#082 Doing Well and Doing Good — Deena Shakir (Partner Lux Capital)

Deena Shakir is a partner at Lux Capital, where she likes to invest in underdog entrepreneurs building breakthrough companies to accelerate advances and equity in human and population health. She's led investments into companies like Maven Health, a unicorn in women's and family health, and SteadyMD, a telehealth company. She has a very interesting background. She studied at Harvard and Georgetown School of Foreign Service. She was then a Presidential Management Fellow at the US Department of State. She directed social impact investment at Google.org, and she was also a partner at GV, previously Google Ventures. She's been named a top 30 under 40 in healthcare by Business Insider and top 9 women to watch in venture capital by the Wall Street Journal. She's a member of Fortune's Most Powerful Women and a lecturer at Stanford Graduate School of Business. We talk about her story, how her network is one of her most important assets, and how much VC fits into philanthropy and doing good. I hope you enjoy. So Deena, would you mind telling me a little bit about your story, particularly how you got to where you are today?

How much time do we have? I'm happy to. Sure. So I am a partner at Lux Capital. The journey starts a long time ago. This is not what I thought I'd be doing, you know, when I was growing up in the Bay Area, or even when I was in college, or even when I was in grad school. But at the same time, I can't imagine myself doing anything else now. The journey begins even before I was born. My parents are both immigrants from Iraq and made their way to the States in the '70s for my dad and the early '80s for my mom. And that was really, you know, a big part of my identity growing up was knowing in the wake of war after war and sanctions and, you know, 9/11, just how fortunate I was, the serendipity of my existence and my birth in the Bay Area and not Baghdad. And that really drove a lot of my early ambitions and to this date is a driving force for me in terms of thinking about my North Star of impact and also, you know, why I work as hard as I do, just realizing the chance that I have and that I can't lose it. So growing up, you know, I really thought I was going to do something to prevent, you know, another 9/11 and to help build bridges and use this sort of hybrid identity that I've had that was always so natural to me to help, you know, bring these parts of the world closer together. And that at one point thought looked like it might be as a journalist. At another point, I thought it might be as a public servant. I actually did do that, both of those things, for a little while. And eventually it became clear to me that tech was increasingly a way to achieve impact and to build bridges, and perhaps to do so in a way that would be more efficient, in some cases be more equitable. And that was something that I needed to, to learn how to do. This It was around probably 2010, 2011 when it became clear to me. At the time, I was at the State Department, and I had joined State actually because I was covering a speech that President Obama gave in Cairo in 2009 when I was interning with the BBC in DC, where he talked about a better way of doing development and diplomacy with the Muslim world that was really grounded in technology and in entrepreneurship. And so I was working on public-private partnerships with big tech companies that, you know, and increasingly startups at the time. This is right when software started eating the world, really, you know, the heyday of, of that era of innovation. And I was coming out to the Bay Area a lot, which is again where I grew up and really where I never thought I would live again because, you know, as a child growing up here, there wasn't really a lot to do if you weren't working on semiconductors or chips or maybe early days of software engineering. But if you have these global aspirations, you'd go to DC, you'd go to New York, you'd go to London, you'd go overseas. And so coming out here, I was really surprised. I sensed the center of gravity was shifting geographically out west in terms of tech, that it wasn't just this like separate esoteric sector, but actually a way of doing a lot of things better. And at the same time, the Arab Spring was getting started in the region. And, you know, topic for another podcast in terms of where that went. But at the time, you may recall, we were all kind of hopeful about the prospects for democracy. And, and so I really felt like tech was playing a role and enabling change and revolutions and impact on the ground. So I set my sights on joining a tech company, but not on the periphery in policy or, you know, or in marketing, which would've been a more natural fit if one exists for somebody with my background who studied social studies and Near Eastern languages and civilizations and who did her graduate work at the Georgetown School of Foreign Service. No, I wanted to work in product, and no one knew what to do with me. They had no idea why I thought I had, you know, the audacity to, um, to, to apply for these roles. I got hundreds of rejections. I still have a lot of those emails. Um, but eventually got lucky and got a, a great role in product partnerships, which is where I would end up staying for the next 5 to 7 years. Um, at Google and got to work on some really cool early stage initiatives on a team that doesn't exist anymore, where, uh, I, you know, often be the first business person to come in Whenever an ambitious PM or engineer had a moonshot idea, and that is how I ended up really getting exposed to healthcare beyond the fact that I come from a family of physicians, much to their chagrin. I never went down that path. I think for a hot minute I thought maybe I'd be pre-med until I realized that required taking organic chemistry. And, you know, up until recently, my dad was still telling me, you know, you could still go to medical school. And I'm like, Bob, I'm, I'm in my mid-30s now. I've got a career. Like, I love diligencing companies with you, but, um, I, I don't think I'm gonna go back, uh, and, and be a doctor myself, but I love working with doctors and I love funding doctors and I love working in health tech. So I ended up helping to build what eventually became Google Health 2.0, not 3.0 or 1.0, but, uh, a, a little, uh, a little in between there. And that's what led me to venture. It was getting exposed to the potential around 2013, 2014 of technology. And healthcare and the opportunity to help improve lives through technology, but also realizing that big tech was not gonna be the source of innovation. And I knew this because I tried. We had hundreds of engineers working on this product, and at the same time I was meeting incredible entrepreneurs who were getting started with their companies, many of whom are now unicorns, some of which we've since invested in. But at the time they were bootstrapped and they had you know, uh, very few people on their team, very few dollars behind them, but they were doing more than my team of hundreds of engineers. And so that's ultimately where I realized where I wanted to be was, uh, helping to grow and scale a lot of those companies. Um, and I ended up connecting some of them with people I knew who were in VC. I wish I had thought to invest. I didn't even have the mentality of a, of an investor at the time. I had the currency of my network, which is still kind of my greatest asset. And a lot of those folks ended up making investments. So got the itch to join VC and ended up joining GV.

