Checkmate & Balance

For a long time, I thought playing it safe was the right way to improve. In chess, that meant choosing solid openings, avoiding sacrifices, and focusing on defense. I liked positions where nothing could go wrong. If the game stayed under control, I felt comfortable.

But when I was around twelve, my progress stalled. My rating stopped improving. I drew games I should have won and lost games slowly instead of decisively. I remember feeling frustrated and embarrassed, especially after tournaments where I walked away knowing I hadn’t played badly—but also hadn’t played to win.

When my parents hired a chess coach, he noticed the problem almost immediately. My style was too cautious. I was so focused on avoiding mistakes that I wasn’t creating chances. I waited for my opponent to fail instead of forcing the game forward myself. I wasn’t taking responsibility for the outcome.

At first, his advice made me uncomfortable. He pushed me to play more aggressively, even if it meant risking material or entering unclear positions. To me, that felt reckless. I had built my entire approach around safety. Letting go of that felt like letting go of control.

But over time, I realized that my fear of mistakes was holding me back more than any actual mistake ever could. By trying to protect myself from losing, I was also preventing myself from improving.

What I’ve learned is that playing it safe can feel responsible, but it can quietly limit you. It keeps you in familiar territory, where mistakes are smaller but progress is slower. Real improvement requires discomfort. It requires accepting short-term failure in exchange for long-term growth.

I still value control and preparation. But I no longer confuse safety with strength. The moments that have shaped me most—difficult losses, uncertain decisions, uncomfortable choices—have all come from stepping outside what felt safe.

When my economics teacher first explained compound interest, I'll admit—I didn't think it was that big of a deal. Sure, your money grows over time. So what?

Then she showed us a simple example: investing $1,000 at age 16 versus age 30. With a 7% annual return, that early investment would be worth over $21,000 by retirement. Starting just 13 years later? Only $10,000. Same contribution, half the result.

That moment changed everything. I opened a custodial investment account with my parents' help and started putting in money from my part-time job as a Chess instructor. Not much—just $50-100 a month when I can. But knowing that this money is working for me, growing exponentially over decades, makes every teaching session at the Elite Chess feel more purposeful.

I've been learning about index funds, ETFs, dollar-cost averaging, and the importance of starting early. Finance isn't just about making money—it's about making smart decisions that compound over time, literally and figuratively.

Update: (September 17, 2025): I had chosen a passive investment strategy. I invested in S&P 500 ETF fund SPY a year ago. It's up by 20 percent since.

I started teaching chess when I became a junior in high school. I joined Elite Chess in Naperville, Illinois, excited but also nervous in a way I hadn’t expected. I had spent years competing in tournaments, preparing openings, and analyzing games. I knew how to play. But teaching felt different. This time, I wasn’t responsible just for my own decisions—I was responsible for someone else’s first experience with the game.

On my first day, I was assigned a small group of students between the ages of seven and nine. None of them had ever played chess before. Some didn’t even know how the pieces moved. As they sat down, swinging their legs under the table, I realized how exposed I felt. I couldn’t rely on instinct or speed the way I did in tournaments. I had to slow down and explain everything from scratch.

I remember feeling nervous as I picked up the pieces. How do you explain something that feels obvious to you but completely unfamiliar to someone else? How do you keep kids engaged when they don’t yet see why the game is interesting? I worried that I would confuse them or lose their attention.

The first lesson was simple. We talked about the board, the colors, and how each piece moves. The rook moved straight. The bishop stayed on one color. The knight jumped, which immediately became everyone’s favorite. The students asked questions I had never thought to ask myself. Why can’t the queen jump? Why does the knight move like that? Why does the king only move one square?

At first, I struggled to answer without overcomplicating things. Teaching forced me to confront how much of my own understanding was automatic. I had learned many ideas through repetition, not explanation. Now I had to break those ideas down into clear, simple thoughts.

As the weeks went on, I started to see changes—not just in my students, but in myself. When a student made the same mistake repeatedly, I couldn’t just correct them and move on. I had to figure out why they were making it. Was it confusion? Was it fear of losing a piece? Was it that they didn’t yet understand the goal of the game?

