From Consulting to Law School and Back with Ashwin Aravind (pt. 1)

In this episode, I reconnect with Ashwin Aravind, Head of Operations at Lightyear. Ashwin has been a high-octane performer all his life, spanning school and career. Starting with his undergrad years at UC Berkeley, where Ashwin majored in Molecular and Cell Biology as well as Business Administration, we follow his forays into consulting and law school before ultimately transitioning to the tech sector. Ashwin reflects on the proactive and strategic nature of his career decisions, consulting mentors, and evaluating trade-offs, only to recognize in retrospect how some choices didn't align with his true motivations.

We wrap this conversation with him finishing law school, foregoing the bar, and returning to consulting. Stay tuned after this discussion for Part 2, where we discuss his transition to tech and operations.

00:00 Introduction to the Push-Pull Podcast
02:27 Meet Ashwin Aravind: A Journey Through Education and Career
14:11 Early Career Decisions and Consulting
15:31 The Law School Decision
29:35 Experiences at Stanford Law School
35:38 Questioning the Law School Grind
38:07 Exploring Other Interests at Stanford
41:01 Internships and Realizations
46:05 The Consulting Pivot
51:13 Navigating Post-Law School Decisions
01:00:16 Final Decision: Consulting Over Law

Transcript

Varun Rajan 0:06

Hey, I'm Varun Rajan. Welcome to the Push-Pull Podcast, where we interview professionals about their career transitions, particularly the push and pull factors that inform those transitions. Today is the first part of my conversation with Ashwin Aravind, the head of operations at Lightyear. Ashwin and I both grew up in the Bay Area and went to uc, Berkeley, together for undergrad. It was amazing catching up with him. I introduce him with his title, but we don't actually get to his current role in this discussion. This is going to be another two-parter. Mann's career has so many twists and turns starting as a Molecular and cell biology major. as well as a business major at the Haas school of business, to consulting to law school, and then back to consulting before ending up in tech. Today we'll follow the twists and turns of his journey through law school and why today, even though he embodied the grind set to set himself up for that path, he's not a practicing attorney. Ashwin is so thoughtful when he reflects about every transition, and he goes into such vivid detail about how he approached his ambitions and so humble when taking note of when he was wrong about the decisions that he made In these interviews, we often touch on how we typically can't or don't articulate our true motivations for making a jump. We typically make a gut decision, rationalize it in the moment, and if we're lucky, truly understand ourselves with the benefits of hindsight down the line. Ashwin definitely has some of that too, but more importantly, he often displays the opposite, which is super interesting Throughout his education and career, Ashwin was so proactive and incredibly strategic in how he planned out his next moves. For the most part, he was able to articulate to himself except for some important pivotal moments that you'll hear us talk about exactly what path he was about to take and why he constantly consulted friends, family, mentors. He weighed trade offs, assessed his strengths against the opportunities in front of him. And when we look back on it years later, he found that even though he knew why, he made a lot of the decisions that he made at the time, in retrospect, they were often the wrong decisions. If you've ever looked back on your education or career choices and said, I thought I knew I chose exactly what I did, but looking back, I wasn't being true to what actually mattered to me. This discussion will totally resonate and it definitely did with me.

Varun 2:40

Okay, we're here with Ashwin Aravind, the head of operations at Lightyear. Thanks so much for being with us Ashwin.

Ashwin 2:47

Yeah, thanks Varun. I'm very excited to be here. my name is Ashwin. I lead ops here at Lightyear, here, metaphorically for a remote company. So here could be really anywhere. I've worn many hats over the years, which if the folks in the audience get to know me is both like literal and metaphorical. I'm a big hat collector, so you can probably see my Cal hat.

Varun 3:06

Love the Cal hat.

Ashwin 3:08

Like many, operational kind of, professional hats over the years. last few years I've been in tech. Prior to that I went to law school with this like vague notion of being an attorney. And then before that I. I studied biology, molecular sub biology in college. I had a, again, a vague notion of wanting to get a PhD in the sciences and maybe becoming faculty somewhere. so my career has gone all over the place and like the last, we'll call it 12 years since I graduated but I think like the through line through all of it is just trying to find something that's very meaningful, To me. both kind of something that resonates personally, but also something that pays well, I think ultimately the world we live in today, and for the things that I like in my personal side, like I need something that kind of finds a good balance between like meaningful professional growth and a decent salary

Varun 3:56

Totally.

Ashwin 3:57

support myself and a family that I would like to have.

Varun 3:59

Absolutely. If I were to ask you about the very beginning of your career, how far back would you go? Would you start in undergrad? thinking about what you were doing next?

Ashwin 4:10

Yeah, for sure. So I grew up in the Bay area, went to Cal for undergrad. So obviously there was a lot of stuff that I actually did. Like you would imagine, like you, I was like Indian American growing up in the Bay Area, looking to go to college, like one does, right? To try and build up the college resume, one of which was actually spending like a summer at Cal doing research. And I think that gave me a little insight into being like, oh, snap, maybe I don't have to be a doctor when I, go to college and graduate. there's more that I can do in the hard sciences and the life sciences. and so like when I entered college, like the thought, the thinking I had in my head was, all right, I think, I don't think I wanna be a doctor, but I do like this idea of being in the life sciences, doing biology, doing research, maybe in cancer. and then seeing where that takes me. And so

Varun 4:52

It is super cool. What was the, what did you say? It was a, it was an internship or a fellowship that you had, before you, you went to Cal.

Ashwin 5:00

Yeah, super basic internship. It was like a friend of a friend Sham who worked at a lab. I was like a postdoc at a lab in Berkeley. great guy. and like we, he literally would take pick me up every morning or I'd get dropped off at his place every morning, like my junior year, summer, I want to say.

Varun 5:15

Yeah,

Ashwin 5:16

up to Cal. I do some stuff, I guess in a lab, supporting his research or supporting the research, maybe some of the other folks that are there. and then come home, five or 6:00 PM each day. And that was my junior year, summer. That, and like studying for the SATs

Varun 5:29

of course.

Ashwin 5:30

shout out to Excel. Test prep in Milpitas.

Varun 5:34

what were the kinds of things that, that you were working with during your internship and what was it about it that made you feel like, oh, okay, I could see myself doing more of this? it sounds like you had a little bit of a clarifying moment from this where you were like, oh, maybe this is, like an avenue for me that I didn't think about before.

Ashwin 5:51

Yeah, honestly, fall into this like archetype of, I was a very gifted child that didn't know what the hell he wanted to do, right? And so rather than taking a top down approach, which obviously I'm at like 16 years old, like what top down approach, right? It's what are all the things I can do and then start exploring? It was more what are the things that people slightly older than me have been doing? And let me see if I can, tug on a few strings. and that was part of that, right? That during that timeframe, which was like the late s like mid to late s there were a lot of inter, there were formal programs like at UCSF or Stanford or whatnot that a lot of kids are applying to that I applied to too and I didn't get. And so for me this was like how like still wanted to try and get that experience, then using more informal means of getting it. and then the research itself, again, because this wasn't a formal program like some of these other ones were, it was really more like I was doing, I was just riding shotgun with Shyam as he was like doing his work. and so like he would get me obviously trained on the various protocols that he was in the lab and then, like gel electrophoresis or whatnot. And then I would do like very small contained experiments in favor of the work that he was working on, which at the time, focused on use, if I'm remember this correctly, it was like the use of an anti-malarial compound called artemisinin, I wanna say in breast cancer,

Varun 7:09

Wow.

Ashwin 7:10

CF 10 a breast cancer cells. So it was of stuff that honestly went over my head. Like the most exposure I got to this space prior to this was AP biology. I. Or it's like AP bio. There's some hands-on work. We were doing like lab work, quote unquote, but a lot of it was just like rote memorization. This was like my first ex like exposure, true exposure to actually being in a lab doing stuff that was cutting edge in a way. and using standard protocols that folks across the world were using as well. But I'd only read about, briefly say in a textbook like that really thick AP biology textbook.

