Not just you know evaluating people that sounds pretty negative. But just kind of how do you look not intuitive things? I think a lot of times people focus a lot on the school people went to or whether they worked at Google or not and those, you know, our may be predictive or important but I like to kind of understand people based on their core traits versus, you know, just kind of tags on their resume. And so I think a few things that I look for is this founder market and I think you know, Brock's is a great example.Welcome to worth a podcast for my brother Ethan and I had the unique stories of young people in the tech world will talk with them about their backgrounds current work books that have profoundly affected their lives and a lot more to understand how they think and the impact I want to make this is the podcast that we wanted to listen to but it didn't exist. So we made it ourselves. Thank you means of New York, but for young people shaping the tech ecosystem to check out episode transcripts and join our mailing list. Please visit worth Dot card.com that's card with two r's Link in the show notes. Let's begin in this episode. I'm joined by Jess lie, twenty-three-year-old VC at summer capital and former partner at Rough Draft Ventures. We talked through Justice decision to not return to Morgan Stanley after her Junior Summer her experience working for multiple y combinator back startups and have she thinks about Career Development. Hope you enjoy Jessica thanks so much for coming on the show really excited to have you on yeah, thank you for having me really appreciate that. So you have a pretty extraordinary set of experiences to your name for someone who is just only graduated from college this past year. Can you tell our listeners a little bit about your background and your childhood? Yeah. Totally so start with childhood. I was born actually in Indiana nearby Purdue both my parents were graduate students doing their phds and electrical engineering there and they unfortunately we weren't able to raise me due to financial constraints. So I actually went to China at a very young age like 6 or 7 months. So definitely still an infant and grew up there with my grandparents and aunts and uncles and cousins so pretty big extended family you from Different parts of China and my dad's side as well as my mom side. And then once my parents were in a better place financially and had moved to New Jersey where they still live. I went to join them in early Elementary School and stayed in the u.s. Specifically in New Jersey since then up until of course College. So for college, I went to Harvard and I studied applied math with a focus on economics and computer science. I just graduated. Did earlier this year from Harvard in May of 2019 and throughout College? I was pretty involved with a few different things. I guess my own personal background even starting as early as late middle school and high school was in public markets investing and that was my first exposure to what I'd say later became my current focus and probably my longtime professional folk guys. I really enjoyed the process of analyzing and understanding companies Industries and Collating between different data sources both qualitative and quantitative and but then wanted to work more closely with these companies, which I obviously couldn't do in the public markets and so felt like Investment Banking would be a good way to do that. And so did my last summer that summer 2018 in investment banking at Morgan Stanley and their Tech coverage group and had a positive experience great learning experience, but felt that ultimately the focus there was too short term and to transactional at least or my taste and so wanted to do something that would blend what I liked about banking which is working closely with companies and what I liked about public markets, which is analyzing and understanding companies in a long-term more intellectually honest way and so found myself inventor, especially towards the latter half of college working with different funds including General Catalyst through rough draft Global Founders Capital Romulus capital on female Founders fund and then after school joined Soma Capitol earlier, This year in August actually as their first full-time hire. I'm working on all sorts of things and some of that will talk a little bit about later is a seed stage sector agnostic geography agnostic fund focused on y combinator companies. Very cool. So you did touch on this a little bit, but I'd like to begin with some of the operating rules you've held at startups. So you have experience working for Alpha and a low part of Y combinator spring and winter 2019 batches respectively as well as Lux, which was actually acquired by Volvo the comment car manufacturer in 2017. So beginning with Lux the product that the team was working to build was essentially an app that allowed you to order an on-demand valet. To meet you wherever you are and park your car for you. Is that right? Yes, that's correct. So what was your experience like working with the founders Curtis and Craig over at locks? And what did your day-to-day look like in that role? Yeah, totally. So this is my freshman year of college actually, so I was in Cambridge, Massachusetts at Harvard. So I was actually working more so did a day with the Boston team and the founders were based in SF and headquarters were there as well. So Boston was kind of a newer Branch or more experimental Branch for them and it was a pretty small team when I And obviously I'm not full time since I was a full-time student, but there were just three full-time people and one other interns we were in this pretty small space in downtown Boston. And and the reason why I took on the role, first of all was because I had gone all this advice from my dad and from other older people with more industry experience that working at a start-up and whatever way was a really great training ground because you're able to wear all kinds of hats and be able to learn more skills than you would at a large company where you might probably be pigeonholed in a particular role. And so I definitely felt that way working at Lux in the early days, especially in this early Branch within this already pretty early stage company. And so basically I focus most on