We weren’t born woke; something woke us up. And there’s a difference between being woke and staying woke. so much of this work is making sure that people stay woke. deray mckesson
In August 2014, DeRay Mckesson started sprinkling into all of our time lines with messages of peace and progress and perseverance. On the ground in Ferguson, Missouri, shoulder to shoulder with the protestors and conscientious citizens facing down the police force in the wake of the death of Michael Brown, Mckesson was among the best fonts of information in real time about what was going down, what was happening next. On Twitter, he spoke with a clarity and urgency that could not be ignored. But it was his astounding patience and grace and poise in the chaos that—along with his signature quilted, blue Patagonia puffer vest—turned him into the charismatic frontman of a gathering coalition of organizations often associated with Black Lives Matter. Not just an aggregator or even reporter, Mckesson’s peppy resolve (“We will win.”), and his regular bits of inspiration (“I love my blackness. And yours”) in the year and a half since, have made him the voice of “the movement,” as he calls it.
Born and raised in Baltimore, Mckesson, now 30, studied government and legal studies at Bowdoin College in Maine, where he was student-body president. He would go on to work as a teacher and school administrator until the movement called him out of the school halls and into the streets. And in April 2015, Mckesson returned to his hometown, helping to bring comfort and direction to a city in total disarray following the death, after an injury sustained while in police custody, of Freddie Gray—receiving, for his work there and elsewhere, several accolades, including Teach for America’s Peter Jennings Award and the Howard Zinn Freedom to Write Award. And he doesn’t seem too keen to take up stakes again. Days after we photographed him for this issue, Mckesson announced his candidacy for the mayoral election in Baltimore, and just a few weeks ahead of the crucial Democratic primary in that race, Mckesson got on the phone with his pal Jack Dorsey, co-founder and CEO of Twitter, to talk about what’s to be done next, about the power of tech, and making one another feel a little bit less alone.
JACK DORSEY: Okay, DeRay. I just want to start with a very simple question, which is: Why? Why are you doing what you’re doing?
DeRAY MCKESSON: You know, so much of it was about telling the truth in public. I had under 900 followers when I first went to St. Louis. And I, like so many other people, was pushing back against the police department that killed Mike Brown. And social media allowed us to tell the world about what was happening. The why in terms of protest was to put these things into the public space that had not been there before, with a goal of pushing systems and structures to change. And then, in Baltimore, I realized that we had the opportunity to actually change people’s lives in ways that have an impact today, tomorrow, and the day after. I can do that work from the inside, too.
DORSEY: What was it like growing up in Baltimore?
MCKESSON: Both my parents were drug addicts. My father and great-grandmother raised us. My mother left when I was 3. Both my parents are recovered now. But we grew up in a tough neighborhood. I remember sleeping on the floor when the gunshots got too close. And we moved so we could be in a different neighborhood and go to different schools. Much later I was a teacher, and the thing I loved about being a teacher is that so much of any success I’ve had is due to people who cared about me who didn’t necessarily have to. There were all these adults in my life who pushed me to see things in myself that I did not see. Baltimore is a beautiful city. I started doing a lot of community organizing back in 1999 and met so many great people in neighborhoods all across the city. And that was an invaluable experience. Don’t your parents live in San Francisco now?
DORSEY: Yeah, they just moved to the Bay Area from St. Louis, Missouri. You met them! You met them in St. Louis.
MCKESSON: I did meet them. They’re on Twitter!
DORSEY: My mom posts a tweet every morning for sunrise and every evening for sunset. [Mckesson laughs] They were among the first 50 people on Twitter.
MCKESSON: I didn’t know your mother was on Twitter until Square went public; she was there at the New York Stock Exchange.
DORSEY: She opened the whole Stock Exchange. All of capitalism began on her watch. [both laugh] But tell me more about your parents, how that impacted your childhood.
MCKESSON: Because my father raised us and he was going through the process of recovery, so much of my childhood was seeing adults put their lives back together and seeing people become whole again. And that process has been really powerful in terms of shaping the way I think about the world now as an adult. Because I know that we are not our worst mistakes. We are more than our pain.
DORSEY: What’s something about Baltimore that no one knows?
MCKESSON: I think people who are not from here think the Inner Harbor is the only center for culture or fun in the city, and there’s so much more to Baltimore. The Harbor’s a beautiful place, but there are so many gems embedded in other communities that don’t get as much visibility. I think about how much we all listened to the radio back in the day. I have fond memories of the radio. And I think that the image of the city outside of here is either the extreme of, like, the Harbor or The Wire. Aspects of both of those things are true in the city, but that’s an incomplete story. There are so many communities that have such distinct personalities. And I hope that we can figure out how to give them a similar visibility, places like Sandtown and Hillen and Edmondson Village—all deeply rich communities, culturally.