Varun 7:43

When you got to Cal, what did you end up majoring in? Where did you think, your career was gonna go and, did that change at all over the course of your time there?

Ashwin 7:53

so I majored in two things. I majored in molecular and cell biology, which kind of is a, it's an extension of what we were just talking about. and then the second major was business administration at the Haas School of business. Now, Berkeley is a little bit unique, or Haas is a little bit unique in that the business degree is a two year degree. So you spend the first two years, a year time at Cal. Taking the prerequisites and then you apply during your sophomore year, and then if you get in, you spend the balance, two years, junior and senior year in the program. and so the first two years of my time there, it was primarily biology focused and like hitting different prereqs. There's no guarantee of getting into the program. So usually people, the way people like work, it is like they hedge, which between business or econ and if they get business, they go to the business school. If they don't get business, they become an econ major. So I was looking at either of those two. then in parallel, and this is like more where my personal side kind of comes into, I love history. So I was also taking history classes, with an eye towards potentially triple majoring

Varun 8:47

Wow.

Ashwin 8:47

as well. the course over the, over the course of the four years, like the biology stayed the same. The business office I got applied to, got into, and then I'd say the same history. I think I just ran outta time to take enough courses to actually be able to major in it. But,

Varun 9:02

Do you have a particular focus within history? I,

Ashwin 9:06

Everything.

Varun 9:07

yeah.

Ashwin 9:07

still study history, like on my own today. I just finished reading a book. quick shout out to Dan Jones Powers and Thrones.

Varun 9:14

Oh.

Ashwin 9:15

fascinating look at what the stuff that happened like in the mid middle ages and some tie-ins to kinda interesting parallels between stuff that happened then to like what you can see today in terms of an example is like double book accounting and banking. so the history for me was more like a lifelong passion. and business though were focused more on a career. what do I think I want to do when I graduate? The interesting thing about all this though is like with biology, spend some time in research labs. while at Cal and I think pretty early on I came to the conclusion that I did not want to get a PhD, and pursue the kind of academic route in the life sciences. I. And I had already made a decision that I wasn't pre-med. So like that I think I took off the table before even arriving at Cal. I just, of that maybe was just like a bias against that bias for wanting to defer into either pre-med or engineering, especially at a place like Cal, where like you're surrounded by folks that kind of have those aspirations. And I think when I started, first very first class at Cal was Chem one A it was in Pimentel Hall two, think was one of the larger halls at Cal. And there were like 500 students crammed into one lecture hall. that was actually one of three concurrent kind of cohorts. So I think that class itself, chem one A had 1500 students,

Varun 10:31

Wow.

Ashwin 10:32

the majority of whom were pre-med at that point. But I think it's like that knew it wasn't pre-med while kinda spending time taking these classes and talking to PhD students and postdocs came to the realization as well that like the path of becoming like a tenured academic and the life sciences is a brutal one. I think the thing that taught me was I wasn't passionate enough to commit years of my life to something that had a non-trivial chance of just going nowhere. And I met enough people that were caught in this conundrum of having spent a number of years either pursuing a PhD or finished a PhD after seven years now are like their second post postdoc and they're still trying to figure it out. I was like, I'm not, I can't commit to that. that's something that kind of gives me genuine kind of pause,

Varun 11:17

Yeah. And going back to the pattern of seeing people who are like, couple years, few years ahead of you, trying to understand what you can about like the treachery in their path or the opportunity right. to inform what your own decisions would be. Yeah. I.

Ashwin 11:33

and that's something like I'm very grateful for because that muscle of just being comfortable asking a lot of questions of older folks, it's not something I really flexed a lot when I was growing up. more often than not it was more like my parents or like the very various aunties and uncles would tell me what the other older folks were doing or you see what they're doing. But I wouldn't pick up the phone or send an email and be like, Hey man, like I, you're a few years further along this path than I am. Do you mind just like giving me five minutes or 10 minutes of your time just to chat about. What you've seen and did it go the way you wanted it to? and I think that steered me well in that cir both that circumstance, but in future kind of circumstances too, where was able to glean from their life experiences that like, oh man, that's really not something I wanna spend a lot of time on. but as it turns out, like I still really enjoyed the life sciences and as I was going through undergrad, I think I was looking at other options. Obviously being in the business school, you seek like consulting, banking, accounting, maybe going into tech. Like at this point, this was the, the late OTTs, early 2000 tens where like that second phase of like tech was starting to pick up coming out of the great recession, healthy job offers were starting to float right with kind of folks graduating from college. and so like I was looking at what else I can do, but I still really liked biology and I was very good at doing well academically, which again, coming back to like my upbringing. well in school still mattered. I know now, and this is maybe like of the wisdom of just getting older and now being in the industry and like hiring people, grades really don't matter all that much. Grades truly are just a proxy for, in part how hard you are working towards something. But think my own lived experience on the biology side of my majors taught me that because I had me, at least that my sleep schedule may have, has maybe has impacted this, but I had, at least at that point, I had a very strong memory and a very good like ability to like logic, my way to answers that allowed for me to like cram and do very well academically. Biology was like incidentally one of those majors that I could optimize for, where it's if I needed to have a high GPA for applying for jobs or eventually apply to law school, I. Doing well, like finding a major where I could do very well in academically, even if that major itself contributed very little to my professional success directly. The GPA still mattered and stuck with biology, both from a, it was still interesting, but also because I knew I could just crush the classes and then bank the bank. The GP,

Varun 14:08

you stuck with biology, you stuck with the MCB major and part of it was just like you, you knew you could achieve in it. tell me a little bit about, tell me what came next. You're considering all of these offers, like where did you end up going after you, you graduated?

Ashwin 14:23

decided I didn't want to be a PhD. Decided, definitely decided didn't want to be a doctor and I wasn't an engineer. So what are the other options that are there? Coming outta Haas again, the major things that folks were doing were banking, consulting, some accounting, and then some tech. what I ended up doing was going into consulting, which I'd say like maybe not majority, but there was a plurality of folks coming out of Haas that went that path. and for me, consulting was an opportunity to really explore. So in my career, I've had two stints in consulting and then a third kind of internship when I was in college. all three of these stints were meant more as like exploratory things. I knew very from the very beginning, the goal was never to stay in consulting long term, which I know is cliche and most people say that, but. I always found the idea of just jumping from project to project a little bit dissatisfying in part because, I don't know, maybe this is it's informed by me playing a lot of video games that involve building cities or building simulations. I like seeing the end output. if I'm gonna put in a ton of work, like I, I don't wanna simply do a project and then leave it and move on to the next thing. I really do wanna see if it actually mattered or not. and so consulting, I obviously didn't have as true flavor of this going into that first job, at LEK when I was in Boston. But I did know that it wasn't gonna be for more than a few years at the very, like very most. and at that point too, had more or less coalesced in my mind that I wanted to apply to law school. So the decision for law school, I think comes from a few different areas. The first, again, coming back to like my childhood, did speech and debate, did some, I was part of this class called We the People, which is like constitutional civics debate. and spent a lot of time my senior year talking about the constitution, different things. there was always some kind of Latin interest in being an attorney and you watch TV shows like Suits or Boston Legal or whatnot, and you get excited about, oh my God, being litigator. That's pretty cool. So there's like this vague concept of being an attorney. And then as I was going through college towards the tail end, I was like, I think between having the likely prerequisites so good GPA, good reference letters, that sort of thing. I was talking to a few friends who were like, yeah, there's this thing called IP law, intellectual Property law that might be interesting. it like marries your hard science background with,

Varun 16:40

Yeah.