the operations and I think what I did mostly and what I liked about it was just how in the weeds I guess you could say I was able to get in terms of the business operation. So it wasn't just super high level like, you know siloed in this Making a pitch deck or something like that. It was super on the ground. I would be interviewing potential valets. I would be going to the garages if there were any issues. I would be monitoring. There's this bird math sort of software bird's eye view software that we would use to understand kind of the flows around the cities where there were problems and your valet looked like they were lost or taking too long and then we would check in on those and we would also do inventory counts to make sure we have the proper jackets and Daughters and things like that for valets and so obviously it wasn't, you know, super sexy if you will work of like strategy or whatever people kind of like to talk about but I think it gave me a really good taste of what actually building a company in the early days in these small team settings and really ironing out core processes that will no doubt change, but be really instrumental to the foundation of a particular sector of the business in this case Boston. So really enjoyed Experienced and learned a ton from everyone involved. So Lux is obviously a startup that you worked with back in 2015 moving us into a startup that you're actually still currently working for. I do want to talk a bit about your work for Alpha. So for our listeners who do not know. Can you talk a little bit about what else it does and what specifically you do for them right now? Yeah, totally. So Alpha is a super exciting platform. As you mentioned. They were part of the most recent y combinator batch and actually they started internally. Y combinator is the YC women's Community. I think four Founders and YC internal team members and he's an investor friends, but actually spun out of I see earlier this year. So January of 2019, which is pretty recently but they've grown incredibly so it's kind of starting from the ground up in January. They've on-boarded over 18,000 active members and basically the way I like to describe it as we were talking about earlier before recording. It is very much like a red a 4 Women inventor attack and startups, but of course unlike Reddit where there can be both helpful as well as some strange things. What's nice about Alpha is that it's a curated Community not so much in the sense of being selective or a leader exclusive but rather everybody in order to post anything you do have to have an account and on Alpha and accounts aren't you know, just randomly made you do have to be vetted and by some standard just basically to make sure your genuine woman. Inventors startups or tuck and have good intentions when joining the platform. But once you're on the platform, you can post, you know, kind of anything within reason and you can also post anonymously since we understand that lots of people might have more sensitive topics that they want to discuss or even you know, how to share some details about their situation that would make them identifiable. And so we do respect people's privacy and once they are on the platform they able to post about really anything that's on their mind and what's been really great about the platform and I've seen it Definitely first hand is how transparent and supportive it is so obviously there's lots of talk on Hinton and on Facebook and things like that. But you know, all of these conversations are really polished if you will and and you know, not super transparent and does don't really touch upon and the taboo issues that are so super important. And so people on welfare are able to talk about things like their fear of being fired or they just got fired or they aren't able to launch their startup and they're going to have to show too. Down or they're facing sexual harassment at work, or they're not able to pay their bills because they move to a new city like SF that's very expensive and are working as a founder or you know, taking a lower salary as an early stage startup employee. And so basically people are able to really speak their mind and really get to the heart of issues very efficiently and but not only just are these grievances or questions, but still receive super actionable super relevant super supportive comforting. Feedback from all members in the platforms. So it's a really great Community with a range of Ages of Women in all of these relevant Industries all around the world and to really love it and in terms of my current role, so I work with them as head of content and that basically means that I run all of the featured post. So if you're on Alpha and you go to the hashtag Spotlight, that's where all our featured Post Live and basically I interview some people usually busier and more high-profile women and then also, And all other women who are interested in writing a featured posts to edit their post and bring them in and share them on the site as well as through our social networks. So you touched on how important it is for not just women but women in Tech in particular to have a candid place where they can talk about different issues in the workplace. Who do you kind of see and this is not to say that there is, you know, a one-size-fits-all or a prototypical user for the platform. But who do you see is kind of a type of user that Alpha can really help out that this community is really built for Yeah, definitely. It was a little bit of a biased view since I'm kind of on the side of things but I think since starting Venture what I've realized and startups as well that we haven't worked full time at a start-up so can't speak as much on that fine. But I think vendor and and perhaps startups to is a very isolating industry. It's kind of strange because we think of a typical schedule but VC and they're constantly running around to events and coughing meetings and they have all these 3045 minute. Meeting scheduled throughout their day really back-to-backs you feel like it's a super social and you know, really rich community and you also think about how small and connected the VC world is which is all very true. But I think what ends up happening is that all of these 3045 minute conversations coffee meetings, even the