[F5] College Admissions Essays
Writing = Thinking | Essays that worked for Princeton, UPenn, Harvard, Stanford, and the Thiel Fellowship
Welcome to another Free Friday! Today’s post is the fourth of a new series I’m doing with Altos Ventures’ Director of Research Nick Chow. In this series, we’ll share five pieces of content, whether they be books, booklets, novels, movies, tv shows, reference guides, or anything else, grouped for a specific reason.
We’re still experimenting with the format of Friday 5s, but for this one we’ve split it up into two parts. If you have any suggestions or feedback, please feel free to share it with us on Twitter, Substack (respond to this email or comment below), or LinkedIn.
Theme: Why we grouped these essays together.
Letters: The full text of the actual essays and where the author chose to go and what they’ve done since graduating.
Previous Editions
Theme
"Writing is thinking. To write well is to think clearly. That's why it's so hard."
— David McCullough
There’s a core discipline that is fundamental to nearly every successful investor and entrepreneur: clear thinking. And there is no better test, nor demonstration, of clear thinking than writing.
Today’s Friday Five is a collection of college admissions essays that offers a unique lens through which to observe that discipline in its earliest form.
The college admissions essay is a rare, universal exercise in America. What makes these essays particularly valuable is not their role in securing college acceptance, but what they reveal about the writer's mind at a particularly formative stage. Before jargon, industry knowledge, or professional polish clutter an individual’s mind and shape their identity, these essays expose the raw mechanics of thought—how these future entrepreneurs and investors organized ideas, confronted uncertainty, framed ambition, and made sense of their experiences.
KG Note: For examples of writing at another formative stage, see this F5 where Nick and I cover some of our favorite first shareholder letters.
These essays were written by individuals who would go on to build companies, manage capital, and navigate complex decisions as investors or entrepreneurs. At the time of writing, they weren’t pitching to venture capitalists or drafting shareholder letters—they were teenagers, tasked with answering a deceptively simple prompt: Who are you, and where are you going?
For most, it is the first (and perhaps only) moment in youth when writing carries such significant personal stakes. It demands introspection, coherence, and persuasion. And because the outcome feels consequential, students apply a level of effort and thoughtfulness unmatched by typical academic assignments. Nearly everyone who aspires to higher education must face the blank page and articulate their story.
In hindsight, patterns emerge. The ability to distill complexity into clarity. The instinct to frame challenges as opportunities. The early signs of narrative competence—the same skill later used to align teams, attract capital, or communicate a vision to markets. These are not accidental traits. They are reflections of disciplined thinking expressed through writing.
For investors and entrepreneurs, this discipline becomes a competitive advantage. Whether drafting investment memos, shareholder letters, or internal company updates, the ability to write with precision forces clarity of thought long before decisions are executed or capital is deployed. It sharpens judgment, exposes flawed reasoning, and aligns action with intent. Poor writing often signals muddled thinking—a costly liability in fields where ambiguity and complexity are the norm.
This Friday Five serves as a reminder that the foundations of clear thinking are often laid long before professional success is visible. The college essay, typically viewed as a hurdle to admission, can in fact be an early indicator of cognitive rigor and self-awareness—traits that compound over time.
David McCullough was right. Writing well is hard because thinking clearly is hard. But for those willing to embrace that difficulty, the rewards extend far beyond the page. They manifest in better decisions, stronger narratives, and ultimately, more resilient careers.
As you read these essays, consider them not as relics of youthful aspiration, but as blueprints of minds learning to think through the discipline of writing—long before those minds shaped companies, portfolios, and industries.
KG Note: If you have kids (or grandkids) who are applying to college, this may be valuable for them as examples of exemplary writing and storytelling that is not just technical or creative, but creative and technical.
Essays
Essay #1: Princeton (by Nick Chow)
Why I hate Rafael Nadal
I hate Rafael Nadal with a passion.
There you go. I said it! So please, stop giving me that look. From the reactions I get, expressing my dislike of Rafa is like committing some unforgivable crime against humanity. How can someone have the heart to criticize a man who gives everything on the tennis court, furiously chasing every ball like it’s match point, sweat flying from his glamorously long locks? How can someone dislike a man who hosts charity matches, still lives in a small house next to his parents, and captivates millions with his charmingly-accented English and earnest smile?