This is broadly a debate that comes up on Twitter a lot, on VC Twitter, in terms of how hard you should work as well, which is loosely related to this. And I just wanted to ask, especially during your coming up, maybe, and maybe you are still in your coming up, but especially during your 20s, like how hard were you working?

I mean, I've always worked really hard. It's just like what makes me happy. I don't, I mean, when you're working on things you love, you're, loving what you work on. So you're, it doesn't feel like something that you resent or that you don't wanna do. I mean, to this day, like it's usually a struggle between sleep and working for me, cuz I do love to sleep too, but I kind of wanna keep doing what I'm doing. So that's always been, been the case for me. Uh, I mean, there are some things that I had to study in school that I maybe didn't love too much, and that, that was a different story. But, um, that's just part of my DNA and it, it's, it's something that, um, I don't really know how to be any, any other way.

Another interesting part you said was that the currency of your network and how instrumental that was in everything you've gone on to do. Can you give me a little flavor of tips, tactics, or anything that you think you've done throughout your career that's been helpful in building that network?

Yeah, I think I was able to punch above my weight class really early on in my career, which is something that enabled me in retrospect to to build an incredible network and to get exposure to ideas and insights and decision-making, uh, in, in ways that maybe would've taken me decades otherwise. And a lot of that had to do with the platforms and the rooms that I was able to be in even before I could earn a seat at the table. You know, I worked with people who had the seat at the table, and so I could, I, I could observe, I could watch, I could get insight into, into white spaces and ideas. Um, and that's something that, you know, again, even, even in high school, um, was the case. And I started a, a math a magazine in high school that, you know, was sort of a counter to the school newspaper. And I was able to get interviews with people who, you know, might not have taken my call if I just wanted to grab a coffee and shoot the shit, or God forbid, pick their brain. I hate those words. So that's where that started. And then in college, I, you know, I was financially independent. I paid for college by myself. I won a bunch of merit awards, but I also worked. I always worked multiple jobs and Some of those were not so glamorous, but others were pretty cool. I got to work at the Kennedy School and meet a bunch of these high-powered diplomats and business leaders in some cases as they were coming to speak to the university. I remember working on a scholarship that I helped start for students from the Middle East. And we had at the time Mohamed El-Erian, who I think he was with the Harvard Management Company and then, of course, went off to PIMCO. And I was the staff person. Person who was like literally printing the name tags and stuffing them and getting paper cuts from that. But I got to be with him in the green room and spend some time and ask him about his ideas. And that was incredible. I mean, even to this day, that'd be a really hard meeting to get. And so, you know, having that access was really tremendous. And then eventually when I was at the State Department, I was in the room where, you know, it was in the arena, it was where things were done. And again, got to have that perspective. Even at Google, you know, being the person who was sort of leading their healthcare efforts, I had a calling card and people took the meetings, the major decision makers at some of the largest in, in, in the case of healthcare, which I ended up, you know, working on the largest health systems and payers and pharma companies. Like, you know, I may have been in my mid-20s and, and, uh, kind of been, you know, a name no one had heard before, but I got to take those meetings and those meetings not only enabled me to develop connections over time that literally are still valuable to a lot of my portfolio companies, but they gave me insight into where the white space was for innovation. What were the customers looking for? What were they missing? And because I've had this natural connectivity desire my whole— I just love that. I love bringing people together. It brings me joy. I love that socially. I love that professionally. That's what I did. So I'd meet these folks and I'd separately meet entrepreneurs and then I'd put them together and deals would get done. Uh, you know, that's, that was my job actually when I was at GV was, and we'd track those things and we were able to track like hundreds of millions of dollars of revenue opportunities that were created as a result of literally e-intros. And frankly, that's a lot of what, what a VC does.