Ashwin 16:40

a lawyer, with the fact that it could be potentially lucrative, from a financial standpoint like. I guess I put the thinking together almost from a first principle standpoint. It's like I could put A with B2C and the output is IP lawyer, which pays well and I can, do a thing. in retrospect that was terrible rationale and like reasoning for going to law school, but ex-ante. It sounded very good in my head.

Varun 17:09

Yeah, it's, it sounds like I'm hearing a couple of different things, like in the, this early part of you figuring out what you wanna do is you're trying to see what people around you are doing. You're trying to, you are trying to aim for what's gonna be lucrative and meaningful. And also I. There is this skillset that you have with consuming and remembering a bunch of information, doing that really e efficiently, effectively, and like just being really good at school. that's the, that's something that I think you really banked and not only being able to use logic in your ability to see things through, like in your actual coursework, but that's also how you were constructing what your next step would be. it's I have this and I have this and then this, it like points in this direction and this makes sense to some degree. is that fair?

Ashwin 17:55

that's very fair. And I think there's like always gonna be the hubris of late teens, early twenties, I can do anything I want. I will brute force my way to the right answer if I need to. and again, as my college experience and my, K 12 experience taught me, I have successfully brute force my way to the right answer with cramming for exams or whatnot. So some bad lessons learned along the way that had good kind of outcomes, So I think that's what led me to this notion of, okay, let's apply to law school. Let's see where we can go.

Varun 18:25

and to be clear, you had this idea about law school, like even while you were an undergrad, you said you went into consulting to have exposure, knowing that you'd want to be, somewhere more long-term outside of consulting later, did you think that there was a possibility that consulting could point you to something different other than law school? Or were you okay, whatever I find in consulting that find, that's like maybe resonates is gonna be a post law school thing? how were you actually thinking about it at the time?

Ashwin 18:55

It's a great question. I think I just used consulting somewhat as like a, I don't know. It was, what's the right kind of a framing here. It was just more of something I needed to do during that period between like leaving undergrad and then figuring out what's next. paid well. I was gonna, I was in a new city. I grew up in the Bay Area, went to

Varun 19:16

It is a, it's a gap year with good pay and prestige.

Ashwin 19:20

Exactly the prestige and like maybe there are things that I might figure out professionally that kind of take me away from the law. so maybe like to use like legal jargon I suppose. there was a rebuttable presumption that I was gonna be, that I was gonna go to law school, but if consulting actually showed me something else to rebut said presumption, maybe I go do that instead.

Varun 19:39

Yeah.

Ashwin 19:39

And I think it's funny'cause like I, when I was in Boston working at LEK, I lived with three other guys. just, we had such a good time that year, living in Cambridge and they, we all worked the same firm. One guy, Nick was a year ahead of us, and then the two other Brandon, Derek, we were all the same year. And I think it's the, our experiences were slightly juxtaposed where I think those three were definitely not looking at going to something else afterwards. Like they were in, they were gonna do consulting. They were gonna do it for a couple years and then figure out, do we stick around? Do I go to business school? Do I go do something else? whereas like I I was, I took the LSAT at the end of September. I already was like starting lay down the pieces to go to law school, just as I was starting at my time at LEK. and then I started to get offers from Law schools from January onwards. call it four months into my time in consulting. Like I already had what the next set of steps like. and so by the time, like January, I got into Columbia and Cal, like I think in. In I got into Stanford, I think maybe Harvard as well.

Varun 20:38

Wow.

Ashwin 20:38

March, Chicago, like those were like the fall, like the five schools, right? That's five. The five schools that I applied to. And so by like March, I already had my next steps mapped out. Now there's a difference between having the next steps ma mapped out and like them actually me being the right next steps, which like, again, in retrospect is like, bro, it's you gotta think about these things. But I think this kind of comes back to this maybe like a theme in like my early life. It's gold stars and brass rings. Like when they're in front of you, it becomes so hard to say no to them. It's like, oh, Harvard wants you. And it's oh, as like you're an Indian American, like Harvard, you take Harvard accepts you. You're like, your mind is you lose your mind at that point. and like I live, I lived in, what was it, central Square at the time. That's one T stop away from Harvard Square. So I can already like. I can already visualize myself literally moving one like subway stop over and like living, there, like at that point, like rationality. takes a back seat, just like the emotional kind of the swirl of it all where oh, I can see what I'm doing already, like life is gonna be good. which is then funny because I don't, it didn't necessarily impact like my work output, it made it harder for me then to actually have a rational dialogue with myself to be like, you now have gotten in and you have to make a choice. You have not yet made a choice. Is this the right choice to make?

Varun 21:58

Yeah. Yeah.

Ashwin 21:59

And I also, which I probably should have thought of too, was like you could have deferred, like a lot of these law schools offer deferment by one or two years. if I wasn't prepared to make that choice, should I consider deferment? That's not something I took seriously as an option. Maybe should have.

Varun 22:15

Yeah. you've definitely touched a lot on this not necessarily being the best decision for you. At what point did you figure that out? What, what gave you the information that you were so lacking or not looking for in those months, prior to, acceptance and, and knowing that you were gonna attend?

Ashwin 22:34

Yeah, that's a funny question actually. fast forward a few months to 4th of July weekend. a few friends and I went down to Martha's Vineyard, from Boston. just it's I guess this is my first time on the East Coast, like living on the east coast, doing east coast things. They were like, oh, let's go to Martha's Vineyard. It'll be fun. This is what folks do, out in New England. and like by all accounts, it was, we had a phenomenal time. We drove down, we like took the, ferry from Hyannis port over to Martha's Vineyard. But what st what still stands out to me? This was in July of 2015, so it's like almost 10 years. Like we're coming up on the 10 year anniversary. we are on the cruise or the cruise. The, the sh the ferry back from Martha's Vineyard to Ana port, after a full day in the sun. And we're having a good time. And one of my friends just asks me like, out of the blue, it's Hey man. Like I know you're pretty set on going to law school. I think at this point I was like maybe one or two weeks from giving notice as well that I was gonna leave the consulting firm to, to go to Stanford. why, like what, what drove this decision? it's interesting that you're looking to leave consulting within a year, right? Most people are gonna, they'll try to stick around for at least two before making that, that choice. And obviously because I'm already leaving within that first year, it's, I probably had to put the pieces in motion before, into the fir like early in the first year before any of that. Before we really got serious about being consultants. and I still distinctly remember not being able to answer that question like distinctly like, why are you going to law school? And I was like, I don't know, like straight up, like I don't know. It's, it made sense to me and when I was like putting together the materials, like it, it just made all the sense in the world that I should go be an attorney. IP law was a thing to do. Like I can marry the things I've studied historically with when I was at L-E-K, L-E-K kind of does a lot of work with like pharmaceutical companies and whatnot. So there was like with pharma, right? As an aside, pharma in large part is based off the patents that are derived, from the, like the research that they've done. And also based on FDA regulations that allow for certain drugs to reach market after, going through certain phases of. Of testing. So there's like a he heavy like regulatory and IP component to understanding the pharma market and being able to consult for pharmaceutical companies. So there's also like a part of me that was being informed by my day-today, that kind of gave me more assurance that, okay, yeah, I can also leverage some of the work that I'm doing to like help in this journey of being an IP lawyer. But in that moment, like all the rational reasons, all the reasons I sold myself, they they evaded me, like they eluded me. And I think that's like probably the first moment where I was like having it a like non-trivial level of doubt that maybe I shouldn't be going to law school. but then again, it's we were all exhausted. This was like, seven or 8:00 PM ferry, like dark out, like taking a ferry back. Like maybe this was just me being tired and not actually being able to, like truly think through the whys. But again, like it still stands out that the question was asked, like directly and unambiguously. and to me it wasn't like it was a big group, it was just like we were chatting on the ferry ride back. and like I just failed to answer it. I just did not have anything to say.

