Chapter One: Home and Neighborhood Chapter One
HOME AND NEIGHBORHOOD
“In 1944 a sixteen-year-old Black student in Columbus, Ohio, won an essay contest on the theme ‘What to Do with Hitler after the War’ by submitting the single sentence, ‘Put him in a Black skin and let him live the rest of his life in America.’?” —Matthew Frye Jacobson, Whiteness of a Different Color: European Immigrants and the Alchemy of Race
I don’t remember what I was wearing when I ran from my 250-square-foot apartment to Google’s mammoth Chelsea office, which took up an entire city block.
I probably had on cargo shorts to survive New York’s sweltering summer heat. Or maybe I wore them to look “Googly” in the office. I can’t say.
But I remember clearly stepping into the building and staring down the cold, sterile corridor at the elevators. My brain was paralyzed. I wanted to turn and run out and hide under the covers and call my friends and scroll the horrifying words and images on Black Twitter. Even that seemed better than what I would do instead: shuffle along, into and up the elevator to the fifteenth floor, where I’d be greeted by my oblivious colleagues with a shit-eating grin on my face.
The night before, George Zimmerman had been ruled not guilty of second-degree murder in the shooting death of seventeen-year-old Trayvon Martin, and I was not okay. I was full of grief and fear.
I did not feel Googly.
If my coworkers cared or could tell I was in pain, they didn’t show it. And I did just enough to make sure they couldn’t sense my anguish. I trudged through a micro-kitchen stocked with Greek yogurts and organic snacks to my cubicle. I asked my colleagues about significant others and babies and dogs who were all very important to them. They were as willing as ever to filibuster about these characters in their lives. A couple asked how I was doing. I knew the question was an empty gesture.
Good. Great. I’m fine. Whatever will check the box that we were done and let me get to my seat.
It seemed inhumane that I was expected to show up at work and send emails like any other day. I had seen the photos of Trayvon. That kid looked just like me. I wondered how my coworkers could look at me and not see him. But perhaps they couldn’t really see him and they couldn’t really see me.
Well, one of them could see me—Andrea Taylor. Dre was Stanford-educated, and light enough to pass for white, but she chose not to. She emerged at my cubicle with her hair in a big, curly bun.
“Come on, let’s go,” she said. I followed her.
Dre led me into an overly lit meeting room. She touched my hand, lightly.
“Chad, I can tell you’re not okay,” she said.
How could she tell if nobody else could? I’m almost sure I didn’t cry, because my mom had taught me since I was ten years old that Black folks weren’t allowed to cry at work.
The fear of death was on me. I thought I was hiding it well, but Andrea could smell it in a way none of my white colleagues could or cared to. Their apathy felt personal. Andrea’s comforting presence reassured me I was not alone, but icy loneliness was otherwise a common feeling for me in certain corporate environments.
Andrea sat there beside me, holding on to my arm. Maybe I yelled, maybe I just sat there. I really don’t remember. She knew why I was hurting but she let me tell her anyway. It wasn’t that an innocent kid was dead. It wasn’t that his killer was acquitted. I’d known as long as I’d known anything to expect such atrocities from this country, our home. That was on brand.
What hurt me was that I was expected to smile and drone and punch out mind-numbing emails and laugh at my coworkers’ corny jokes and affirm their experiences without receiving affirmation in return. I knew what Andrea was about to say. She was hurting too, but she processed the pain much more stoically. She gave me three minutes to be emotional. And then…
“Okay, Chad,” she said. “C’mon, we have to get back to work.”
I knew she was right. As two of the very few young Black people at Google, we both felt immense pressure to perform at the highest level. I couldn’t risk squandering my opportunity because of feelings. If I did, would the same opportunity be available for someone like me next year? Would I be able to support myself? The cost of trading time at my desk for time in the conference room, sorting myself, was too expensive.
And for those few minutes I spent in the conference room, I wanted to apologize to my father.
My dad is a tough guy. He’s a college athlete. He’s a lawyer. He was born in Detroit, in the 1950s. Growing up, he shared a bed with his older brother in the kitchen. His father was an army veteran with a sixth-grade education. During the 1967 Detroit riot, one of the deadliest in American history, my dad sat with his father in front of Grandaddy O’Neal’s small laundromat bearing shotguns in case the mostly Black rioters didn’t notice or care that their business was Black-owned.
When I was six years old my family moved up-county, from a small townhouse on the Maryland side of the D.C. border to a quaint cul-de-sac, and this, I think, made my dad keep a very close eye on my sister and me as well as our white neighbors.
We moved from a modestly sized brick townhouse to a single-family house with a two-car-garage. Our old neighborhood was diverse, with a number of Black and Latinx families. Our new neighborhood was mostly white. Our old neighbors were an eclectic mix of government employees, teachers, and laborers. Our new neighbors were more affluent white-collar professionals. We had moved on up
. With its square lawns, tall trees, and general American Dream–iness, our new neighborhood resembled the gated community where Trayvon was murdered for being Black after the streetlights came on.
But what I saw, as a child, was a giant playground. I was six, the age where I wanted to explore on my own. I thought I would ride my tricycle down our street or trudge through backyards adjacent to ours, as freely as the white kids in our neighborhood did. My father knew better. Like Andrea at Google, he knew there was a different set of rules for me.
My dad was a hands-on father. Not in the physical sense—in fact I can’t remember ever being spanked by him. But he paid close and constant attention to my every movement. He coached my youth basketball games and was particularly firm with me compared to the other players’ parents. After every game and every practice from age six through fourteen, he would run through a list of detailed questions about specific plays and decisions I made. These intense discussions often felt like emotional interrogations.
But if I tried to slither out of the questions for a bathroom break, or hide behind my mother, he was always there, on the other side, waiting with fixed intention.
“Why didn’t you shoot the ball more? What did you see when you made this decision? Why are you passing the ball to James so much? Do you think he’s a better shooter than you?” he would say, plowing through one question to the next before I could answer.
Every discussion was followed by another—a meta-discussion on how basketball principles we explored related to life decisions.
“Every shot you pass up is a missed opportunity, Chad. What do you think happens to Black boys who grow up passing on opportunities in this world?” he asked.
It all felt very urgent. Everything felt urgent.
He approached my schoolwork with the same hovering fervor. We’d sit side by side at the dining room table every night, mowing through hours of homework, studying for tests, arguing, struggling, learning together. The white neighborhood kids would show up at the door and ring the bell to see if I could come out and play.
My dad would crack the door just enough for them to see me sitting there in front of a table covered in books and scattered papers. The white neighborhood kids would ask my dad if I could join them outside, and he’d quickly, gruffly, inform them that I was unavailable. Slam. Click. He’d shut the door, shaking the bottom two levels of our three-story house, then snap the lock closed. He wanted them, and me, to get the message that I would not be joining them anytime soon. Perhaps never, if that’s how long it took for me to finish my homework. At times, I felt trapped.
But I had my father in my house. Many of my Black friends didn’t.
As I grew, my high school coach took over my basketball training. Coach Pigrom was only thirty, a Black man who had played college ball at HBCU Hampton University. He was even more no-nonsense than my dad, but still my father hovered and pressed. He’d watch my basketball practices from the gymnasium window. He was the only dad who did that. When my teammates and I lined up on the baseline of the basketball court for sprints, a few would make jokes about my dad, who was always there watching. I was embarrassed, but I guessed that underneath their jokes was harmless envy. They loved to spend time hanging around my dad, maybe as a proxy for their own.
We’d pile into his Acura SUV on weekends and he’d drive us across the county to high school football games, teenage dance clubs, parties, and fairs. Five, six, seven of us Black teenagers would fold into the back of his car and rap along to Kanye West’s College Dropout
album, which had just come out, or my dad’s favorite, Tupac. When we arrived at any destination, my dad would usually go inside to inspect the premises then sit out in the parking lot, watching the door.
I’d try to push him out of his watching. I wanted to assert myself as a man I’d yet become, and to me that meant I needed to get out from under my father’s supervision. Sometimes I’d sneak around after curfew to see girlfriends or go to parties. As I grew, I wondered what or who my dad was always on the lookout for. I’d find that out later.
When I turned fifteen, my dad realized that he couldn’t be everywhere I was, so he laid out very clear rules for my conduct in our upper-middle-class neighborhood.
- Always protect your freedom.