event happy hours things like that are super superficial and that you know, you kind of go through typical conversation points like sharing deal flow and and you know, kind of Of making introductions and giving your elevator pitch and this and that but you never really kind of build those strong relationships built on could have a true understanding of each other both, you know the with the congratulations stuff as well as the more difficult challenges. And so I think what's really great about Alpha is that it kind of brings this virtual community with certain in-person components. You can certainly meet up with people in local areas and but kind of brings this virtual community that talks about real issues. Is to people who might not have the types of you know, working spaces or a company is or where cultures environments to do. So and I'd say that's particularly at least in my experience and obviously bias since I am and BC and particularly true of you see that I think of startups as well you think of Founders and they're usually either sole founder or co-founder, but they're very lonely doing their own thing, you know working maybe from home by themselves without kind of this huge team culture. To be able to share and form friendships with yeah, those kinds of deep bonds and relationships. I think are just really valuable not just in Tech but really for any industry that you work in and I do think that Jess is downplaying it a bit in terms of some of the folks on the platform, but are there any users in particular that you're just so proud to have using and giving advice to young people on this site? I know you guys do have a lot of really impressive than accomplished women using the platform already. Yeah, definitely. So lots of exciting people we have the CEO and founder of the wing for example, and then we also have had Eileen from Cowboy Ventures founder of cowboy Ventures common do an AMA which is super exciting and then we've also had the founders of Birchbox do an AMA as well. And then I've also interviewed Larisa who's the first employee of Brock's which is very exciting and then I also Recently interviewed use dry martini who is actually a un Goodwill Ambassador and she her story is pretty famous. And basically she escaped Syria and on a dinghy with lots of other people and their engine sink and to jumped into the water and tread water for 3 hours to save the entire boat and bring them to I think an island off of Greece where they were meant to go and then she was one of the members of the refugee Olympics team back in Rio and is trying to Compute for a Tokyo. I'm so super exciting woman kind of all across the board and both in traditional Taco as well as startups as well as VC and also kind of more social movement and human rights human rights movements as well. Those are some extremely cool people to have in your platform. I myself am a huge fan of I lie lie at Cowboy Ventures and then Marissa, obviously as you know, one of those first employees at Brax, I'm sure an extremely valuable source of information. Ocean and advice just for a for young women in Tech. We will link to Alpha in our show notes. So Switching gears here a bit from startups to venture capital a role that you took on during your college Years was the position of a partner at Rough Draft Ventures, which is for those who don't know a VC firm run by college students that invest in businesses created by other college students. So first off, what was your experience like with rough draft and what led you to the role in the first place? Yeah, definitely. So rough draft is probably the highlight of my college experience. I can't commend enough so really love day and basically in terms of what I loved most about it, I think and this is kind of where even my love for Avengers started. I think you know what a high level I had mentioned before what I like about venture has the ability to work Hands-On with Founders, which I couldn't do obviously in public markets world and then still have that intellectual honesty Capital alignment incentive alignment long-term. That I didn't really see in banking but I think that was just sort of my high-level honors in and I'm sure kind of everybody's head level understanding Adventure as well. But I think rough draft really gave me the taste of what working in Venture would be like and I think what was really cool was so for a little bit more context rough draft is basically part of General Catalyst. We operate right out of the DC fund. So but then we don't, you know, obviously engage in other DC internal operations who are kind of this Standalone entity with the support of GC so we weren't staying alone in being lost or being resource list. We of course had the immense and wonderful network of GC and their support but then we also were able to have full agency over the company's resources and invested in and so it was really cool in a really unique experience that I don't think I'll probably have again for a while until you know, I make GP at a fund of course down the line and so I think rough draft is a really cool experience because you weren't just I think typical analyst and Associates understandably. But unfortunately are you know just kind of a cog in the wheel sourcing sourcing we're doing just for Kelly operation just really seeing one part of the process. It was really cold out rough draft was that we owned our full sourcing process and owner full investment evaluation process and a little bit less in the portfolio operations front just because the propeller was so large and there was partner turn over a year to year of people of course graduating from the respective schools and but still were able to really see the life cycle at least from the investing friend. And so basically what What we did there was there was one partner at every school sometimes too, but not too many. So you were really able to master your campus. If you will versus, you know, having like 20 people on campus and stepping on each other's toes. And so I was obviously focused on Harvard College and I was just old partner during my year. So the school year of 2018 through 2019 at Harvard and and we had some Partners at HBS and then worked pretty closely with other Boston Schools like MIT Brown and Stern Babson and Etc and