The Exchanges

Q a lot of value back to founders where they haven't had the time to do competitive analysis on pricing and everything in between. So totally get you there. Only exceptional companies deserve exceptions. Is there one company or a situation that just most stands out to you? You've invested in the canvas of the world and many other great companies. Is there one where that was very much the case?

A Yeah. I mean, look, I think the Canva investment for us at Shasta was an exception on so many different dimensions. And so it's obviously the one that stands out for me personally, you know, the company was based in Sydney, Australia. It was raising, um, a convertible note at a twenty-five million dollar valuation cap. Um, it had no revenue yet. It had a bunch of early signs of product market fit, actually, like, you know, several 100,000 monthly active users of Canva who were using the product really aggressively. It was growing 30 to 40% every month. It broke a lot of the traditional rules. And, and so, you know, we thankfully decided to make that investment, but there were all sorts of reasons to let it go.

AI assessment note: “I think the Canva investment for us at Shasta was an exception”

Q And so we have that, and in terms of, like, types of LPs, we have, obviously, there's the corporates, there's pension funds, there's funder funds, there's high net worth, family offices, all the different types. How did you think about that, and do you agree with the common wisdom of, you know, oh, endowment funds, they're, they're so stable. Is that true?

A Yeah, so we, we wanted some diversity, and I think we have about 15 institutional LPs, we have six university endowments, uh, you know, I think Three other foundations. So we're a little bit weighted towards endowments and foundations, but we have a bunch of fund of funds, and we have a couple family offices as well. And so we like that mix, because while the endowments are great names, and they are long-term oriented, there's still some level of risk of having an entire endowment based LP base, because they may all sort of have the same denominator effect issues at the same time. They also perhaps tend to be more aligned in what they care about, and so we, in general, like the diversity, and that's what we prioritized.

AI assessment note: “endowments are great names, and they are long-term oriented, there's still some level of risk”

Q Can I ask you, we've spoken about kind of dysfunctions within venture partnerships. Kind of extrapolating that, there's also the LP relationship. Before we talk about kind of dysfunctions there, you know, I know many of your LPs, I'm sure we probably share some. How did you select the LPs that you work with for Footwork?

A We had three things that we thought about when we raised our first fund, and we actually ranked LPs based on these three dimensions. And they were, one, what's just the Quality of the relationship with the people. We really tried to prioritize people who we built relationships with, who we really liked as humans, who we wanted around our proverbial dining table as a firm in, in this first fund. Second, we thought a lot about just, are these people who have seen what world-class looks like, and will they push us to be world-class, which is what we want in, in, in our firm. And third, we thought about the mission Uh, values of the institutions themselves and whether they were institutions that we are really excited to make money for and be partners with. And so those were the three, uh, dimensions that we prioritize. We, we assigned like a one through five rank on each of those. And then at a macro level, we were really lucky in our first fund. We had about four hundred and fifty million of commitments for a hundred and fifty million dollar fund. And we ended up raising one hundred and seventy five million and realized that's incredibly fortunate for a first time Fund. But what we thought about as we were constructing the full LP base was just having a little bit of diversity across both check size and type of LP. And so we wanted, you know, a nice mix of, uh, of LPs where, uh, y…

AI assessment note: “We had three things that we thought about when we raised our first fund”

Q a lot of value back to founders where they haven't had the time to do competitive analysis on pricing and everything in between. So totally get you there. Only exceptional companies deserve exceptions. Is there one company or a situation that just most stands out to you? You've invested in the canvas of the world and many other great companies. Is there one where that was very much the case?

A Yeah. I mean, look, I think the Canva investment for us at Shasta was an exception on so many different dimensions. And so it's obviously the one that stands out for me personally, you know, the company was based in Sydney, Australia. It was raising, um, a convertible note at a twenty-five million dollar valuation cap. Um, it had no revenue yet. It had a bunch of early signs of product market fit, actually, like, you know, several 100,000 monthly active users of Canva who were using the product really aggressively. It was growing 30 to 40% every month. It broke a lot of the traditional rules. And, and so, you know, we thankfully decided to make that investment, but there were all sorts of reasons to let it go.

