Posts Tagged ‘life’

Making My Own Luck

When I was 15 years old I worked as an intern at an New York-based Internet marketing company, MediaTrust, who happened to be one of the fastest growing private companies in America during the summer of 2009 (Inc. magazine ranked them #9). And I loved it. From taking the train into New York City every day, to becoming introduced to Shake Shack, and daily trips to Jamba Juice with my great friend Herwig, I learned a lot by even just walking the streets. This was the summer when “I Gotta Feeling” by the Black Eyed Peas was at the top of the Billboard charts, and I know that Herwig and I truly felt like lucky guys.

During my exit interview with one of the leaders at MediaTrust, Trip, exposed me to two thoughts which have influenced my behavior ever since:

  • Don’t rely on luck. Make luck happen for yourself.
  • Communicate better. Many of life’s problems are rooted in communication failures.


Those two pieces of advice have stuck with me because this conversation was one of the first moments when I realized that my destiny is up to me to determine.

I never had great grades in school, so I didn’t often feel that I could control the destiny of getting into a great college. But when it came to making things on the Internet and selling them, I knew I could make my own luck by reading online and then performing experiments with the knowledge that I had gained. And so that’s what I did, and that’s where I excelled.

When I learned about Y Combinator and Paul Graham during that same summer from my co-workers at MediaTrust, I became inspired to find a repetitive problem in my life, and mechanize a solution with technology. I learned that I could make my own luck with the right preparation and the right opportunity. But perhaps equally important, I learned that thought leaders in technology companies and startups, such as Paul Graham, are great communicators.

Paul Graham’s essays gained the loyal readership of programmers and other hackers, who provided the seed for what became Reddit and then Hacker News. Likewise with Peter Thiel, his book, Zero to One, is now one of the best selling business books of all time. Their clarity of thought is the product of years of thinking deliberately on how to distill their experience and intuition into words. It’s something I admire very much about them and seek to emulate in all of my communications.

Looking back on my experiences since 2009, it’s clear to me that many of my “lucky” successes were developed by a combination of me vigorously pursuing a specific goal, in addition to clear and succinct communication that helped to relay my story. From writing to the Thiel Foundation about how I wanted to change the world, to my application essay at Wake Forest, to writing about “bacn” on the Glider blog and having that picked up by BBC News, my great strides have relentless execution and strong communication at their core.

I’ve spent much of the last six months working on the first part of this equation, making my own luck: writing code, drawing user interface designs, and purely executing. I am building a flight deals application: Concorde. I believe the last six months has been one of the most creative periods in my life. But I know that my dedication to writing has lacked focus during this time. Over the coming months, I am aiming to share more about my specific decisions for why and how I am building Concorde, because I’ve gotta feeling that my success depends on it.

Ciao and arrivederci.


01 2016

Four Words

Tomorrow I will begin what is likely to be my last school year. My fifteenth “first day of school” (I skipped a year of college). Optimism and uncertainty abound, like any student about to embark on a new year. There’s a lot to look forward to as a senior at Wake Forest.

Although I’m sure I will learn quite a bit in my classes, I’m certain my experiences outside of the classroom are the ones that I will cherish the most. I didn’t fully realize this when I first arrived in Winston-Salem, but I now understand that my classes are a vehicle for helping me interpret the world outside of the classroom. Recent experiences such as a conversation with the CEO of one of the world’s largest tobacco companies, mourning the death of one of the greatest Americans (Maya Angelou), or a day on the set of a feature Hollywood film have all come unexpectedly — and I’m sure my mind will continue to expand in ways that I can’t predict.

My english professor last spring was one of those people who fulfilled on his potential to “change the way you think”. He didn’t begin our course with a syllabus; he began with four words.


adj. Intended to ward off evil.


adj. 1. Excessively determined. 2. Having more than one determining psychological factor.


n. Indignation or ill will felt as a result of a real or imagined grievance.


adj. 1. Of or concerning the appreciation of beauty or good taste. 2. Characterized by a heightened sensitivity to beauty.
n. 1. A guiding principle in matters of artistic beauty and taste; artistic sensibility. 2. An underlying principle, a set of principles, or a view often manifested by outward appearances or style of behavior.