Through spending time with these people that you, you know, across academia, policy, business, is there anything that you learned through them by osmosis that you started to pick up that you think has been useful for your career?

Absolutely. I mean, I think, again, this is something that you can really only observe through osmosis. You're not going to get it necessarily through conversations, but if you can observe how decisions are made, if you can, you know, see how negotiations get done, if you're, you know, CC'd on these emails that are going back and forth about, you know, facilitating partnerships and all of that, that it's not like I was sitting there taking notes on, you know, here, here, here's the business book I'm gonna write about what I learned being surrounded by leaders. But it was, it, it, these were things that I was absorbing and adapting into my own, into my own ethos, into my own way of doing things. And that continues to be the case. I mean, what an incredible privilege to be in this job where I get to spend all day meeting with brilliant people who are literally, you know, putting their lives towards the work that they're, that they're championing as founders and to be able to observe and learn from them. And I think there's often this, you know, this, this sense of the power dynamic or the power law, as Sebastian Mallaby would call it, between VCs and investors. And that may be the case sometimes, and that may have been the case historically. but there is a hell of a lot that I learn constantly from them, even as I am coaching in some cases, guiding in some cases, uh, a lot of the founders. And that's, that guiding and that coaching comes from the fact that we have this unique wide lens into various different stages of companies as we invest in, in multiple stages, different, uh, sectors and so on. And we can help do that dot connecting, which again is sort of my, you know, what brings me joy or sparks joy.

With networking and dot connecting being so important in VC, of course, building relationships, these sort of things, it's something naturally that happens that you, you kind of do unconsciously. But I was just wondering if, you know, you must be at the stage now where you've met hundreds of thousands of people. Do you have any kind of strategies you use, any frameworks or anything that you do to kind of maintain these relationships, keep them going? Or is it purely just something that just, you just let it happen?

I wish I had a better strategy. I'm terrible at CRM. I've never been good at it. Um, I know some people are very systematic and have like calendar reminders, reach out to this person, reach out to that person, and so on. I mean, I have things on my to-do list that have been pushed for years now. Like, that's really difficult to do. So a lot of it is just, you know, it is sort of our job, uh, as, as VCs to, to try to connect the dots. And, you know, we're not just meeting founders, we're meeting talented people who may end up being excellent board members for our company or customers for those companies or hires for them, et cetera. So, um, being able to kind of have— it doesn't really scale to a certain extent, but being able to have these, these various different parallel streams in your mind and connect the dots is great. It's also really difficult. And there are things that I should do that I frankly don't remember cuz I'm in Zooms all day and I might even think, oh, I should connect that. So, you know, there's, there's an element of productivity and task management that I'm sure would make this more efficient, but I don't think this is the kind of thing you can automate. You know, and I know cuz I've been on the other end of like somebody's, you know, auto email saying, just checking in, you know, da da da. Like that's not the most effective way to do it. The, the best types of partnerships are one where there is a mutual value and benefit. In fact, even when I'm helping, when I'm doing diligence for a company and I'm looking at one right now, and I'm very careful to make sure that if I'm asking them to take time to speak with someone, that could actually be a in many cases, a potential customer for them. And that other person could have a valuable partnership with that, you know, so trying to make sure that there's always that kind of accretive value across the board and being, you know, having those things be top of mind to the extent that you can.