- No hats, du rags, or headwear of any kind in the car.
- Drive below the speed limit. If you get pulled over, put your hands where the police can see them. Don’t make hard eye contact with the officer. Address the officer respectfully as sir.
- You can play with white kids in the neighborhood, but don’t go in their houses.
- Don’t get your sense of self-worth from depictions of Black people in the news, popular music, or popular movies and television. They will destroy you.
- Avoid interactions with the police.
I bristled at these rules, but I followed them, like all the rules that came before. My dad never really yelled at me off the basketball court. He never had to. I knew that he wanted to protect me. I don’t know how I knew, but I just knew.
When I was in middle school, maybe twice a year, my dad would follow my school bus as it weaved between white neighborhoods picking up “Gifted and Talented” kids to take cross-county to our public school. The shrewdest preteens recognized I was insecure about being a Black kid who lived in a nice neighborhood with attentive parents, because that way of being ran counter to stereotypes. So they needled me when they saw me sweating over my dad’s “overprotective” hawking eye.
“Hey dude, isn’t that your dad
? What’s he doing?” one of the white kids would always ask, loud enough to catch the other kids’ attention—and shame me. I’d shrink lower into one of the green leather seats of those big yellow buses and clutch my black JanSport backpack. I’d pull out my three-ring binder and busy myself with extra credit math problems to take my mind off of my humiliation. Then I’d peek around the side of one of those big stiff seats, out of the bus’s wide back window and we’d make quick eye contact, my dad and I. I’d sneer. He would just smile back at me.
This one time, Trevor Willock, the cool
kid with slicked hair whose father had divorced and married much younger, blurted out:
“Does your dad think the bus driver’s gonna forget where our school is? What the hell is he doing back there?”
The coolest among us had started cursing by then. I wish I’d known the answer to his question. I do now. If I could go back, I’d give my twelve-year-old self the answer so he could spit it at Trevor.
“He’s protecting me, Trevor. From being Emmett Till or Trayvon Martin or some other little memorialized Black boy. He’s protecting me for as long as he possibly can, before it’s out of his control,” I’d have said. Instead, that day, I just squirmed deeper into the green leather seat.
I’m not sure if my dad clocked all my eye-rolling and sighing back then, but I know for certain he ignored me if he did. He was determined to fulfill the most important duty of fatherhood. He was on a mission to keep his Black son alive.
The danger my dad was always defending against came in many forms, some of them confusing. It could be a white woman walking her dog off leash in the park; it could be a racist neighbor overzealously playing out his American hero fantasies with a gun; it could be a cop who woke up on the wrong side of the bed. Whatever the danger, my dad was committed to keeping me under his supervision until I was mature enough and savvy enough to protect myself.
My father protected me by enforcing an elaborate set of rules. A decade later in a Google conference room, Andrea did the same thing, in her own way. She knew that what I needed, even if just for a few minutes, was to be seen. I needed for a moment to have my humanity affirmed. I needed to be with another Black person who understood the emotions boiling inside me; to nod and give me permission to be broken for a moment. And then I needed her to look me in the eye and tell me to get back to work. She provided me the safety to cry at work, but only for a moment in private. Because she knew, like my dad, that regardless of my feelings, my fears, and the danger I faced every day, that I needed to get back to that desk and do my job just like I needed to get on that bus every day and go to school and learn. Because my life and my livelihood depended on it, as well as the life and livelihood of the next Black person to come after me.
While my father seemed to focus on rules that maintained my family’s physical safety, my mother pushed my sister and me to strategize and achieve. This was her way of giving us financial safety. She taught us the importance of education, corporate advancement, and earning as ways for us as Black people to protect ourselves down the line from misinformation, financial predators, and unexpected disasters. The four of us—mom, dad, sister, brother—sat down for dinner as a family nearly every weeknight in that three-story house on the cul-de-sac. My parents took turns cooking while my sister and I set the table and listened to Stevie Wonder playing in the background. My late maternal grandfather’s paintings adorned the yellow walls of the kitchen. He was a lieutenant colonel in the army and a Vietnam veteran. His paintings depicted people alone with nature. A bullfighter awaiting a charging bull. A camper alone beside a bonfire at night in the woods.
The television was always off. My Xbox was unplugged for the night so I wouldn’t try to rush through a meal to get back to it. A ringing house phone went unanswered. Door-to-door salespeople stopped coming at dinnertime, because my father warded them off. Before an unsuspecting Jehovah’s Witness or Cutco knife salesman could even open his mouth, my dad would make waste of him.
“We don’t want any and if you keep coming back here it’s going to be a problem,” he said before the guy got a word of his spiel out.
My parents protected dinnertime because it was their chance to listen to us, and to teach us who we were and where we came from, before the outside world could force its Eurocentric perspective into our developing minds. And that sort of enrichment required a high level of insulation and focus from all four of us. No distractions.
My mom was an executive at Verizon for most of my childhood, and she ran our kitchen like her boardroom. Dinnertime was regimented. Each time we sat down at our rectangular wooden table, we’d first say grace together. We took turns speaking to God on the family’s behalf at each sitting. Then, my mom would recount the activities of the day at her Fortune 500 employer. By twelve I was familiar with rebrands, layoffs, mergers and acquisitions, initial public offerings, stock options, office politics, and the unstated rules of corporate culture. My mom engaged us in these conversations not as children, but as thought partners. We were invested spectators as she ascended the ranks from entry-level MBA to senior director over the course of my childhood. Race was an important factor in every discussion.
She’d ask what my sister and I thought she should tell her white male boss about her white female subordinate who’d been undermining her for weeks. She considered our thoughts and feedback carefully. I was eleven, my sister fourteen.
We’d brainstorm together with my father until we found a solution we could all live with. We were a mini war room. My mom often reminded us that business was a game, with rules, and additional nuance and risk for Black people. But like any game, it could be solved, and won. I found over time that living as a Black person is a game of its own, with the highest stakes and a similar set of rules.
In high school, I began to jot down the rules in business that I learned at our dinner table boardroom. I’ve paraphrased some of them here:
- Money controls all important decisions. The closer you sit to the money, the more valuable and safe you will be as an employee.
- Someone, somewhere is accounting for you as a human with a dollar amount attached to your name. That is your capitalist value. Your leverage (or lack thereof) can be reduced to that dollar amount. Be aware of it.
- In hard times, company culture craters. The leverage created by the money you make the company and the strength of your relationships is your safety net.
- In good times for a company, opportunities for promotions and growth emerge, and the money you make the company and the strength of your relationships are your leverage to access them.
- Always make your boss look good to her boss and make sure your boss knows you’ve done so.
- Value is measured by outcomes and not process. No points awarded for trying hard. No bonuses for sending the most emails.
- Do your job first before helping others to do theirs. You will never be rewarded in a way that feels adequate for helping other people do their jobs, especially if that aid comes at the expense of your job. Do your job.
- If you report an issue about a colleague to Human Resources, know that two people will thereafter be examined closely and considered potential threats to the business: the person you reported and you.
- Don’t cry at work. Don’t do it.
ED BAILEY “Call it what you want. I’m still here.”
Ed is an executive coach for Silicon Valley leaders and an NFL agent and business consultant. He formerly led teams in Sales and HR as an executive at Google and LinkedIn and as a business management consultant at McKinsey & Company. He earned his MBA at Stanford GSB and his BS in Mathematics at Michigan State University.
When I started working at Google, the execs called Ed “Papa BOLD.” He was a sales executive, but in his spare time he built Google’s Building Opportunities for Leadership and Development program to help hundreds of Black and brown young adults get hired at Google. I was one of those kids.
I was walking through one of Google’s main campus hallways when I first saw Ed. He stood out as a big Black man with broad shoulders and a full beard. Ed was giving an orientation talk to the new hires. The Google employees, mostly white, wore company-issued hats with silly pinwheels to announce their newness. Ed was more dignified, all six-foot-three of him, wearing a Chicago Cubs T-shirt and shorts.
The audience members were quiet and attentive, jotting notes as he spoke. Ed captivated those white people. I watched from the back row as he plowed through his lecture with no notes, holding his body upright with complete confidence. He owned the room. That struck me. And he spoke from his belly, not shrinking his body or raising the pitch of his voice to make himself unthreatening.