AI assessment note: “the Canva investment for us at Shasta was an exception on so many different dimensions”

Q And so we have that, and in terms of, like, types of LPs, we have, obviously, there's the corporates, there's pension funds, there's funder funds, there's high net worth, family offices, all the different types. How did you think about that, and do you agree with the common wisdom of, you know, oh, endowment funds, they're, they're so stable. Is that true?

A Yeah, so we, we wanted some diversity, and I think we have about 15 institutional LPs, we have six university endowments, uh, you know, I think Three other foundations. So we're a little bit weighted towards endowments and foundations, but we have a bunch of fund of funds, and we have a couple family offices as well. And so we like that mix, because while the endowments are great names, and they are long-term oriented, there's still some level of risk of having an entire endowment based LP base, because they may all sort of have the same denominator effect issues at the same time. They also perhaps tend to be more aligned in what they care about, and so we, in general, like the diversity, and that's what we prioritized.

AI assessment note: “while the endowments are great names... there's still some level of risk”

Q I'm really intrigued that how are we seeing software eating the cart then for you?

A So, so an example of this is, you know, Tesla has a 30 person team working on autopilot, which is their Autonomous sort of cruise control and lane changing and lane keeping, uh, software and application that's live today in, uh, in Model S's and Model X's. So they have, Tesla has over a 100,000 cars with autopilot that are out there on the road driving and collecting data and automating highway driving to the tune of millions of miles per week. They are gathering that data. They're gathering it from the car itself, from the camera at the front of the car, from the other sensors in the car. And they're able, therefore, to use that data set to improve the autopilot system very quickly. That's leading to an advantage around data, around software. It'll lead into advantages around the hardware and the capabilities they build into future vehicles like the Model three. And that's already happening for Tesla. And so that's one example of how software is eating the autonomous transportation space right now.

AI assessment note: “that's one example of how software is eating the autonomous transportation space right now.”

Q Can I ask you, we've spoken about kind of dysfunctions within venture partnerships. Kind of extrapolating that, there's also the LP relationship. Before we talk about kind of dysfunctions there, you know, I know many of your LPs, I'm sure we probably share some. How did you select the LPs that you work with for Footwork?

A We had three things that we thought about when we raised our first fund, and we actually ranked LPs based on these three dimensions. And they were, one, what's just the Quality of the relationship with the people. We really tried to prioritize people who we built relationships with, who we really liked as humans, who we wanted around our proverbial dining table as a firm in, in this first fund. Second, we thought a lot about just, are these people who have seen what world-class looks like, and will they push us to be world-class, which is what we want in, in, in our firm. And third, we thought about the mission Uh, values of the institutions themselves and whether they were institutions that we are really excited to make money for and be partners with. And so those were the three, uh, dimensions that we prioritize. We, we assigned like a one through five rank on each of those. And then at a macro level, we were really lucky in our first fund. We had about four hundred and fifty million of commitments for a hundred and fifty million dollar fund. And we ended up raising one hundred and seventy five million and realized that's incredibly fortunate for a first time Fund. But what we thought about as we were constructing the full LP base was just having a little bit of diversity across both check size and type of LP. And so we wanted, you know, a nice mix of, uh, of LPs where, uh, y…

AI assessment note: “ranked LPs based on these three dimensions”

Q Final one. Footwork in five years time or 10 years time. You can choose, but you said AUM's not the metric we should be measuring. Most firms always scale. What does footwork look like in the 10 year frame?

