💎New Year, No Resolution

December 26th, 2024 – my co-founders and I decided to put a halt to our startup. Bootstrapping to $200k in revenue and spending the past summer at a startup incubator in Harvard, I didn’t expect the journey to end here. 

I’m heading into 2025 completely lost. 

Would I bother trying if I couldn’t win? 

During the summer of 2022, it was almost impossible to make our first sale, recruit committed workers on our team, or even convince my family this was “worth” my time.

We started with no funding, no brand advantage, no ethos, and no“industry experience”. 

In other areas of my life, the incentive to be disciplined was clear. 

Studying with a good routine and strategy, instead of doom-scrolling online, will boost my odds of performing better on an exam. 

Working out consistently for a few months, instead of comfortably laying in bed, would get me in better shape. 

The formula wasn’t complicated: sacrifice something today to obtain something better tomorrow.

With startups, I would be losing in both the present and future.

The sacrificial effort wouldn’t guarantee anything.

The rough vision was to employ a zero-to-one strategy and dominate a small market in the Bay Area that could afford high-ticket consulting packages. If we could grow organically through word-of-mouth referrals with at least 70% gross profit margins, we could invest in developing an LMS (learning management system) and tech platform to scale up our early career mentorship platform. 

Although we experimented with multiple pivots, starting with peer-to-peer admissions consulting to a project-based learning program for aspiring knowledge workers in tech/engineering, we never knew whether any of this would work. 

We made an educated guess and left the rest to us making a million mistakes and trying our best to learn from them. 

I had no clue when a big financial payoff innovative breakthrough could occur.

I’m an underskilled high school kid without a college degree. Besides, many founders start their companies after reaching the pinnacle of their domain. 

I haven’t reached the pinnacle of anything.

Deepening Self-Doubt 

How much capital do you invest upfront? How do you bootstrap if we aren’t getting a loan or equity investment? How do you create a competitive offer with minimal experience? Which methods will allow us to validate our idea? What customer acquisition strategy is going to be scalable? What projects are going to be “high leverage”? Where can we find hires who are committed to our company's mission? What is our mission statement? What are the most high-leverage skills our team needs to learn? How do we optimize our personal learning while enabling the company to grow? 

I never felt prepared to answer these types of questions. 

Public education systems have to draw boundaries of rigidity to be systemically employed for millions of students.   

After all, the basic building blocks of any subject require proficiency in pattern recognition, repetition, and memorization.

If I complete a set of math problems, I know which ones I got right and why I got them right. If I got something wrong, there was an answer key that told me what the correct solution was, and an instructor could guide me if I got stuck. 

However, it wasn’t so helpful when I got tossed into a storm, stranded alone without someone telling me how to escape. 

What happens when our lead flow or marketing funnel is completely broken? That can be a symptom of 100 different problems, and solving 99 of them could get me nowhere until I found the one that moved the needle forward. 

That might spark frustration, believe I wasted my time, stagnated, and could’ve spent the time on a path that would guarantee some progression. 

Why not get an internship, learn from an experienced management structure, and acquire skills currently in demand? 

When we had little to no revenue, Jesse, Ishaan, and I would hear our friends secure internships at JP Morgan, Goldman Sachs, Google, AWS, and a laundry list of prestigious companies. 

I felt happy for their success but couldn’t help but question if our strategy was worth it.

Especially when others were paving a path of stable progression while we second-guess everything.

The Unspoken Constraints of Autonomy 

Many of my older friends who secured their dream job in big tech were left unsatisfied. Something was missing. They wanted to pivot toward startups and obtain more “autonomy” in their daily work life. 

I would highly encourage anyone to contemplate this as a worthwhile goal

(Or else I wouldn’t have been involved with Collegiate)

However, the benefits of ownership become glamorized to the point where people aren’t presented with an honest consideration of its drawbacks. 

For a VC pitch, founders can project contagious enthusiasm, excitement, and confidence for their company. However, in the day-to-day operations, most people I’ve met  – who are serious about their venture – don’t walk around with a glowing smile on their face, feeling elated about the newfound “freedom” and “autonomy”  they have. 

(You’ve won in life if your work provides you with bliss. However, I’ve found that increased responsibility, ownership, and discretion don’t entirely reinvent someone’s life from misery to joy).

Most likely, they’re under a time bomb to hit an OKR, scaling goal, meet some exigent obligations with users/customers, manage their burn rate, etc. Most importantly, they don’t have an exact formula, proven “framework”, or methodology built on years of precedent to solve a novel problem that hasn’t been validated by the market yet. 

This was a long-winded way of me saying, I needed a decent reason to keep pursuing Collegiate. 

Searching for an Unshakable Northstar. 