That process changed how I thought about learning. I began to notice that improvement doesn’t come from being told the right answer once. It comes from understanding the reason behind it. Watching my students slowly gain confidence reminded me that mastery starts with curiosity and patience.

Teaching also changed how I handled mistakes. When a student blundered a piece, they didn’t feel embarrassed the way competitive players often do. They laughed, reset the board, and tried again. That attitude stayed with me. I realized how much energy I had spent over the years being afraid of mistakes instead of learning from them.

Perhaps the biggest lesson teaching gave me was perspective. Chess had always been about performance—ratings, wins, losses. Teaching stripped all of that away. What mattered was whether a student felt excited to come back the next week. Whether they felt proud after spotting a checkmate pattern for the first time. Whether they believed they were capable of thinking through a difficult position.

By teaching beginners, I relearned the fundamentals of the game and, in many ways, the fundamentals of learning itself. I learned how important clarity is. How patience matters more than speed. And how understanding something deeply means being able to explain it simply.

Playing chess taught me how to compete. Teaching chess taught me how to think. And that lesson has stayed with me far beyond the board.

Junior year hit me like a truck. Four AP classes, chess tournaments, Chess tutoring,numerous school clubs, college prep, and somewhere in there, I was supposed to maintain a social life and get enough sleep. Spoiler alert: I wasn't getting enough sleep.

By October, I was burned out. My grades were fine, but I felt like a robot just going through the motions. That's when I had a conversation with my guidance counselor that changed my perspective.

She asked me: "What do you actually care about?" Not what looks good on a college application, not what your parents want—what lights you up? For me, that's chess, maths, understanding finance, and writing. Everything else? It's important, but it's not my passion.

I started saying no to things that didn't align with my goals. I dropped a club I'd joined just because "it looked good." I set boundaries on homework time so I could practice chess.

The result? I'm still busy, but I'm energized instead of exhausted. I'm learning that balance isn't about doing everything. It's about doing the right things and giving them your full attention.

I play middle on my high school volleyball team. It’s a role that demands focus and quick decisions. You’re expected to be alert at all times—blocking, transitioning, reacting in seconds. But on that day, at the end of an important conference game, none of that mattered. The game came down to one point. And that point was mine to serve.

The gym was loud. We were tied, and whoever won the next point would win the match. I remember holding the ball and trying to calm myself. I had served hundreds of times before. This was supposed to be routine. But the weight of the moment made everything feel heavier.

I tossed the ball. I served. And I missed.

The ball didn’t go over the net. The whistle blew. Just like that, the game was over.

For a moment, I felt frozen. Then the realization hit. We had lost. And it was because of me. I felt shocked and ashamed. My face burned, and my mind replayed the serve over and over again. I didn’t know where to look. I felt like I had let everyone down.

As a middle, I’m used to thinking of myself as part of a system. But in that moment, the mistake felt painfully individual. One action. One point. One loss. I remember thinking that the team had worked so hard, and I had undone it all in seconds.

What happened next is what stayed with me.

My teammates didn’t turn away. No one blamed me. No one looked disappointed or angry. Instead, they came over and put their arms around me. They told me it was okay. They reminded me that we win and lose together. Their support was quiet, steady, and sincere.

That support meant more to me than winning ever could have.

I realized then that humiliation doesn’t come from making a mistake. It comes from feeling alone in it. And what my team gave me in that moment was the opposite of that. They made it clear that I was still part of the team, still valued, still trusted.

That experience changed how I think about failure. It taught me that being part of a team means being supported not only when you succeed, but especially when you don’t. It also taught me how important it is to offer that same support to others when they’re at their lowest.

I still remember that serve. I always will. But when I think about that game now, I don’t remember the loss as much as I remember the way my teammates stood by me. In the end, that moment taught me something far more lasting than how to handle pressure. It taught me what it really means to belong to a team.

In the winter of 2024 and early January 2025, I interned for a month at a logistics company. The company operated several trucks, and like most logistics firms, its drivers were paid based on the number of miles they drove. Each driver had a fixed rate per mile and typically drove between 2,500 and 3,000 miles a week.

At first, the system seemed straightforward. Miles multiplied by rate equals pay. Simple.

Then I helped calculate and run payroll. They used ADP to handle payroll online.