A Yeah. We, we perhaps add, uh, one or two equal general partners to our group. Who are re-founders and co-owners of the firm with Mike and me, but most importantly, we've, we've been able to already work with a handful of really special founders and companies, um, where we've been their lead series A or C partner. Again, that probably in, in five, five to 10 years is not going to show up with distributions and DPI, but hopefully it shows up in just The fundamental nature of a couple of the companies that we work with, and their scale and revenue, their business fundamentals, the impact that they're having on markets, and on hopefully creating categories. And so, you know, Mike got to work with a woman named Katrina Lake, the founder at Stitch Fix, from five people to 10,000 people, and from zero revenue to a couple billion in revenue, and we hope that we get to work with a handful of Katrinas, of Melanie Perkins from Canvas, Of Jonathan Regis from the Founders Dogs. We hope to work with a handful of those folks over the next 10 years.

AI assessment note: “perhaps add, uh, one or two equal general partners to our group”

Q And so you think LPs don't do that well?

A I don't think that they spend enough cycles on it. Um, but I actually think some of the great ones do. Um, and of course I'm biased here. You know, we had LPs who did, I don't know, 30, 40 references that we heard about on, on us, uh, each. You know, we were heavily scrutinized on us as people because so much of our strategy is really just about the two of us, Mike and me, and our ability to make decisions in the partnership that we have. That's where we found LP GP fit with our LPs, is the folks who really dug in on us as people and how we make decisions, and who ended up fortunately supporting us.

AI assessment note: “I don't think that they spend enough cycles on it.”

Q are told Sorry, I'm going here, but I'm interested to hear your thoughts. Don't speak to the associates. Like, it's the GPs who make the decisions. And I'll be honest, I say that too, especially at growth. We don't have time for spinning cycles on associates. Like, just go to the GPs. I can introduce you to them. Do you agree with the advice on just go to the GPs?

A I think it's case by case dependent. And there are so many folks who've grown up in the industry to become Incredible investors who started off at the bottom of the ladder at a firm, and so you just don't know who those people will be. I think that you're better off as a founder judging based on the actual conversation you have, which sometimes may be a lot better with the youngest person on the team versus the managing partner of the firm, and sometimes it won't be. I always give people a chance, whether it's the founders who, you know, Come in through not that warm of an introduction or purely cold. Uh, I always try to review what they're saying and I'll quickly write an email back saying, uh, not interested, comma, thanks if it truly is, is not a fit. But I've always kept that mentality. I started at Insight Partners in New York where I was bottom of the ladder as a summer intern and then an analyst. And so I obviously have bias on this dimension. Um, But I do think that there are people who are really young in our business who are really thoughtful, and that a conversation with them might actually lead to some learning for you as a founder, and it may even lead to an investment, as it's done for me several times in my career on the venture side.

AI assessment note: “I think it's case by case dependent.”

Q You know, when a fund's done well, when the manager then returns with, I'm managing my own money now, you're like, well done. Uh, best board member you've sat on a board with, and why them?

A I'll put one that I miss right now working with, which is, uh, Vas Nadarajan at Excel. Vas and I were also at Insight together, um, in the summer of 2010. He left soon thereafter to join Excel, so he's been there, I think, for about 12, 13 years now. He led the seed round in Frame.io, where we did the Series A with, with them at Shasta, and so I got to work with Voss and, and founder Emery and, and the team there. You know, I picked Voss because I think he's, he's not that well known, but he's got a great portfolio. Frame.io was acquired by Adobe for, for 1.3 billion dollars a couple years ago. Um, as an example of that, a segment was another one that, that he, he did. But as a board member, he just asks really thoughtful questions. He sticks to just what's most important to prioritize as a company. And in my peer group and sort of our generation, although you're younger than me and I'm younger than Vaz, I still think of us as sort of the same generation. I think he's one of the best and probably hasn't gotten the credit he deserves for that.

AI assessment note: “Vas Nadarajan at Excel... as a board member, he just asks really thoughtful questions.”

Q You said about your, your wonderful partner. I do have to touch on fatherhood. It's such a special, but also significant change to life. There's so many ways I can take it. I think the biggest one that I'd love to understand is if you could advise yourself one thing and call yourself up the night before your wife gave birth, what would you tell yourself? Oh man.

