How to Deal with Being the Rule, Not the Exception


TRISTAN WALKER, twenty-nine, stands out in Silicon Valley because he is one of the few successful, black men in an industry that is definitively less diverse, and definitely more perverted than SCOTUS; those judges don’t even know what sexting is! And Justice Alito is probably still trying to make that floppy disk work– Hobby not-so Knobby if you catch our current.

Anyway how Tristan Walker came to make a cameo at the Val party is the stuff of lore.

His story goes as follows:

Walker emailed the founders of a certain well-known Internet company, Dennis Crowley and Naveen Selvadurai. He didn’t get a reply. He emailed them again. He didn’t get a reply. After the eighth such back-and-non-forth, he finally received a note from Crowley: “You know what, I just may take you up on some of this. Are you ever in New York?”

Walker went to New York and spent the next week with Crowley and Selvadurai. He then went on to run business development for their little company: Foursquare, the social networking app that allows users to keep up and meet up with friends.

For many Millennials – those confident, social networking, children of ego-boosting Baby Boomers, born roughly between the early 1980s and early 2000s – some seeking job security, or their own lucky break, Walker’s story serves as a great lesson in perseverance.  Wasn’t it Winston Churchill after all, who said, “If you’re going through hell, send eight emails?”


A few years ago, after boomeranging back home post college (contrary to the promise of my prestigious degree, I was earning ten dollars an hour as an intern), I saw an old man at the corner of a four-way intersection by my parents’ home, clinging to a stop sign. He was hunched, gray in the patches of what remained of his hair.

He had a face like junkyard scraps, fulgurating with sadness.

In his free right hand he held tight to a stack of letters, their crisp white corners, angular and exact– a sad contrast to a jaw line that was no more. His feet turned inward on his shoes, bowlegged and bent wrong, and his legs, unable to support his weight, shook as if tornado winds were whipping at his feet.

But the air was calm.

His knuckles, giraffe-patterned with age spots and scabs, were taut under the pressure of his grip, and his pants, held up by a rope, were losing a fight with gravity. But he couldn’t let go of the pole for fear that he would fall down, so he lost his pants instead.

I watched from the driver’s seat of my own car as folks in 4Runners and BMWs, sentried by the anonymity and privacy that cars provide, pulled to stops and gassed their pedals again, taking nothing with them but the thoughts in their own heads and leaving no more than emissions behind. No one so much as hesitated.

I didn’t move for minutes, until finally a driver behind me gave me a honk, a tap on the tush, insisting that I too, roll on.


On July 16, 2011, two years after Tristan Walker sent his original email to his future employers, he posted that correspondence on his blog.

Hey Dennis and Naveen, it read.

How’s it going? Hope all is well!

My name is Tristan Walker and Im a first year student (going into my
second year) at Stanford Business School (originally from New York).
Im a huge fan of what you both have built and excited about what you
guys have planned for FourSquare. It is an awesome , awesome service.

The next two paragraphs are ripe with fairly standard cold-call vernacular: “I know you guys are probably getting inundated with internship-type requests”…”Thought it’d be worth a shot!”…”Im hungry.”

The only part that really stands out throughout the text is Walker’s refusal to use apostrophes. There’s no grand business plan or game-changing strategy. Nothing that would, at least on the surface, convince two guys whose company is now valued at over 700 million dollars, to respond. And yet, one did, even in the face of Walker’s mixed case (that capital S) faux pas.

Perhaps it was the double awesome that hooked the founders, whom he also reminds to “stay awesome!” in his signature. Surely his pending MBA from Stanford’s GSB didn’t hurt his chances, but to say, as others, such as IA Ventures’ Ben Siscovick, have, that “if you are outside StartupLand looking to get in, read this then read it again – this is how it’s done,” is a tad misleading.

It’s more than misleading. It’s dangerous.


Millennial. It sounds like the brainchild of the Chrysler marketing team. It sounds like you could slap some LED lights and vegan leather on us and sell us to some old white guy who can’t afford an Audi.  And sell, Millennial has. Never has so much been written about a generation that has done so little.

Cue the uproar.

We lobbied for flip-flops at work and won!

Time and Forbes won’t stop writing about us!

Granted, the articles are always a little harsh on our lack of soft-skills, communication, and interpersonal abilities. They play up our inability to think creatively or critically, and point out that we can’t solve problems, or write well. While they’re at it they pile it on that we can’t organize team projects, show up on time for work, or press a button-down. Which, obviously: ironed shirts don’t go well with flip-flops.