Varun 25:54

Yeah. Wow. And so there's a signal there, but a signal that could, at that point, at least, maybe be swept under the rug, what comes next?

Ashwin 26:04

a few weeks later, give notice. I do what I thought everybody does, took a few weeks, went to Europe, do the whole like Euro trip, like solo backpacking. Come back from Europe, settle back into the Bay area, start law school.

Varun 26:18

real quick, you got into Harvard, Columbia. why did you choose Stanford? Were you trying to get closer to home?

Ashwin 26:25

yeah. I chose Stanford for a few reasons. I think there's some more like banal reasons and then there's some more out there reasons, not all equally weighted. I think the most, like more of the banal piece of this was my family's from the Bay. obviously went to college in the Bay, tons of friends in the Bay Area, and I think there was like a level of just homesickness, where it's like I just wanted to come back to, being able to eat my mother's home cooked food, a weekend. I'm just so so just so desiring. I lived in Boston, I'd come back to the Bay. Maybe I came back to the Bay maybe three or four times over the course of the 10 or 11 months that I was there. So think that kind of fed into it. The second reason. I think was more tailored to. Stanford obviously has a very strong IP program. I think it's one of the best IP programs in the nation, if not the world. So that's tied into like my thinking about why I'm gonna law school in the first place. and then that it was like IP coupled with tech where like tech, I think having grown up in the Bay Area, like my dad worked at like Intel and hp, it's like being in the tech environment is something that was very familiar to me. Then you go to Cal or of big companies came outta Cal, right? And a lot of folks that I knew, the engineers mostly at that time were gonna work at tech companies like in Peninsula and whatnot. And so for me too, it was like, okay, IP Tech, they all came together. It's if you're gonna go do this stuff that involves technology, either from a legal standpoint or not, Stanford again is the right bet. And then this is probably the more out there reason for it as well. So Taylor Swift has this song called Style. Which it has like a very specific beat, and like sound that reminded me of, I think it was like an ad from Apple from like the eighties and I was born in 91, so this is like before I was born, but I heard this like melody of about the melody a lot when I was growing up. For whatever reason the song style reminded me so much of that commercial. But more broadly of the Bay Area and like the Rolling Hills, if you're like driving on two 80 and like you see the Hills and that music is coming on and weirdly enough, I don't know if that song dropped in 15 or 14, but it was on the radio a lot. Like when I, like in February, March, April, like around that time when I was making my decision to pick which law schools and like weirdly enough, Taylor Swift then actually has a role to play like building up the nostalgia factor so much for the Bay Area. I don't, again, I don't even know if style has anything to do with that Apple melody or what. I don't even know why or where that connection comes from, but that's what is in my head. that I, that, that would, that also played like a pretty serious role. And just felt so nostalgic for the Bay Area and I was hearing this song a lot and I was like, I just gotta come back.

Varun 29:01

Yeah,

Ashwin 29:02

in the bay.

Varun 29:03

the,

Ashwin 29:03

no knock to any of the other schools, great

Varun 29:06

of course. I don't

Ashwin 29:06

as

Varun 29:07

think anyone's gonna leave listening to this podcast being like, this dude was talking smack about Columbia.

Ashwin 29:15

yeah, so that's, that, that's all it was. I had fun enjoying, visiting the other schools and obviously I lived down the road from Harvard, so it's like I a few opportunities to go visit. my parents also came through and they bought the Harvard swag and there's a picture of us in the Harvard Quad, think like my mom is like wearing a Harvard Law like jacket and like my dad's looking really proud and there's like me, But yeah, no, Stanford, I think there was a deep personal resonance for the Bay Area coupled with what seemed like the right, it seemed like the right environment to be in for what I thought I wanted to do

Varun 29:45

Yeah. Yep. Totally makes sense. okay, so you get there, you were talking about, Stanford's on a quarter system. what do you encounter when you get there?

Ashwin 29:53

Yeah, so Stanford being on the quarter system is interesting. So Cal obviously is semesters like we started in late August and we go from there. Stanford being on the quarter means we started in late, like mid to late September, but for the first years or one Ls as they're known, we started a bit earlier than the, like the two Ls or the three Ls in part because at that point Stanford's first quarter curriculum was probably one of the more rigorous amongst all the big law schools in the nation.

Varun 30:19

I.

Ashwin 30:19

We had four doctrinal classes and all doctrinal meant was like, these are foundational, like out, like classes that tie to foundational topics in the law. and really meant to set the tone and tenor for the rest of like your legal education, but also that's the base upon which you then will practice law down the road depending on which area of the law you go into. four doctrinal classes and a legal reading and writing class again meant to help teach you how to exactly write a brief or write a memo or whatever it is. maybe less relevant if you go do m and a work or corporate work more relevant if you want to be a litigator. But at that point, most folks are still figuring out one or the other. So everybody takes that class. reason that I'm bringing this up is because we started before the two Ls, the second years, the three Ls and the third years showed up, very much felt like a bootcamp where there were, Stanford is a law school. Each class is fairly small, like 180 JD students. it's smaller than my high school. Like my high school graduating class was like 500 kids. So it's like this was, I'll call it a third, the size of that. so you got to know people either immensely well, or you very at the very least, knew everybody by face and name and like you maybe had one or two conversations with'em. It's also because of the rigor of the four doctrinal classes in legal writing. It really is a crucible, like it truly was a crucible that we were all going through together. what that meant though was as with any crucible, and I'd actually consider Cal to be a crucible as well, right? When you're in huge classes and the ability to do academically, especially in the business school side of things like hinged on, like getting one correct answer versus not. that could be the difference between an A and a b plus. this too was a crucible where it was for most of us first time going through anything like this. We had to do like maybe a few hundred pages of reading before each class, like get us prepared to what we had to get done. this also then helped truly confront the question perhaps why am I here? and do I actually enjoy doing this work that kind of would prepare for my eventual time as an attorney? Or am I here to do school and crush school the way I approached Cal back in the day?

Varun 32:28

did it feel comfortable to you, the crushing school aspect of it? did it feel familiar, compared to your time at Cal and in high school and stuff, the kind of things that you were indexing on? No.

Ashwin 32:41

no. This is a very different beast. law school is not meant. Law school is like at its core, it's supposed to be a vocational school, right? It's meant to prepare you for a very specific career in the law. I. And that's something when I talk to like prospects that are looking to go to law school or folks get into Stanford on occasion, I'll hop on the call with folks. that's something I'm very clear about. if you're gonna go to law school, be prepared to practice the law. Don't go to law school'cause you wanna do policy work, don't go to law school'cause you want to go run for office. Don't go to law school'cause you think that'll look good on a resume to go be CEO of a company. Like there are better, less expensive, and more like efficient paths to getting to those outcomes than going to law school. Investing the time and the money. and then not practicing afterwards just to go pursue something else. And then when you're, so then you take that environment and you like, you see the students that go there. There are students that are like me that kind of fell backwards into the law, so to speak. Like they did very well academically. They didn't know what else to do. They applied to law school. Like I think you're always gonna see that cohort. I. You may actually see more of that cohort now with the macro environment. when folks

Varun 33:48

Totally. Law school applications are up, significantly, right? Yeah.