A Uh, well, first I would say, uh, go to the airport sooner than you think. Um, our daughter was born less than 30 minutes after we left the house. Fortunately, we live less than five minutes from UCSF in San Francisco, but that was the craziest 30 minutes of, of all of our lives. Um, and fortunately it was incredible, and, and my wife is a total hero and champion. But on a more serious note, what I think I would, I would advise myself is, You think you have a bunch of control over your life, and you kind of do have a bunch of control over your life right now, but tomorrow you suddenly are not going to have a bunch of control over your life. Like, all these things are going to be out of your control as a parent. You, you can't control exactly who your kid is. You can't control how they're going to behave in certain places and dimensions of life. Um, you know, you, you think you have the perfect childcare set up, but Stuff's gonna go wrong. You're gonna have to keep adjusting your schedule. And so you sort of have to embrace the lack of control and the surprise that is gonna come from all of this experience. And I think the joy of parenthood is in the randomness and surprises of it. And so it's still something that I'm comprehending, but that's the first thing that comes to mind.

AI assessment note: “what I think I would advise myself is, You think you have a bunch of control”

Q I'm really intrigued that how are we seeing software eating the cart then for you?

A So, so an example of this is, you know, Tesla has a 30 person team working on autopilot, which is their Autonomous sort of cruise control and lane changing and lane keeping, uh, software and application that's live today in, uh, in Model S's and Model X's. So they have, Tesla has over a 100,000 cars with autopilot that are out there on the road driving and collecting data and automating highway driving to the tune of millions of miles per week. They are gathering that data. They're gathering it from the car itself, from the camera at the front of the car, from the other sensors in the car. And they're able, therefore, to use that data set to improve the autopilot system very quickly. That's leading to an advantage around data, around software. It'll lead into advantages around the hardware and the capabilities they build into future vehicles like the Model three. And that's already happening for Tesla. And so that's one example of how software is eating the autonomous transportation space right now.

AI assessment note: “that's one example of how software is eating the autonomous transportation space right now.”

Q Brilliant synopsis. Well done. Not many people can do it. It's a very hard question to sum up your life in a minute and a half. Um, but, but in terms of the operational experience, I'm intrigued. How pivotal do you think that was to forming you as an, as a VC? I mean, did that really lend to your style now, do you think?

A So I got that taste of entrepreneurship by being on the founding team at, at Artsy, which is a place to discover art online. Um, Carter Cleveland, who founded the company, had the idea, um, And I got to work with him on it, and I was 19 at the time, and he was 21. That taste of building a product, uh, struggling to find product market fit, does inform me today in venture capital because it helps me empathize with founders who are going through that same struggle. But now that I've been in venture capital for five to six years, the venture experience trumps the operating experience at some point. It absolutely does now for me. And, and so I think the venture experience now informs much more what I, what I do every day with finding new companies and deciding which ones to invest in and, and trying to be helpful to the ones that we have invested in.

AI assessment note: “That taste of building a product... does inform me today in venture capital”

Q dive today into the topic of autonomous cars. It's something we're both very passionate and excited by, probably because I haven't learned to drive yet, but, but let's, so let's discuss that. I want to dive straight in. But it's not, it seems relatively simple, but there is a variant on self-driving cars to a degree, so could we start with a definition and a walkthrough of the different stages?

A Sure, it's a great question. It's the National Highway Traffic Safety Administration that's come up with a formal classification system for autonomous vehicles. The ones that are, and it goes from level zero to level four, the ones that are most interesting, the ones that I think about are level three and level four automation, and level three is where You have a driver at the steering wheel, but the driver can fully cede control of all safety critical functions in the car to the car itself, but the driver still needs to be present. Level four automation, which is pipe dream, you know, in many movies and the things that we fantasize about is where a vehicle can drive autonomously without any driver control. So it can actually drive without anyone in the car. Um, and so level three and level four are the two stages that I think are most interesting to know about when it comes to autonomous transportation.

