Logan Miller


Flippant Detroit by Logan Miller

I am scribbling furiously on a yellow legal pad as Zach and I spew ideas back and forth.   We have about 45 minutes until our flight boards, and at the rate we are brainstorming, it seems we are going to need every second.  I no longer notice the stifling air in the terminal waiting area, or the pleather seats that my sweaty ass is stuck to.  My vision is tunneled between the faint blue lines on the paper as I try to keep up with the relentless flow of thoughts jumping in and out of my mind.  I grasp at one of these ideas and miss, watching for an instant as it recedes into the infinite black space somewhere in the back of my head where all the best ideas are inevitably lost.  Just as quickly as it disappears, Zach’s voice cuts into my thought space. “Where are we going to manufacture the shirts?”

            This oddly practical question tears me from my imaginary thought universe and plants me firmly back in real life.  I lift my eyes from the yellow page and look around, suspiciously eyeing the older woman across from us.  Although she still has bulky, paisley-patterned luggage from the mid-20th century and appears to be fast asleep, I can’t help but think she has been quietly listening and conniving to steal our idea.   Zach makes another attempt to pull me back to reality. “Literal bro, I told you she’s not gonna steal our idea.  Where should we be based out of?”

            I reluctantly stop narrowing my eyes at the older spy-lady and consider the question.  My eyes drift back to the illegible scribbles on the paper in my lap. “Uhh… let’s see.”

            Scanning over the excited mess of ideas, I pull out the key elements – upside down pockets, “flippant,” funny commercials, useless, seamstresses, party.  As I scramble to put these together, something starts to crystallize, an unfamiliar and strange notion – I think it might be a plan. We have the business idea, now we need a place to start it. “Well, everyone goes to the Bay area for start-ups, so we obviously can’t go there.  Seattle’s pretty much played.  Nebraska could be tight.”

“Too much grain,” Zach shakes his head, “my allergies would be brutal.”

“Ok.  And East Coast is out – too crowded.  What about the South? Mississippi?”

Zach looks at me skeptically.

“Good point. So that leaves Alaska and the Midwest.  I feel like we should try a new spot first, we can always move it back to Juneau.

“Word…” Zach stares out the window as China Air takes off down the runway, quickly tapping his Blackberry on his leg.  I traverse the map of the U.S. in my head, hunting down cities, sizing up their potential.  I’ve made it to Albuquerque (way too dry – a “hard no”) when Zach straightens up.  His shoulders pull back quickly and his phone starts bouncing on his leg.  After 20 years I can always tell when my brother has a great idea, and this is what it looks like. I know what he’s thinking before he says it, but still can’t wait to hear it. “We’re going to Detroit,” he says with an ironic grin, and leans back on the pleather seats as he puts on his wide-frame grandma sunglasses. 

Five months later I am sitting in a basement office across from Professor Waldron, Chair of the Religion department at Middlebury College.  He only has five minutes to spare before an important meeting in some other chairs, with some other chairs, or Chairs. Despite this, he is deeply focused for a moment in the way of people who meditate often, thinking about my question.  Although he moved away from Detroit at sixteen, this still makes the religion professor one of precisely two people I know with direct ties to the motor city.  I start to think about the question again, “Was it…”

“Yes,” he starts.  “It was fun. I used to go to shows downtown.  But really we lived in the suburbs, everyone did.  Terribly designed city…”

I start to space out.  I’ve heard this before from every possible media source that covers Detroit.  Poor city planning, collapse of the auto industry, unsustainable tax base, complete economic failure, train-wreck of a city (SUV-wreck?), possible economic rebirth founded on Quickenloans (owned by billionaire Dan Gilbert) and micro-craft-wood-working shops (owned by small-scale dreamers).  I space in as he slows down.  We are standing outside his office in the dim basement hallway in which the dirty linoleum floors and unpolished wood doors seem to suck away any remaining light.  “So that’s really all I can tell you about Detroit.  I have to get to this meeting, I’m already late,” (he wasn’t) “but I am curious – why does your generation think Detroit is so cool?”

            I am caught off guard, initially perplexed by the grotesque basement and now at my own ignorance. “Well, I mean… I guess I don’t really know,” I stutter as he hurries away in the uniquely rushed gait of adults who think they are late for important meetings.  I stare stupidly at the piece of scrap paper in my hand, covered with scribbled questions for other people to answer.  I slowly put it into my pocket and amble toward the dark-stained wood doors, wondering if there is someone flippant enough to help us learn about Detroit.