As I went through the numbers, I noticed how much additional money the company was paying beyond the drivers’ wages. Taxes I had barely thought about before started to appear everywhere. Employer payroll taxes. Contributions that never showed up on a driver’s pay stub. Costs that were real, recurring, and unavoidable.

What surprised me most was the scale. The employer paid close to 15% of the payroll in additional taxes. That number added up quickly. When I looked at the total cost per driver, the gap between what the driver earned and what the company paid was much larger than I had expected.

Until then, I had vague idea of taxes mainly as something individuals paid. Income tax. Deductions on a paycheck. But running payroll showed me a different picture. It didn’t matter whether the tax was labeled “employee” or “employer.” At the end of the day, it was still a cost tied directly to labor.

And that realization stuck with me.

If that extra tax burden didn’t exist, the money wouldn’t disappear. It could go somewhere else. It could mean higher pay for drivers. More flexibility for the business. Greater room to absorb slow weeks or rising fuel costs. Instead, it became a fixed expense that shaped every decision around compensation.

Running payroll made me see how incentives work in the real world. Companies don’t just decide what they want to pay—they decide what they can afford. Drivers don’t just see their gross pay—they feel the limits of a system shaped by costs they never see.

This wasn’t a political realization. It was a practical one. Payroll turned abstract ideas about taxes and labor into real numbers with real consequences. It showed me how policies translate into everyday decisions, and how hidden costs often matter more than visible ones.

Before this internship, I thought of payroll as an administrative task. After running it, I understood it as a window into how businesses actually function. It changed how I think about compensation, incentives, and the difference between what looks simple on paper and what is complex in practice.

I started interning at a San Francisco–based venture capital firm in June 2025. Unlike many short-term internships, this one is ongoing, and I can continue for as long as I choose. That structure has made me think less about quick takeaways and more about building a long-term understanding of how venture capital actually works.

The firm is a ten-million-dollar fund focused on early-stage, AI-first B2B companies. One of my first learnings was that the firm often invests alongside lead VC firms rather than leading rounds itself. Before this, I had assumed that every VC firm played a similar role in deals. Seeing how smaller funds collaborate with lead investors helped me understand how capital, expertise, and risk are distributed across a funding round.

The general partners are Northwestern alumni, and the culture of the firm reflects that connection—direct, analytical, and focused on fundamentals rather than hype. Conversations center on product-market fit, incentives, and execution, not just big ideas.

In the coming months, one of my responsibilities will be building cap tables and dilution models for startup founders. This is something I’m especially interested in learning, because it sits at the intersection of finance, strategy, and fairness. How ownership changes over time affects not just valuation, but motivation and control. Understanding that trade-off feels essential to understanding startups themselves.

I will also be attending pitch deck presentations and sitting in on conference calls with founders. At first, my role is simply to listen. I’m there to observe how questions are asked, what concerns matter most, and how early-stage companies explain uncertainty. I’ve learned that listening carefully is often more valuable than trying to speak early.

As I gain more experience, my responsibilities will expand. I’ll be calling portfolio companies to gather updates and helping write newsletters for the firm’s limited partners. That process—turning many small updates into a clear, accurate picture of progress—is something I’m looking forward to learning. It requires judgment, precision, and restraint.

What stands out to me so far is how much venture capital depends on clarity rather than certainty. Most decisions are made with incomplete information. The work isn’t about predicting the future perfectly, but about understanding risk, incentives, and people well enough to make thoughtful bets.

This internship is still ongoing, and I’m aware that my perspective will continue to change as I learn more. I plan to use future posts to reflect on specific lessons as they come up—about founders, funding, and how decisions are made when the stakes are high and the outcomes are uncertain.

For now, I’m focused on listening, learning, and building a strong foundation. That feels like the right place to start.

As I started learning how to build cap tables and dilution models, I realized that every cap table tells a story. Not just about ownership, but about decisions, trade-offs, and consequences that can last for years.

The first theme I noticed was the trade-off between control and capital. Every time a founder raises money, they gain resources—time, talent, and runway—but they give up a portion of control. On paper, dilution can look small. A few percentage points here, a few there. But over multiple rounds, those decisions compound. What feels reasonable early on can become meaningful later.