basically Source companies from different parts of the campus and invested in them and supported them regardless of the investment outcome. And ultimately what I really liked about rough draft. I'm was specifically I think kind of pertinent to the Boston ecosystem. So unlike SF or New York or really any part of the country, I'd say Boston startups are super research of men. There's a lot of spinouts from labs and PHD programs things like like that and so on the one hand, it's these really cool really interesting super technical Founders and I would never in a million million years be able to you know, go in and build their product or invent their invention for them, but I felt like I was really able to help them with everything else. They had never seen a pitch deck before and he would have turned she was or even knew what GTM said for or you know, what a business model was. And so I was actually able to help them in these very tangible ways of providing feedback on their deck explaining kind of a whole Side to them explaining the Venture funding and raising process. And so it was really cool to be in the room with some of the smartest people in the world probably but still actually be able to help them whether it was just through advice or being a friend or believing in their idea and the early stage and or unit, providing guidance and capital along these lines. I'm and so that was a really cool experience and lastly in terms of to your earlier question of how I got involved with drugs. So it is kind of a bit of a murky. Process my I don't think there was kind of a standard application process. But basically I had met Peter Boyce and who's the founder of rough draft and now with gc4 I think the past seven years since he graduated from Harvard say met him at different events at Harvard and he was super active on the Harvard's campus when he was a student founding Harvard Ventures and Harvard and both groups. They had participated in and so I was able to meet him as well as Natalie who later led up our GP and And some of the private partners and so is able to kind of get an interview and work my way into the group. Yeah, it sounds like you had a not want to put words in your mouth, but it does sound like you had an extremely positive experience with rough draft. And one thing that I think really does set it apart from other funds is really the ability for Founder's to be working with their peers and other folks their own age. So are there different things that you saw coming up over and over that maybe Founders were missing or struggling with her things in particular that you felt like you were uniquely qualified. Or good at helping founders with I guess what I'm getting at is is there something that you can take across your experiences with rough draft that you can say definitively you know, what this is what Founders are missing or this is what Founders are neglecting that maybe folks on the other side of the table can help out with more. Yeah, totally. I think especially with the Boston ecosystem perhaps less ferrino consumers right up Sir passions are absurd things like that. But especially with the research of an innovation that was coming out of Boston a lot in indefinitely out of Harvard in particular. I think what I was really able to help founders with was kind of take their idea and I obviously just takes time so it wasn't like it was, you know done and achieved overnight but kind of help them in brainstorming different ways, even if it's not something they totally Don it's obviously very hard to execute an in very kind of research oriented spaces, but basically kind of create a sort of roadmap to commercialization, which is what BC's always want to hear and you know, we all know that plans are probably not or very theoretical and in probably not going to stay true forever and there's going to be lots of edits and challenges and mishaps that come up along the way but at least for the sake of presentation and even just for the sake of the team itself, so they have some Direction and this plane could stretch out over the course of a year or two years or three years. So it's not like I saw the whole life cycle of it, but basically sitting down with them to understand kind of the their idea and usually it was pretty moonshot or is very theoretical so I wasn't even trying to understand every single micro layer, but the macro idea of the impact they were trying to have as well as where they were with their product or their research and being able to you're not map out step by step the future but be able to I have helped out in sort of like an 80/20 way. Even of targeting here are the Milestones that you need to reach, you know as a company and as a vc-backed company in order to reach your own impact goals as well and kind of here's how we would reverse engineer the steps that the core steps you need to take to reach those milestones and then here's how you would communicate it to a potential hire or potential partner or the FDA or VC in particular. And so I think that was kind of a really specific value guy. and that I was able to have in that, you know, I'm obviously still working on there certainly many investors who have more sort of commercialization Biotech research experience or able to coach on this but I think especially for those Founders who are super super technical in their brain is super wired to focus on the technical aspects kind of thinking taking a step back and thinking more about practicality and reality and business and kind of those things that feces want to hear and those things that ultimately are may be best for actually building a business versus just doing research in the I buy in bridging that Gap and whistling that I was super passionate about still am really interested in and was really cool to just not even just see like the business grow and the founders get funding and things like that. But Envision the impact they're able to have especially with health care products and things that you know can really change human lives. Absolutely. So moving us into present-day here. You're currently an investor at Summa capital for those that don't know so much capital is a seed stage fund that has invested in the likes of Lambda school house party and cruise automation among others suggest as an