Ambition is overrated. 

I used to believe it was a virtue worth aiming at. My classmates, parents, and relatives all told me to dream big, desire more, and work hard to achieve as much as I can. 

This trait isn’t inherently good or bad.

It depends on how it’s leveraged. 

Ambition is a multiplying force that helps people materialize whatever desire resides in their hearts. 

Dictators are frequently labeled as “ambitious” but do terrible things. 

To a much lesser extreme, I was taught to look up to ambitious students, ambitious entrepreneurs, and ambitious athletes. 

To be transparent, I wasn’t always thinking about some grand mission I was embarking on while completing 1099 contracts or LLC paperwork. 

There was work to be done, and I had to complete it. 

But every once and a while, there was a spark that would burn, the feeling of wanting to conquer, compete, and build a unicorn company. No matter how low the odds of building a company with a billion-dollar valuation, simply visualizing such a grand achievement would energize me and get my heart racing. 

Growing up in the Bay Area, I was socialized into enjoying competition for the sake of competing. There was a challenge with nearly impossible odds and I wanted to win. 

It didn’t take me long to realize this would be entirely unsustainable. Moreover, something just didn’t “sit right” with me. 

I wanted to leverage ambition as a tool to inspire me, not an end goal to become consumed in a zero-sum game.

It ran contrary to why pursuing Collegiate was so appealing to me. Making room for a winner didn’t mean a loser was created. We can build, sell, hire, and leave our mark in a way that makes the pie bigger for everyone else.

From a practical perspective, an overly ambitious mind can also be counter-intuitive. 

The more ambitious my desire, the more I suffered from the gap between my present and future self. 

Let’s say I told myself, “I want to be financially independent when I just started undergrad”. From there, my mind will start calculating all the milestones I need to hit. This could require me to perform well on each midterm, final exam, assignment, and research paper, apply to multiple jobs, prepare for interviews, ace each stage of interviews, perform well on the job, and upskill while I do have the job so I don’t get replaced, etc. 

Doing well in any stage of the process won’t feel rewarding because there are another 50 steps I need to complete. Slip through the cracks once, and I feel like the entire purpose for hitting this goal is out of reach. 

Applying this mindset to Collegiate, whenever my mind was fixated on a long-term goal, taking the small steps to get there didn’t even feel gratifying. I was constantly reminded of how far I was instead of how far I’d come. 

Becoming consumed by ambition ignites burnout; after all, what do I expect when progress produces pain?

The more I punished myself for pouring effort, the more I had to compensate by squeezing a finite supply of willpower – making it harder and harder to reinforce consistency. 

“I’ve got so much more work to do”
“I’m still not good enough”

That’s why it was difficult to fully embrace or accept acknowledgment or praise from others – even when it was sincere. 

My mind was running computations on how behind I felt; drowning in a pool of expectations that weren’t visible to others. 

Again, ambition is not entirely bad; it can be used to spark desire and cultivate action. However, the fuel needs to be carefully managed. 

It can get me to my destination, but polluting my consciousness could only get me so far. 

On the flip side, I’ve also been told: “Just do what makes you happy”

I certainly don’t want to spend my entire life feeling sad, but chasing an emotion is not the most noble or fulfilling end I can aim for. 

Not only is it a fleeting emotion that can largely be out of my control (unpreventable illness, layoff, poor job market, car accident), it doesn’t bring the most out of my potential. 

Eating Chipotle makes me happy. Playing Smash Brothers Ultimate makes me happy. As chill as this lifestyle would be, I believe there’s more meaning to my existence than grubbing and gaming. I’ve been doing this all winter break and haven’t felt more miserable. 

Seems like I’ve been exhausting every option. 

I don’t want to chase happiness. I don’t want to be mindlessly ambitious, nor do I want to sit around and do nothing either.  

What’s left? 

I was drawn to taking unfamiliar challenges with Jesse and Ishaan because I was developing, growing, and revealing strengths to myself that I hadn’t noticed before. 

I wanted to solve unfamiliar problems for the sake of becoming dependable to people.I care about while uncovering the mystery boxes of my own capability. 

This is also why video games are so addicting; you get to “level up”, experience rapid progression, and encounter a challenge that’s adjusted to your current skill level. 

People only end up rage quitting when the game becomes too hard or get bored when it remains too easy. 

Seeking out the right challenges is a skill that I took for granted; I continue to struggle with this because most tasks are imposed upon us on autopilot.

“I need to study for a test, I need to prepare for this meeting at my job. I need to clean my room, I need to complete this assignment, I need…”

It was surprisingly uncommon for me to hear someone say: I’m “choosing” to do X for Y reason. 