Ashwin 33:53

they are spiking. but for a lot of the folks that are there, with families, like a non-trivial number of like folks who are veterans too, that are like more than a few years out of a formative undergrad experience. they're there because they, they have a fundamental belief that they wanna be a lawyer and therefore they will work towards that belief. and that's like law school generally. And then like when you're at a place like Stanford, these are folks who are not just working towards that belief, but they are exceptional, They had to do very well on like an undergrad to get the grades and other accolades, like Rhode scholarships or whatnot, to be able to apply and get into places like Stanford or Harvard or Yale. Columbia, Chicago, Cal, I'll just throw'em all out there. NYU that's where my wife won. have to, to work. It's like very hard and honestly have a non-trivial amount of luck in certain things to be able to get into this school. And then that then comes like full force when you're in class with them and you see who these folks are. Like they will do the hundreds of pages of reading and they'll put in the time to then think through, okay, what are the next set of questions that I should be thinking about? they're gonna be immensely structured and like taking very rigorous notes. And then, when they're writing their briefs or they're whatnot, they're like the people that you're with. And I'm, this is one of the things I'm deeply appreciative about law school for. are very serious individuals. granted, like they have levity in their off time and whatnot, but they're very serious individuals that really do raise the caliber of everybody else around them. And you see this in other environments, like you go to like early Facebook or whatnot, right? People talk about the same thing. The thing though that I realized was am, I'd like to consider myself to be very serious and smart and hardworking. But because I didn't have a fundamental belief in actually wanting to be an attorney, it became harder for me to actually keep pace, if that makes sense. At a certain point, this is not necessarily in like the first term, but over the course of three years, probably closer towards the end of like my first year, I was like, I do, I really care enough to keep grinding and keep putting in the work when I know this isn't for me. Whereas like in college, I could brute force my way to getting an A. It's much harder to brute force your way to getting, and at Stanford didn't have like real grades, they had honors and pass. It's to get that, that like honors or get a book prize for the top person in the class, like to get that. Accolade, you really had to work really hard, and smart'cause there's just too much material to necessarily go over. So you really had to understand what pieces mattered, what pieces didn't, and then be able to make a cogent argument on the base of that. and so that's like where maybe some of the dissonance that I was able, I was comfortable living with K through 12 of I didn't really care for this subject matter, but I'll get an A'cause that's what I do. That's the dissonance I lived with in college. biology. It's interesting. It's definitely interesting. Or physics, it's interesting, but I'm not really, I don't actually care to take this concept any further. I just need to understand what Cullum's law is so I can get the a on that physics exam and then move on to the next thing. You couldn't really do that in law school. And that kind of it led me to a place of just making a decision of I continue to take classes at the law school? And there's certain courses that were like notorious for. There's a cohort of folks called Gunner. These are folks that are gunning, quote unquote, to go do the most prestigious things. Go clerk for a federal judge, maybe go clerk for the Supreme Court one day. go work at the biggest white shoe firms in the world where they're making a ridiculous amount of money. Getting all the brass rings. Do I really want to spend my time in classes or in environments surrounded by folks like that where the, it is hyper competitive, but I'm not really sure what I'm getting out of it Or do I wanna spend time in places like the business school or the engineering school where Stanford is a phenomenal school, kind of end to end. I say that wearing Cal Hat, and I say that as one who hates the Stanford football team. No offense like Gilberts, but Stanford is a phenomenal school. and so I had to ask myself the question, okay, if I only have 24 hours in the day and I'm only here for three years and I'm. I'm like paying a few hundred thousand dollars right? To, for the privilege of attending this school that I have to pay Uncle Sam for afterwards. Do I spend that time the law school or do I explore other things? And the decision I ultimately made was, it has to be other things. Like it cannot simply be law school

Varun 38:24

Yeah. Yeah. And so what were those other things that you ended up exploring while you were there?

Ashwin 38:30

Stanford does make it relatively easy to apply to classes in other parts of the campus. I think that's one of the smarter things that they have done to try and ensure that there's more crossbreeding of ideas. and likely, one of the reasons why you see so many startups coming out of Stanford that are pretty cross-functional in terms of their founding team. It's like you'll see the CEO type coming from the business school,

Varun 38:51

I.

Ashwin 38:52

are a lot of classes where the business school and the engineering school kind of have cohorts of students sitting next to each other, being able to build stuff Law school less And I think this is something law school's tried to fix in like the last seven years since I've graduated. It's like doing more cross-functional work, we'll call it across campus. but I took classes like engineering school, CS classes, where I'm sitting next to like year olds, learning how to code for the first time or like taking more like advanced kind of coding classes or whatnot. I took classes at the business school on like investing, private equity investing. I'm a big sports head, so it's sports, business management, hearing folks come in from various corners of the world talking about how they manage sports, some of whom were lawyers, who had made the transition from, being an attorney at a firm or something to then running a business, which obviously has special resonance for me.'cause at that point wasn't sure if I wanted to still go into the law for a few years. Kinda similar to consulting, right? but it was really meant to give me a breadth of like just, okay, what else is here? think part of what I didn't get at Cal, which I think Cal that point about a little over a decade ago, did not do a good job of, but they do a better job of today is promoting more of that kind of cross-functional kind of collaboration, whatnot. Stanford I think was a lot better about that I had a few friends who actually dropped out, not from Stanford but from other programs where they tried it for a year. They realized it wasn't for them. they went on to do some amazing things'cause they followed their passion. And I think in many senses, like maybe that was what I should have done. It's like I, if I cynically got a, gotten what I needed from Stanford, like I got the degree I got the name of the school on the resume at the law school too. So that kind of commands a certain prestige. I didn't necessarily need the JD if I wasn't gonna practice.

Varun 40:35

Yeah.

Ashwin 40:36

And so I have a friend actually who I think, like he attended Stanford Business School for a day and then dropped out and like he then fundraised in the back of that, right? So it's I probably got the value I needed, and could have gone into saved two years of like my prime twenties going and doing something else. But I think part of me too was a little risk averse where I wasn't sure what that next step was. Like. My buddy obviously knew he wanted to do a startup. Some other friends knew they wanted to get into politics. I didn't have that. I didn't know what I wanted to do. And so Stanford gave me a bit of a safety net to be like, all right, you're still paying for this privilege, but you at least can justify why you weren't looking at other, doing other things during that period while you're in school. And I spent one summer, in government DC trying to see if okay, maybe like regulatory work might be interesting. I spent a few quarters doing, I was part of an IP practicum, and then a couple other quarters in the IP clinic, like doing actual IP, hands-on IP work, like writing briefs. I once, I spent my second summer working at a white shoe firm in New York, doing half the summer in m and a work, half the summer in patent litigation. Again, exploring like, is this something I really wanted to do? work at a big firm? Did I wanna live in New York City? did I wanna do m and a work? Did I wanna do patent litigation work? so I ate from the buffet,

Varun 41:47

Yeah,

Ashwin 41:48

I, I took myself, we used to have this restaurant called Sweet Tomatoes. It's sun for RIP,

Varun 41:52

right. RIP.

Ashwin 41:54

RIP. So good. but it's like going to, you go to the buffet counter, right? And I want to try this. I'll take one scoop and if it tastes good, I'll take more. more often than not that one scoop was enough for me to throw the spoon in the trash and move on to the next,

Varun 42:07

This is super interesting, man. it, it feels to me, it sounds to me like you started to approach a law school almost like you were approaching consulting the first time around. this is something for me to do. It comes with a prestige. It's, it's an expensive, level of prestige, but it does provide some level of like safety and security that, like you're a law student at Stanford, while you're doing all of this exploration, while you figure out do I commit to this or not? and so because you've committed, there's this expectation that you stay there for three years. So the momentum and the kind of what's the word that I'm looking for? I think there's like an inertia

Ashwin 42:46

to it, right?

Varun 42:47

Inertia. That's that. Yeah, that's it. That's it.

Ashwin 42:49

there's a certain inertia that just leads you like, all right, I'm here. I'm surrounded by some really successful people, which I've graduated. It's been seven years since I graduated. So now you're starting to see where their final form is, like evolving to right. Folks who have like successfully run for office folks that are on the cusp of making partner with their law firms. Like can now appreciate that for a lot of these folks, the work that we put in three years ago is actually bearing fruit in a very meaningful way. but I think the challenge that I always faced back then was like, did I even care for those outcomes necessarily?

Varun 43:19

Yeah.