investor with Soma Capital. Where does your focus line a daily basis to find the world's next great Founders and startups. Yeah, totally. So I think in terms of our own differentiated and we've always talked about buying a proprietary deal flow. And this is to provide a little bit more contacts that we are a y combinator focused on sort of similar to a liquid to Pioneer fund Rubble fund. And for those listeners do part of those funds are very basically index the top in our case 10 to 15% obviously in quotes because to can really say except in hindsight and it's around 20 to 30 companies per batch and of course as Oh, oh, I know YC has two batches per year once with a demo day in March and the other in August and and so we're sector agnostic and geography agnostics or ultimately just looking for really strong Founders really strong teams and really strong founder such teen Market fit. Then we understanding of the product and the market might and probably should have many cases change tomorrow or the next day or sometime in the future, especially in the seat and precede stages, you know, even at YC demo day. Tuning the most companies don't yet have revenue or have only a little bit of Revenue and are mostly kind of been the Ella Y and pilot stage or can a freemium the free part of the premium stage. And so you really don't feel like metrics and things like that or super predictive and we know that Founders will pivot throughout by see after YC in order to kind of find that fit for themselves and tried even different channels for getting the word out there about their product and then of course the product changes in subduing the market changes in the Suppose seesaw effect kind of ensues and it's something out overnight. So I think we really look for teams that are strong that will figure it out and in terms of doing that so outside of you know, just figuring out who's in YC. We rely a lot on our portfolio companies as well because Founders usually no Founders and are able to you know, provide a stronger referral and recommendation for us and for so much more broadly been, you know, just us putting ourselves in a cold email ever could and so you really rely on Our Network and specifically founders of fact it helped in the past as well as investor friend. So we don't ever lie drowned at this stage. We always co-invest and so we have a lot of collaborative industry relationships or never, you know, fighting very aggressively for allocation on or you know terms or anything like that. I'm receiver founder friendly very investor friendly as well. And so we will get a lot of deal flow from our unique investor Network to and in terms of kind of my day-to-day so obviously during YC season for the bookends of those Indian month and a half in advance of demo day as well as a month after its pretty heads down focus on meeting companies closing deals winning allocations things like that, but really outside of Y combinator season, so right now which is right now, for example, I'm although January kind of things start up again, and we've been focused on raising her third fund actually. So that's going to be targeted to be around a hundred and fifty million. So we're really excited about that and it's really more of a follow-on. and to double down on emerging winners in our current portfolio, so it will be very exciting to really build those long-term Partnerships with our current portfolio, you know, even Beyond just providing help or just being around but actually being able to use super pro rata and really Provide Capital behind our words and behind our conviction and I think it's a really cool strategy as well because we have built this really robust portfolio with some of the names you mentioned for example, and we also have this informational Advantage when it comes with a and the B because we invested The seed and we've been getting you know, the quarterly monthly reports from all these Founders. We've been working with them on the ground. We've been understanding them and so we understand them better hopefully have better relationships with then and also know their business and their traction and metrics and everything like that better to be able to invest with greater conviction and at more favorable terms in later stage deals and that's been a big focus. And I think the other thing I've been doing as well is catching up with current portfolio companies, and I think initially when I started at so At first obviously you have a pretty large portfolios. It's pretty common in the seed stage. We have a little over 200 companies at first. I was kind of overwhelmed frankly with the size and was like, you know, I never would be able to build really meaningful relationships with I'll do a hundred companies and that's probably true at least, you know in a limited amount of time but I think what I have been doing since then is kind of turning it around on a tent or not. Just seeing this as a challenge but rather, you know, we have 200 companies. Yes, it does. God to be calling all the time and I probably won't be calling all of them all the time, but we do have this information on them. And so kind of leveraging the size of the portfolio as a value add for other members in the portfolio group of companies. So, for example, we have this company that's building the pill pack of Latin America there very early. We just invested in them and they've been going through some typical, you know business challenges around scale and things like that. We were one of the early backers of out to Pharmacy for example, which is basically Us has done really well with a pill pack like model and they're a bit later Sager quite a bit later stage. And so I was able to share some learnings from alto with this line America company and so basically doing things like that thinking of intuitive as well as less intuitive connections and to put companies in touch with each other or just share learnings. And then the last part I'd say is kind of the broader relationship developments are interviewing for another team member. We're also going to continuing to develop our investor relationships, which Again is kind of where the deal flow is partly come from and then also just kind of the broader Community doing different events or Founders for investors and thinking