AI assessment note: “National Highway Traffic Safety Administration that's come up with a formal classification system”

Q And talk to me, okay, so as we said, both very passionate about this space, but what's the source of excitement for you, and why is it now for self-driving cars? Why, you know, the year of What's it for you?

A So for me, I think there's a few categories. I focus more on the consumer side at Shasta, and we do a mixture of consumer enterprise and connected hardware investing, and I think across, across those areas, there's a few categories that will lead to trillions of dollars of shift in spend for consumers over the next couple decades. I think housing and real estate is one of them. Healthcare and medicine is another. Consumer finance, a third. But if you had to push me to focus on one, I would go with autonomous transportation and self-driving cars, because I think that disruption in how we move around can have the largest impact across the most number of industries over the next couple decades. And, and why now, going back to the definitions we just talked about, we're almost at level three, where cars can, can drive themselves, albeit with a driver at the steering wheel to ensure safety and as a backup. And that's amazing. Elon Musk said in In December, 2015 that Tesla is two years away from a self-driving car. So, you know, now we're in 2016 and he said that the Tesla will get there in late 2017. You know, the why now for me as a venture investor is that I do believe we're almost at level three vehicle automation and, and the timing is now for, for huge opportunities around, around this stuff.

AI assessment note: “why now, going back to the definitions we just talked about, we're almost at level three”

Q And so for those legacy auto traders then, Uh, is M&A the only real solution to adapt, adapting to this new industry, or can you have kind of corporate innovation from beneath? Do we have corporate innovation from beneath? Uh, BMW maybe have their intelligent cars. I don't know, but is M&A the sole solution, do you think?

A No, I don't think it is, and I think we should give the auto manufacturers some credit. You know, I think many of them have expected this to happen for a while, and have built teams in-house Working on this stuff. You know, I, I believe GM has a pretty big team working on autonomous transportation, and they had that for many years pre the acquisition of Cruise, and I think BMW, Daimler, several other companies have groups in-house working on autonomous transportation. I think the big question is, though, whether their approach will lead to success, or whether a new entrant And a new type of approach, something like Uber or Lyft, for example, or Google or Tesla, will actually lead to, you know, the approach that catalyzes this autonomous transportation revolution.

AI assessment note: “No, I don't think it is, and I think we should give the auto manufacturers”

Q I mean, I, I look about 25 years older, it's, uh, the venture game is having its effect on me. The thing I'd love to start on is, I think we change how we invest so much, um, in time, and if you were able to cool yourself the night before your first day investing, what would you advise yourself on that cool?

A Two things. One, Is actually a piece of advice one of my partners at Shasta gave me pretty early on, like probably in the first couple months, which is don't look at the title on your business card, which at the time was associate at Shasta Ventures. Just think about yourself as a venture capitalist and do as venture capitalists do, which is find, decide, win, help, and exit. So the five components of our, of our day-to-day job and venture. And that advice I think was really profound. It sort of unleashed me and Um, and it's the advice I give young people in venture today, which is again, don't, don't look at your title. Don't think about exactly what the role is. Just think about yourself as a VC. And I think you'll be better off for that. And then the second one that came to mind is exceptional companies deserve exceptions. And it's a mantra that I've tried to always have in my venture career, which is yes, you have this model of how you want to invest, um, this dream idea of portfolio construction and the profile of company that you're looking for. But It's so often the ones that you consider an exception for, the ones that just blow you away, that feel like outliers, that end up being the ones. And so I've always tried to have that in the back of my head, which is at the end of the day, all of our, all of what we're doing in our job is searching for the outliers and the tru…

AI assessment note: “Two things. One, Is actually a piece of advice one of my partners at Shasta gave”

Q I totally get you. On the people side, We all make mistakes. When you review people assessment, what have you made a mistake on that you have changed or should have seen?

