I’ve been meaning to write this post for a long time now. At first, I planned to write a reflection on the one-year anniversary of our startup, compiling all my personal thoughts and learnings from a year of working on a startup. However, I ended up procrastinating, and, in the time since, I ended up leaving my startup. I planned to combine that reflection with an explanation of why I ended up leaving, but due to a combination of procrastination as well as not being completely ready to write down everything, I never got around to writing it.

I’ve started writing this blog post on various flights, but I’ve never really had the time to finish. I’m currently writing this on my flight from Asia back to SF. Hopefully this is the flight where I finally finish this essay.

At this point, I think it’d be easiest to first explain why I left, and then wrap up with any other thoughts about my general startup experience, both for the sake of personal reflection as well as documenting my life decision making for the future.

I left my startup on May 11, 2023, meaning that it has been over two months since I left. My memory is a little hazy, but I remember enough of my decision process to write down the general jist.

reasons

The main two reasons why I ended up quitting were: location and startup life.

location

I grew up in the Bay Area, and, as a kid, I never really had any complaints with the area itself. The academic environment was extremely competitive, which, now that I’m older, I realize had a negative impact on my mental health as a kid. That being said however, when I was growing up, I never really thought twice about it. That was pretty much the only life I knew, and I didn’t consciously hate my high school/the Bay Area the same way many of my peers did.

In fact, upon moving to NYC, I didn’t really like the city. I experienced pretty intense culture shock from going from Dougherty Valley High School, where virtually everyone I ever interacted with was Asian, to Columbia, where there were far fewer Asians. I also remember thinking that people in my high school were generally smarter than the people I was meeting at Columbia (yes, I know this is a weird thing to be thinking about, and no, I no longer think about things like this), which also negatively impacted my opinion of the city. Going from San Ramon, which has huge, open parks where you can have long stretches of complete silence to not being able to see the sky due to NYC’s buildings, the constant noise of the city, and crowded sidewalks was an additional jarring change.

But by the time freshman spring semester rolled around, I had started getting used to NYC. By the time sophomore year came, I had fallen in love with the city and all the nice spots it had to offer—I felt like there was an unlimited supply of fun things to do and a huge diversity of areas to explore/people to meet. When the pandemic hit in 2020, I made the decision to go back to NYC rather than do the year at home. While I do think that was the right decision, I spent the majority of my time that year in Philly due to certain circumstances (long story), which I do sorely regret. Sometime at the start of that year, I realized that I had completed enough credits my first two years at Columbia that I could very easily graduate a year early. Columbia had a masters program that I could easily append on to the end of my undergrad degree, and I also decided to apply to Stanford.

Looking back, my reasons for applying to Stanford were rather tenuous. Upon graduating high school, part of me was rather upset that I was attending Columbia, which in my mind was a second rate school compared to some other schools (e.g. MIT)—this was a big point of frustration for me, since I genuinely believed I performed basically as well as I could’ve throughout high school. Even now, looking back, I’m not sure what else I could’ve added to my application if I could redo high school all over again—there’s an undeniable amount of entitlement in that sentiment, but the end result was that 17 year old me felt that it was supremely unfair that I didn’t get into what I considered top tier schools. This was exacerbated by the fact that most kids who did get in to these schools tended to flex this fact on me, which irked me to no end—this was probably one of my biggest pet peeve at the time. At the end of senior year, I thought that if I could attend Stanford for graduate school, I could finally right this feeling of injustice.

Secondly, at the end of high school, I got much closer to my friend as we spent considerable 1-on-1 time together on college applications. I remember several conversations where he challenged my goal of becoming a physics professor one day—when asked why I wanted to, I had no good reasons. In comparison, he was able to articulate such clear reasoning behind his dreams of doing a tech startup and becoming a billionaire one day. When I now reflect on these conversations, I think the stark contrast between his intense conviction and my own lack of convinced me to adopt his goal as well—I switched my intended major from physics to computer science, and I started gearing my life/college career around a life of startups and programming. When junior year of college rolled around, I had a sense that Stanford was the place to be for college startups—Yale and Columbia have much smaller entrepreneurship cultures in comparison.