I devoted endless months trying to figure out what was wrong with me. For after all, the problem with hating Nadal is that it reflects more on me than on him. Nadal is a perennial underdog … and after all, how can you root against the underdog?
Full disclosure: I have always been a diehard Roger Federer fan. I first began watching tennis in 2006 and loved Federer from the first moment. His forehand was a controlled arc of destruction; he moved over the court like it was part of a complex dance. He seemed unstoppable; no one could oppose his grace and God-like precision. Unfortunately, I would be proved wrong.
Federer is sponsored by Mercedes; Nadal … by Kia. Somehow, that sums it all up.
I remember it so clearly when I first saw them play. I was watching the 2007 Shanghai Masters Cup semifinal. At first, I laughed at the contrast. Federer was his usual sharp self, ripping forehand winners while gliding across the court. I almost felt sorry for Nadal, the skinny teenager in the bright blue muscle shirt, scurrying along the baseline to retrieve Federer’s shots. But then, Nadal’s tenacity began to trouble Federer, and Federer actually began to sweat. Was Federer showing signs of his mortality?
A day of trauma I will never forget: Sunday, July 6th, 2008. The day that Nadal beat Federer in the Wimbledon finals. It was terrible to witness, but ironically Nadal winning is not what bothers me. What really irks is that people root for Nadal because he is the underdog. This never ceases to amaze me. People view Nadal as a fighter. Regular people can emulate the way he plays. He constantly fights and scraps for points, running down every ball, while Federer plays effortlessly and glides on top of the court. Nadal is all too human; Federer seems like a machine. Federer is sponsored by Mercedes; Nadal … by Kia. Somehow, that sums it all up.
Yet when looking objectively at this historic rivalry, Nadal has a 22-10 (accurate as of Oct. 2013) -advantage in their matches. Nadal is in his athletic prime; Federer is slipping toward the twilight of his career. Not to mention that Nadal seems genetically engineered to defeat Federer, as though some higher force was trying to stop Federer in his quest for unrivaled dominance. His high bouncing topspin gives Federer nightmares, and his doggedness frustrates Federer. Nadal is far from an underdog. So I suppose my ultimate problem with Nadal is that he’s portrayed as the brave challenger to the invincible Fed, tireless in his heroic quest to unseat the Swiss Maestro.
So that’s what I really hate about Nadal: the incorrect narrative surrounding him and the romanticized light the world bathes him in. He’s not just Goliath — he’s Goliath pretending to be David. Underdog status is too important to squander on those who don’t deserve it. There are underdogs out there, and the world should save its cheers for those who need them. Nadal will do just fine without our misplaced emotional support.
Just one thing. After spending so much time writing about my hatred of Nadal I realized something. A come-from-behind kid from a Spanish fishing village who lives next to his parents and leads a simple life. He can’t be that bad … right?
And that’s the problem. Say what I will, hating Nadal will always just be a hair out of reach.
Nick chose to attend Princeton University, after which he joined Wellington’s quant group. After Wellington, he attended Stanford’s Graduate School of Business, and today is Director of Research at Altos Ventures. You can read his GSB essay here.
KG Note: Nick didn’t want to include his essay/put it first, but I insisted.
Essay #2: University of Pennsylvania (by Eddie Dalton)
Cuatro Cuerpos
I know we’re complete strangers, but so were Eliel and I once. This past summer, I spent two weeks in Nicaragua with four other provincial selectees, witnessing international development and human rights conflicts first-hand. During the five nights we spent in San Andres, an indigenous Miskito village nestled in near impenetrable Nicaraguan rainforest, I met Eliel. I doubt I’ll ever see him again, but in the short time we spent together, I struggled with the most challenging and humbling experience I’ve ever encountered.
Miskito is Eliel’s native language, and the broken Spanish I could muster reduced our conversations to pathetic hand gestures and constant laughter. Yet, we kindled on implicit connection in spite of the stammered silences between our fruitless attempts to communicate. At least we both understood “perdón?” As time passed through, what I dismissed as initial awkwardness drove an insuperable rift between us. I couldn’t talk to him. I was mute, eloquence voided, rendered useless (and speechless).