about the brand behind the organization to suggest. I do want to zero in on one thing that you said, you know that you guys are looking for really strong Founders or founding teams. What are some of the traits or characteristics that you guys look for when trying to identify these types of really strong founding teams? Yeah, totally. So actually recently wrote an article nice that I was really excited about writing. So I really like to think about you know psychology and about people and not just, you know, evaluating people that sounds pretty negative. But just kind of how do you look not intuitive things? I think a lot of times people focus a lot on the school people went to or whether they worked at Google or not and those, you know are maybe predictive or important but I like to kind of understand people based on their core traits versus, you know, just kind of tags on their resume and so I think A few things that I look for is this founder market then I think you know Brock's is a great example because the quick back story is that both the founders had built this fin tech company that sold at a very high valuation before they even entered College. They're literally high school students and they were both, you know Tech Geniuses that had fintech in their blood when they went to YC they wanted to build a VR company is VR was kind of taking off as an industry back then in the valley at least and at Stanford where they had been at school before they dropped out on but Course, you know, they're really smart and B are mean it's kind of dead now according to kind of a lot of people but back then we are was really On The Rise. And so you think this would be the perfect combination, but actually there wasn't founder market fifties where I've been Tech Founders who are super smart, but they still were fin Tech Founders and then when they pivoted to work on projects, obviously, you know, everything kind of collect and they've been actually the fastest company to become a unicorn and part of that or large part of that I'd say is this found in Market fit so, you know finding that in and seeing NG what really is it about this founder? That's not just making them talented and isolation, but the most talented and most capable person to solve this job. And I think also especially in the early stage when you're looking at Founders who aren't serial entrepreneurs is obviously most Founders. They shouldn't be ruled out of course, but I think you really want to look for people who will stick it out because sometimes you have really smart people who are also really hard working, but it's hard to say whether they would really survive that entrepreneurial Journey. So I think it's really important to Look at people's backgrounds of have they done something ridiculously challenging just for fun have they even had like research experiences where their whole sample for example and in like a lab research studying has been destroyed after like a year or two years worth of work. And did they just give up after that or did they keep going and put together a really good pieces or paper or presentation or whatever and things like that and I think also people with chips on their shoulders and that sounds pretty cliché, but I think the way in which Which these people see the world is that it and it's kind of more of a call option and then than anything else and so when they when you know, when you ask them what would happen if you filled they're not very scared of it. They feel like yes, you know failure is sort of an inconvenience but you know, nothing more than that and the opportunity that they can get from taking a chance is so much larger than the potential for failure and I think also just are looking for really good altruistic people because ultimately there isn't a real way to rationalize becoming a founding It's not going to lead you to and media wealth or fame or anything like that. Maybe you know down the line in the future, but the odds are so slim and the time line is so long and the interim is so hard and so looking for people who really put the problem. They're trying to solve the for themselves and their team behind themselves aren't able to changes people to meet the needs of their team, especially as it grows and you know, they need not just, you know a Founder team to lead but a true CEO they can lead a large team. And so kind of thinking about you know, just people who are really good and really patient and really diligent and really willing to evolve and input others and put the team in fourth idea and really be selfless ultimately. So not just, you know, obviously asking them like if their selfless or not because they're not going to say that's very weird, but I kind of even talking about having them talk about instances where they performed or behaved in the certain way and I think so many times people as investors focus a lot on like oh in the seats are like, oh is this Patrick 60 years it 61.5. I'm in sometimes that's important. But usually it's not because data in the seed stage is really not predicted and of the future for some of the reasons mentioned with all the pivots and everything and lack of data. And so I think what I like to focus more on is just how founder see the world. So seeing how they think and and you know being able to extrapolate that to core traits and behavioral features. That would be actually more fundamental because you know this 6160 number is probably going to change tomorrow. I might not even be relevant by the next hour but these core traits of Founders are probably something they've had since their childhoods or since birth and they're you know, truly their instincts and maybe they'll change those people over time, but they really kind of evolved and around those instincts going to Pivot around those instincts with those instincts being kind of a grounding characteristics and I think I try to get at those and obviously it's hard to tell but try to get it though. They're getting to know the founders and their life story and how they see the world and asking questions that are more along those lines and then you know kind of what is this metric or what's the growth or things like that? So zooming out from more of a qualitative circus at the seed stage of venture investing moving towards