gladly. So, the fund is an investor who believes that we are living in a collaborative economy, and I don't think that's a particularly controversial statement These days, but the way that we frame it is we're living in an economy where the hub and spoke model of creating value and the centralizing of resources and the centralizing of distribution and the centralizing of production is an anachronistic model that was dying in the Network-driven model with nodes, and collaboration, and peer-to-peer, and liquidity directly between microparties, be those smaller firms or individuals, is the mode that's going to come and dominate, and that's, you know, the promise of the internet. But we think, beyond that, that there's a really, really important implication to this, and that there's a trend that's, that comes right alongside it. And that implication, that trend, is one where, since every individual node Is now connected to every other node because of the internet and because of these networks that are open. That means that every consumer, every potential employee, uh, even companies themselves, uh, have an obligation and have an opportunity, and I think increasingly have a trend where they are trying to align their interests and align their value sets. And so from a consumer standpoint, I'm purchasing stuff that is reflective of The value set that I have about the world. As an empl…

AI assessment note: “the fund is an investor who believes that we are living in a collaborative economy”

Q How did you get over those hard times then of loneliness and of, you know, credit card debt at a young age? I mean, was there a kind of vision in your mind that drove you on?

A There, there wasn't, it was the way that I, you know what it actually was, was I didn't feel like I had that much of a choice, so I felt like this is the path that I had chosen, this is the path I was on, and all I really had the opportunity to do at that point was to see it through to the best of my abilities, and to, to turn, to turn lemons into lemonade, and so one of those things, too, that a lot of people often think about is that it's, it's the actual purity of one's vision, and the And the real promise of this great dream of success that drives people when sometimes it could be, I don't really know what else I could do. I don't really know what else I would do. I'm doing this, so I got to keep at it at least until I can finish it so that I can do something else. And so it was in some ways less of a sort of a glamorous and a really easy to tell story than I didn't think of anything else really.

AI assessment note: “There, there wasn't... I didn't feel like I had that much of a choice”

Q Mm-hmm. And, and, and now you're at Collaborative, as you mentioned there, so can you give us a little background on the fund, your investment thesis, the stage that you like to go in on, and, and any preferred themes?

A Gladly. So, the fund is an investor who believes that we are living in a collaborative economy, and I don't think that's a particularly controversial statement These days, but the way that we frame it is we're living in an economy where the hub and spoke model of creating value and the centralizing of resources and the centralizing of distribution and the centralizing of production is an anachronistic model that was dying in the Network-driven model with nodes, and collaboration, and peer-to-peer, and liquidity directly between microparties, be those smaller firms or individuals, is the mode that's going to come and dominate, and that's, you know, the promise of the internet. But we think, beyond that, that there's a really, really important implication to this, and that there's a trend that's, that comes right alongside it. And that implication, that trend, is one where, since every individual node Is now connected to every other node because of the internet and because of these networks that are open. That means that every consumer, every potential employee, uh, even companies themselves, uh, have an obligation and have an opportunity, and I think increasingly have a trend where they are trying to align their interests and align their value sets. And so from a consumer standpoint, I'm purchasing stuff that is reflective of The value set that I have about the world. As an empl…

AI assessment note: “we think that the actual outcome of a collaborative economy is one that's impact-driven”

Q And do you think then that this theme specialization results in the higher returns for the fund overall? Do you think that's, that's the kind of secret sauce, or do you think stage specialization is there's often this kind of divergence between, ah, we, we don't have, we're theme agnostic, but we're only series A. Which one do you think is kind of more effective to be?

A That's a good question. I think that any theme being Fully candid is used as a way to be efficient with one's time. And so, at the end of the day, somebody, somebody in the venture community said to me, you don't have to do every good deal. You just have to only do good deals. And so, I'm going to pass on plenty of really excellent companies. In fact, the best investors of all time have passed on 10 to more companies multiple times over each of them. And so, There's this world in which I need to figure out a best way to be efficient with my time. I need to figure out a way to look at companies in a way that I can fundamentally process. Sam Altman tweeted something a couple of weeks ago saying that he estimated there were between four and 6000 seed stage companies looking for funding every year, which means more than 10 a day every single day, and there's no way you can do that. So you need some sort of a heuristic or some sort of a tool whereby you can decide on a point of view and say, I noticed stuff outside of that point of view, and just hope your point of view is more right than wrong, and that you can find the winners within it. And I think that's true about stage, and I think that's true about theme. And so that can go for both. It's just a matter of, can you find enough of a way to constrain your sample set, and then within that sample set, optimize for getting lucky, b…

AI assessment note: “I think that's true about stage, and I think that's true about theme.”

Q And then in terms of Uh, skipping many, many stages now to the, to the exit and the dream of many a VC. Uh, you've written that there should be kind of further alternatives other than just the, the rather limited IPO or acquisition that we frequently hear about. What, what sort of, uh, other solution then do you, do you suggest? How can we expand this narrow funnel?

A That's a good question. Uh, the first, a tiny bit of background, which I imagine that your listeners will, will have been abreast of the news that Fidelity is marked down a bunch of companies, and the implication that I have of that is that these companies, which are private, are in some ways starting to get treated like public companies, and so, you know, their future prospects are being valued in real time, uh, by investors, which is not so different than how a public company has to deal with stuff, and And can, that can go up, and that can go down, and that can happen within the context of a financing and not. Uh, so there's that piece, which I think is worth just making note of, but we live in a, a world, and, and after Sarbanes-Oxley, which, uh, was a piece of, uh, legislation and act that was passed, I think, in 2002, it's become fairly burdensome to be a public company. The SEC just puts a fair amount of Restrictions on being a public company, and so even for those companies that have free cash flow, that have EBITDA, and want to raise money from the public at scale, it's not necessarily the most attractive thing. And so, and so that's, I think, part of what's contributing to these massive, massive funding rounds that are fundamentally private, even though they should have gone public ages ago for some cases, and in some cases not. Uh, but what I do think is Worth thinki…

AI assessment note: “if you can find ways to profit, then you can find all sorts of ways to exit”

Q And then in terms of Uh, skipping many, many stages now to the, to the exit and the dream of many a VC. Uh, you've written that there should be kind of further alternatives other than just the, the rather limited IPO or acquisition that we frequently hear about. What, what sort of, uh, other solution then do you, do you suggest? How can we expand this narrow funnel?

A That's a good question. Uh, the first, a tiny bit of background, which I imagine that your listeners will, will have been abreast of the news that Fidelity is marked down a bunch of companies, and the implication that I have of that is that these companies, which are private, are in some ways starting to get treated like public companies, and so, you know, their future prospects are being valued in real time, uh, by investors, which is not so different than how a public company has to deal with stuff, and And can, that can go up, and that can go down, and that can happen within the context of a financing and not. Uh, so there's that piece, which I think is worth just making note of, but we live in a, a world, and, and after Sarbanes-Oxley, which, uh, was a piece of, uh, legislation and act that was passed, I think, in 2002, it's become fairly burdensome to be a public company. The SEC just puts a fair amount of Restrictions on being a public company, and so even for those companies that have free cash flow, that have EBITDA, and want to raise money from the public at scale, it's not necessarily the most attractive thing. And so, and so that's, I think, part of what's contributing to these massive, massive funding rounds that are fundamentally private, even though they should have gone public ages ago for some cases, and in some cases not. Uh, but what I do think is Worth thinki…

AI assessment note: “freedom is a free cash flow, and if you can find ways to, to create net income”