He believed that the behavior of the characters in the literature (and life) is often rooted in these words; thus a useful interpretation mechanism. I hope to keep these words in mind during this next year.

Go Deacs!


08 2014

Inflection Points

On the last page of a few recent National Geographic issues there has been a section named “The Moment” which describes a “moment of peak energy”, an inflection point, discovered by one of their photographers on assignment. The idea behind this special photo blurb is that each cover story has a decisive moment which captures the most authentic energy of the subject.

My thoughts are often similar to a reporting photographer waiting to capture the essential moment of their subject: I have an undying fascination for observing moments in life during which we come to realize happy and painful truths. This past winter was no exception.

I am writing this post to dive deeper into what it means to re-evaluate yourself and the beliefs about the people who surround you. First I will begin with an excerpt from an interview of David Foster Wallace’s opinion on great art, and then I will take a look into some of the work by Marina Keegan.

Great Art

Wallace describes that great art requires a selfless emotional leap in an interview originally published by Larry McCaffery:

Really good work probably comes out of a willingness to disclose yourself, open yourself up in spiritual and emotional ways that risk making you look banal or melodramatic or naive or unhip or sappy, and to ask the reader really to feel something. To be willing to sort of die in order to move the reader, somehow.  … Maybe it’s as simple as trying to make the writing more generous and less ego-driven.

I am proud of this blog in many ways, but one recurring self doubt is that I am overly mechanical in my writing; I am unready, unwilling, or unable to disclose how it really feels to be in my shoes. Any of my close friends will tell you that I speak of a few key influential moments in my short life, some of which I was able to capture here: We Weren’t Born To FollowPeer Groups, and Peer Groups Continued. Unsurprisingly these posts (including this one) have coincided heart-break in business or life, and for better or worse.

You would also probably not be surprised to learn that these “sappy” posts don’t quite produce the SEO home-runs that an exposé of Rap Genius might bring, for example. But the page views aren’t my key metric here. This is just my brain to your brain, my heart to yours.

It’s my goal to begin publishing writing that brings out my emotion more often than I have in the past.

Marina Keegan

One great writer I discovered during my time away from school is Marina Keegan, a graduate of Yale in 2012 and the victim of fatal car crash shortly afterward. Despite the tragic nature of her death and unrealized post-college ambition (she was due to begin writing for The New Yorker just weeks later), I learned that she had an uncanny ability to narrate some of the most pivotal moments in life.

Through a series of short essays in The Opposite of Loneliness, Keegan captures three significant life lessons that I have been able to relate to in my own life. I’ll explain these lessons with help from a book review in the Pittsburgh Post-Gazette and then offer my anecdotal evidence. It is my hope that you may identify with these moments as well.

I’ve named these lessons “The Cheat”,  “Fleeting Happiness”, and “B-team”.

The Cheat

In “The Ingenue,” a young woman catches her boyfriend cheating at a casual game of Yahtzee, throwing into question everything she believes to be true about him.

This is the gut feeling when your whole world spins 180 degrees. It’s important to note that the cheating action is insignificant but the overarching moral dilemma is profound.

What do you do in this situation? What I would probably do is step onto an orthogonal vector: a diverging observation point in which judgement is neither made or discarded. In one sense, the insignificant cheat is exactly that, no stakes, nothing to lose. In a more rational sense, any cheat signifies a moment of indignity.

I’ve found that we humans tend to have an irrational amount of good hope for the person we love or admire. It’s easy for infatuating feelings of a special person to override any judgement derived from an insignificant cheat. In other words, the complex and multidimensional nature of humans covers up our own unique flaws and our ability to see them in others.

I am suggesting that we pay closer attention to these seemingly insignificant moments because they are the small actions that constantly define us. In any outcome we have the ability to forgive others, and that’s important.

A couple of years ago I remember this painful feeling the first time I watched one my good friends smoke a cigarette. I was absolutely mind-blown that someone I trusted so deeply had happily accepted a life of routinely smoking cigarettes. We are still close friends, but in that moment my expectations were temporarily shattered as if I didn’t really know that person.