One thing I don't understand about VC is that, say, early on, say you've started a new fund or something, and it looks like the feedback loops for VC are at least 5 to 10 years before you know you've done a good job essentially. And the thing I don't understand is that sometimes it seems like someone starts a new fund and then within 2 or 3 years they've started a new fund. And I just basically, I don't understand how you can measure performance in maybe an objective way prior to that, those returns coming in. So I just wanted to ask you broadly, like how do you know you're doing a good job early on?

You have no idea. That's the thing. There, you know, it's a big challenge for anyone going from operating, especially if you've worked on building and launching things, where you have these quick feedback loops. You can, you know, gauge NPS, you can look at conversion, you can look at, you know, there's so many things that you can track. And when it comes to investing, a lot of the things that you think you can use to track earlier on aren't really meaningful. If you're looking at markups, that doesn't— and that might look good in the short term, but you don't know what that looks like in the long term. We've seen plenty of things get, you know, marked up and valued even in public markets, you know, at a, at an incredible, um, number, and then they tank. So, it, it is very difficult to know in the short term. And so often when people are like, oh, you're killing it, you're doing a great job, I'm like, how do you know? I, you know, so you don't, uh, it, you know, there are sort of more non, um, you know, non-quantitative or, you know, or, or softer ways to, to think about it. Are you getting access to the best deals? Do you know about them? So if we see some, you know, announcements coming out of of companies in areas that we are interested in or looking in that are done by, you know, other competitors or top-tier firms, and we didn't even know that was happening, that's a failure on our part. So, we need to know, we want to be able to get those meetings. And, you know, that's one way to make sure that you're at least onto something, but that really does take a long time.

I've been reading The Power Law as well, and I'm about halfway through. And one of the feelings I get from reading it is just how amazing VC looks and how much of the world they've changed, how much good stuff happens because of VC. And I wanted to just ask from your perspective, how much of that do you think is true? How much do you think as a VC you have the potential to really change the world and do have a great impact? And how much of it is just a basically like a cost-benefit thing? Like this X will make me money, Y won't, that's what I'll do. Like how do you think of that?

I mean, I think it's both. I don't think it's a dichotomy. You know, I actually taught a class at Stanford last quarter called Deconstructing Impact. And part of that, you know, came from my own personal journey where I've always been trying to seek a way to have impact. And I've done it in the public sector and I've done it in the nonprofit and philanthropic sector and I've done it in international aid and I've even done it as, you know, as a journalist and now, and then as a technologist or, you know, uh, as a sort of product person and now as a VC. As a VC, you, I have the word capitalist in my title. And again, I took me many, many years to realize that this sort of Venn diagram between doing well and doing good does have an area of overlap, at least as I see it, and that it, It's not as black and white as I may have seen earlier. So there are a couple of ways I think that you achieve impact through— at least I believe that I do through, through what I'm doing. Number one is, who are your LPs? Who are you making money for? And this is something that was very important to me as I looked to, you know, a few years ago when I was thinking about leaving Google and GV, the next firm that I'd be at. And it is a big, heavy responsibility to be a steward of capital for major endowments for, you know, educational institutions, for hospitals, for, you know, philanthropies. That is a big deal. And I take that very seriously. So it's not only that you're, you know, as we call it, investing in matter that matters and helping to, you know, to propel industries forward, some of which are working on very difficult, hard things that take a long time to get there that may, you know, help to work toward making our planet you know, and our climate healthier, making human lives better, making, creating more jobs, opening up new channels for the economy, but also in doing so generating returns for our LPs. And so there's a lot, there's a lot to it there. And, you know, I think that's a nuanced way of understanding the role. Not to say that, you know, I'm Mother Teresa or that any of us are. Obviously at the end of the day, like this is, it's a capitalist function. But I do think that there, that it has the potential to do some real good in the world.