I heard him before I saw him.  I was at a mining camp in Alaska during the summer when Flippant was conceived, and we were listening to new rap songs as we stared at excel spreadsheets.  A hysterical, high-pitched voice, careening over a raunchy beat, came blasting through the portable speaker on the portable table:

“31 years old so I done been through all that dizzert

Came up off the porch straight serving off the crizzurb

Long time ago, I don’t do that shit no mo’

This the last time I’m a tell you, wanna hear it?

Here it goes!”

He sounded like he was about to lose his mind, and we could feel the hysteria as we quit pretending to work, and jumped around the wall-tent, industrial rubber rain gear flopping around spastically.  I listened to that song dozens of times before I laid eyes on Detroit rapper Danny Brown.  I still remember the first time I saw him.  An untamed poof of messy black hair hung off of one side of his head, and the other half was shaved. His eyes were squinted, possibly even closed, as he grinned maniacally and joyfully, proudly displaying his lack of front teeth.  This man wearing a collared shirt and bow polka dot bow tie was confidently displaying what looked to be a mild case of insanity. 

To be honest, I wasn’t sure what I was looking at, and I got nervous.  I looked away from my computer screen, attempting to find something more comfortable and familiar to occupy my vision.  My eyes scanned the room, coming to rest on my overflowing pile of dirty clothes.  I rested my brain for a second, but quickly became bored of the soiled garments, and found myself drawn back to the face on google images.  By all typical standards, this man was definitely “sketchy,” but his complete joy and confidence were overpowering. 

Danny Brown embodies a relatively unknown side of Detroit – he brings an edgy type of fun, which seems to casually say “Yeah man, come do hard drugs with me…hahahahaha… just kidding….hahaha.” 

In an interview, he speaks about moving to the East side and switching schools as a 6th grader: “Niggas shootin, niggas stabbing niggas everyday like what the fuck is goin on? Hahahahahaha I don’t wanna go to that school no more. Hahahahahaha.”

The guy is crazy, and it’s beautiful.  Danny exudes a confident, genuine, inspiring insanity.  The kind that little kids have right before their parents yell at them to stop acting like lunatics.  He exudes freedom – from expectations, conventions, standards and the mundane – the freedom that Detroit represents, that we are going to try and find.



After weeks of talking about the “D” and listening to vulgar Danny Brown tracks at full volume, we make the decision to leave on a Friday evening in March, during a dinner of chocolate milk and chicken nuggets in the dining hall.  We stuff down our final nuggets (who knows if we can find food in Detroit?) and burst out of the dining hall to make an overnight break for Detroit, where we will meet Zach on this leg of his cross-country road trip.  But in order to find the secret freedom and opportunity that we think is hidden within Detroit, the first challenge is getting to Detroit, and because I spend all my money on T-shirts, I don’t have a car.  Fortunately, I have a fiercely loyal friend, Mike Peters, the Chief-Chief-of-Efficiency at Flippant, who is coming along.  I met Mike on the second day of college, although at the time he looked like he should have been starting high school.  We were both trying out for the hockey team, so after a few weeks of time-honored male bonding including lifting weights, grunting, objectifying girls and drinking light beers until we puked everywhere, our friendship was solidified. We have since expanded our interests to include feminist blogging, fashion design, and drinking vodka out of large plastic bottles, but our friendship is stronger than ever.  Unfortunately, despite being a great friend, Mike doesn’t have a car either. 

We call Brent, the third member of our Detroit exploration team, and get his voicemail. Brent is a Southern-raised Episcopalian who has since left his traditional upbringing behind and through a tumultuous journey including goat herding, orgies (not with goats – as far as I know), and lots of caffeinated kombucha, has finally landed himself in a routine of meditation, skateboarding and celibacy.  We check our email and see that Brent has too much homework this weekend to go to Detroit, so we grab skateboards and T-shirts, and hop in his car.  We stop briefly at a friends’ funk band concert to watch him rip the drums, are wished safe travels while everyone jokes about us getting shot, then settle into Brent’s beat-up Volvo and start driving west.