more of a quantitative protests in the world of Finance. You also spent some time working for Morgan Stanley as an investment banking analyst and their San Francisco office. What was that experience like and what ultimately LED you to decide not to return to the firm. Obviously. This is a very prestigious job. It's one that's pursued by so many different college students at tops. Was can you walk me through your decision not to return after getting a return offer during your summer there? Yeah, totally I think of the way in which I saw banking is that it's actually truly is a really good career for maybe the majority of the world. I think it's really helpful for four things in particular. The first is if you and banking as and you know a bank at a prestigious Bank like Morgan Stanley the first is if you're looking for a brand name on your resume, maybe you didn't go to the College of your dreams and then you're kind of lacking in that department. Apartment but still want to prove your worth on your resume. So that's really good. But of course, I had gone to Harvard student feel like I needed to collect another brand name and the near-term future and the second is for people who may be studied liberal arts or true humanity is in school and haven't done it, you know much in the way of quantitative analysis and want to brush up or learn those skills. That's super valuable. But I had that applied math and had come from a point to get background from an early age. She didn't really need that and I say the third is if people Like they're locking and work ethic or just want to work on work ethic more. I think it's kind of a boot camp that really puts people in shape, but I had always had you know, maybe even too much anxiety about work and about organization and so didn't really feel like I needed that in the last days of people are super dead set on going into private equity and I personally know private Equity is a great industry, but personally never felt that kind of need to be in the industry and all costs and so felt like kind of all those boxes definitely applied to Too many many people and be the majority of the world's but didn't really apply to me and so felt like banking wasn't a really good fit for me. And I think kind of as you're talking a little bit about earlier before recording. I feel like so many times people theoretically go to you know schools like Harvard to be able to do risk themselves, you know, even if things go bad badly in the future you're still able to say, you know, I did go to Harvard on the certain level of IQ, maybe EQ competence work ethic things like that and then, you know, obviously Leverage your network and whatever and but I think what ends up happening is that people in actuality in this, you know, obviously it is pretty intuitive and probably what most of us would do but they end up becoming addicted to be resting themselves and collecting titles and totally fine to not work in private Equity or banking if you really love the job and you really love the firm and just like how this close connection to it and many people do which is awesome. But I think you know more people than Not end up going into these industries for the wrong reason and mainly for collecting those titles and and they feel like they need to climb this ladder to somewhere. You know, I'd go to Harvard then I go to banking that I go to business school. Then I go to private equity and then I, you know make partner and but kind of what is this all for and so I just felt like it was a ladder to nowhere and it's kind of endless de-risking loop and I wasn't really taking this job and there's so many, you know, good reasons like the job, but I felt like the reasons I was doing it for weren't The right reasons and so I felt like I needed to kind of take me made out of FO Philippe like and as Anita become a founder or you know grow and like go to the middle of nowhere and like do something super random, but I feel like I need to take this First Leap of joining a smaller firm and I'm more up-and-coming firm in an industry. That's still you know, prestigious PC is great. But, you know a little bit kind of off the the main course if you also she relative to my classmates and you know, the broader School in the herd mentality that exist there and So that was kind of my experience but I really loved my summer they are the team is super smart and I think no I already had pretty good work I think going into it, but I think my work out they got even better afterwards even just over the course of a summer and we were able to Morgan Stanley's pretty active in their tuck practice. So we were able to do three IPOs just during my nine weeks over the summer and I was able to be a part of all three of those and they're all pretty different companies. When was Domo software and one was blue energy, which is energy tuck and As Joe knows which is more consumer Hardware consumer electronics. And so really interesting exposure are really great hard-working Innovative team blue support of analysts class and you know the work itself and obviously it's not the most glamorous but did feel like I learned a lot especially in the way of how we operate in and work in teams. So entering our final portion of the show, we're going to dive into a couple shorter questions some fun facts if you will. Are you ready to get started? Yes. Yes, perfect. So if you could go back in time, what advice would you give yourself before? You entered college? Would you change anything about your path thus far? Yeah, I think kind of grand to Harvard. I had this I made my identity around my strength and my strengths were everybody defines her strength on a pretty relative basis. Like I'm good at math because I won this math competition or because I was ranked first in math in my class and coming from high school and I went to a small high school but really any High School doesn't compared to Harvard or really any large University of that caliber. And so I'm I had this kind of existential crisis if you will going into School because you know sort of not being at the top of my class which is very natural, but it was kind of a core part of my identity and I started to lose my identity because I was like, you know, who am I without these strengths? And so I think what I would