This is a bit of a broad question, but in your story and your journey, you've mentioned, you know, you've done a lot of different things and tried a lot of ways of kind of making a positive impact on the world. In what ways is VC in that whole journey, is it satisfying? In what ways can it be unsatisfying? Are there things that you like about it in that context and things that there are some drawbacks as well?

Absolutely. I mean, they're— at the end of the day, we're not philanthropic by, you know, by mission, right? So what that means is if there are things that are very capital intensive and could make the world a wonderful place and should exist in the world, that doesn't necessarily mean that they're venture-backable businesses. So, you know, there, there are many things that are venture-backable or could be venture-backable, and And that's what we— our sweet spot. We love to see things before they're obvious, et cetera. But there are also things that we look at that we think are wonderful and should exist in the world, but they're not going to create the kind of value and the kind of returns we need to for our LPs. And so, you know, this is why I have some healthy skepticism around the notion of impact investing or, you know, this sort of hybrid social innovation. I've worked in and around those areas for, you know, for over a decade before coming into venture. But I think it's really important to be absolutely crystal clear about what your mandate and role is. And it is ultimately, as a steward of capital, to generate returns for your LP. You can and should ground yourself in the, in values and avoid, you know, the types of things that could make a lot of money but are just bad for the world, right? And that could be around, um, you know, certain types of energy. It could be around, um, you know, addictive substances. It could be around, you know, uh, things that might, you know, push medication in a certain way. Like there are a lot of ways that things could go awry. And so as long as you keep that, those values at your core and how you think about what you want to do and how you evaluate what you're doing, I think there is a tremendous potential for good.

I've always thought it would be interesting if there was some kind of scientific study or some kind of analysis of what makes a good investment and particularly a good VC investment. And I'd imagine that if this was being done, it would kept proprietary, wouldn't be shared freely. But are you aware of this kind of thing being done? Has this kind of been looked into? Because I think there's a lot of assumptions that are made that, you know, you need a mission-focused founder, and maybe it's the case that you don't need some of those things, or maybe some of the assumptions are incorrect. So, like, are you aware of any of this analysis going on?

You know, it's a science and an art. There are certainly quite a few firms who have either built their own or in some cases licensed different types of, you know, data services who claim to take certain inputs that are publicly available and analyze, or at least help source or help filter. But frankly, I think if this is something that can be done quantitatively and algorithmically, like, why do we exist? And it reminds me sometimes of speaking to physicians who think, you know, who are skeptical about the types of bots and algorithms out there that can diagnose. But this is ultimately, it's a human, it's a human business and it's about people. And again, like there are things that you might look retrospectively and say, you know, so-and-so graduates from these top schools ended up creating these big companies or people who worked at this, you know, McKinsey or went to HBS or so on. But if I think about some of the top companies that I've invested in and the top co-investors I love to invest with, they don't fit any of those molds. And, you know, I invested in a company called Moss, which was founded by Amira Yahyaoui, who was a human rights activist in Tunisia. She built a company initially intended to help students, college students pay for college. She never went to college. Now she's, you know, built a challenger bank that's helping students have their first debit card. She was stateless. She was a refugee who couldn't even open a bank because she she didn't have, you know, a standing and passport. So how, I don't know how algorithmically I could have come to realize how incredibly special she was and how powerful that business would be. And I think that's the case for a lot of folks. And that's part of why we love to invest before it's obvious. And that's kind of the edge you can get.

In the investments you typically make, what percentage do you think is you picking a good one? And what percentage do you think is then the kind of support and things later on that you offer that kind of enhances whatever doing, like what kind of split do you think goes on?