When a tall, square-jawed blond man in the front row tried to interrupt Ed’s spiel with a question, Ed drove straight through the man’s interruption without skipping a beat. Ed gave the man a wink to let him know he clocked him and that he’d get back to him after he’d finished his train of thought.
I knew so little as a twenty-two-year-old working for the first time in a large company, but I learned quickly that to excel I’d have to get white people to listen to me. I thought that to get their attention, I’d have to emulate them. I thought I should dress as they did and talk as they did and shrink in moments when they didn’t want me around. I call that process of changing to appease white people “racial duality.” I showed up as a “whiter” version of myself when I thought it would save me. Many Black people feel forced to adopt this process, this reality of dual selves, to be palatable and included, especially in corporate worlds.
When I interviewed Ed, I wanted to understand how he commanded the respect of white people as a big, Black man from the hood. I wanted to explore Ed’s ability to connect with white people in a way that seemed so effortless. I wanted to learn from his mastery of racial duality.
I thought mastering racial duality was a form of Black Magic, an ability that could help Black people manipulate situations. But Ed finds racial duality to be a painful burden—one he’d had to carry since he was a kid, to survive his old neighborhood. I was struck by Ed’s conviction in his belief that Black people actually lose more than we gain by switching back and forth between personas to accommodate white people. Chad:
To start us off, can you run me through the geographic stops from your life dating back to childhood, and your focus in each one of those stops? Ed:
So geographically speaking from zero to eighteen I was in Chicago, I grew up in one house my entire time there, on the West Side of the city in the midst of a neighborhood where a lot of gangs and gang leadership resided but it looked okay from the outside. In other words there were lots of houses and bungalows and stuff but the freaks really came out at night.
From eighteen to twenty-two I was at Michigan State. In between there I spent a summer in Minneapolis and I spent a summer in this town called Lodi, California, which is a wine manufacturing town. The big employer there was the General Mills plant, which is why I was there. From twenty-two to twenty-four I lived in downtown Chicago, where I was working at McKinsey. And then twenty-four to twenty-six I was at Stanford at the GSB, but I was one of the few folks that lived off campus both years. From twenty-six to thirty-four I basically lived in Los Altos, that comprised both my Google era and my LinkedIn era. And then I got my place in Sacramento when I was thirty-four and I’ve been here in the Bay Area ever since. Chad:
What was your purpose at each one of those stops? And what was your relationship to your race? Ed:
Both my mom and my dad grew up in families with at least five kids that were very poor. So both of my parents were first-generation projects. My mom lived in a condemned house, my dad lived in some of the worst projects in Chicago his entire life. So resources were never plentiful for them and they didn’t really care about that kind of stuff. In addition, both families were Jehovah’s Witnesses, so there was a level of separatism there and both my parents really didn’t get along with their mothers as they became adults.
All of that led to a scenario where my parents moved to a nicer part of the west side and basically away from everything they grew up around. So I was always different as a child from the rest of my family. I was different from cousins, aunts, uncles, and stuff on both sides because of that distance. I was different both in terms of philosophical distance as well as actual distance, because my mom and dad both had cars but no one else in the family had vehicles. So we could get to them, but they couldn’t get to us. So my experience outside of school was just me, my mom, and my dad. And then when my brother was born he was added to that.
There was always a challenge for me to connect to my family members and cousins. They were having conversations about common experiences and then I would drop into their environment and I couldn’t relate. I didn’t play with the toys because my parents believed toys were distractions. I didn’t watch the TV shows or listen to the music they listened to, so there was no connection there. I had to learn at an early age how to be in an environment and connect while not being connected. Chad:
How did that translate once you started school? Ed:
Up to eighth grade, I was part of a gifted and talented program, so I didn’t go to the neighborhood schools. I might see the neighborhood kids for an hour or two on weekends, but I was separate from them too. That led to something my dad and I always talk about: neighborhood rules. I wasn’t allowed to talk to the neighborhood kids about how smart I was. I wasn’t allowed to talk about what kind of stuff my family had in the house. I wasn’t allowed to talk about the experiences I had because in my dad’s perspective—and he was right about most of it—in the type of neighborhood we were in, people see that stuff and they try to take it.
My house was probably broken into every year for ten consecutive years, and I would see some of the neighborhood kids with the toys they stole. But yet, I had to figure out how to get along with them. That was an interesting experience, and particularly with guys, that led me to not build close relationships with men for a long, long time. There was no trust level there. I knew that for guys my age and a little older—call it eight to twenty years old—it was every man for himself and guys were trying to get anything they could at all costs. If they had to sell drugs or rob people and take stuff from others, even their friends, they would.
I could never trust the decision-making of the guys where I lived, so I’d never get in the car with them. I would rarely even walk places. Those became saving characteristics for me, because there were times where I chose not to go on a ride and the group in the car got shot up. When I explain this to people, some say that feels kind of separatist or kind of extreme, but it actually saved my life on multiple occasions. You can call it what you want. I’m still here. Chad:
Did those habits of separation follow you into the classroom? Ed:
When I got to school it was a non-Black world. There were white people, there were Hispanics, there were Asians, but basically all the smartest kids in that part of Chicago were in one school, and even among that group I was sort of extra-gifted with math and analytics. So on one hand I was a competitor with my classmates and on another hand I never got to spend any time with them because my parents didn’t believe in me spending the night in other houses because of all the religious stuff. I wasn’t going to birthday or Christmas parties or anything like that. So I had to learn to support people from a distance. I had to learn to show people that I knew something was important to them without having the ability to participate.
Those three major dualities forged my personality: separation from family, separation from neighborhood, and separation from my peers, at school and in social environments.
When I got to Michigan State, I was really excited about being able to be friends with people of color on my level academically. But I quickly realized many of the other students of color weren’t nearly as prepared to be successful. Many of them lacked fundamental tools to be successful there. I spent a lot of time helping them, tutoring them, coaching them to make sure they got through classes so they could stay at school and so I could have friends. I lost three or four close friends over the first couple years because they just couldn’t hack it academically. As I took on leadership responsibilities at the dorm and on campus, I had to stay grounded so I could still be one of the crew. I had to make sure I wasn’t automatically alpha. I had to learn how to lead when it wasn’t what I wanted to do but it was necessary for the best outcome. I had to learn to lead my friends in structured environments and then just be one of the people in unstructured environments, and I had to learn to identify the difference between the two types of environments.
On the flip side, I still had to find ways to relate to my honors college folks and scholarship folks who weren’t Black. So when I decided we were going to put on a Kwanzaa celebration for the first time in Michigan State’s history, a lot of my fellow scholarship kids were like “Why are you doing that? Why are you trying to accentuate Blackness so much? Is there a problem?”
Later, when Student Body president elections came up, all the candidates were white males and they were searching for someone to just diversify the ballot. My name came up. I had already agreed to enter the pool of candidates before I realized why
my name came up. But when I found out they just needed someone of color on the ballot, I felt like I needed to win
. I thought I needed to win so people’s behaviors and thoughts would change. The feeling came from things I experienced when I was younger. I thought Yeah, I might be an outsider for things beyond my control, but don’t discount my abilities based on that. And don’t think that because I spend a lot of time on the brown side of campus that I don’t have the white credentials and capabilities.
I won the election by connecting with students who felt disenfranchised, and it led to one of the biggest learning experiences of my life. I learned what happens when you achieve something that you don’t really want or care about. To boil it down, you end up not doing as well and making yourself look bad in different ways. You end up going through heartache because you fight what you can’t do versus what you want to do when they don’t line up. And I think that is a big downside of having to go through racial duality. You end up in situations when you have to choose between solidifying or debunking the world’s view of you or solidifying or debunking your own version of yourself. That leads to what I call “Ghost Chasing” or this internal struggle between which person is real. You end up with multiple personas, and it gets difficult to manage them after a while. Chad:
What does that look like? Ed:
In college I did an internship for two years with General Mills. Loved it. Very diverse company. Learned a lot. Had a lot of support multiculturally. I was excited about pursuing that opportunity as a place to work after college. I felt comfortable there. Then this magical thing that I knew nothing about called McKinsey & Company dropped out of the sky and decided to interview at Michigan State for the first and last time over the course of a twenty-year period. Even though I knew General Mills was better for me, McKinsey was more prestigious. And so I did what I did with the student body president election. I made sure I killed it and I got the offer.