A common ground that I had taken for granted didn’t exist, and it was like learning English in a grade one classroom again, two short weeks after setting foot in Canada for the first time. I thought back to persuading countless debate panels into medals, smooth-talking girls into dates, improvising presentations. i was right there, in the middle of the rainforest, but no words came, none were understood. I was a deaf man in Carnegie Hall, watching the concert happen and never hearing a note. I wanted to ask Eliel how he could be so happy when he had nothing. How on earth he had learned to beat box. I wanted to ask, but I withdrew from our fruitless exchanges, defeated by each shortfall after another until this rather-lose-it-all-than-lose-at-all mentality replaced shy conversation with mutual silence. I began to wonder how I could be a doctor, travel the world and save lives. I needed to be able to connect with people like Eliel, even without the words.
From then on, we had entire unspoken dialogues through cockamamie charades and gesticulations that no one else understood. We were both sixteen, but fate had designated us to lives that were almost destined to never cross, and coincidence had trumped fate. Coincidentally, despite how disconnected we are, he has the same suave walk and casual hair flip that I do, and we shuffle cards the exact same way.
The last evening I spent in San Andres, Eliel approached me with a worn deck of cards. We did nothing else the entire night, shamelessly defying the language barrier that had condemned understanding between us. Between the countless futile explanations and failures (and fits of hysteria), the modest breakthroughs we made were proud victories, and I gave, hands-down, the most innovative theatrical explanation of blackjack to date. One of the last games we played that night has a winning hand called “Cuatro Cuerpos”, which is when one person holds all four suits of the same number card. Eliel won the round. The next morning, he handed me the two of clubs and the two of hearts, and I never saw him again.
College admission is a lot like revealing a hand of cards in a game we haven’t quite mastered. Mine are face up on the table. I am ever grateful for the shortcomings that intimidate me. Out of these downfalls comes renewal, but out of renewal comes permission to stumble again. J.M. Barrie, the author of Peter Pan, tells us that “we are all failures — at least the best of us are,” because failure is triumph incognito. There are no roads to San Andres. The only way to get there is by canoe on the Rio Coco, eight hours into the heart of undisturbed rainforest. It’s a rare sanctuary from hastiness and uncertainty, primeval and almost otherworldly. To get there, we follow the “second star to the right and straight on ‘til morning.”
Eddie went on to attend the University of Pennsylvania, where he studied finance at Wharton. He went on to cofound a startup that was later acquired, worked in private equity at a firm with $30bn+ in AUM, and was an investor at a hedge fund with $50bn+ in AUM. Today, he writes One More Thing.
Essay #3: Harvard (by Jeffrey Wang)
Some people study best at the library. Others occupy a corner in a coffee shop where inspiration and creativity flow with cappuccino. Personally, I do some of my best work while sipping a one dollar plus tax McIced Tea at a plastic table on which my laptop and a book rest. The subtle scent of grease fills my nose and the shouting of order numbers rings in my ears. I've found an unconventional place of contentment beneath the Golden Arches.
I'm home alone on a hungry summer night when I discover the McDonald's near my high school. The refrigerator is empty, preventing me from cooking, so I decide to become Mickey D's daily customer number sixty million and blank. I walk in, order food, and sit down to chow. In the middle of my feast, I realize that there is nothing on my mind but my surroundings and my stomach. I'm completely at ease; no pretension exists in this global franchise that has more stores in the world than people in my town. I briskly walk out to my car, grab a book, and return to study for a few hours that I've realized were some of the most restful yet productive I had had for a long time. I've spent many more hours at McDonald's since, usually just to use the space to work or even just meditate on weekends that might otherwise have been lazy.
I don't claim that McDonald's is the perfect place to be. The commotion of the kitchen and indelible buzzing of pop music often make it hard to do things like appreciate the structure of certain biochemicals or follow local politics. When a high pitched voice begging for a McFlurry interrupts Charlotte Brontë's beckoning for me to decipher the symbolism behind a lightning-struck chestnut tree, I'm whizzed from the English countryside back to this American burger joint.