So when one day I randomly got into Stanford (I wasn’t really even thinking about it), I kind of just went with my gut and decided to accept it. I knew I liked meeting new people, and I figured that a change of scenery would be a great way to do so. I also knew I used to have reasons for wanting to do this back in high school, but by this point, those reasons had pretty much all but faded away. Accepting my admission was probably the biggest regret of my life, and I do think that it would’ve been avoided had there not been a pandemic—I had absolutely zero clue how socially isolating graduate school was, and that the numbers of new people I was meeting through undergrad would slam to a halt in grad school.

I strongly disliked my year at Stanford. I had decided to do grad school rather than working as a quant for two main reasons: to meet more new people and I figured it’d be easier to drop out of grad school than quit my job as a quant. I quickly realized that most people are at Stanford grad school for very specific reasons, almost none of which include socializing (I’m not including law or MBA students as those social circles never overlapped with mine). In undergrad, social life is a big part of why people are there, and you have a lot of what I deemed “passive socializing”—you see people in dining halls, lectures, parties, clubs, events, etc. In contrast, I felt like most Ph.D. students were focused on their research, and many masters students simply aren’t there long enough to want to form lots of deep friendships. People are also just in a different stage of life, where they’ve already had their fun in undergrad/made their lifelong friends. In contrast, I was still extremely desperate for the fun social life that college years promise—I had few months at the start of freshman year before I ended up in a relationship that sucked up all my social life. By the time I ended that relationship/was ready to socialize again, COVID hit and I graduated early—so in effect, I had a few months of fun college life, and I spent my year at Stanford desperately trying to chase that high again and failing to reach it. This was all while I could see all my friends having the best times of their lives in the senior year at Columbia—I also missed my girlfriend quite a bit, as we were doing long distance (she was also at Columbia).

The fact that Stanford was located in Palo Alto did not help at all. Restaurants close super early, and there is no night life. It’s deathly quiet, and there’s basically nothing to do—I was legitimately so depressed by the area. I think the factors listed above definitely reinforced my negative associations of the place, but when my startup team planned to live in Palo Alto for another year despite my earnest objections, I already knew what another year in Palo Alto would be like. At the time, I justified it since startups were something that I’d wanted to do for such a long time, but I consciously noted that I was making a big personal sacrifice by agreeing to live in Palo Alto versus even San Francisco or San Jose (NYC is not even comparable).

This might sound weird given that I quit my startup, but my year working on my startup was significantly better than my Stanford experience. My house would semiregularly host medium-sized parties, which I had a ton of fun at. A lot of my high school friends had graduated/were working in the Bay Area, so I could hang out with those friends. I had made a handful of close friends at Stanford that I still continued to hang out even after I took leave from Stanford. The fact that I lived in an 8 person house meant that I had quite a bit of the passive socialization that I missed from undergrad: from having random conversations with my housemates in the kitchen/living room to playing sports in the park. The FOMO of watching everyone live out senior year of college had also passed. But I think the biggest difference was that I finally felt like I had purpose to my life—I was pursuing my dream of working on a startup with my friends, whereas my year at Stanford was a complete waste of time.

But perhaps comparison is indeed the thief of joy. There were countless evenings where I scoured my brain for something fun to do with my friends, only to end in disappointment. My frustration continued to build as I felt like if we were living in NYC or basically anywhere besides Palo Alto, I wouldn’t be struggling like this. There were countless moments where I sat there depressed, genuinely wishing with all my heart that I’d never experienced all the fun that NYC had offered me in the past. I thought that if I didn’t remember, then perhaps I could be content like the rest of my peers with Bay Area life, that perhaps my past memories were the reasons why I was so discontent. I think that if you talked to me at that time about why I was upset, it would be clear that I had an intense fear of missing out on my youth—this fear was multiplied exponentially by what I mentioned earlier losing on on so much collge from the pandemic/graduating early.