Ashwin 43:21

And that's where between the crucible of law school kind of really forcing you to ask the question, but I want to keep spending time in the here and now. In the short term, the here and now to do this. And then for a lot of those folks, the answer was maybe not yes in the short term, but the answer was, it was answered for them in the longer term. It's but I do want to go to work in a law firm and I wanna be a partner. I want to go do these things. That having a legal background form might be helpful. that I think helped convince them to stay locked in. couldn't do that. Like I, I didn't see both a short-term kind of outcome here that I wanted to optimize for. And I, I definitely didn't see a long-term outcome, but part of that eating from the buffet was trying to ask the question of, is there a long-term outcome that I could optimize for?

Varun 44:03

Yeah.

Ashwin 44:03

what I ended up learning was in eating from this like buffet and asking myself. Each of these questions. I also wanted to make sure that I have a regret three years, five years, 10 years afterwards being like, oh, I should have probably tried this thing when I was in law school.

Varun 44:19

Yeah, that's fair. Some, somebody brings up some particular thing that sounds good on paper, but you weren't able to try working in DC doing policy work, and you're like, oh, that actually could have been really interesting. I wish I'd at least put myself through that. And, then tho those what ifs pop up. But you were operating to minimize the what ifs.

Ashwin 44:35

I recognized I didn't need to be in all of these classes that were required to get the notice, like the notice I needed from say, a Supreme Court judge for, to be a clerk on the Supreme Court or something like that. So the ability to try different things that didn't necessarily ladder up on like the same path that some brass ring helped a lot. Where I can I can try something from here and I can try something from there. And if I like this, maybe I can, click in a little bit more and go one, one step further.

Varun 45:00

this was like.

Ashwin 45:01

did,

Varun 45:02

This was a moment where you were seeing all of the kind of like proxy metrics for success and outcomes like the grades and performing up to the level of or beyond your other peers that all of your other peers were like dead set on. This was an environment compared to your prior academic environments where you were able to say actually, I'm just not as committed to this, so let me take a step back and see what else I can get out of this. that, that sounds like a real, honest and like meaningful pivot in terms of what you were putting your attention to being in an academic environment.

Ashwin 45:33

I think it's a great summation. and it stands in contrast to Cal, where it's like Cal, I was optimizing for the GPA, So I sacrifice taking, getting like that history major. I sacrifice, just doing other, like being able to eat from the buffet, like a study of abroad, right? But like I didn't get much opportunity to travel in college because I had to do internships or research or whatever it was. I had, I was double majoring and the majors had a lot of requirements. I was intentional in law school not to make that same mistake. and it was reinforced by the US understanding that brute forcing didn't get me the short term outcome. I cared for brute forcing. I also didn't care for the longer term outcome that brute forcing may potentially bear fruit.

Varun 46:16

Yeah, totally makes sense. and the other thing, we, we haven't had a, chance to really dig into like push and pull factors in your transitions, because I think like you've been, up until this point, it sounds like you've been relatively proactive in figuring out what step was gonna be next for you. And so I'm curious with the internships, like the, all of the things that you were trying in the buffet, what were the things that you liked and didn't like about the work that you were actually exploring? The potential pathways, post law school,

Ashwin 46:44

Yeah. I think the first caveat I'll throw out for a lot of this, and probably important for the audience as well, is there is way too much luck that just goes into so much of what opportunities open up before you.

Varun 46:56

I

Ashwin 46:56

It's like right time, right place, this was my experience and if I had to rerun this simulation 10 times, I like to get 10 different outcomes. so like with the DC internship, I did my one L summer. I was working in DC at one of the kind of three letter agencies for one of the commissioners. and granted, the commissioner had different politics than I did, but part of my reason for joining this internship was just like, get to know the other side a little bit more. understand what they cared about, what they didn't care about. Humanize them too, a little bit too, right?'cause you grow up in the Bay Area, it's very blue. And so for me, I just wanted to open my, it wasn't just like a professional opening of the eyes. It was also like, I just wanna know more about these folks. in addition to that, I also wanted to see if working in government was something that was interesting to me. Granted again, current environment, maybe working in government might be a little bit more difficult. But like back then, I. Government was seen as a very, it was a relatively lower paying role than going to a big firm, but was stable, right? And it's like you'd get to the office between nine and nine 30 and you would leave between four 30 and five and you would leave like your, you'd leave your literal machine at work, There's no, I'm in tech now, right? I'm fully remote. I might be clocking in at 8:00 PM, 9:00 PM 10:00 PM there was none of that. It's when you left work, you went home, you could maybe have family and some kids like you can spend the rest of the evening with them and then you wake up the next morning, you can prepare your kids to school, drop them off at school, maybe have a hardy breakfast, and then come in and you can do that. The other piece about government too is like people that are there, by and large, they had a very clear mission and their mission was, we want to make the United States a better place to live. which is not a mission that's necessarily shared in private practice, where in private practice it's like. Yes, I wanna as defend the interests of my clients. But for a lot of folks, especially more junior folks, it's just wanna get the bag. it's like the goal here is to get the bag. If I can help people along the way, great. so it's, the ethos is slightly different. And so I wanted to see if that ethos, again, parts of it map like resonated with me. Like the idea of serving others resonated a lot. parts of it, as I mentioned before, like being on a financially stable footing was paramount. that didn't resonate. But I also wanted to know if like maybe ante. I didn't know what I wanted,

Varun 49:14

Yeah.

Ashwin 49:15

I thought I wanted the finances. But then I go there and I see these guys have a phenomenal life and they get paid well enough to live a good life. that's it for me. I think what I learned during that experience though, is it just wasn't, and I think that's is part of why I left the law and part of why I left the law. Generally it's the law moves slowly and I think in government. The law should move slowly and they should measure twice, cut once because you're impacting thousands if not millions of people with the decisions that get made very different than operating in a startup or even at a company, right? Where it's like the total radius of like the damage could, is far more limited and that can be meaningful. But for me, at that stage of my life, it just wasn't like, it was like I needed to be in an environment that was moving faster where

Varun 50:00

Totally.

Ashwin 50:00

to outcomes. and obviously the pay didn't exactly contribute favorably in that direction.

Varun 50:04

Yeah.

Ashwin 50:05

the second role then was, the following summer where I worked at a law firm, right? So I kept the cop the opposite experience. I was in New York. so faster pace of life generally. And then at a law firm, things are moving a lot faster. And I think there, there's like a different set of learnings for me where I didn't really know. it meant to practice as an attorney, like at a firm, just what I'd seen on tv. Like you watch suits and you're like, yeah, let's be Harvey Specter guys. that'd be freaking awesome. but that's that's not at all what it is. Like it's a lot more mundane. it's a lot of just like pushing paper. And I think there too, it's yes, you're, you have impact because you are the backstop for like a billion dollar deal or like you're the guy or woman or whomever that's like going into court, right? To argue for on behalf of your client. But even that happens so infrequently that it's mostly just pushing paper. there too, it's like you're working really long hours and maybe you're getting good outcomes for your clients. But I couldn't come to care for that. And it was similar to like consulting words. In part. You do a lot of like work on behalf of your customer, but ultimately it's it's the customer who then has the business to run. That then continues afterwards. And I think that's also like where I started to have that the. The inkling of maybe I should return back to consulting post law school as a bit of a re-pivot into the business world and try to figure out where it is that I wanted to play.

Varun 51:25

tell me a little bit more about that actually. how did that inform, because I'm, I hear a couple of different things when I talk about this particular internship experience working for clients, and then the consulting, like what you had done before, right? One of the things you said about consulting was like, Hey, I can do something for my clients, but I'm not able to stick around and be really invested in the wins and how they like manifest in terms of outcomes Long term here, it's something similar, but like you are seeing the wins. Like the win is what you're doing for your client, right? Like the, it's seeing that, that outcome right away. But it sounds like you also weren't. it was still in a position where you felt not as invested in each client. and, there's a long set of questions, but it's I'm just trying to make sense of what were the kind of like parallels and, differences that you were seeing between these two worlds and how did that inform actually wanting to pivot back into consulting post grad school?