But I defend my newfound habitat despite its imperfections. While attention-catching sights and sounds sometimes divert my attention, they've helped me to work by forcing me to focus harder. Better yet, I've found meaningful the array of diversions I've experienced, from a conversation with my quirky, retired seventh grade English teacher about how fast (not quick, he had taught me) life passes by, to companionship with employees here like Milly, who works the cash register, and Maureen, the manager. As far as why I've settled on McDonald's as my choice of refuge, the only other two fast food restaurants in my town don't have adequate places to sit, the town library has short hours, and my thrift prevents me from frequenting the local coffee shop. McDonald's has two sittings areas with power plugs at every table, is open 19 hours a day, 7 days a week, and has a quite tasty dollar menu. For this, McDonald's speaks to me. Sometimes, I put down my pencil or stop typing into a Google Doc to just appreciate the simple utility of the location in a sort of wistful way. I see my life as a sort of quest to find ultimate authenticities, and while I know that there will be more truths to discover and that they will most certainly be more difficult to find, my being content at McDonald's is one conclusive victory.
Physicist Richard Feynman once described the world as a "dynamic mess of jiggling things." He was referring to the literal behavior of the atomic world, but I believe that the modern, macroscopic world, where even watches and glasses will soon bombard us with stimuli, fits this description just as well. With so many things jiggling in front of us, it's becoming harder and harder to focus, stop moving, and simply be content. I've learned that contentment can exist in imperfect and unforeseen places when you simply observe your surroundings, adapt, and maybe even eat a french fry.
Jeffrey went on to attend Harvard College. Today, he is the Cofounder of Exa, an AI search company that has raised over $22mn in funding from Lightspeed, Nvidia, and Y Combinator.
Essay #4: Stanford (by Garry Tan)
Screams of Silica
Grains of sand have feelings too. As environmentalists bicker over trees, who will be there for the billions upon billions of grains of sand out there? Soon, entire deserts of sand will be harvested for silicon! These poor creatures will be decimated and irrevocably altered into ungodly silicon wafers. It is time to rise up and fight for our silicon dioxide crystal brothers and sisters.
We've all heard the analogy... If cars evolved like computers, they would cruise comfortably at 10,000 mph, get a million miles to the gallon, and if it broke, you could go to the store and pick up a new one for a dime. Moore's Law of exponential growth has been a godsend to Silicon Valley. With computer technology doubling in speed and complexity every eighteen months, people spend billions annually to replace last year's models. Countless multitudes of crystals of silica are being sacrificed for a short use of but a few years. Moore's Law has resulted in the systematic murder of these unassuming, innocent, naturally occurring crystals.
At the same time, Moore's Law has kept the computer the domain of a privileged few. Prices continue to be beyond the range of affordability for many. Even today, fewer than 40% of Americans own computers. Technological advancement will eventually hit a wall. Moore's Law is not an absolute. Computers have always been getting faster and cheaper. Someday, with that quest for speed out of the picture, cheap will be the name of the game. Imagine the horrors as the other 60% rushes down to the store to buy the next 100 gigahertz Intel Octium VII Pro for $9.95 at the local Fry's Electronics. The horrors of such an age would make the systematic slaughter of silica of today look like children building sandcastles.
The prospect of computers everywhere not only threatens the fate of sand particles everywhere, but also the place of ignorance in society. With information exchange and dissemination at everyone's fingertips, where would ignorance and tyranny go? Evil dictators around the world would be displaced as computer-engendered thought and communication tears millions of minds from abject poverty and subjugation and transforms them into organized, united and educated masses. The world would be at our fingertips. The great WWII-era scientist Dr. Vannevar Bush once postulated a device called the Memex, which would augment the mind with hypertext memories. The rise of ubiquitous network computers could be just the augmentation of humanity that the doctor ordered.