Once discussions about signing a new lease rolled around, I felt an insanely strong sense of unease and anxiety. The thought of being stuck in Palo Alto for another year genuinely terrified me—the previous two years had already taken such a heavy toll on my personal happiness, and I was convinced that another year would actually break me. Being in the Bay meant I was sacrificing essentially all other aspects of my personal life for the startup, which exacted a much heavier emotional toll that I expected prior to that year. We as a startup team decided to move to San Francisco, and two of our housemates would also join us in the same place. I definitely was happy about this decision, but it would be a stretch to say that I was completely content. I still consciously knew that I was making a sacrifice if I were to live in SF versus NYC, where girlfriend/100% of my college friends are. Visits/outings to SF only confirmed these feelings for me—night life didn’t feel the same, the streets at night stressed me out, and the food/activities felt the same or worse as NYC. One of the things that eventually pushed me over the edge of quitting was a realization that even if our startup took off in a raging success, I’d most likely be stuck in SF for another 5-10 years—this was something that I didn’t think I would be okay with, even if I did achieve my “startup dream.”

I sometimes wonder, if my team had wanted to live in NYC from the very beginning rather than Palo Alto, would I have also quit? A big part of me feels like I wouldn’t have. However, this is a rather futile exercise as in reality, it was clear that my team and I were not on the same page in this regard, which I believe is not due to the fault of any of us—but I do think that it reveals a deeper set of differences in terms of values/personalities, which fed into this particular incompatibility. I could never understand why they wanted to be in Palo Alto, and, vice versa, my co-founders never fully understood why I wanted to leave so badly. At the end of the day, I felt like it would be very wrong of me to force them to move to NYC just to keep me happy/productive, and another part of me questioned my own commitment to the startup dream if something as trivial as where I live could rattle my dream to the core like that.

startup life

This is where my memory gets pretty hazy, since it was a bunch of little things over the course of the entire startup. It essentially boils down to the fact that the work that I had to do for startups was not what I expected at all.

What I expected to be doing for work seems naive in retrospect, but I thought doing a tech startup would mean working on interesting technical problems, learning about lots of cool new tech, honing my technical/engineering skills, thinking about how business ideas slot into society/human psychology, scaling a company (i.e. hiring, picking an office), lots of camarderie of weathering out startup storms with three of my closest friends, the list goes on. The reality of startup work is a lot harder than I had expected, both in a direct sense but especially in an emotional sense.

The majority of early-stage startup work boils down to sales/marketing. The tech is actually arguably the easy part, particuarly with my team (the four of us are all technical). But even before sales and marketing, you first need an idea—my team and I were predominantly stuck in what’s referred to as “pivot hell” (we kept pivoting from idea to idea once it became clear that the previous one wasn’t going to work). I’ve described a lot of our process in startup logs I’ve written in the past, but to rehash it, we employed a process called “hypothesis sheet testing.” We would first pick an industry, write down a bunch of hypotheses we’d have about said industry, and then do a combination of research/call people in said industry to either confirm/reject these hypotheses. As we did that, we’d write down more and more specific hypotheses, until we’d essentially created a giant tree of knowledge spanning an industry. The entire time, we’d be searching for any potential opportunities/problems that we could come in as a startup and solve. Some questions would require building product/prototypes to find answers, which was the only fun work.

I genuinely found this type of work similar to what I’d imagine slogging through mud in the middle of a humid jungle being eaten alive by bugs would feel like. It was work that I felt like I was bad at, and I didn’t like doing it (definitely a causal relationship here). There’s also an overhanging cloud of realization that, on any given day, you might have to throw away all your work. Doing a startup straight out of college is also a weird experience compared to almost any other job because there’s nobody telling you what the right thing to do is, because, surprise, there’s often no right thing to do. There are only wrong things to do, which we did plenty of, but it’s hard to realize in the moment—you just know that you have to keep working super hard, but the moments where you are forced to scrap all your hard work never get easier (for me, they got exponentially worse as I started losing more and more hope).

In March, we decided to pivot away from our largest project yet (Orchard), which really demoralized me. I had actually felt months prior that we needed to pivot away, but since everyone seemed to want to continue working on it, I had mentally convinced myself that Orchard was the idea that we were going to continue pushing through on, no matter its flaws. So when the decision to move on was made, it affected me quite deeply. After that point, just showing up and doing work every day demanded a tremendous amount of personal mental grit. I hoped that it would get better over time, but when May rolled around and I still didn’t feel better, I started worrying that I wouldn’t be able to see the startup through to the end.

