Leveraging your privilege
Thanks for being here with me in this #vanlife of a podcast publication where you’re always exactly where you want to be or at least on your way with a good podcast on. Today, though, we’re trading in our van for a bus pass.
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I’ve been wanting to tell a personal story, and I was looking for a way in. I have a story about a hard time in my life, but I don’t want to be ungrateful for my obvious privilege. I also want it to be relevant to podcast listeners and creators, so my lens has to be wide enough to encompass you.
This week I listened to an episode of Climbing Gold, and the the way to tell my story materialized for me. The episode helped me see my own story in contrast to someone it featured, and I wanted to write about that contrast. I’m going to write about the entrepreneurial leverage of privilege, and how three different people, Malik Martin, Anna Sorokin, and I have used it.
Unpacking this term I just made up, it’s is probably just a long way of saying “working that hustle.” It’s about using the privilege people grant you from the external clues they perceive to gain access or favor with them. It’s about getting just the right access or favor to be really meaningful (that’s the leverage part), and it’s about making something out of that access or favor to move yourself higher on the capitalist pyramid (that’s the entrepreneurial part).
What if you’re Black and born in a poor neighborhood in Memphis?
Your privilege is like a credit score that people can figure out with a first impression. If you’re Black like Malik Martin and grew up in Memphis, then your privilege score, historically, is at absolute rock bottom. Martin grew up in the mostly Black neighborhood where, in an unlikely twist of luck in 2018, former Hollywood producer Tom Shadyac (known for comedy blockbusters like Ace Ventura: Pet Detective) decided to open a climbing gym as a community hub.
Martin describes his first impression of the gym as “Narnia” in a place where things like that, “They're not accessible for like the vast majority of the people who lived there.” What he was used to was, “poverty and hopelessness.” He says:
I'll try to paint this picture. I want you to understand if you wake up, your parents are absent (both of them) wherever it may be—like legal problems, or drug issues, or they're working all the time. And they're not very productive in their child's day-to-day life. You have no resources or food, and you’re overcoming that day-to-day. Like figuring out how you're going to maneuver—what you're gonna do. Sometimes a good day is just, ‘I want to eat today.’
From that place, Martin had no privilege to trade. He says, “Nothing's ever going to change, but you're still hungry.” But despite his lack of privilege, he learned how to make money. As a kid, he discovered he could trade labor for cash and started a business called Two Guys and a Rake.
When the new climbing gym was set to open, he was working as a freelance photojournalist. He went there to take some photos, and they offered to let him climb for free for a couple weeks before the opening. Director of Operations at Memphis Rox, John Hawk, noticed Martin returning to the gym several times during that pre-opening because, as Martin says, “being a freelancer means that you have a lot of time on your hands.” Hawk offered Martin a job at the gym.
With that small favor, Hawk extended his own privilege to Martin, and Martin leveraged the hell out of it. He is now an outspoken and loved influencer advocating for the gym and for representation for people of color in the climbing world. He was featured in the annual Reel Rock film series with the short film Black Ice that has been grabbing headlines.
Please listen to the episode. I laugh-sobbed the whole way way through. Martin is the most engaging and fun personality I’ve heard on a podcast in all of 2021. He’s a treasure. I’m so happy that Climbing Gold used its place of privilege to give him a spotlight.
What if you’re me, and 23, and broke as hell?
I’ve told this story a hundred times. I love telling it because it felt like a triumph during the lowest period of my life, and as I tell it, I feel that positive, successful, energy again. But recently I’ve reexamined it for what it really is, not a triumph over adversity, but a moment in time when I, a young, healthy, white guy learned how far I was able to stretch my privilege.
Shortly after 9/11 I was laid off from my software developer job in Downtown Denver. I was two years out of college and had every opportunity to save money but none of the maturity, so I skidded into unemployment with only my last paycheck’s wages in the bank.
It’s hard to imagine a time when someone with a computer science degree couldn’t get a high paying job within 24 hours, but the summer of 2002 was not good for young tech people. No one was hiring, and if they were, there were plenty of people with five or more years of experience ready to scoop up available jobs. My other entry-level friends left the software game altogether. Marco got a job at Home Depot, Jonathan became a teacher, but I was determined to stay in software and stretched my unemployment checks as far as they would go.
Those checks didn’t stretch far enough to continue the lease payments on my car, which eventually got so many parking tickets that it was booted then later impounded. They didn’t go far enough to pay off credit card debt or student loans, so they went into collections. And they didn’t even quite cover paying rent on time, but the property manager let me pay rent about 30 days late for several months. That wiggle room on rent was surely because my property manager thought I looked like the “type of person” that would eventually get it together.
Too broke to spend time in indoors, which always requires buying something, I just started walking around my Capital Hill neighborhood. I struck up conversations with whoever would talk to me. A few of us started meeting outside every morning and sitting on the steps to the three story apartment buildings we lived in. There was the former Marine, the lost soul sailing instructor who for some reason lived in Denver, a couple of homeless guys in their early 20s, and all the people that walked by and in and out of the buildings.
Usually by noon we had scrounged up enough loose change to afford a 12 pack and we made a run to the liquor store. We’d offer beers to passers by, and they would sit on the stoop and hang out with us. Before you knew it, they’d be back with more beer. After two months of doing this, we sometimes had a crowd of 20 people sitting on the stoop. We even started getting hassled by the police. We owned the stoop!
“What are you doing tomorrow, Paul?”
“You’re looking at it, Jon. Stoopin’ it.”