Even though all my friends were going back to General Mills and I knew I would have a support system there and I knew I would be in a place where I could be happy at work, I chose to do the shiny thing by going to work at McKinsey because as a Black person, sometimes to get ahead and get opportunities, you have to do the shiny thing. Chad:
Why? What does it cost you if you don’t choose the shiny thing? What does it cost you when you do choose the shiny thing? Ed:
First, when you’re in what I’ll call high achievement environments
, there’s always the recognition, implicitly or explicitly, that there have been very few if any people of color who have done what you’re doing. If you’re at all sensitive to the outside world, you realize you’re not just representing you. There’s something on the front of the jersey that you wear that becomes more important than who you actually are and what you care about. And that’s why I think, in many cases, pursuing the shiny, known, visible opportunity, even if it’s not best for you or what you want, becomes an important decision for Black people.
What does it cost you when you don’t
pursue the shiny thing? Well, I think what it costs you is the opportunity to learn what other parts of the world look like, and to go into places you wouldn’t have had access to otherwise. And to learn from people, learn from circumstance, learn emotionally how to deal with all of it. And more importantly, if you don’t do the shiny thing, it can cost other people like you the same opportunity in the future. Oftentimes, in those environments, you’re the gatekeeper’s first chance to experience a Black person who has the capabilities that you have. And the gatekeeper’s experience with you is going to define whether or not they’re open to more experiences like that for people like you. So shoving what they believe to be a gift back in their faces can be unhealthy. It can lead to doors closing for many more deserving, better fitting Black people who come behind you.
But the cost of pursuing shiny objects is twofold as well. For one, as a person, you can waste your time pursuing things that aren’t for you and suffer emotional pain when those things don’t go well. Even if they do go well, you know that you aren’t doing what you’re meant to do and you can’t enjoy life the same way. For me, that was particularly painful because I’ve always had a really good sense of what I wanted to do in my life, and the McKinsey choice led to a bunch of decisions that I made that weren’t in the best interest of my personal happiness. Instead I continued to pursue exploring and entering slightly forbidden worlds to learn for the sake of advancing Black people.
Take my experience working at McKinsey for example. After undergrad, I made this decision to go to McKinsey and I didn’t know what the hell McKinsey was. I knew they helped other companies do stuff, which to be honest, where I’m from, didn’t make much sense to me. But everyone said it was the hardest company to get into and the best company to work at, so I went. And, boy, was the world opened up to me. It exposed me to simple things. For instance, my family never went out to eat growing up, and I had never been to a nice restaurant before I worked at McKinsey. I had never been around wealthy people. I had never been around executives. I had read all the books and articles and stuff so I could have conversations, but it was just a really foreign environment. I had grown up opting out of foreign environments that weren’t comfortable, for survival. This was the beginning of a period where I was starting to process the fact that what I actually had to do was opt into foreign environments in order to be successful. My comfort zone said hell no, but I knew that to trailblaze for my people I had to.
I learned a lot at McKinsey, but it wasn’t very fun for me because I thought the work was really inefficient. There were times where I was sitting there waiting for someone else with more authority to allow me to do something that I may or may not have thought was useful. I didn’t have much time to spend with anyone except my girlfriend because I was on the road all the time for the job. The money was great, but it didn’t feel worth it at the end of the day. And most importantly, I never wanted to work there. Chad:
What was your relationship with whiteness at McKinsey? Ed:
I didn’t really see it that way at McKinsey. If I look at my class of business analysts, there were twenty of us. There were three Black people in that class. I was the only Black male. And then there were seventeen white people. Thirteen of us were men and four were women. Within that group, we were just peers trying to survive McKinsey and there was no relationship with whiteness or Blackness or race or anything. We were just twenty young people trying to survive the madness that is working in a high-stakes business.
But my relationship to Blackness was interesting. McKinsey’s Black network was called BCSS or Black Client Services Staff. Its origin was in Chicago. The first couple Black partners were from Chicago, and I worked in Chicago while I was at the company. Also, the most important person in any consulting firm—which is the person who does the assignment of analysts to projects—was also Black. And so, because of that, I had access to a power structure that gave me an opportunity to understand McKinsey in a way that was actually kind of unfair. It was the rare corporate environment where I had access to rare information as a Black person. That was really important for me in some pivotal moments. But it also underscored to me why it was so important that I made sure I did what I could to open doors for other people. Chad:
You said earlier that something problematic about duality is that you can end up with multiple personas. Did you feel that in your experience at McKinsey? Or did that develop elsewhere? Ed:
I actually didn’t feel that at McKinsey. But the only reason I would say I didn’t feel it is because McKinsey was life for those two years. There was no outside life. There was no other person I had to be. And so there wasn’t as strong of a duality conflict—I just wasn’t myself. I was just completely in another persona for those two years. And I think that had an impact on me. I was almost completely a character at that point. Chad:
Considering the path of your life—from grade school to college, McKinsey, Stanford, Google, Cisco, LinkedIn—the entire path. How would you quantify the percent of space in your brain occupied by managing the various personalities you needed to display at each stop? Ed:
That’s a really good question and I was hoping you’d get to that. Middle school, I’d say 80 percent. High school, 40 percent. Undergraduate school at Michigan State, 60 percent. McKinsey, 95 percent. Stanford Graduate School of Business, 5 percent. Google, between 50 and 85 percent, depending on what I was doing. LinkedIn, 95 percent. Cisco was probably 50 percent. And now, 10 percent. Chad:
And what has it cost you to spend so much of your brainpower managing personalities within yourself? Ed:
Three years on the couch with my therapist twice a week. It cost me and several other people fun experiences because I was dealing with depression, social anxiety, PTSD, and the results of having to deal with all of that. It probably cost me two promotions at Google, one promotion at LinkedIn, and at least one promotion at Cisco. Chad:
You’ve made it clear that there were costs to your energy and mental health in managing dualities. What did you learn from that twenty-five-year process? Have you used or wielded any of that for success? Have you been able to fine-tune the muscles for your own advantage? Ed:
I think that because I spent a lot of time by myself, throughout my youth, I did develop a capability to think independently and to only be moved by better information and not by who it was coming from. And I think that is an advantage that plays out today and will play out in spades as my life continues to evolve. I think that I understood the importance of doing my own research and creating my own perspectives on things and fitting other people’s information into that, versus starting with other people’s information and then figuring out how much I could do with that until I have to start thinking for myself. Chad:
Do you feel like you have enough perspective and distance to opt in or out of duality? Ed:
My visceral answer is I think I’ve always tried to opt out of duality. I now have enough information to know why and when and how to exercise duality and to do that in a healthy way that’s not self-destructive for me and other people. I always intellectually and emotionally knew the concept of duality was stupid and no one should have to go through that, but I also logically understood that in certain situations duality was unavoidable. But it took me a very long time to come to grips with exercising duality in a healthy way versus fighting and being willing to murder myself internally or externally to avoid it.
JASON CRAIN “I recognized that white Kansas City and Black Kansas City were two totally fucking different things.”
Jason is a tech and restaurant entrepreneur, startup advisor and investor, film producer, product owner at Amazon, real estate investor, and world traveler. He cofounded Partpic, a visual hardware recognition software, later acquired by Amazon. Before that, he was an executive at Google and Shazam. He is also chairman of the board for ScholarMade Achievement Place, a charter school in Little Rock, Arkansas, founded in 2018. Jason’s achievements landed him a place in the 2016 Forbes
30 Under 30 manufacturing list. Jason earned his MBA at Kellogg School of Management and BAs in Marketing and Spanish at Morehouse College. That’s where I met him.
Jason was the first of our friends to get rich, and he did it by building a company and selling it. In this interview, I was prepared to ask him about the process of raising money as a Black entrepreneur. I wanted to know the ways in which having money has affected his life. But Jason took control of the conversation and steered us to a more compelling topic: his experience growing up in his neighborhood in Kansas City. Jason highlighted two important experiences that made him a successful entrepreneur.
The first was the time he spent as a kid working with his father. The men on Jason’s father’s side of the family ran a nightclub in a rough part of Kansas City, where, as a teenager, Jason learned to run a business, from stocking the bar to counting the money in the register at the end of each night. It was hard work, but everyone worked hard. The second was the time he spent with his mother’s family. His mom’s side of the family faced constant struggles, including murder, poverty, and teen pregnancy. That gave Jason fuel and purpose to provide relief for himself and the people he loved. Jason stressed how both sides of his family influenced his outlook and shaped his success. Though some might see Jason’s mom’s side as a disadvantage, he never did. It drove him.