Yeah, I mean, I'm— you're reading the power law, so it's interesting because there are very, um, dichotomous views on this topic in venture today. Um, and you know, there's data that, if you wanna look at data that proves that both work, right? So there's definitely some investors who are very hands-off and for them it's about the picking and the indexing and then like let them, let them do their thing. And there are others who are more closely involved. Fundamentally, you don't want to be operating as a co-founder. You don't want to be investing in companies where you need to be the one making those decisions. So it is really important when you pick that there is that level of trust. Now, that being said, of course, as, as VCs, like, we have convening power, we have a certain network, we also have the ability to see challenges across companies that are very valuable insights to the founders. And so a lot of what we end up getting, you know, getting involved in is often, you know, coaching them through difficult decisions, recognizing if somebody, you know, may not be the fit that they're looking for, you know, helping to notice those kinds of signals and signs, and using that network and convening power to facilitate partnerships. And, you know, it's, it's a very different conversation when a, when a VC fund with a large portfolio is talking to a major C-suite executive at, you know, a Fortune 10 or 50 company and helping, helping them understand who should they be partnering with, who should they think about as they are trying to solve some of their key problems. That's It's not a sales conversation, but in doing so, I can suggest things to them that they might not necessarily have ever thought about. And in doing so, I can create, help to create access for those companies and founders who may not have ever gotten a foot in the door at that level. That is really powerful. And that's something that, you know, that we do a lot of.

You mentioned that at Luxe, you're going to do some more of your own media broadcast kind of stuff. And I know that there's some firms that that's actually a very critical part of their DNA is media and putting out content. Why is that becoming so important?

Again, one of those things that people have very mixed views on. I think I honestly was also skeptical myself. Like when I first started investing, I didn't really have a strong Twitter presence. I wasn't doing a bunch of podcasts. You know, I've always loved public speaking because I was a nerd in high school who like used to compete nationally and, you know, I'm one of those weirdos who like loves and gets energized by doing that rather than fearing it. But, um, I never understood why do VCs talk so much? Like, why are they on Twitter all the time? How do you even do your job and tweet like that all the time? And then over time it kind of became clear to me a couple of things. First, by virtue and by the privilege of the job that we have, we are seeing a lot of things and having access to, um, incredible brilliant minds who are working on solving really challenging problems. And getting on boards and helping them work through that. And so again, because we have that, that vantage point not only across different sectors but also across different stages, I mean, some of the boards that I'm on range, or, you know, the companies I've invested in, some of which aren't, you know, aren't board seats, from literally new co, one person and a deck, all the way through pre-IPO. And so that, you know, I think enables us to sort of pick up on trends and patterns. And that's why I've always loved reading some of the most prolific, you know, VCs' blog posts and tweets and so on. In terms of podcasts and all that, I mean, it's kind of a— people joke around like, oh, you don't need a podcast just because you're a VC. And there are other media out there as well that you can employ. But what I think what some of us realized over time is, oh, these are actually really interesting insights, and it would be, you know, it'd be good to kind of scale those conversations and be able to you know, to, to, to get that message out. It's also really important to build a brand because of what you asked earlier. How can you, you know, if you haven't been doing this for 20 years, you don't have, you know, 50 exits to point to, how can you be known for what you know? Not for just be known for the sake of being known, but for the, thesis that you have for the, the things you can bring to the table. And in an increasingly competitive world where we are literally fighting to get into the best deals, it's a helpful input for founders.

From living with physicians, from working with many physicians, I was really curious to hear where do you think physicians are myopic? Where do you think they miss things? And where do you think they really excel? Where do you think they do really well? Like what of analysis have you had of that group?