Fleeting Happiness

“Baggage Claim” also explores this same concept as a young couple visit a store that sells unclaimed baggage, and the thought of the personal photos deleted from the found digital cameras forces the male narrator to contemplate the fleeting nature of happiness — how quickly happy moments occur, and how quickly they can be erased.

Keegan is emphasizing that nothing lasts forever. Most of us work so hard to build up towards certain goals, but one slip up can reduce that progress to nothing.

The Swedish House Mafia reminded their fans of fleeting happiness during their final performance at Ultra Music Festival in 2013:

Remember your last day in school? This is our last day in school. We can tell you how it feels, and that we are sad, and that we are ending Swedish House Mafia together.

but they reminded us that fleeting happiness does not always have to be an unhappy memory:

…or we can tell you how it feels to have played for one million people on this One Last Tour. We can tell you how it feels to look in people’s eyes, with their hands in the air, with smiles and screaming at you because they love your music.

During this time of year (end of the school calendar) it’s impossible for students to not think about how things were vastly different a year or six months ago. Sometimes even less than than that, just moments ago.

When I lived in New York in one moment I would be dancing with my friends late into the night. Moments later I was alone in a dark apartment facing my own psychology, thirsty, hungry, and awake.

Or the moment when you leave the table at the last family holiday dinner. The last page of a thrilling novel. The moment your cell phone screen cracks. And of course the moment that ends a relationship.

One of the most important lessons I learned after leaving college is that everything can change instantly. Withdrawing from school and moving to California instantly removed me from a social support structure. Eventually the fleeting nature of my happiness pushed me towards a different course. I needed to make a change in my life to optimize for happiness, and by returning to Wake Forest I got the instant change-back that I needed more than anything else.

From my experience the cliché “you don’t know what you’ve got till its gone” stands true.


“Cold Pastoral,” the most striking short story, is a melancholy exploration of love in an age where our past never really leaves us. Claire, a college student, learns of the sudden death of a casual lover. Claire’s mourning process is full of anxiety as she grieves for someone she shared a bed with but whom she ultimately didn’t understand. This leads Claire to a painful universal truth: namely, that we are not guaranteed leading roles in other people’s stories, no matter how much we feel we deserve them.

This is probably the hardest lesson because of the line right here: “we are not guaranteed leading roles in other people’s stories”. No matter how hard we beg for forgiveness or try to improve our situation, we are not guaranteed unconditional love. Every person deserves to be loved, but I don’t think from and to whom is something that you can choose all that much.

This lesson is the hardest to accept because your past continually affects you whether you like it or not. My english professor this semester regularly projected his skepticism of the word “closure”. Yes, in a mechanical sense any situation can be terminated and escaped, but the term “closure” is really just a coping term. Both good and bad life experiences never truly leave you.

Fortunately at Wake Forest and in the startup world I’ve found a handful of people that deeply care about me. When I see any of those people leave my life it has always left a feeling of emptiness inside. In just a moment you are moved from someone’s front and center vision to the periphery. Despite real feelings making it hard to embrace this change, we have to move on and be thankful for the past.

Extrapolating this lesson further, I see this lesson applying to many tough moments in life: the classic story of a childhood sports saga when a kid doesn’t make the “varsity” team and gets sidelined with a “less talented” group of peers. When a person doesn’t get the job promotion they feel that they so much deserve. Or when a divorced parent is not granted custody of their child.

. . . 

So, if people are fundamentally flawed, happiness is always teetering, and our leading role amongst people we care for is not guaranteed, what should we strive for? My friend Paul Dejoe often reminds me that striving for sincerity is the best we can do:

We forget that we are just passing through this world so we put emphasis on possessions and status when all we have to leave behind is how we’ve made others feel.

Paul suggests that we all want to be relevant to other people but he says that the only thing of true relevance is how we make others feel. Perhaps if we are more generous and less ego driven, then we can be better people through the sincere energy in our interactions.

I’m talking about the moment of when you decide to speak up in class instead of sitting back in mutual acceptance. The moment of when you say “hi!” to the stranger in the elevator instead of pretending like they are just air. The moment when you don’t cheat at the causal game of Yahtzee. These are the decisive moments of peak energy. These are the inflection points.



05 2014