A The first thing that comes to mind, and I apologize that I, I didn't really look at the questions before coming in here, so that wasn't on the question. All of this is, all of this is unscripted. The first thing that comes to mind though, Harry, is there's this difference between the ability to fundraise and the ability to build a business. And so I have been sucked in and seduced by founders that can tell a great story, that are great in a handful of one hour sessions and in person for the first time, who feel like they're magnets for talent, who know their business inside and out, it seems, and who are great at fundraising, and so attract multiple term sheets. And what I've seen happen a handful of times is that They are not good at the fundamentals of, of building the product and building the team of actually finding product market fit or growing the product market fit that we thought that they had. And that there's that huge difference between fundraising and business building. And I think that's showing up all over the place right now, right? Like there were so many companies that were able to fundraise in 20, 21 that now don't have P and L's and fundamentals that to show for, for the vision that they told.

AI assessment note: “I have been sucked in and seduced by founders that can tell a great story”

Q are told Sorry, I'm going here, but I'm interested to hear your thoughts. Don't speak to the associates. Like, it's the GPs who make the decisions. And I'll be honest, I say that too, especially at growth. We don't have time for spinning cycles on associates. Like, just go to the GPs. I can introduce you to them. Do you agree with the advice on just go to the GPs?

A I think it's case by case dependent. And there are so many folks who've grown up in the industry to become Incredible investors who started off at the bottom of the ladder at a firm, and so you just don't know who those people will be. I think that you're better off as a founder judging based on the actual conversation you have, which sometimes may be a lot better with the youngest person on the team versus the managing partner of the firm, and sometimes it won't be. I always give people a chance, whether it's the founders who, you know, Come in through not that warm of an introduction or purely cold. Uh, I always try to review what they're saying and I'll quickly write an email back saying, uh, not interested, comma, thanks if it truly is, is not a fit. But I've always kept that mentality. I started at Insight Partners in New York where I was bottom of the ladder as a summer intern and then an analyst. And so I obviously have bias on this dimension. Um, But I do think that there are people who are really young in our business who are really thoughtful, and that a conversation with them might actually lead to some learning for you as a founder, and it may even lead to an investment, as it's done for me several times in my career on the venture side.

AI assessment note: “I think it's case by case dependent.”

Q argument with founders, not the argument, but the debate, when they have a multi-stage fund and a seed fund, and they say, hey, these are all These are our options. How do you actually advise them on taking the money, and they have much more money available to them from the larger funds? I guess my question is, is it always better to take the smaller round, do you think?

A Look, I think it is dependent on the investor, of course, so that the variables that would go into my thinking are, um, the firm, the, the partner at said firm, um, and sort of the match of that to the type of business, and, and the capital match to the type of business, because there are some companies That actually do need more capital in the early days, and that will benefit from that, and so I, I struggle to have a general, um, piece of advice on that front, but of course, based on Footwork being a stage specialist firm at early stage, we only lead early stage rounds, we only lead and we only do early stage, I have a bias towards the stage specialist.

AI assessment note: “I think it is dependent on the investor, of course”

Q I totally get you. On the people side, We all make mistakes. When you review people assessment, what have you made a mistake on that you have changed or should have seen?

A The first thing that comes to mind, and I apologize that I, I didn't really look at the questions before coming in here, so that wasn't on the question. All of this is, all of this is unscripted. The first thing that comes to mind though, Harry, is there's this difference between the ability to fundraise and the ability to build a business. And so I have been sucked in and seduced by founders that can tell a great story, that are great in a handful of one hour sessions and in person for the first time, who feel like they're magnets for talent, who know their business inside and out, it seems, and who are great at fundraising, and so attract multiple term sheets. And what I've seen happen a handful of times is that They are not good at the fundamentals of, of building the product and building the team of actually finding product market fit or growing the product market fit that we thought that they had. And that there's that huge difference between fundraising and business building. And I think that's showing up all over the place right now, right? Like there were so many companies that were able to fundraise in 20, 21 that now don't have P and L's and fundamentals that to show for, for the vision that they told.