I heard stories about founders who raised aggressively in the early stages, prioritizing growth and valuation. The company succeeded. The product found traction. But over time, their ownership shrank, and so did their influence. Some eventually lost control of the company they started. In a few cases, they were even fired from their own role. The cap table didn’t just record those outcomes—it explained them.

Another theme was fairness versus leverage. Early-stage founders often have limited leverage. They need capital to survive, and investors know that. The terms of a deal reflect that imbalance. Option pools, liquidation preferences, board seats—these details may seem abstract at first, but they shape who benefits and who bears risk.

I learned that “fair” doesn’t always mean equal. It means aligned. When incentives are misaligned early, the effects show up much later. A cap table can reveal whether a company prioritized short-term survival or long-term balance.

One story that stayed with me was about a founder whose company reached a high valuation on paper. The headlines would have called them successful. But after multiple rounds of dilution and complex preferences, their actual financial outcome was far less clear. They were technically a multimillionaire, but with little liquidity and limited control. Someone described them as “paper rich but penniless.” It sounded exaggerated at first, but the numbers made it real.

I even heard the phrase “homeless multimillionaire.” It sounded almost unbelievable, but it captured the same idea: wealth on paper does not always translate to security or freedom. The cap table explained why.

What surprised me most was how early these stories begin. Many of the outcomes I heard about could be traced back to decisions made in the first few rounds of funding. Choices made when the company was small and uncertain shaped everything that followed.

That’s what makes cap tables so interesting to me. They aren’t just financial documents. They are records of judgment. They show how founders balanced ambition with caution, growth with control, and optimism with realism.

As I continue this internship, I’m realizing that understanding venture capital isn’t just about evaluating ideas or markets. It’s about understanding incentives and consequences. The cap table is where those forces quietly accumulate.

It looks like a spreadsheet. But if you know how to read it, it tells a story—sometimes a hopeful one, sometimes a cautionary one, and almost always a revealing one.

Before interning at a VC firm, I had a simple picture in my head of how venture capital worked. VC firms raised money, sat on it, and waited. Founders lined up, pitched, and hoped to be chosen. VCs, I assumed, held all the power.

That picture turned out to be wrong.

One of the most surprising things I learned is that VC firms are also under pressure—real pressure—to deploy the funds they raise. Once capital is committed by investors, it does not help anyone if it just sits in a bank account. That money needs to be invested.

What changed my perspective even more was seeing how competitive the VC landscape is. There are many firms, often with similar strategies, all chasing a limited number of truly exceptional startups. For “hot” startups, it isn’t the VC deciding whether to invest. It’s the founder deciding which VC to accept.

In those cases, VC firms actively try to convince founders to take their check. They emphasize their network, their experience, their value beyond capital. The dynamic looks nothing like the one I had imagined. Power shifts quickly when demand exceeds supply.

This competition creates another reality. Smaller or newer VC firms often invest in startups that are promising, but not breakout successes. These companies may return 50x or even 100x. That sounds impressive, but in venture capital, it often isn’t enough.

The reason is the model itself. Most startups in a fund fail or return very little. A few big winners have to make up for everything else. Without those rare, extreme outcomes, even solid individual investments can lead to average—or disappointing—fund-level returns.

Seeing this made me understand venture capital less as a world of dominance and more as a world of trade-offs. VCs aren’t just evaluating founders. They are managing timing, competition, portfolio risk, and pressure from their own investors.

That shift in perspective stayed with me. Venture capital isn’t just about picking winners. It’s also about navigating constraints—many of which are invisible from the outside.

And sometimes, the side that looks powerful is working harder than anyone realizes.

In late October 2025, I attended TechCrunch Disrupt at Moscone Center West in San Francisco, sponsored by the VC firm I intern with. The conference brought together hundreds of startups from around the world, displaying new technologies and business models. It was my first time at a flagship event like this, and I was immediately struck by the energy and ambition on display.

I had been assigned a specific task: talk to founders, understand what they were doing, do a quick, intuitive analysis of their market potential, and introduce them to our firm if they were raising funds. Walking through the exhibition halls, I couldn’t believe that I was interviewing founders who might be wildly successful in the future. Some of the companies had just launched, while others were already gaining traction.