Ashwin 52:19

it's a good set of questions and it's, I think it is important to raise in part because when you think of consulting or banking or a lo being a lawyer, right? It's service industries, where you're working alongside a customer or your client to go do things And you are right that like ultimately as a litigator, your goal is to win, And then on the corporate side, m and a or cap markets or whatnot is to close deals. Whatever those deals might be, there is like a very clear outcome that you're going towards. The outcomes though, for me, were not satisfying. Yes, we win. But then you move on to the next thing. What, like, where does that win then build into, which I think is somewhat not, it's not something you see a ton of in the law. The law is very project oriented, you're not necessarily moving on to a follow on stage of that project. You might just be moving on to something entirely different. Ultimately the lawyers are the ones giving advice on the legal matters. But as I've come to appreciate having been, become an operator, in my years since law school, the lawyers ultimately are there to say yes or no. But if you're pushing a lawyer to say yes, you'll get them to say yes.

Varun 53:23

Yeah. You serve the client and their, you know what they want at the end of the day.

Ashwin 53:27

of the day, the business matters more than the lawyer itself. And so maybe that's a little bit different in litigation where it's like the only person that can really advocate outside of pro se work, like the only person that can really advocate is the lawyer. But there too, it's like litigation is very, it's very, self encapsulated. It's like there's a specific lawsuit that's happening and maybe the lawyers or the kings of the kingdom for that piece of it. But then they're not then impacting necessarily the rest of the business. At most. It's advice, it's like an advice or, they're providing advice to the rest of the business, but it's not directly impacting where the business goes, how they're making money, et cetera. And I think that's like where like the, it somewhat broke the illusion for me. being a lawyer is all powerful and whatnot. It's like at the end of the day, you are advising folks, and this is obviously more true on the corporate side where if I was at one firm, but there are like 15 other V 15 firms, like there are 15 other firms that I can call, or 14 other firms that I can call up to the exact same work. as a lawyer are very fungible and like relationships matter, but ultimately the skillset is very fungible. That kind of turned me off. There isn't, there wasn't, I didn't find meaning in being, I could be like a partner that's getting paid two and a half million dollars a year and I feel high and mighty, but you're like, ultimately you're still at the beck and call of the customer. the customer is

Varun 54:44

highly paid, high prestige, but replaceable at the end of the day.

Ashwin 54:49

fungible.

Varun 54:50

Yeah.

Ashwin 54:50

fungible and the era. And we were at that point, like at the very beginning of, we'll call it the era of ai, and there were like a lot of conversations around Stanford, around oh, what's the role of AI and this and that. I was still looking at IP somewhat, and obviously I was spending a little bit of time dabbling in the corporate m and a side of things. These are areas of the law that are very heavy on like precedent and like using existing materials to craft the next set of materials. If you now think of like the evolution of gen ai, LLMs and what they're able to do, it's like a lot of people, like a lot of cynics call it like glorified auto complete. I think it obviously goes beyond that, but if a lot of the work that these lawyers are doing involves like taking existing deal structures, like replacing the name of the company at the top, some deal terms, but like copying deal terms from other deals, deal deals that they've done, at a certain point you have to ask yourself the question. Where's like the event horizon of if you join in, if you're like a super junior, like associate, either you lose out on that role entirely or your role like just evolves in such a way that you're no longer like actually doing like lawyering. It's like you're doing more like managing an LLM that's like doing the work instead. but not necessarily an LM. There are other kind of tools here too, but I don't know. I, it, I got very cynical as a result of I didn't know where the career was going and even if the career was still going in the way it had been going for the last 40 years without necessarily the outcome I cared for, when ultimately I cared to be the guy in the room making the decision for the business itself.

Varun 56:15

So there, there was some attraction to being the decision maker that came as a part of it. And this is actually a perfect, like push and pull, right? There's some level of okay, hold on. there's more actual like decision making, maybe some creativity, and obviously actually like ownership when it comes to being in the actual business and like making a business decision. Whereas you didn't get that, and also you saw this kind of like macro level picture of like whole, is this work that I'm doing actually new generative in any way? Like, how is this gonna change in the future? and it just ends up being like, you just, it's like templates on templates, like getting really deep and in the weeds and like very detailed, but like you're copying and pasting a bunch basically is how you're seeing it maybe.

Ashwin 56:56

yeah.

Varun 56:57

yeah,

Ashwin 56:57

isn't to say that the work that the lawyers are doing isn't valuable. Like

Varun 57:00

of course. Yeah.

Ashwin 57:02

who will push back on maybe some of my characterization here. But I think it's one of those areas where I think about this too right now is ops in my current role, it's a lot of what a gen AI tool might be able to do. Can replace what junior associates do, and if the junior folks aren't getting the same training today as they were previously, does that necessarily make them as good of an attorney or a lawyer or an advocate, the road or like you've now put in so many reps, you build that muscle memory that may not come about. Obviously that is one example here of a reason why I wasn't bullish, perhaps on a career path in this space.

Varun 57:35

Yep.

Ashwin 57:35

primary reason, but it led back to when you start thinking about the various outcomes and you kind of risk adjust your ability to achieve set outcomes. This was one of those factors that increased the risk for me in a way that I didn't, maybe by itself wasn't sufficient to make the path, the path un like less than palatable, but it moved me in that direction.

Varun 57:56

Totally, that, that makes perfect sense. Yeah, it is act actually really interesting because the thesis of the show is really that the more explicit that we get about our motivations, helps us make better decisions in the future. the thing that I'm hearing from your whole career trajectory so far, is that like you were doing a lot of that, articulation of like why you were going to, towards specific things, why you made certain decisions, like going to law school and then finding out that logic was not necessarily pointed at things that would truly resonate with you. the things that you're probably like most grateful for doing were the things that were like gut decisions. you took that approach of being very explicit, and then found in post that maybe that wasn't what resonated. one question I would have before we move on from law school, let's say, is like, knowing all that you did now and then, you go back into consulting, what would you have thought about differently, with any of these things like going into law school, let's say for the first time? some of the stuff is you see it when you get there, right? And so there's no substitute for that too. and maybe that's the answer, but I'm curious if you have a, in retrospect, I might have considered X, Y, and Z instead, given what I know now

Ashwin 59:05

I think with law school, that's probably the one I could answer like directly. It's like only go and I, again, I tell this to everybody I talk to who's interested in gonna law school only go to law school. if you want to be a lawyer, like you may not know, you may not have confirmation about being a lawyer. Like you kind have to get to law school and then summer and whatnot, you can build some evidence base just by being a paralegal or other things, even though that's not exactly being a lawyer. But don't go to law school if you're not set on being a lawyer, at least initially going in to law school like that. I think you do yourself a massive disservice on that front because law school, it is expensive. It will take years off your life that you could otherwise be spending towards other pursuits. and like in my case, the opportunity cost was, had I stayed in consulting and followed the path that other folks had done, like there was a financial opportunity cost, like I went. A few hundred grand in the hole instead of making a lot of money, doing other things. maybe joining tech, I probably could have had more control over my twenties, in a way where when you're in law school, you're almost like you put in a capsule don't go unless you have conviction that you want to be an attorney. And definitely don't go if like you're only using this to jump into other things.

Varun 1:00:12

I think your emphasis on law school is like a vocational school is is actually like really apt given everything that you've told me. okay, so you're wrapping up at law school. how did you end up back in consulting? Did you have a few offers on the table? what were you looking at? going towards?