Selecting something “worthwhile” to work on, over a prolonged period of time, was more complicated than I thought. 

New Community, New Identity.

“You shouldn’t care what other people think”

In reality, I still do. At least from friends and mentors that have my best interest in mind. 

I don’t believe people can optimally function without adequate feedback from their social environment. 

I don’t believe I could sit in bed, contemplate my life’s purpose, and forge an identity in isolation. 

Knowingly, or unknowingly, my reason for taking action has been colored by the influence of my parents, peers, and the rest of my environment.

When I spent the past summer in the Cambridge house, I was introduced to lifestyles and attitudes that were foreign to the culture I was accustomed to in the Bay. 

Stat-padding a resume didn’t hold a candle of significance: everyone cared more about an intrinsic drive to solve problems that mattered to us. 

Here were the qualities they cherished instead: eagerness to help others, learn for the sake of learning, encourage self-awareness, and grow for the sake of giving back to others.

Each resident was… “Wholesome and Cracked”. 

One person I met was working on a solution to clean up toxic waste, but I presume he didn’t go to bed believing it was his childhood dream to reduce the sludge levels across America. 

Although, I bet it was intellectually stimulating for him to evaluate and take a stab at problems that haven’t been solved before. 

I wanted to lean in closer to see how I could see the gray lines between what I was learning, excited to find new angles I could create to demystify a problem. 

I even got the idea for pivoting our startup from a Gen-Ed class I was forced to take in college, titled: American Legal Culture. 

Learning the historical developments of how lawyers were trained – from a one-on-one apprenticeship model to a mass-produced, socratic style of education – gave me hints on the technical issues that arise when scaling personalized career mentorship. 

Collegiate became a giant target that I could always aim at, everything that felt “meaningless” now had a newfound meaning.

Closing the Chapter. 

That target is now invisible. 

I’m sitting alone in my room, unsure of what the next step is. 

There is no big mission, big project, or big initiative to look forward to. 

I’ve been sitting at home playing Mario Kart with my older brother and big backing the Cali Tacos at Spartans. 

One of the driving reasons we stuck with Collegiate was to optimize our learning, growth, and development. The business was no longer a vehicle that served that purpose. 

While I was diving into the rabbit hole of YCombinator’s YouTube videos, Paul Graham’s essays, and Sam Altman’s blogs on startups, I was sold on a narrative that I still believe has merit: Regardless of the immediate financial outcomes, choosing the path of startups will yield asymmetric, compounding growth. 

Innovation sounds flashy. “Asymmetric” growth seemed pretty cool. Was I going to start accumulating intellectual superpowers? 

What isn’t as mainstream, however, is the same monotonous routine that people who want to escape in a corporate landscape can grossly intensify when starting and operating a company. 

With Collegiate, the proportion of time we spent on what was “needed” and “feasible” for the business increased, while the time we spent on accumulating new skills plummeted.

While we weren’t going financially underwater, we also weren’t hitting the aggressive revenue goals we wanted for scaling the consulting side of our business.

For most of my posts, I try to write about something that inspires some hope or optimism, either to myself or someone else that can resonate with my story

This time, I just want to give in and feel cynical. 

I’ve been religiously looking at the glass half full for these past two years, telling myself I’m going to reinvent myself, learn, and be able to confidently tackle the size of any problem. 

As of now, the entire cup appears empty. 

I’m starting from ground zero again, switched my college major, and don’t know which community I belong to now. 

I know I won’t feel like this forever; I have to get up because the alternative is giving up on everything. 

I refuse to quite quit on my own life, no matter how bad or unexpected things can get. 

Aiming up is the only choice I’ve given myself, but I don’t know what the next target will be.

To Ragu, Agrim, Andre, Shashank, Tanay, and Amandip, thank you for believing in our vision and dedicating uncountable hours – even when Jesse, Ishaan, and I didn’t have everything  “figured out” and were constantly putting out fires. 

To Jesse and Ishaan, thank you for believing in me. I never considered myself as someone worthy of becoming an “entrepreneur”. I didn’t hold myself with much confidence in high school, and the two of you significantly altered my perception that I don’t have to wait for permission or abide by traditional pre-requisite standards in society  – I can just do interesting things if I want to. 

Becoming a cofounder was a decision that wasn’t solely driven out of career and educational alignment.

After the late-night We Work sessions at Bishop Ranch and genuinely leaving each day with excitement, I joined for the culture.

And I stayed to help us bring the best out of each other. 

Even if the cup looks empty right now, I’m glad we spent these two years – filled with memories of warmth and mutual respect. 

I don’t know where any of us will end up but that’s partially why I have hope for the future.

It’s the only resolve I currently have.