AI assessment note: “I have been sucked in and seduced by founders that can tell a great story”

Q I spoke to one of your friends, uh, actually a mutual friend of ours before the show, speaking of confidence and vulnerability, and they said the challenge that I have with Nikhil is that he is one of the great ones, he just doesn't believe it yet, and he kind of feels like he should be someone maybe that he has to be sometimes. Do you think that's fair?

A In the early days of my career, which I still consider it to be, I mean, I'm, I'm, I'm 34, I've been in venture for, I guess, 13 years since I started as a summer intern at Insight. There's an insecurity that comes from not yet having, uh, delivered in distributions, many, many multiples of what I've invested. An insecurity that comes from having started a firm that, uh, has so much To prove. Everything to prove. An anxiousness that we'll have, that I'll have until we've many times over returned our first fund. But I also think that I know who I am more than I've ever known. You know, I think I'm able to authentically be myself. I think I've sort of been able to find my voice as a writer over the last three, four years of trying to do the newsletter As consistently as possible. My hope is that footwork is an embodiment of sort of who my partner Mike and I are, and that we express ourselves fully authentically through the investments we make and how we conduct ourselves as a firm.

AI assessment note: “There's an insecurity that comes from not yet having, uh, delivered in distributions”

Q And so you think LPs don't do that well?

A I don't think that they spend enough cycles on it. Um, but I actually think some of the great ones do. Um, and of course I'm biased here. You know, we had LPs who did, I don't know, 30, 40 references that we heard about on, on us, uh, each. You know, we were heavily scrutinized on us as people because so much of our strategy is really just about the two of us, Mike and me, and our ability to make decisions in the partnership that we have. That's where we found LP GP fit with our LPs, is the folks who really dug in on us as people and how we make decisions, and who ended up fortunately supporting us.

AI assessment note: “I don't think that they spend enough cycles on it. Um, but I actually think”

Q Brilliant synopsis. Well done. Not many people can do it. It's a very hard question to sum up your life in a minute and a half. Um, but, but in terms of the operational experience, I'm intrigued. How pivotal do you think that was to forming you as an, as a VC? I mean, did that really lend to your style now, do you think?

A So I got that taste of entrepreneurship by being on the founding team at, at Artsy, which is a place to discover art online. Um, Carter Cleveland, who founded the company, had the idea, um, And I got to work with him on it, and I was 19 at the time, and he was 21. That taste of building a product, uh, struggling to find product market fit, does inform me today in venture capital because it helps me empathize with founders who are going through that same struggle. But now that I've been in venture capital for five to six years, the venture experience trumps the operating experience at some point. It absolutely does now for me. And, and so I think the venture experience now informs much more what I, what I do every day with finding new companies and deciding which ones to invest in and, and trying to be helpful to the ones that we have invested in.

AI assessment note: “the venture experience trumps the operating experience at some point.”

Q Fantastic. And then sleep. You're very into sleep. Uh, obviously we are too being, uh, Uh, big Lisa fans here. So what is it about sleep that really excites you?

A So consumers spend, people spend about a third of their life sleeping, and we definitely do not spend a third of our money, uh, on sleep. And so there's a disconnect there between how important it is in our lives and, and how much we spend on it. And then if you think about it, you know, technology is not really altered for the better how we sleep. In fact, some would argue that technology has worsened how we sleep with, with phones, you know, waking us up and, and other forms of technology being, uh, interference on our sleep. And so I've been looking for a while for entrepreneurs and companies that, that are using technology to dramatically improve the way we sleep. And I'm still waiting to, to find the right investments there, but I'm hopeful that someone cracks, you know, how, how we can get to sleep better and how we can stay asleep for longer.