I admire Jason’s perspective. One side of his family showed him how to provide a living; the other showed him the urgent and dire need to provide a living. Jason underscored that these experiences were the source of his Black Magic: he felt the need to provide resources, and learned the ethic to create them. Jason:
I’m Jason Crain, I am a Kansas City, Missouri, native. I currently live in Atlanta, Georgia, and I work for Amazon.com as an entrepreneur in residence and product manager. I’ve been in technology my entire career, starting at Google, then went to Shazam, then started my own tech startup in computer vision. We sold that startup to Amazon.com about eighteen months ago, and my responsibility now is leading data acquisition for our computer vision team and integrating our Partpic technology into Amazon’s mobile app. Chad:
How did you grow up? What did your parents do for work? How were you raised? Jason:
I grew up modestly in Kansas City. I saw a lot, on both sides of the spectrum. My parents had me when they were in high school. My mother had me as a senior in high school at seventeen years old, and my father was just eighteen, and they didn’t have much. My mother was one of seven kids. By the time she had me, all five other sisters and her one older brother already had multiple kids. So she grew up around young parents. My uncle, her brother, was murdered—shot and killed at a skating rink—so I never got to know him but I got to meet his kids in other cities.
On my mother’s side, pretty much everyone is still living below the poverty line. They struggled with teenage pregnancy. They lived in not so good areas and had to fight the battles of living in Kansas City without having much.
On the other side, my father came from a divorced household, but a household that was grounded in Christianity and the Baptist faith. They didn’t have a lot either but they lived a different life from my mother’s family. My grandfather, who is the only person in my immediate family to have gone to college, took that college degree and was also an entrepreneur before me. He spent his whole life savings pursuing entrepreneurship, and to some degree you could consider it a failure, but he was able to create a life for my father. That life wasn’t full of riches, but it was a life grounded in responsibility and working and doing whatever you gotta do to provide for your family.
My great-uncles on my father’s side were also all entrepreneurs. They were fairly known in the Kansas City area because they owned a nightclub called Epicureon, which I now own with my father. That nightclub was a staple in the Black community. The club provided outlets for me and my brother to work from the time I was old enough to walk—whether it was just yard work at the club or stocking the bar in high school. My job was to make sure that the bar had liquor every night. And I had a key and I was responsible for going in and filling the bar. My father’s side of the family provided me with structure, foundation, and religion, and a focus on working and hustling and doing whatever you gotta do.
My mother’s side of the family showed me struggle. Folks were in and out of jail, but that was the side I spent most of my time with. My mother had five sisters and two or three of them had at least five kids. So I had hella cousins. In elementary school I had cousins in every grade at my school. We ran the school.
So while I was being raised by my mother’s side of the family, my father’s side of the family provided that structure and guidance that made it possible for me to be successful. Chad:
You’ve built a career in the tech industry primarily. We worked together at Google, you were an equity owner at Shazam, and you cofounded Partpic. Now you’re an entrepreneur in residence at Amazon. None of those places are filled with Black people. None of those places are even representative of the national demographics in terms of Black and brown people. You are a Black man under thirty-five from Kansas City with what you just described as a humble beginning. How have you been able to navigate those kinds of environments to plow your way to selling a company for millions of dollars and establishing yourself as a leader in technology? Jason:
I think it starts with what my family instilled in me, which was a need to provide. I saw how lack of access and resources impacted both sides of my family, but my father’s side of the family was a shining example of an ability to push through and work through it regardless of the outcome. That determination and motivation is really the backbone of my success. Most times I didn’t know what I was doing or know what the outcome of my actions would be. I was just doing what I thought I was supposed to do or what I was told I was supposed to do at each stage.
One of the things that changed my life was going to my high school. I went to Kansas City public school my entire life until my freshman year of high school. At the end of my eighth-grade year, the Kansas City School District lost its accreditation, which forced me and my family to make a decision on whether or not I was gonna stay in the Kansas City public school system and risk my high school diploma being meaningless to colleges or go to a private school which cost a good grip of money. But one of my older cousins on my father’s side had been to that same school. It’s called Rockhurst High School, an all-male institution. My cousin was a football star there and went on to play at University of Oklahoma during the early 2000s when they won all those national championships. To this day, he and I are probably the ones that our family look toward for continuing the legacy of building middle-class success in my family.
I went to Rockhurst, which was where all the rich white folks in Kansas City sent their sons. It was, and still is, one of the best schools in the nation for sports and academics. But for me, personally, it was where I recognized that white Kansas City and Black Kansas City were two totally fucking different things. The experiences that my white high school classmates lived every day were so far out of my reach, even with the success of my uncles, it was incomparable. We had totally different lifestyles, totally different access to resources. My friends in high school all had cars when they turned sixteen. And not just cars, but BMWs and Mercedes and Suburbans. They all traveled for holidays. They had lake houses and vacation homes and had been out of the country multiple times and their day-to-day life was just a different experience from mine.
I made one friend in particular at Rockhurst—Gil—who remains one of my best friends today. His family basically adopted me when it came to Rockhurst culture because his parents grew up humble in middle Missouri, where drugs are rampant. Some members of their family are still crackheads to this day. So they grew up modestly and worked hard to become very, very, very successful and very wealthy. In hindsight, I think they must have seen some of that work ethic in me and wanted their son to be around me, because they took me in. They are responsible for taking me out of the country for the first time in my life. They even paid for it, though my father was very hesitant to accept help or money from a white man. Gil’s family took me on some of my first and best experiences of my life and just changed what I thought was the norm. They set a different precedent for what I wanted my norm to be for my family now and my future family.
Recognizing the difference between my life and theirs, and then taking real effort to insert myself into those new experiences is a pattern that I have pursued my entire professional career. I’ve had to be unafraid to take the chance to engulf myself into a new experience and to think holistically about what I can get out of it and how I’m gonna get it. Chad:
You touched on accessibility. In my experience, inroads to opportunities that gave me new ways to see the world—like Google—have generally come from relationships with Black people. You mentioned Gil’s family, from high school, who exposed you to new experiences. But have you been able to identify allies and Black champions for yourself in your career? Is that something you have worked on? Is that something you’ve gotten better at over time? Jason:
That has definitely been my experience. There have been allies throughout my professional career who didn’t look like me, but I wish there were more. At Google, my mentors were Black people who put their arms around me in a way that made it comfortable because they recognized how difficult it was to be successful.
But in my first week at Google I was sitting in New York in the office with my manager, Kevin, who was white. I learned that I should always ask questions to make my managers feel good, so they would provide me with solutions. So I asked a question: “Hey, I’m really having a hard time learning people’s names and you do such a good job of it. I always see you socializing with people. What’s your secret?” And he started laughing. Then I realized that I was the only Black man in the entire building. And that’s what I said, and he confirmed.
He said, “Yeah, that’s why it’s so easy for them to know your name because you are literally the only one here who looks like you.”
At that point I stopped going to work looking for comfort or to feel comfortable. I went to work looking to work. That was my only thought. I’m going to work and I’m going to work my ass off and I’m gonna work better than anybody else.
That was all I was thinking about. And I did. I worked hella hours. I was always the first one in and last one out. I wore a suit every day in the Google office, which nobody does. I needed to work and I needed to prove myself. I worked and that was all I did.
In terms of allies in the professional place, I think they’re extremely important but I don’t think I’ve figured it all out. I’ve been able to start and nurture relationships because I connect with people at their most vulnerable states of fun. Some people might call those vices instead of fun, but I like to look at those activities in a positive light. Those moments of smiles and laughter and energy are where I connect with people the best, whether they’re older or younger. And those moments might take place at a bar or smoking a blunt and connecting or talking about nonprofessional things or whatever.
Being able to connect with people at that level helps them recognize my loyalty. They return that loyalty because I meet them at a vulnerable place—a positive, vulnerable place. A lot of my real relationships professionally started over fun. I had a meeting with one of my first managers from Google, who is now trying to recruit me to his team at Facebook. I remember getting drunk with him and writing on his face with a permanent marker as his intern. At the time we just laughed at it, but it was one of those nights where you build a bond forever.