With the help of several Nos energy drinks we make it to the US-Canada border at Niagra Falls before dawn, and stop at a gas station where we are offered oxycodone pills for sale by the young attendant.  While we appreciate the hospitality, we are about to cross an international border, and have to politely decline.  Canada is brutally foggy, obscuring what I imagine to be breathtakingly average vistas of flat grass and power-lines. We emerge from the fog mid-morning as I emerge from a three-hour nap with lumps of a soggy donut from breakfast still occupying the back of my mouth.  Mike is focused like a stalking lion with eyes on the road – the current target of his insatiable thirst for competition and conquest, which has been lacking an objective since the end of his hockey season.  We pull into the customs lane, smugly holding our U.S. passports.

“Where are you going?”


“For how long?”

“Just the weekend.”

Now we have his attention, but the customs officer doesn’t seem quite as amused by our trip to Detroit as others have been.

“Why are you going to Detroit?”

“For a school project.  And we are thinking about moving our company there.”

“What’s your company?”

“Flippant.  We make T-shirts with upside-down pockets.”

“Hmm.” The officer checks a box on his form. “What’s the purpose of that?”

“So that the pocket can’t hold anything.”

The officer looks at us briefly to see if we are laughing.  We aren’t, but he can still tell we are loving this, and he isn’t happy about it.

“Who owns this car?” He asks, referring to the scrappy Volvo with North Carolina plates being driven by two college students from Alaska and Maryland, respectively, on their way from Vermont to Detroit for the weekend. 

“Our friend Brent.”

“And he let you take it to Detroit?”


The officer looks skeptical.  Apparently he doesn’t have any friends like Brent.  Then again, not many people do.

“Ok, just pull over there for a minute and wait for another officer.”

Having successfully set off every red flag possible, we enjoy our first hour in Detroit by sitting on metal benches in a chilly customs office, answering the same questions again, and watching a parade of tired and much less suspicious black and middle-eastern people endure questioning.

Twenty-four hours after leaving Vermont, and one week after that night of watching Danny Brown interviews, we are sitting in Brent’s Volvo with Zach, engine sputtering as we stare at a school in the East Side of Detroit that could easily have been Danny’s new school.  I am violently nauseous. I struggle to keep my eyes on the cracked and potholed pavement as our Volvo creeps through a zone of rubbly houses and empty lots in one of Detroit’s infamous East Side neighborhoods.  I wonder yet again what exactly makes Detroit special.  The end of Danny’s interview plays in my head:  “If you never been anywhere else, then it’s all there is to you, and you be happy with it, and you live every day, then you die one day.  Welcome to Detroit man.  It ain’t much, but its mine.”

It definitely ain’t mine yet. It’s only two o’clock in the afternoon, and I have a crushing headache that is screaming at my stomach to vomit.  Zach slouches in the seat next to me, a   similarly pained look dragging at his facial features as he vacantly watches the sidewalk crawl by.  As two brothers raised in the rainforest of Southeast Alaska, this is by far the poorest (and blackest) neighborhood we’ve ever seen, and that fact is making us sick.

“Whaaat the fuuuck?” Zach groans – apparently he’s not sure either.

“You really think it would be that bad of an idea to get out of the car?” I ask for the sixth time that hour, glancing at Zach, then at Mike in the back seat, waiting for someone to tell me it is. 

“Dude, I’m telling you, what’s the point?” Mike reiterates.

Mike is from just outside Baltimore, and has seen many neighborhoods like this.  He’s also been jumped.

                Zach and I emit weak sigh-groans, and we continue driving. I am experiencing what seems to be every unexpected side effect from the Cialis infomercial, and now I think I know why.  My own racism is making me physically ill.  I am too scared to get out of the car, in the middle of the day, because we are in a poor, predominantly black, neighborhood in Detroit. Yet oddly enough, there is no real danger in sight.

                 Not only has every person we have encountered over the last twenty-four hours been exceedingly friendly and generous, but in this particular neighborhood, there aren’t even people in sight. On a rational level, I can’t fathom what I could possibly be afraid of at this moment, yet I am still terrified, and this racist, classist paradox is enough to make my skull start collapsing in on itself.