Ashwin 1:00:28

Yeah. My, my journey back to consulting is an interesting one. I actually, so I was, the summer I was interning at the law firm in New York. the law firm actually had a Starbucks in the, on the ground floor. I actually applied to BCG in the Starbucks. I think it was like a Saturday. I only applied to BCG and McKinsey I interviewed McKinsey didn't get the offer. BCG was a little bit more of a journey because like they wanted to interview me in the fall during like their fall recruitment cycle. I think early September or late August when I was in India for my cousin's wedding. And so there's no way for me to make it. And because BCG has a pretty rigorous, schedule for like, when they do these interviews, the next interview slot that I could get would've been in April. So I had to wait for most of like my three L year. and so at that point, it's like I didn't have a consulting offer or anything for most of like actually my entire three all year. instead what I was doing was like, I still had a notion of wanting to return to the law firm, be a lawyer. I was like talking to a few folks who were in, at like tech companies. maybe I joined Dropbox or one of these guys that are like in the peninsula ways from Stanford, so I can get coffee and talk to some folks. But I think the reason I didn't pull the trigger on moving forward with any of those processes was this like albatross of debt hanging around my neck it was difficult for me to say yes to a startup in part because to keep in mind, I only had a year of work experience before law school. So it's like I, yes, I went to Stanford and yes, maybe some places might treat me as a post MBA hire, but like I didn't have a lot of work experience that I could hang my hat on. And like any entry salary offer would've been woefully too low for me to be able to start servicing the debt that I had.

Varun 1:02:15

Yep.

Ashwin 1:02:16

and this was still ZIRP, like this was 2018, right? So there was still like a ZIRP environment, so maybe the equity pays off in a big way. But Uncle Sam doesn't care about the equity value

Varun 1:02:26

Right.

Ashwin 1:02:26

of ISOs. Uncle Sam needs cash, like cold hard cash, at a ludicrous interest rate, like it was all unsubsidized or whatever the term is. I think it's on subsidized. so I was paying like the interest was like accrue, accruing over the course of my three years, then it continued to accrue even afterwards, practically I needed to find a way to get refinanced. and I could not get refinancing unless I had a certain salary threshold. So startups were off the table. And then a lot of tech companies were off the table too because like they would effectively treat me as somebody who was like 24 or 25 coming in with maybe a year or two of like work experience and like that. Like I just couldn't afford that.

Varun 1:03:07

Yep.

Ashwin 1:03:08

this is also one of those areas where it's important to note when I went to college, like I got a lot of scholarships, but my parents helped bridge the rest. that was their kind of promise. It's, we'll pay for your undergrad. But, and this was something we had a very explicit discussion on. They would not pay a dime towards my law school. Like any grad school I did was on my was on me. and so I'm very grateful, right? And appreciate the privilege that I had going into college as a result. But what that also meant though, is I had to take full responsibility. I couldn't fuck around, quite candidly, I could not do that coming outta law school. I had to make a decision that made sense. And so to that extent, it was like the law firm, obviously a very lucrative route that a lot of folks obviously used to pay off their debt. Consulting was another one of these very lucrative opportunities that could pay a decent amount of money. there are other reasons too, but that was one of the primary ones. and I think the last piece of it too was putting aside the financial situation and like how much I'd get paid. I also just didn't know what I wanted to do. I did less than a year of consulting and before law school. Then I went to law school and now I'm coming back and trying to be like, all right, let's go back to the business world. Let's do a thing. But the business world is amorphous. There isn't one thing in the business world, right? It's literally you're talking about all the various facets that are part of a business. It could be finance, it could be ops, it could be sales, it could be strategy, it could be whatever, marketing, whatever it is. I did not have enough understanding of what was going on. And I knew that and I was like, all right, I could maybe try for a BizOps role'cause that's very generalist. But I think the thing I struggle with was I'd be competing against kids that are coming out of BCG or McKinsey or Bain or whatever it is who probably had that toolkit and were able to like actually succeed in role. And for me it's like I had less than a year of work experience, And that was like three years. I was just three years removed from, said less than one year of work experience. I'm smart and I'm capable and I'm hardworking, but there's a certain refinement you get from actually being in the workplace. And I see it now, right as leading ops. It felt very risky to take that step and then tack on like the financial piece and whatnot, where you're like, shit. Like now if I get this job and I suck at it and then I get fired and I have to pay these loans off, like I am screwed.

Varun 1:05:15

Yep.

Ashwin 1:05:16

consulting then seemed, in a weird way, it made a lot of sense because they did have this a d, c program where it had some comfort in knowing that okay, they have kids that are coming outta PhDs that have probably also never worked to going into a PhD program. And so I will at least have Something that'll give me structure to figure myself out. And I had like less than a year of consulting experience already. So if there's a, if there's one job that I could probably ramp up on faster, it'd probably be consulting than anything else. and then consulting obviously paid well. And I think last piece was there was a travel component, I used to go to India every year as a kid growing up. I feel like that is a somewhat quintessential experience for a lot of

Varun 1:05:58

Totally. Yeah.

Ashwin 1:05:59

particularly those who grew up in the bay. It was like, parents obviously miss seeing their parents and like siblings and whatnot. So like travel has been a fundamental part of my life since I was like, very young. but like my Euro trip in 2015, I think opened up a level of wanderlust that I indulged in law school. Like I visited a number of places. That one was in law school and I wanted to keep that gravy train growing, going, growing and going, I guess it's both. and consulting gave me that too. It's we're gonna pay you really well, you're gonna get the exposure to a bunch of different things, both functional areas, different sectors, and we're gonna pay you to travel. And I'm like, all right, dude, this seems like a really good setup for me. That kind of checks a bunch of boxes that I was worried about. and I think that's also then where I probably made a less than rational decision of putting all, like most of my eggs in that consulting basket, where it's I applied to McKinsey in the fall, didn't get it, B, C, G, and like I was anchoring a lot on that BCG opportunity coming through. because I was putting so much weight on getting the BCG offer. I also didn't study for the bar all that much. I tried, like I, I gave it four days of I won through know civil procedure and criminal procedure and trust in estates. And I was like, you, I saw a notebook full of just rewriting like my barbary kind of the book that I had, to like, to learn stuff. But my heart was just not in it. And then the weekend before 4th of July, like that Friday I had my final round interview. and like miraculously it went well. miraculous in the sense that I was very grateful that it did go well. But this is also like having done many cases that went poorly. this was a case that I objectively crushed Like I prepared for it. I went through it. I was firmly in control and I felt it and it felt great. And so I had high confidence getting to get, I was gonna get the offer and then I ended up getting it the following week, and then I had a choice, do I now what do I do now? I still had committed to going back to the law firm, but I, that was the, like the safe, like the fallback of sorts. and I had this BCG offer, and this is like when I then spent like the next week having a number of conversations with just as many people as I could get. Like a hold of some people that were in consulting, some people that were at different law firms, friends, some partners that I knew kinda over the course of my time at law school. some people that I hadn't talked to in years that were just like, some of the smartest people I know. So it's if I gave you something fresh, first reaction, does this make sense or not? And came to the conclusion that I think this is the right next step for me. I need to get off, like firmly get off the path of like the law, set it like this, set it aside, put it behind me, and move on to the next thing. And called up the firm, let them know I was reneging on the offer. I had to pay back. I think like they had paid for my, like the barbery, the bar prep course. So I had to pay it back for that. faxed in like my withdrawal from like the New York bar. Be like, I am not taking the bar exam. Thank you. But no, thank you. and then I don't know, like a week or so later, whenever that start date was, maybe two weeks later. and then, yeah, then it was like off to the like that's like when, that was like probably the moment where there was like that firm. the last, maybe two and a half years before that, there were like small breaks in like my path the law, but it was never like a full break. that's the moment where I was like, yeah, I am never gonna do this. this

Varun 1:09:26

Yep. Totally.

Ashwin 1:09:29

yeah.