I try to replicate that as much as possible. Chad:
But now you’re far from an intern. Compared to when you started at Google as a twenty-year-old intern, how much of your cultural identity, how much of your full self, including your Blackness, do you bring into the work space? And how much do you lean into your Blackness now compared to ten years ago? Jason:
It’s night-and-day different. Ten years ago, I did not bring my total Blackness into the workplace. I felt like my Black skin was probably too much for them to handle in the first place. They had to get comfortable with seeing my Black skin and not associating that with negativity or poor work or whatever bad thoughts prejudice puts in people’s minds. I didn’t feel comfortable enough being Black, which is one of the main reasons I think a lot of Blacks are not successful in tech companies—especially Googles and Amazons—because they don’t feel accepted into the culture. The culture is not made for them. It’s made for the masses of the white majority.
I didn’t feel comfortable going into work and talking about my favorite type of hip-hop or talking about Black cultural events like Carnival or HBCU homecomings. I couldn’t talk about that stuff because I didn’t have anybody to talk to about that stuff. So much of my Blackness I either hid or I focused it where it was welcome. At Google, the Black Googler Network (BGN) was where I could focus my Blackness. It was like I was Black Jason outside of Google and inside I was whoever they wanted me to be. But with my BGN friends I was Black through and through, because in BGN I found cultural acceptance. I recognized in those environments I stood out, not because I was more Black than anybody else, but because I was Black and I was observant of our white surroundings and I was able to kind of bridge those two things together.
The difference between who I am now and who I was then is that through my career, I have continued to see the value in my Blackness and the value of that perspective. I’ve also learned that, in being entrepreneurial and starting Partpic, I shouldn’t
hide my Blackness. I should
talk about Black things. I recognize that I am a Black founder with a diverse team of Black and white employees, and when I was at Google my white colleagues didn’t try to hide their culture from me. At Rockhurst, they didn’t try to be Black for me or show me Blackness, they only showed me what they knew—which was their white privilege. Which is fine, I don’t judge them for that. That’s not their fault that they were born into that position, but the point is they don’t tiptoe around their whiteness. And as a founder, now I don’t have to either. The Wiz
is my favorite movie. I made a point to encourage my employees to watch it. While it might be a minor example, it’s an example of something I wouldn’t feel comfortable as an employee at Google saying early in my career. But now I have no problem asking what Black Lives Matters means to my employees or leading those kinds of conversations. When we started Partpic, we did those things. We played hip-hop music in the office. It was just this idea of recognizing that we are Black. We’re not going to hide the fact that we’re Black, and while that may be uncomfortable to some people, evidence of Blackness is not a bad thing. And I’m going to keep pushing you. And you might be uncomfortable, but it’s coming from a place of giving people access and a viewpoint into the world of Blackness and the people that are shunned because of their Blackness. So, today I am much more confident in the idea of who I am and what value I bring because of my Blackness. Chad:
Think about a Black twenty-one-year-old coming into adulthood realizing she’s in charge of shaping her future. Where can that person find comfort, advantage, leverage, strength? Where can she find that within her Blackness? Where would you say, “This is where your identity can create advantages for you”? Jason:
That’s a difficult question because of how diverse we are as Black people and because of all the things we need as individuals. We all need different things to be successful. Some people just lack confidence. Other people lack skills. Others lack other things. But to identify that one source of strength or truth for Black kids, I would first say family. For me it was family and faith. So that’s how I did it. It was the fact that my family, even my mom’s side of the family that was all fucked up, what they did believe in was being a family and holding each other down. Regardless of what they did and who they did it with, at the end of the day we had a family bond.
My father’s side was responsible for giving me faith and religion and spirituality. That’s where I found confidence, but every Black kid doesn’t have that.
I live by the phrase know thyself and live accordingly
. That phrase has meant something different to me as I’ve grown up. Especially the live accordingly
piece. So, I would say: anchor yourself in you. Anchor in asking yourself who you are, what you want, and what you’re willing to do to get it. If people ask themselves those questions and are truthful about the answers, I think the identity of self can become strong enough to appeal to outsiders in a way that creates opportunity. If you’re doing something you love and if you are passionate about what you’re doing, people will see. Once people see, then you become accessible to other perspectives, ideas, and experiences. That access to new perspectives creates more opportunities. But first it starts with you. Nobody can be you for you. You have to do that on your own.
DR. LYNN MCKINLEY-GRANT “There’s a double-edged sword. They used to make you feel inferior just because you were Black. But now they try to make you feel inferior because you may be more educated than them. They’ve been duped by the Trumps of the world and the white privileged men.”
Dr. McKinley-Grant earned her MD at Harvard Medical School. She is a board-certified dermatologist, author, researcher, and associate professor of Dermatology at Howard University College of Medicine. Dr. McKinley-Grant has practiced dermatology for over twenty-five years in Washington, DC. She is president of the Skin of Color Society and a member of the American Academy of Dermatology and National Medical Association and has been listed in Washingtonian
magazine as one of the area’s “Top Doctors.” Her special area of interest is using the arts to train physicians in making accurate diagnoses in all skin colors.
But for most of my life I’ve known Dr. Grant as Aunt Lynn. Her daughter and my older sister went to preschool together, and our families have maintained a friendship across the DC/Maryland border for three decades. The Grants were always a force in the DC metro area; a regal Black family living in a beautiful brick house striped with growing ivy.
Every Christmas Eve my parents, my sister, and I would load into my dad’s Acura SUV and take the thirty-minute drive into the city to park among the BMWs, Lexuses, and Mercedes-Benzes lined out front the Grants’ house.
Inside, Dr. Lynn and Dr. David Grant and their daughter Davlyn would greet us with warm apple cider and sweet potato pie. The house was full of Black professionals and their families loudly singing “The Twelve Days of Christmas.”
Sometimes I felt a little out of place at the parties, because I thought the 16th Street Black people who lived in DC were richer and more proper than us suburbanites. But then Dr. Grant’s friends, who’d migrated from Harlem down to DC, would come in, dressed to the nines, and truly
party. I didn’t feel out of place then; I felt happy and entertained. After a few spiked ciders, some would break into their version of “Theme from New York, New York
,” complete with eye-high Rockette kicks.
Black doctors, lawyers, dentists, professors, politicians, musicians, engineers… they all came through to celebrate. The wine flowed from eight until the last few families trickled out after midnight, and I wondered, What were they celebrating? Why were they so happy to see each other? Why so many cheek kisses and hugs and joyful shrieks to accompany the off-key Christmas carols?
Based on my observation of Dr. Grant and her friends, I thought Harlem must be some place where all the Black people were rich and well dressed and well educated. In our interview Dr. Grant set me straight. She informed me that Black people in Harlem in the fifties struggled just like Black people everywhere else. But the advantage her neighborhood offered was its community and the high expectations that community instilled in its young people. There was an explicit agreement among Harlemites at that time that children would excel academically and professionally, and that would lead them to give back to the community. Dr. Grant was taught by example by her mother and her neighbors. That’s why Dr. Grant hosted Christmas Eve every year, to make sure we as Black kids with opportunity, surrounded by white people at school, knew our elders, and knew that they would hold us to the same high expectations.
In Harlem, Dr. Grant learned that Black Magic is passed on within communities. In DC, on Christmas Eve, she made sure to share that magic with the next generation. Chad:
So what do you do and how were you educated, Dr. Grant? Lynn:
I am a dermatologist and an internist. For most of my career I have taken care of patients but combined that in an academic setting with teaching. And some writing also. I went to college and medical school, did the whole thing. Growing up I was in New York and then we moved to Washington and then we moved back to New York. So there were always changes in schools. I went from first year in public school, and a teacher yelled at me or something so my mother put me in Catholic school. In Catholic school the teachers would beat you, but it was a very good structured education, you know.
In fourth grade I was taken out of Catholic school because I wanted to become Catholic and we were Episcopal, so that wasn’t going to work. So I ended up going to a private school where you called the teachers by their first names. It was a very liberal school in New York. I was just in elementary school then.
And then we moved to Washington, DC. Something that triggered me was that I realized in New York I really grew up in an all-Black community. I grew up in Harlem, you know. My family is Black, educated. White people existed, but they really weren’t a big part of my life until I went to private school. And then I really thought all white people were Jewish, because that’s New York, you know. So I learned more about the Jewish culture.