                   In my defense, of myself, to myself, Detroit has certainly developed an infamous nature over the last half-century. The city rose to stardom in the early 1900’s as an automotive manufacturing giant, and was home to over 1.8 million people by mid-century.  But today, this population has sunk to less than 700,000 people, with 40% of the population currently living in poverty. 

“We’re literally only scared because this neighborhood is poor,” Zach reminds me, “This is so ridiculous.”

I couldn’t agree more, yet my vision is starting to blur.  I scramble for answers.

“Yeah, but, uh… you don’t think it’s still dangerous?”

                   Detroit has the highest violent crime rate of any major U.S. city, averaging approximately one murder per day.  But after talking to many Detroiters about crime during our trip, few of them had even ever seen a gun here, let alone a violent crime.

                   We continue our bumpy ride through the near-empty streets while seeking a neighborhood to live in this summer, then stop at a burger joint we heard about, and I vomit in the parking lot.  I smile weakly and slouch into the backseat of the Volvo, and the smell of my puke clings faintly to my sweatpants for the rest of the weekend.  A day later, full of P.F. Changs, white guilt, conflicted ideas and complex emotions about Detroit, we are heading back to Vermont. We say goodbye to Zach for the next ten days, and after two more detentions at the border, we arrive home to our safe, white, privileged, liberal arts school.



It’s 3:45 am on a Tuesday and we are about to have a breakthrough.  Ten days removed from Detroit, we are sitting on pieces of a couch at Flippant HQ (my dorm room), three joints and 25 beers into an executive meeting about our corporate culture.  Zach and I are slumped on the larger piece of couch, taking sips of Busch light and watching a time lapse of mountains in Austria, still trying to figure out what exactly Flippant is.  Ben is lying in bed, chipping away at a business plan so we can convince our parents to give us money.  He is one of Zach’s best friends from Alaska and is visiting for this spring break week.  Ben, a nerd with an incredible eye for photography and a 6’4” athletic frame, is studying business at MIT, and is our media guy.  

“Tomorrow we need to get some shots of attractive girls in our shirts.  People need to think they will look good wearing them,” Ben says from across the room.

Zach and I both roll our eyes, thinking the same thing. Zach takes another sip of comfortably warm beer from the blue can, tasting his next words.

“Ben, that’s not the point.”

“Yeah, but we could sell so many shirts.”

“We know. But anyone could do that, it’s easy. The whole idea is to make a completely different kind of company.  It doesn’t matter if it works.”

I nod to agree.

“If it’s fun, it’ll work, and the only way it will work is if it’s fun. And creative is fun.” I add.

Ben mumbles to himself for a few seconds.

“Ok, that makes sense, I just don’t want it to fail.”



I open my ancient gateway laptop and start composing an email to the COO of Life is Good to discuss more branding strategies. Zach is perusing YikYak on his iPad and occasionally rolling tobacco cigarettes. He finishes a particularly beautiful cig and starts to light up.

“We still need that tagline,” he says as he takes a puff, “Flippant is…”

“It’s tough to get one line,” I say for the tenth time tonight, “How about, Flippant: do what you feel.”

“That’s not bad,” Ben mumbles from his bed “or… Flippant is confidence, upside down.”

The Austrian train on the high-definition screen in front of me is taking a very slow turn around the side of a mountain to the soundtrack of our indie-surf-rock Pandora station.  

“Flippant is not, not creative,” adds Zach.

I chuckle at the line as I think about Detroit – a city that represents a similar paradox. It is a national symbol for failure.  But at the same time, is just another city filled with businessmen and loud cars and gummy sidewalks and people curled up on the sidewalks with blankets.  I like to think a city can’t die, because a city is also an idea.  Even at its lowest point, Detroit is filled with people who love it, who love the idea of Detroit.  Like Flippant, I’m still not sure what that idea is, or what it means.  I do know that we can’t put it into a word, or condense a complex and beautiful idea into one phrase.  But while Detroit is the realization of millions of stories, lives and moments, Flippant is just, well – us. 

This is the challenge – creating Flippant is about discovering who we are.  Our dad always told us to “stop acting so flippant,” to take things more seriously, show more respect, be mature.  Ten years later, we know what we care about and what we love, yet we are still flippant, or now, Flippant.  We might leave the upside-down pockets and Detroit behind, starting tomorrow.  But whatever we do will always be flippant, and every idea and action we create will bring us one step closer to finding out what Flippant is.