AI was the dominant theme this year. Many companies were applying AI in creative ways to solve old problems or build entirely new business models. One company that stood out to me was focused on disrupting the real estate market. The founder explained that they had learned from the failure of Opendoor, a twenty-year startup that targeted sellers—a much harder segment to crack. Instead, they were focusing on buyers. Their approach used AI to send listings, provide comparables, and even set up appointments with seller agents using conversational AI. It was an efficient, tech-driven way to handle what is traditionally a slow, manual process.

I thought their model had potential and introduced the founder to the general partners at my firm. They are currently in advanced talks. It was exciting to play a small part in connecting a promising startup with investors and to see how the industry moves quickly when ideas and technology align.

Attending TechCrunch Disrupt was a unique opportunity to observe firsthand how innovation, AI trends, and venture capital intersect. Beyond seeing products and pitches, I learned how investors evaluate ideas on the spot, and how founders adapt lessons from the past to build better models. It gave me a glimpse into the scale, speed, and thoughtfulness required to succeed in early-stage investing.

For me, the experience reinforced that learning in venture capital is not just about spreadsheets and numbers. It’s about talking to people, understanding markets, and seeing opportunities emerge in real time.

In the summer of 2025, I interned at a hedge fund in New York for two months. The fund focused on equities and options, and I spent most of my time analyzing companies, building financial models, and observing how the traders and portfolio managers made decisions.

One of the first things I noticed was that no one treated any outcome as certain. Even the most confident investment idea came with caveats. Before this internship, I had thought investing was about predicting which stocks would go up or down. I quickly realized it was more about thinking in probabilities—assigning likelihoods to different scenarios and planning for multiple outcomes.

During the internship, I also learned how to use financial performance indicators to support probability-based thinking. I analyzed P/E ratios, EBITDA, and other ratios to evaluate a company’s health and potential. I learned how these numbers could help estimate probable returns and identify risks.

Options were another key concept I encountered. I learned that they could serve two purposes: as a hedge against potential losses and as a way to amplify returns. Using options thoughtfully meant considering probability distributions, not just guessing the direction of the market.

For example, when evaluating a stock, the team would consider the base-case scenario, the upside, and the downside. They would ask: “How likely is this outcome? What would happen if it doesn’t go as planned?” The focus wasn’t on being right, but on preparing for a range of possibilities.

Thinking this way changed how I approached my own analysis. I began to quantify uncertainty, consider alternative scenarios, and focus less on predicting the future and more on managing risk. It also helped me understand why diversification, hedging, and options matter—because even well-researched ideas can fail, and the probability distribution matters more than any single outcome.

By the end of the internship, I realized that thinking in probabilities is not just a hedge fund skill—it’s a way to approach decisions in general. It encourages flexibility, humility, and attention to risk. That perspective will guide me in both finance and everyday decision-making long after the internship ended.

Applying to universities has been one of the most intense learning experiences of my high school years. It’s easy to think of the process as simply submitting applications, but it quickly became clear that it’s much more than that—it’s a process of understanding yourself and communicating that understanding effectively.

Writing essays forced me to reflect on my experiences: competitive chess, volleyball, my internships in venture capital and hedge funds, teaching, and community involvement. I had to think critically about what I had learned from each, and which moments truly defined me. Some lessons were obvious, but others—like the importance of trust in volleyball or thinking probabilistically in finance—only became clear when I tried to articulate them.

The activity list, recommendations, and supplemental essays taught me another lesson: clarity and authenticity matter more than exaggeration. Admissions officers read thousands of applications. They notice when a student is being genuine, thoughtful, and reflective. I learned to focus on conveying my actual experiences, not what I thought would impress.

Time management was another major part of the process. Balancing school, extracurriculars, internships, and the application itself forced me to prioritize and plan carefully. It also reminded me that resilience isn’t about avoiding stress, but about organizing and tackling it effectively.

Overall, the college application process has been more than a series of deadlines. It’s been an opportunity to step back and see the arc of my own growth—to notice patterns in my learning, leadership, and decision-making. It’s also shown me the importance of reflection: not just doing, but understanding what each experience teaches you.

Looking back, the process has prepared me in ways I didn’t expect. It’s given me confidence in my ability to plan, communicate, and reflect—and those are skills I know I will carry into university and beyond.