But most communities weren’t integrated. A lot of my strength and the expectations I had for myself came from the housing complex I lived in. It was a group of very highly educated Black people who were leaders in the community. There was a guy who was an executive at Macy’s and this was in the fifties. In that community excellence was just expected of you. There was no question about whether you were going to college, because your parents went to college. You knew you were going someplace.
I had someone ask me once, “Why do you keep doing more stuff? You’ve done so much. Why don’t you just stop?” I don’t know why I never stopped. That’s something for a psychiatrist to deal with.
Anyway, we moved to Washington when I was in seventh grade and then we moved back to New York and I had to finish school in New York. In New York, to get an academic diploma, you have to do Regents exams. I had to do them all in one year. Most people do it in four years—languages, science, math, history. I got them all done in a year.
At that point I was at an integrated high school in New York, and when it came time to fill out college applications the school told me I wasn’t college material and that I really needed to go to trade school to be a secretary. They said I should be a stenographer or something. They wouldn’t send my applications to colleges. All my friends were applying to Harvard and Yale and blah, blah, blah. So, I sent in my own applications. I didn’t do Harvard and Yale, but I did some of the other schools, like Boston University and Syracuse. But the people running my own school said they didn’t feel that I should go to college. That infuriated
my parents. So I ended up going to Fisk University, which was another great opportunity. But I decided to go on exchange to Colby College because all my friends from high school were going to white schools so I said—well, let me go to Colby.
That was an academic shock coming from Fisk, but I really learned how to study. I majored in Political Science. It was the sixties and I was a revolutionary person. I wanted to “change the world.” When I got back to New York I was part of the Civil Rights Movement but stayed in education—counseling kids about going to college and stuff. I ended up getting a master’s in Counseling. I was counseling college students who were going into medicine and law and I thought that was interesting. So, I ended up going to medical school. I had a friend who was very ill and I just thought, “Well maybe medicine. Maybe I should give medicine a try.” Chad:
Got it. You mentioned a couple things I want to explore. You said that the expectation in your mostly Black community in Harlem was that you would do great things. How were those expectations communicated? How were they instilled? How did they stay with you when you moved out of all-Black communities? Lynn:
There were times I know my mother was struggling financially, but I never considered us poor because she was still working and she worked at the YMCA in public relations. We were both very involved in the Civil Rights Movement, so there was always this thing about giving back and I did volunteer work at Harlem Hospital. We were always helping somebody with something. Because there were always people who were less fortunate than us.
I always felt that our family was kind of important in the community. People would see me and say “well this is Aretha’s daughter.” That meant something important. So I had to really act like I had some sense. The people that we were around, even socially, they really worked hard and so you were expected to study hard. Books were always around. I remember Marian Wright Edelman saying that she could get out of doing chores if she was reading a book. And sometimes that would work in my house.
There were always these opportunities to learn and exposure to new things. We got to take advantage of experiences outside of Harlem. We would go to museums. We would go to concerts. We would do stuff at home. On Sundays, families would get together and somebody always had a piano, so there was singing, and it would be after church so you couldn’t go shopping or anything. Or you’d read poetry. I can remember times of us sitting around reading poetry to each other. First the kids would read some aloud and then the adults would read some. One of Countee Cullen’s wives was one of my mother’s good friends and so we had that kind of exposure. And just listening. A lot of times as a child you didn’t say anything. You just kind of sat and listened to what people were talking about and the struggles they had, but they didn’t talk about that as much. Chad:
I’m writing this book because of my experience starting my career at Google after moving from Atlanta to Silicon Valley. I was working in a nearly entirely white and Asian office and dealing with my learning curves in the ways people engaged with each other and how they talked about work. I was trying to understand the social habits outside the office, and all of this was a gigantic culture shock for me.
I’m writing this book to learn, from people like you, how to find power in our Blackness instead of weakness or isolation.
If a young aspiring doctor grabs this book and flips to your section, what do you want her to find? Lynn:
I would want her to know that she is somebody. That’s really important, because you can lose that. And it’s really different now. White privilege can make white people think you’re taking away something from them. I realize that is the biggest source of prejudice that’s happening in terms of racism. It’s the fact that they feel that you’ve done well and because you’ve done well they are not doing well. So they’re blaming that on you and you happen to be Black too. There’s a double-edged sword. They used to make you feel inferior just because you were Black. But now they try to make you feel inferior because you may be more educated than them. They’ve been duped by the Trumps of the world and the white privileged men.
So, my message to a young person opening this book is that they are somebody. Maya Angelou used to talk about the importance of the sense of belonging. The way I’ve interpreted Maya Angelou’s message is that you can’t be free if you feel like you have to belong someplace. She says, “You only are free when you realize you belong no place—you belong every place—no place at all. The price is high. The reward is great.”I
She talks about really being free and that means kind of being who you are and it sometimes means that you don’t belong; not that you shouldn’t be there, you need to be there, but you won’t feel a part of belonging. It takes maturity to be comfortable with that.
Growing up in New York, and in Jack and Jill, I was the darkest person in the group. Because of that, I didn’t have a sense of belonging. And then when I was at Duke—I was Black, I was a woman. I didn’t belong. Having a sense that you are somebody, that you’re important, that you belong wherever you are matters. We each have an experience to bring.
TARLIN RAY “If I think about my professional career, there has been no mentor in any environment that looks like me.”
Tarlin is an education and technology executive, investor, startup advisor, and former Division 1 college basketball player. Today he is the senior vice president of business development and product management at Kaplan North America. Formerly, he was president of Dev Bootcamp—the world’s first immersive coding bootcamp. Tarlin earned his MBA at Harvard Business School and his AB in Economics at Harvard University, where he played on the basketball team. He grew up in the town of Brentwood in Los Angeles.
I first met Tarlin when I was working for a small tech startup that was bought by Kaplan. Tarlin was sent over from the mothership to take command of our startup, a small coding school that was leaking money. His job, from what I could tell, was to figure out how to make our business profitable or close us down. Tarlin was clean-shaven, sharp. He usually wore starched collared shirts. As an executive, he had clout with Kaplan and they trusted him to take on major projects like our startup. Most of the overlords at Kaplan seemed to be old, bald white guys, and they seemed very comfortable with Tarlin. So I read Tarlin as a company man. That’s actually why I thought Tarlin would be a great mentor. I too wanted to be well paid and trusted by my superiors at the company. I asked Tarlin to grab coffee because I wanted to learn how to climb the corporate ranks. He was generous with his time and knowledge.
When we sat down, Tarlin asked me
a question I had on my list of questions for him
: “So what are you doing here, Black man?” I gave him the Silicon Valley, jargon-y answer. I said I was trying to change the world and make some money. I never got around to flipping the question back on him, so I did, many coffee chats later, when I asked him to participate in this book.
What was he, a Black man from LA, doing in the places he’d been? First Brentwood, an affluent LA suburb. Then Harvard Business School and now the executive ranks of Kaplan, Inc. Tarlin described his upbringing in a two-parent household, with money. I liked how Tarlin owned his privilege. He called out his good fortune. He didn’t pretend to come from a disadvantaged background. But still Tarlin accepted his mission to help other Black people who started with less, and stressed that he will teach his daughters to do the same.
And yet, as he moved from place to place, Tarlin had no Black mentors on his way up. It seems impossible to me. How did he have the confidence to push through glass ceilings without learning from others who had done it before him? I discovered he learned his values from his parents at home growing up in Brentwood. Tarlin’s Black Magic is self-awareness and sending the elevator back down. He understands the rarity of the advantages he was born into compared to so many other Black people, and he uses his positioning near the top of the corporate ladder to help others—like me—find their way through the maze. Tarlin:
I grew up in Ladera Heights and then when I was in seventh grade my folks moved us to Brentwood. Chad:
What was it like growing up as a Black kid in Brentwood? How did you end up as a student athlete at Harvard? Tarlin:
I just need to start with my folks. Both of my parents are from Ohio. My father was one of seven children. You know, the bathroom was an outhouse and he slept in the same bed with his two older brothers. Both of my parents were the first generation to go to college. I was lucky to have them as role models who paved the way for me to understand how to navigate a world where I’m often one of few individuals that look like me.