recommend my former self and in people in this particular situation is to really Define Yourself by your interest because those don't really mean they can change but they can only change on a pretty constructive way and they're going to still be there for you and still for my joy and so provide fulfillment for you regardless of the outcome. I'm so really focusing on those interests and the process of learning and developing versus the outcome because the outcome can be influenced by so many variables that are out of your control. I think that's awesome advice and I really do think it's an important thing for people to remember or just kind of keep at the front of mine from time to time. But what books or podcasts have had the greatest impact on your life thus far and why yeah, so I'd say that my actually favorite podcast. Is this one by Patrick O'Shaughnessy. I'm who runs is that it's very interesting. He actually is a Quant investor in the public markets, but and he runs it's like amazing podcast called invest like Best and and it sounds like kind of cliche and corny but he asked the truly smart as questions some of the smartest people ever and he has this really great way of even like synthesizing what they're saying and kind of providing like the macro view of things which is, you know, kind of more important for most people when they're listening to these things and he features all kinds of people not just in public markets, but actually largely inventor and startups in larger corporations founders. And things like that, he's had people like the founders of Instagram and the founders of Spotify. He said Bill girly and Keith were boy. And so all these really really incredible people and on the platform and it's just been really great to to learn from that and it's been been, you know, one of the most educational experiences that I've had that podcast is awesome. Patrick is such a great interviewer, obviously any opportunity to learn from the likes of go curly and Keith were bought something that's really really cool and just so valuable. So let's fast forward to 6 years from now. What do you hope to have accomplished in your lifetime? And what do you hope to be remembered for? Yeah, definitely. That's a really good question. And I think what I would like to be remembered for is ultimately building taking something from point A to point B, I think a lot of times people and you know are like, oh I joined this company and they were at point B, and they were you know, really rocket ship shipping off to point C and then I was a part of town that was really exciting to see and that's all great. But I think I really kind of want to be in a place where you know where I point a and nobody really believes or very few people really believe in the vision or what we're doing. they understand a and but then kind of having that connection myself and I don't know, you know yet what this will be my having my back conduction and not you know crazy conviction but really evidence driven data driven, but still contouring and conviction in a particular idea or you know way in which I see the world evolving and not just, you know, having this believe in having his ideas, but you know, really really working in the trenches with other people who share that Vision but come with different backgrounds and different viewpoints to kind of make this idea better and really We refine it and stick it out through those tough times and take things take this thing. Whatever. It is from point A to point B, and so really want to be involved in building something really unique from the early days and really kind of taking it from from 0 to 1 if you will. Yeah, I do think there is just a ton of meeting and taking something from scratch or something from just the idea phase and bring it really bringing that into the world and growing that product and scaling the company then obviously that's such a tough Journey so fenders do you need folks like yourself that can help out not just for funding but for support and so many different things along the way but that's a very cool. Thank you. So last but not least. Where is the best place for our listeners to find you Jess? Yes, definitely so few places. The best is probably on medium. So I read a lot there on and you can feel free to follow me there or contact me there on my username. There is justly Jes SLI, and then you can also find me on LinkedIn and feel free to message me there. I also list out my various email addresses depending on you know, whether you're trying to contact me for Alpha or for Soma or for Harvard and talk over something else so you can feel free to read To me there as well. Jesse's been a pleasure. Thank you so much for joining us on the show. Thank you so much for having me. It's been really fun. This has been a surely Tyson with worth. You can find show notes below or at worst card.com that's card with two r's wor th dot CA RR d dot CEO. If you enjoyed this episode, feel free to share with friends or leave a review. We'd really appreciate it. Thanks again for listening.
In this episode, Asher is joined by Jess Li, 23 year old VC at Soma Capital and former Partner at Rough Draft Ventures. We talk through Jess' decision to not return to Morgan Stanley after her junior summer, her experience working for multiple Y Combinator backed startups, and how she thinks about career development. [1:45]: Jess' background and childhood [4:42]: Advice from her father and diving into the world of startups [7:58]: Jess' ongoing work with Elpha (YC S19) - a Reddit type community for women in tech [16:07]: Investing in student-led businesses at Rough Draft Ventures [21:25]: Helping founders to see their blind spots and how VCs can add value [24:43]: Joining Soma Capital and staying on top of 200+ portfolio companies [30:52]: What Jess looks for when evaluating founding teams at the seed stage [36:19]: Closing the door on an investment banking job at Morgan Stanley [41:20]: Jess' favorite podcast and advice for her pre-college self  Worth website - worth.carrd.co Jess' Medium - https://medium.com/@jessli Jess' LinkedIn - https://www.linkedin.com/in/jessica-li-12b74968/ Elpha - https://elpha.com/ Book recommendations - https://www.notion.so/book-podcast-recommendations-59abba1db1db4fc2b9b9a4e08edb0b24 