The last major thing that I didn’t expect about startups was how genuinely hard it is. I’ve talked a lot about how emotionally difficult it is, which I didn’t realize before plunging into the startup life. But the most sobering realization was this was probably the first time where I felt like, wow, no matter how smart my team and I are and no matter how hard we work, success in this world is still very far from guaranteed. Growing up, school kinda conditions you for the opposite realization—if you’re smarter than everyone else and you work harder than everyone else, then you’ll generally be successful. Things that people traditionally find hard/impressive when you achieve it (i.e. prestigious jobs, high scores on competitions and exams, getting into graduate school, groundbreaking research) are relatively straightforward via intelligence, lots of hard work, and the privilege to have those opportunities.

Building a billion dollar company is a different definition of hard in comparison. This is why a lot of books about tech startups/businesses somewhat annoy me. In my opinion, there’s a rather insane amount of survivorship bias packed into those books—the bad/particularly annoying ones promise that if you follow XYZ method, you’ll avoid all the other pitfalls that kill 99.9% of startups. In my experience, there’s an insane amount of complexity packed into the timing of developing technology, evolving society, and your own learnings/knowledge. There are far too many external factors and situation/individual specific decisions to be made that generic advice doesn’t help, and advice that worked for one group of founders at one time for one company can hardly be extended. One piece of super common advice that you’ll hear from startup founders is that they never gave up, even when most normal founders would’ve given up, and that’s why they succeeded. But the survivorship bias is abundantly clear if you start reading startup post-mortems—the startup graveyard is littered with teams with millions of dollars in funding who clearly should’ve given up on their ideas much earlier before wasting years of their/their emplyees’ lives. I believe that advice is free for a reason, and you should always first listen to advice and see if it actually applies to your specific advice before blindly accepting it as dogma because you respect the person giving said advice—you’d be surprised by how often it’s the case where the people who have the most legendary of accomplishments have the shittiest of takes (they also have good takes too, but in general, these types of people have many strong opinions that they constantly voice). They’ve already made it, they can say whatever they want and it doesn’t matter—you’re the one whose life/success hinges upon following their words.

mortgaging happiness

I kinda went on a bunch of tangents there, but essentially I felt like if I had continued working on my startup, I would be mortgaging my happiness for some notion of grand success via becoming tech billionaire. But I’ve changed so much from that 17 year old conversing with my friend/eventual co-founder. In high school, I wanted to win the USA Physics Olympiad so bad as I wanted to be the smartest person my age in the US by some legitimate, meritocratic metric, and above all else, I wanted to get into a top tier college. I pushed my body and mental happiness to very extreme lengths because of how bad I wanted these things—Columbia taught me how bad these tendencies were for my long term happiness, and so I unlearned them. Throughout the first year of college, I was still a workaholic—if I had any free time or if I got more than 5 hours of sleep, I would think I wasn’t doing enough work and start to feel anxious. Switching to 7+ hours of sleep a day genuinely changed my life (I felt like there was color to life for the first time ever), and by the time I started working on my startup full time, I realized that I was far from the ideal, obsessive workaholic temperament that would’ve made me a great founder in high school. The conflicting thing was that I saw that my cofounders had that same drive, and I really wanted to match that—but I had just spent essentially four years unlearning this same exact thing, so should I actually revert to ways that I had worked so hard to better myself on?

I also had decided to do a tech startup at a time where I knew very little about myself, how the world worked, and what makes me happy. I’d already learned from my Stanford experience what happens when you stick to a plan made by a 17 year old, and even though I’ve historically stuck to plans that I’d made several years out, I’d say one of the biggest lessons I’ve learned about life is that it’s essentially impossible to plan life more than a year or two out. The world changes too much, and you gain way too much knowledge that you simply have zero concept of multiple years prior. For example, if I planned my life five years out, and I’m 22 now, then I would truly be living a life planned by 17 year old me, which is actually a nightmare scenario (to me).