My mom was one of the first teachers in her magnet school in Los Angeles. Education was important. My dad was the first Black partner in a major law firm in LA. My dad went to Howard University for law school. One day he made a decision, based on weather, to move the family from Washington, DC, to LA. He was sick of fighting winters and there was an opportunity to go to a major firm.
You asked what it was like to grow up in Brentwood. I would not have been able to handle what was a very homogenous, very affluent environment, without watching my parents navigate being the “only ones”; without watching them navigate how to work with power and gather their own power and create a team-tribe around them. That tribe was made up of other Black folks in Los Angeles who were doctors or lawyers working in entertainment who launched their own businesses. I got to watch and learn from them as well.
So when I got to grade school and I was one of only six Black males in class, I didn’t feel like I was ostracized. We had our tribe. We had our Black student union.
But it didn’t feel like anything could hold me back from taking full advantage of the opportunities there, whether it was student government or playing two sports or being an admissions counselor or writing for the paper. My parents enabled me to feel comfortable, and even though it was a very homogenous environment, as I applied to colleges I felt that anything was possible. I had worked hard, and had a work ethic coming from my folks. I tried a bunch of things in school that were passions for me. I created what I felt was a legitimate CV to go to some of the best schools. I felt like I could hang with anyone. Chad:
You mentioned how your parents grew up. You said your dad grew up sharing a bed with two of his brothers. My father had a very similar experience growing up in Detroit. I just had another conversation with a really close friend from college whose uncle on his mom’s side was shot and killed at a family get-together. Across these conversations for the book, everyone mentions being one degree away from tragedy or poverty. How close or far away does that feel to you? How much time do you spend remembering where your family comes from? Tarlin:
I don’t feel like that place is close. What I do know is that I’m extraordinarily fortunate.
There’s just luck that is involved. I think about my mom’s side—you know, super-talented side of the family—but they’ve had some struggles. My dad’s side, his hometown in Ohio used to be a thriving community because there was industry there. Then the factories left. Now it’s known for its two or three prisons, one of which was the prison highlighted in The Shawshank Redemption
. So I know that I am extraordinarily fortunate to have the opportunity I have, which is why I probably still push hard to not waste that opportunity. Granted, everyone has to work hard. You’re not handed anything.
So I spend less time thinking about how close I am to tragedy or poverty because I’m probably further away. While I was a child and growing up I was probably shielded more from that one degree, unless we were going on a plane to Ohio and hearing some of the stories that our relatives were going through. But I think I’m channeling an extremely rare and lucky opportunity.
When I’m talking to my daughters—I have an eleven- and an eight-year-old—I make sure they know nothing should be handed to them and they should go and give back to communities that are not as fortunate. Because we want to make sure we not only give my girls opportunity, but make sure they are service-oriented in the future. Because we need to spread “the luck” to more people, so they feel as emboldened and empowered as I felt growing up. Chad:
When we worked together, my boss, who was a white guy, said, “You’re going to be working with this guy Tarlin and you’re gonna love him.” He kinda had this look on his face. So I thought, Okay, I know what this means. Tarlin is Black.
I met you, and indeed you were Black and I loved you. I felt immediately a different level of trust than the trust I had with other colleagues. I could tell you what I felt. I could tell you where I was coming from in a way that was different for me than my relationships with most of my colleagues. I’ve had similar experiences with other Black colleagues. Most of the times I’ve found that a door I wasn’t yet qualified to walk through was opened up by someone Black who is older than me.
Have you had a similar experience? Have you found Black people to open doors that you didn’t expect to open? Tarlin:
If I think about my professional career, there has been no mentor in any environment that looks like me. I’ve spent a lot of time in early stage companies. If you look at venture capital, especially in the early 2000s, there were not a lot of Black executives or Black senior leaders. There wasn’t a nod. There was no “let’s go to coffee.” Oftentimes the doors opened from individuals who did not look like me. Which meant that I had to fall back on my ability to relate to people who didn’t look like me, which came from the grooming I had growing up the way I did.
I am currently the most senior Black executive at a large, public education company and there is no one I’ve interacted with broadly that looks like me. I’ve always had a peer set but to have a mentor to help me grow, I’ve often had to look out and not within the company. Chad:
So for anyone else who is Black looking up to you at that company, you look like the glass ceiling to them. Does it feel that way to you? Tarlin:
So I’m the glass ceiling only if I place limits on what I want to do. Chad:
I could see someone looking up and saying, “Tarlin has reached this level in the company. It appears that is the highest level that someone like me can reach within this company. That looks like the glass ceiling to me.” Does it feel that way to you? Has that seeped into your own mindset? Tarlin:
No. Maybe this is just the nature of the work I’m doing.
I left Kaplan after climbing the ladder to go pursue an entrepreneurial venture that I felt was more growth-oriented. I came back to Kaplan to go to a startup born out of Kaplan to build something. So for me, the ceiling is only on what I believe are the opportunities out there, and my ability to partner with an organization to see if I can get supported and funded to do those things. It’s less about someone in a seat.
I feel unencumbered because I feel supported by the CEO and COO to go do this thing. But other individuals in the organization don’t know that. So the last thing they saw was Tarlin, a very senior guy, running a division of Kaplan and closing it down. They have no idea what’s happened since.
I think about work in a different way. There are people who are prone to want to be the leader of a large organization. Those are a small subset. I’m more passionate about trying to build something out of the thought leadership and concepts I think are worthwhile, and then organize a movement around that rather than taking over what already exists. Chad:
Why do you think you’re built to build instead of assuming an already existing position? Tarlin:
For a while I wanted to study second-generation Black children of white-collar families. [My parents] went through the trials and tribulations of proving they could perform. They had to make partner, all that. And once that happens, you get exposed to yes, being a doctor or lawyer is a path you can take. But there is so much more you can do to be self-actualized, to make money, to make a difference. So there was no limit put on me. My wife’s parents immigrated from China, so there was a fixed mindset about the type of work you do to be successful. Other than making sure I got the best education, there were never any other fixed boundaries to stop me from dreaming.
When I was eleven, for two years we moved to New York. My dad was setting up a branch of a law firm in New York. In my fourth-grade class we ran a pizza business. I was the treasurer raising the money for our business. We sent out our salespeople to sell tickets. We’d get the money back, we’d buy pizza wholesale and then distribute the pizza at school on Fridays. Whatever surplus we had we used to go on a trip at the end of the year. I got excited about business and I learned the word “entrepreneur.” You can be your own boss. It’s about how you can take an idea and have fun with it. My parents pushed me to get the right foundation, and I felt like with that grooming there were so many more possibilities for me than what I saw.
I had another friend—who was the son of a partner at my dad’s firm—who was on Survivor
. Does the world become more of your oyster because of the initial foundation you get, because your parents have broken the glass ceiling—and therefore there’s more to life? Chad:
Is there anything valuable that you learned from your experience as a Black man growing up the way you did that helps you in your work? Tarlin:
I believe being able to communicate is a unique kung fu that gives you a continued way to advance. I’m talking about written and verbal communication. I believe with technology tools we are losing that ability to communicate, thus losing the opportunity to learn how to persuade and to engage and to debate. My dad considered asking me a ton of questions to be small talk, but it felt like the third degree. My dad would ask five questions about anything I said I learned or believed, to make sure my argument was sound and tight. I think that ability to articulate ideas—even if you don’t look like everyone in the room—will at least get everyone to pay attention. I think that’s something that’s being lost.
People do a quick assessment of you. I try to show up so that someone cannot make a determination of who I am before
they get to hear what I have to say. I don’t ever want to mute someone’s artistry or their style, but, depending on the environment, I think it’s helpful to remove bias. Remove bias and then get a chance to show them what you really think. To me, that means continue to hone your craft and your communication style, verbally—whether forcing yourself to do presentations, or sitting around the dining room table talking about your day with your children. As they’re communicating, pick their message apart and tell them better ways they could package messages. I believe that is massively important, especially for young Black men and women, because it opens a ton of doors.
Don’t limit yourself to 140 characters. Force yourself to write things long form. Force yourself to write even longer letters. That will help with whatever you do for the rest of your life. I
. “You only are free when you realize you belong no place—you belong every place—no place at all” (Maya Angelou, Conversations with Maya Angelou
, ed. Jeffrey M. Elliott [Jackson, MS: University Press of Mississippi, 1989]).