Sailor Paul was the energy behind all of it. He equal parts generosity and trouble—always drunk, always sunburned, and always listening to Jimmy Buffet. He left his apartment open for people to use the bathroom until it got hopelessly clogged and just stayed that way until he was evicted at the end of the summer.
One day I got an email. It contained an invitation for an interview with a software company in Houston. This would be my first interview in months, but it felt like an impossibility. How was I going to get to Houston?
I asked the company to buy my plane tickets because my credit cards were maxed out. That was the first risk. Some hiring managers would have hit me with a “no thanks” just for that, but they bought the round trip one-day ticket from Denver to Houston. Now all I had to do was get to the airport on the day.
I also needed to look employable which meant that I needed a haircut. Those relationships I’d forged on the stoop were worth something. I asked sailor Paul to lend me $20 for the haircut and he unquestioningly and magically produced a twenty dollar bill. He also gave me a nearly new pair of Sperry Topsiders he claimed his parents had sent him.
With my hair looking high and tight, and my boat shoes deployed, and one of my dress shirts from back when I was employed, all I needed for the day of the interview was to get to the airport.
A perk of working for my previous employer was the all-access bus passes they gave to every employee. Mine had expired, and I hadn’t gotten an updated one before I was laid off. This year’s passes had a red shiny sticker on them instead of a gold one.
Finally after a summer of boozing on the stoop I had an engineering challenge. I tore through my broke bachelor’s apartment looking for the solution, and I found it in the form of a red dry erase marker. I tried coloring the sticker. Passable!
The morning of my interview was hot, and the sweat pouring from my hands as I waited at the number 15 bus stop threatened the dry erase job on my buss pass. I was terrified of getting caught stealing a bus ride. I rehearsed in my mind, “Just flash the pass confidently and duck into the bus.”
When I stepped onto the bus, the driver never even thought that someone with a fresh haircut, white skin, and boat shoes was using a counterfeit bus pass. The drama of the event was 100 percent in my own head.
And throughout the day I continued to use my first impression privilege to grab small favors. I landed in Houston and hopped in a cab. When the cab arrived at my prospective employers office, I told him to wait there while I got money for him. I walked up to the office admin and told her that there was a cab waiting that needed paying. In my head I was panicked, but looking back on it, I probably seemed like a privileged, mildly annoying kid to both the cabby and the office admin.
Lunch that day went the same way. The CEO took me to lunch and I made no move to pay. But by that time I was warmed up. I had made it to Huston with nothing but my driver’s license and a counterfeit bus pass. Nothing could stop me.
I ended up getting the job, and I needed it so badly I would have moved to Houston for it. Fortunately, I got another offer in Denver during the time I was negotiating with the Houston company for relocation expenses. The dot-bomb didn’t last long.
The mindset I had during that time to use whatever I could find from the borrowed $20 to a red dry erase marker has stuck with me for the rest of my life. Over the years, when I’ve asked for shout-outs, introductions, and access for my business, I was taking the same advantage of my privilege that I was when I was flashing my fake bus pass.
What if you know that the non-skin and non-gender parts of privilege can be faked?
Just like first impressions and skin color can unfortunately determine privilege for everyday interactions, it looks like whatever mental formula people use for calculating privilege at society’s highest levels is equally bullshit. Your privilege becomes a cocktail of where you say you’re from, what your parents did, and how you talk. I love thinking about how it can all be faked.
My favorite story of faked privilege is the one of Anna Sorokin. She was a middle class Russian immigrant who spun a story that made her the “it girl” of New York society in the mid 2010s. She made a counterfeit life on Park Avenue for years before it collapsed around her. Take a dip into how this famous piece from The Cut describes her:
Soon, Anna was everywhere too. “She managed to be in all the sort of right places,” recalled one acquaintance who met Anna in 2015 at a party thrown by a start-up mogul in Berlin. “She was wearing really fancy clothing”—Balenciaga, or maybe Alaïa—“and someone mentioned that she flew in on a private jet.”
Even knowing those clothing brands is part of projecting privilege.
“She forged financial statements and lied about her family and her name,” this New York Times article says. She nearly made the transition from fraudster to legitimate entrepreneur by almost landing a huge investment for a night club. If she had gotten that investment and started that night club, she might never have been caught for overextending her “line of privilege.”
What should we do?
After having looked at three different starting points, my hope is that what comes out is that all three of us used what we had in the same way. We leveraged our privilege (even the tiniest scrap of it in Malik’s case) to enlarge our window of opportunity.
But living in a world where the advantages of privilege are unavailable to some people and easily stolen by others, how should we play?
For me personally, the answer is to leave faking it to fraudsters, to create great stuff that people actually love, and talk about it with as much pride as I can muster. This might keep me permanently out of the billionaires club, but f!#$ those a-holes anyway. I’m most interested in a world where people are richly rewarded for creating actual value through hard work, creativity, ingenuity, and persistence. And if we have to bank on whatever privilege we happened to be born with to get started, then we sure as fuck had better offer that same privilege to others that don’t have it when we’ve succeeded.
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True crime chat casts are the most popular flavor of the true crime genre. Among them, True Crime Obsessed is a hit. Sean Williams wrote a profile of the show that highlights how the two hosts played to their strengths to find their audience.
Listen to learn about a well made pillar of the true crime genre, or to get inspiration if you've ever felt like you're swimming against the current with your show.
And here’s a Spotify player:
Thanks for being with me on the bus today! Next week we’re back in the van.
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