Well, I mean, I said my, my father is a psychiatrist. My grandfather, I miss him so much, he was a pediatrician who, you know, lived in Iraq and, and worked for the World Health Organization in the early '50s. He came on a Fulbright and did his master's in public health at Harvard. Apparently there's still a device, an analog device called the Shakir strip, which is used to measure malnutrition, and it's sort of an analog device that can be used, you know, easily in areas where there's no access to care. So I've got an aunt who's an OB-GYN, an uncle who's a cardiologist, my mom is a dentist. I was just always surrounded by that. And I think it is a noble profession. It is an incredibly difficult one. It is one where you can touch humans literally and in a way that you're literally saving lives. It's amazing. So I have so much respect and it's a privilege to be able to work at the intersection of now of business and tech healthcare. Uh, you know, I think some people would joke that, you know, MDs are not necessarily the best, you know, business people. I think it's hard to do both if you're classically trained in medicine. Uh, you know, now that sort of MD MBA thing is quite popular, and I know a lot of amazing people, some of whom we've invested in, who, uh, you know, are brilliant scientist physicians but also are going to be incredible founder CEOs. Like, those things are inconsistent with one another. But the act of company building and, you know, the challenges that come in that role are not necessarily the types of challenges that you encounter in classic clinical practice. And so they, you know, they're not always overlapping from a skill set perspective.

If you'd be comfortable, would you mind telling me about any big failures you've had in your career and what came out of them?

Oh, I've had plenty. I started a company in college that turned out to be a failure. Depending on how you define it, you know, I think it's really nice in retrospect to talk about, you know, how one experience led to another. And again, this is something I talk with my founders about all the time. There, there will be failure points inevitably. There's no way you will not. But what can, in some cases you can't even learn without experiencing that. What can you learn and take that to the next thing? So, you know, I co-founded a, a company that we sold for parts. I, you know, dabbled in a few different industries and like, you know, I went to grad school right away after undergrad, which which I wouldn't recommend to anyone. Uh, luckily I didn't, you know, pay— had a scholarship and didn't, you know, pay for it. But still, you know, there are a lot of things that, looking back, I, I don't think necessarily would have been the choices I'd make retrospectively. But I also never really had that 10-year plan. For me, it was always around, number one, being in a place where I'm constantly learning. Number— and that's why I think this is the job for me for the rest of my life. But like, that wasn't the case before. But because I'd reached a point where I was like, okay, now I, I don't really think I'm gonna learn anything new here and I'm not challenged enough. Being in a, in places where I, um, where hard work and hustle is, is rewarded and not in, you know, being a large sort of cog in a machine where it doesn't really matter if you go, go on vacation, somebody can totally take over, you know, and that you're not like an essential piece of it. And so again, I don't think those are failures per se, but perhaps I did some of those things things earlier in my career when, you know, I shouldn't have been. I should have, you know, I should have taken more risk.

Post-COVID, has VC become less fun? Like, I can imagine that speaking on Zoom a lot, doing a lot of calls, like, is it, you know, I was reading a book on repairing motorcycles and it's this whole thesis on how post-industrialization, the, the world of work is, it's not fun anymore. You don't get that satisfaction of building things with your hands. And, and part of that is just doing virtual calls and things just not being the same as meeting people in, in person. So what has been your experience of that? Like post-COVID, has, have things become less fun for you?

No, not at all. I mean, I don't like Zooming all day. I don't think anybody does. However, it has democratized a lot of things. I mean, I often have no idea where the people are that I'm Zooming with. The friction that it might have required for someone to get on a plane and come to Silicon Valley and waste time, you know, driving between meetings and so on. Like it doesn't matter. It doesn't matter where they are, and it doesn't even really matter in many cases where the company is going to be, depending on, you know, the type of company. So that actually made it in some ways more fun because it was a lot of people that I wouldn't have met otherwise, even outside of founders, like co-investors and other folks. Like, you know, rather than a big hullabaloo about when you're gonna meet and where and how can you set that up and da da da da, it's just like there's no friction. Jump on a Zoom or jump on a call. Um, so in those ways it's still really fun. And now who knows, I'm really trying hard not to look at the data too much, but it's not looking that good. But, you know, hopefully we're at least for now somewhat moving out of this. I mean, I was at South by Southwest, you know, the other, the other day and got to meet so many people in person. And that was really fun and amazing. And although, you know, it was nice not to travel for a while because I have little kids too. So I think that there, you know, we'll figure out what this looks like next. But this morning I had coffee in person with someone and now I'm here, you know, doing a virtual podcast with you. But it's, it's not something that, um, I think there are a lot of positives to it actually.

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