Anyways, whether or not it’s actually better or worse, I value a bunch of things more than ambitions of ultra-grand achievements. I like being able to be happy without feeling guilty that I’m not pushing myself hard enough. I like being able to sleep more than 5 hours a day. I like meeting new people. I like hanging out with my friends without feeling anxious that I’m not working hard enough. I like not having to worry about my family’s/my own financial security. I like my stupid little hobbies in mechanical keyboards and flyfishing. I like the small moments in life, like drinking a good cup of coffee in an aesthetic little cafe you just randomly found, or conversing with a new friend at a new perfect hangout spot that you never return to again. The more things I experienced in life, the more I realizd that I don’t need to be the most successful human being around me to make life worth living. And once I lost that burning motivation, even the end outcome of becoming a tech billionaire lost its appeal to me. Working as quant at my current age provides me with the time, money, and friends to do all the things in life that make me happy.

It’s so weird, I’ve spent the majority of my life unhappy trying to chase happiness, only to realize that it takes so little to make me happy.

And I think this final realization that I’ve changed and the startup dream that would’ve made my 17 year old self happy doesn’t make my current 22 year old self happy, and my ability to leave on good terms was what enabled me to walk away. I don’t think this is me closing the door on startups forever—I’ll chill in quant for the next year or two and reevaluate what I want to do. But the truth is that if I had stayed in startups, I would be constantly mortgaging my happiness for an outcome that wouldn’t even deliver me the same amount of happiness as if I moved to NYC right now.

why I almost stayed

I do want to make a quick note that even though my reasons for leaving startups might seem relatively clear here, the actual decision to leave was one of the hardest decisios I’ve had to make in my life so far. It’s hard to overstate how difficult it is to give up on a dream, especially when you’ve been conditioned as hard as I have to chase lofty ambitions. Even now, part of me is scared that I’m weak, and that by leaving, I’m losing out on my potential and giving up on a chance for legitimate greatness in human history.

The biggest reason, however, was that for the longest time, I was convinced that I wanted to keep doing the startup for my co-founders. It felt illogical that this was the main reason for staying—after all, the reasons for doing a startup should be more intrinsic and independent of your co-founders, right? People I sought advice from regarding this entire situation told me that it’s best to think selfishly in these scenarios as being selfless and staying when you don’t want to hurts your team, but even if I could accept such advice, it felt wrong to me. Through doing a startup, living in the same house, cooking/eating every single meal together, and sharing nearly every social interaction, I developed a relationship with all my co-founders that runs super deep—it really isn’t an exaggeration when people compare co-founder relationships to marriage. I really did see my cofounders as my brothers, and leaving my startup felt like giving up on family. The thought of leaving them was painful enough that I was fully willing to suffer if it meant that I could stick by their sides and see the startup to completion. One of the things that I’ve learned about myself over the past four years is that people are what matter the most to me, and leaving my startup meant losing the most important people to me at that period of my life.

The illogical nature of my reasoning drove me crazy. I so desperately wanted to stay, but it was tough to construct other, more logical reasons that I believed. The more I reflected on this point, the more I realized that this sort of focus on caring more about my cofounders than the startup and its success manifested not just in that decision, but also throughout my time at the startup. I really did try to change for them through lots of personal writing/reflections and trying to revert to my high school productivity-obsessed self, but I couldn’t do it quickly enough. I could’ve done many things better during the startup, and so I am very sorry to my cofounders. A part of me still feels like I let all of them down, and I’m not proud of the impression I left.

So my decision to leave was in part very selfish, and in part a great loss for myself. I partly lose the people that matter the most to me, but I hope my decision in doing so ultimately benefits them too. If I stayed, I was positive my continuingly decreasing morale would’ve dragged them down too as I would’ve quickly been rendered an unproductive and ineffective cofounder.

ending thoughts

Even though it was a really hard decision to make, after making it, I haven’t felt any regret yet. I’m super excited to go back to NYC and see everyone again. But more than that, I travelled for an extended period of time for the first time in my life (it’s also the longest period of time I’ve gone without working). I travelled all throughout Asia (Japan, Korea, Thailand, Vietnam), and it was truly a life-defining experience and one that would’ve never happened had I stayed at my startup. I’m super grateful for all the memories that I made over the past two months, and even more grateful for all my friends that spent time with me to make those memories possible. These past two months healed a considerable chunk of the anxiety I previously had about missing out on college/my youth.

Like I’ve said previously, it’s impossible to know what the future holds, but I can confidently say that in the present, I am happy, and it’s looking like I’ll be that way for a while!