AI assessment note: “there's a disconnect there between how important it is in our lives and”

Q Fantastic. And then sleep. You're very into sleep. Uh, obviously we are too being, uh, Uh, big Lisa fans here. So what is it about sleep that really excites you?

A So consumers spend, people spend about a third of their life sleeping, and we definitely do not spend a third of our money, uh, on sleep. And so there's a disconnect there between how important it is in our lives and, and how much we spend on it. And then if you think about it, you know, technology is not really altered for the better how we sleep. In fact, some would argue that technology has worsened how we sleep with, with phones, you know, waking us up and, and other forms of technology being, uh, interference on our sleep. And so I've been looking for a while for entrepreneurs and companies that, that are using technology to dramatically improve the way we sleep. And I'm still waiting to, to find the right investments there, but I'm hopeful that someone cracks, you know, how, how we can get to sleep better and how we can stay asleep for longer.

AI assessment note: “there's a disconnect there between how important it is in our lives”

Q Do you think this is a winner-take-all market, or will we see a proliferative market in the car industry like we have now?

A Yeah, I don't view it as, as winner take all. That's my current thinking. Now, that thinking might very well evolve over the next six months, the next couple years, but it's a massive market. I think there'll be multiple successful approaches in companies, and I think once one company figures out the best approach, there will be fast followers, just like in the traditional auto industry. The one thing that gives me pause as I say this, though, is that there is such a big software element to autonomous transportation and to self-driving cars, and in software, Companies that have the network effects and the data set to be able to iterate and get better, faster than, than anyone else can lead to when it take most dynamics.

AI assessment note: “Yeah, I don't view it as, as winner take all.”

Q But you did mention Uber there, and so the next logical question for us is, is who owns these cars? Does car ownership fundamentally shift, and how does it, autonomous vehicles, affect the sharing economy, do you think?

A Yeah, another great question, and something I've been thinking a lot about. My current view is that I don't know that there's one, again, coming back to your previous question, I don't think that there's one company that will win this entire market right now, and I think it might actually vary by geography. So in Europe and Asia, where public transport is more prevalent and more used, I do think that a fleet-based approach, where you take out your phone, press a button, and an autonomous car comes and picks you up, But you don't necessarily own that car. Uh, it's shared, and, and you get into it, and maybe it goes and picks someone else up on the way to your next place, and maybe it picks someone else up. I think that that approach, certainly in, in Europe and Asia, it makes sense, because it's more blended into the culture that exists today, and the way people move around today. In the United States, car ownership is, is a big deal, and it's, it's something that's, again, bred into, The culture here. Even though autonomous cars will, I think, be quite expensive and won't be accessible to the mass market, just like luxury cars today aren't accessible to the mass market, I think that there will be a certain part of the population in the United States that will demand owning these cars and having their own autonomous car to be able to call at any time to just pick themselves up v…

AI assessment note: “in the United States, there'll be a blend of Car ownership, and fleet-based”

Q And then, and then finally, before we dig into a deep fire, deep fire, quick fire round, uh, talk to me about, um, regulation and, and the barriers that maybe might stop this becoming as mainstream as we'd like, as quickly as we'd like. What are the, what are the potential problems that you are concerned by for autonomous vehicles?

A Well, to go from level three, where a driver is still present in the car and, and it's kind of a backup in case something goes wrong. To level four, where a driver doesn't have to be in the car, and where a vehicle can drive autonomously without anyone in the car, that's a big shift. That's something that is not going to happen in the next couple years. One of the reasons for that is regulation, you know, governments, I don't think will allow it, ah, until they know that it's safe. I think the other barrier is just cultural. I mean, it's, it's going to be very strange for people to See things move around without anyone purportedly or anyone visibly controlling it. And so I think that's something that, that will take some time to, to shift people's mindsets around. Just like humans have been resistant to change in, in so many ways in the past.

AI assessment note: “One of the reasons for that is regulation... I think the other barrier is just cultural.”