They make us sound like real assholes.

Now, I don’t want to be a traitor to my generation or anything (Clueless reference numero dos), but the thing is: we kind of are. And it’s not because we don’t own three-piece-suits or know how to starch our whites. It’s because we all think we are the exception, when we’re all just pennies hoping that we’re hundreds.

A 2011 study conducted by the research network Affluence Collaborative found that almost 40% of Millennials, “have started a business or expect to do so,” making their entrepreneurship rate 10% higher than the general population. Yet our unemployment rate holds steady at nearly 12%, which is about 3% over the national average.

According to research conducted by Small Business Trends, a full quarter of small businesses won’t make it a full twelve months. By year three, 44% will have failed. By year ten, only 29% will remain. While these numbers aren’t broken down by generation (Boomers and Gen Xers are also afforded the same failure rate), they are statistical failures that 40% of Millennials are disregarding because we all intend to be the stuff of myths the startup kid, the self-made man, the one whose email gets answered.

And that’s why Walker’s story is dangerous.

We’re failing to process that Tristan Walker is the outlier, not the rule. No matter the hardship he overcame or how much intelligence he possesses, his success sounds lazy and it bolsters the dream of Millennials who are not interested in legwork or the fine print of the story.

We’ve seen the damage. We’ve got the numbers. We’ve been warned, but we just roll on by. Some of us get lucky.


All those years ago, when I rolled through the stop sign, I knew something wasn’t right, and when I got to the top of the hill, I made a quick U-turn and sped back down.

The old man had released his grip on the pole and attempted to make it across the street. In doing so, he had fallen. His letters were everywhere. His scabbed hands were bleeding.

No one stopped, and so I found myself at a crossroads. Continue to the comforts and spoils of a home I did not own, or stop and step into the muck at the shore of life’s river.

I pulled my car to right and tepidly walked over to him. He was repeating the same phrase, “I have to get to the bank, I have to get to the bank.”

I gathered his belongings and tucked them under my arm, and stretched my free hand toward him. It took some effort, but we wrestled him to his feet and into the passenger seat of my car. I drove him five blocks to the bank and offered to wait.

“No,” he insisted, “I just needed to get to the bank.”

When I got home I washed his blood from my hands and then I cried. Then I thought about how much easier his day would have been had he done his banking online. Hadn’t he watched those Quick Deposit Chase commercials?


The Millennial generation is the product of a discrepancy between accessibility and attainability.  Anyone can send an email, but the responses are few, and the jobs are even further and far between.

How we got this way is rather simple.

It took a decade or two of indoctrination, of someone telling us that the world was ours, followed by the painful realization that reading Tweets were as close to big wide world domination as many of us would get. Ours would be a second-hand success. Most of us were left to fake it or blame the odds and cede to apathy. Delusions of entitlement headed off work ethic at the pass, and a narrowing spectrum of life experience and a contrary exposure to idealistic extremes left our senses dull.

Technology shoulders some of this responsibility (as does globalization, a weak economy that’s seeing the number of young adults making less than $25,000 increase by six millionand Sean Rad), but technology, for all its 0s and 1s has done something interesting, and slightly ironic: it has turned us into sentimentalists that lack the ability to see, or be lead to the truth. It has made us nostalgic for a history that’s not ours, and as a result denies us the future we desire.

It’s why we say things like: “I miss real photographs,” while simultaneously Instagramming, or why we Tweet, “I like the smell of books.” We’re stockpiling nostalgia, visions that never really belonged to (most) of us in the first place. We’re hoarding the image in our head without the means or the actual desire to put in the hard work. We’re busy surfing the internet wave, without stopping to realize that the wave is wet or that it’s pulled us under. Or when, more often than not, we’ve missed the crest all together.

We don’t appear to want to shoulder any responsibility– like the fact that we refuse to read the fine print, and then collectively uproar that a conglomerate didn’t provide us with the magnifying glass. We’re a bit French (aie)  in that manner. And when someone questions our abilities, we get pretty tetchy.

We want everything, while understanding the value of nothing. We accept everyone while having sympathy for no one. We see the man on the side of the road, but we aren’t going to be the one to stop. We jump in the fire and take a piss on it all at once. Tristan Walker may have succeeded, deservedly so, but for most of us this will not be the case.

We have to be willing to get out from behind the computer. We have to not only pay attention, but be willing to engage. We need unsentimental efficiency to disarm our nostalgia.

We have to willing to get out of the car and get a little blood on our hands.

Because, most of the time, it doesn’t matter how many emails we send.


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