Certainly, the ubiquity of the computer might change society at its core. Sure, it might result in the rise of new media, and the empowerment of the individual on a grand scale. Indeed, it might even result in world peace and harmony among all men. But humanity must not be selfish. We share this planet with the trees, and more importantly, the earth. Can we afford to continue to victimize these helpless crystals of silica? May their silent screams haunt our motherboards as we type away with reckless carpal tunnel abandon.
Garry chose to attend Stanford University and graduated with a degree in Computer Systems Engineering. He went to work at Microsoft, before joining Palantir as the 10th employee. After leaving Palantir, he founded Posterous, a blogging platform he later sold to Twitter. He then joined Y Combinator as a designer in residence and partner, before founding Initialized Capital. Today, he is the President of Y Combinator.
Essay #5: Thiel Fellowship (by Dylan Field)
Tell us one thing about the world that you strongly believe is true, but that most people think is not true. If this belief shapes the way you live, tell us how.
Chocolate is repulsive. Even the smell of it makes me want to vomit. Although I have other beliefs that distance me from the majority, no conviction elicits a stronger reaction than admitting I detest chocolate. As a young child, I quickly realized I was not normal. One of my first memories is of a little girl frankly asking me on the playground if I was an alien. Others simply labeled me as a freak.
Even today, my peers are shocked when I reveal this preference. Just a few weeks ago a girl I was interested in dating offered to share her dessert with me. “Too full,” I told her. “Come on,” she implored. “It’s soooo good. Just take a bite.” Finally, I admitted the truth. At first she just stared at me. Then, slowly, she turned away. “We can’t be friends anymore.” She told me.
According to research into hours of baby videos, I have never enjoyed chocolate. My mother tells me the first time I was allowed to try any sweet was on my first birthday. It was supposed to be a joyous occasion. I don’t have any recollection of the incident, but footage shows me happily sitting in a high chair surrounded by family friends. A guest blows out the candles on a large, chocolate cake and I am fed the first slice. My face changes from joy to confusion to visible disgust – then the video ends. I like to imagine that I spat it back out.
Over the years, I’ve been offered chocolate countless times. At first I refuse. Some people, like the girl I mentioned earlier, are persistent. After I tell people that I don’t like chocolate, they react in one of two ways: either they immediately classify me as a mutant or inquire about the condition. Many ask if I’m allergic. I’m often tempted to lie and end the discussion, but the truth is that I’m not allergic. I’ve forced myself to swallow the black goo before and – besides having the impulse to make myself throw up – nothing bad has happened. I just abhor the taste.
While my hatred is rare, I’m not alone. A fellow chocolate hater and writer for Gilt Groupe found a study by Hofstra University that determined an entire 2% of the population doesn’t like chocolate. My personal theory is that hating chocolate is a recessive trait – my grandma also disliked it.
One day I intend to research the phenomena and find out the truth. Scientists at Nestle wrote in a paper from 2007 that my belief is due to an imbalance of gut bacteria, but I’m not sure if I believe the results given their sample size of 11. Perhaps the researchers are correct and one day my belief will be changed through science. In the meantime, I’m perfectly happy with a simple sugar cookie or a slice of fresh blackberry pie à la mode – vanilla, of course.
Dylan dropped out of Brown to join the Thiel Fellowship. As a fellow, he founded Figma, which was valued as high as $20bn in private markets and recently filed to IPO.
KG Note: While the Thiel Fellowship isn’t exactly a “College,” Dylan wrote it while he was a college student, and dropped out after being accepted, which to us, qualifies it as a formative moment.
If you got this far and you liked this piece, please consider tapping the ❤️ above or sharing this letter! It helps me understand which types of letters you like best and helps me choose which ones to share in the future. Thank you!
Wrap-up
If you’ve got any thoughts, questions, or feedback, please drop either of us a line — we’d love to chat! You can find us on Twitter at @kevg1412 and @nicholasachow, Kevin’s email at kevin@12mv2.com, or Nick’s LinkedIn here.
If you're a fan of business or technology in general, please check out some of our other projects!
Speedwell Research — Comprehensive research on great public companies including Constellation Software, Floor & Decor, Meta (Facebook) and interesting new frameworks like the Consumer’s Hierarchy of Preferences.
Point in Time — Musings on code, capital, and craft.