DORSEY: You’re now running for mayor of Baltimore. What matters most in civic leadership for the city? What do you think is missing?
MCKESSON: I think that integrity with a focus on outcomes is important. Making sure that the processes and structures are things that people trust, are transparent and accountable—that is a part of integrity to me. And making sure that integrity is focused so that we actually do things that will make peoples’ lives better. So the outcomes are really clear: It is about making sure that there’s treatment for people who are addicted, that there are strong schools for every kid—that the integrity has purpose.
DORSEY: You spoke a little bit about education and your background. And we’ve had conversations around skills-based learning. Can you talk a little bit more about why you’re focused on education, and what you might be doing to bring that to more people in Baltimore?
MCKESSON: We talked about it last in the context of social media becoming platforms where people access skills and not just information. I was a teacher. I also worked at Harlem Children’s Zone. I moved back to Baltimore and opened up an after-school, out-of-school program on the west side and then worked in two public school districts, in Baltimore and Minneapolis. And all of that made me really keen to better understand the importance of making sure that our students learn skills every day. Skills acquisition is really at the heart of what it means to learn. I’m always interested in how we scale those opportunities. All across the country, there are these incredible programs, whether they involve coding or creative writing or financial investing. And people either don’t know that they exist or we haven’t figured out how to create real access to the opportunities for students. That’s important work to do. Who taught you how to code? You were part of the team that built Twitter, right?
DORSEY: Yeah, I wrote the first lines of code. But I taught myself just because I wanted to build something. When I was 14, I wanted to build a map of a city. I was fascinated by cities and wanted to visualize them more. When my parents got a computer, I had to understand how to see that on their computer screen. I just did whatever it took, learned the bare minimum necessary to draw on a screen. Then I learned a little bit more and a little bit more. And I found myself able to program. And it became the skill that I could use for really expressing my ideas. I think the cool thing about coding is, it’s not just the expression of an idea, but it’s something that people can actually use, too. I’ve always been fascinated by that concept, how that works. You’re one of the earliest adopters I know, of every technology under the sun. I learn about new technologies and new apps from following you on Twitter. I don’t know how you discover them all, but you’re tuned in. What is technology to you first and foremost?
MCKESSON: I think there are two things. One is that I’m also fascinated by cities. I think that what I’ve come to realize in the last few years is that most of the changes that will impact people’s lives immediately occur at the city level. Did you play SimCity? I was obsessed with it.
DORSEY: I did. I also loved SimTower. I loved going into the building, but SimCity was definitely a passion.
MCKESSON: SimTower? Was that before my time?
DORSEY: That was after SimCity. It was a Japanese programmer who went into the city and wondered, “You have SimCity, but what’s in that tower? What’s actually happening in the apartment building?” And you would build apartments, you would build commercial zones. I didn’t really get into games, but I loved simulators. They were more like toys that you could learn from.
MCKESSON: [laughs] That’s awesome. I think technology is an accelerant at its best. It creates access. Like Twitter—Twitter accelerates the pace at which messages have impact. And the movement is an example of that. I think the other platforms also help messages travel further and quicker than they ever could. And I think that what you see with, like, Google Maps and Google itself, is that, all of a sudden, people have way more access to information and to each other than they ever did before. I think about the work of trying to make the world a better place—so much of this work is urgent. And technology honors the urgency of it, as an accelerant. And so much of this work, we have to do together. Technology allows us to be together without needing to always physically be together.
DORSEY: The past year and a half has really been an accelerant for you and your focus on the movement and what you want to see in the world. We’ve seen a little bit of that from the outside. Can you talk about what the past two years have been like for you?
MCKESSON: It’s so fast paced, you know? August of 2014 was really the first time that I understood that police violence was so widespread. I just, I didn’t know. I knew that it was happening, but I didn’t know that it was happening at the level it was all across the country. Ferguson changed my whole perspective. I think that the community that formed in protest is incredibly strong. And I think that we will see those bonds resonating for years to come. I’m mindful that we weren’t born woke; something woke us up. And there’s a difference between being woke and staying woke. So much of this work is making sure that people stay woke. What comes next is coalition building. Like, can organizers make coalitions that have entrances for people who might not have shared goals but have shared desire in the outcomes? When you think about the gun-control activists and the movement, the gun-control activists don’t necessarily have the same goals. But they want to live in the same world where people aren’t dying by mass shooting, right? And all environmental activists don’t necessarily have the same goals, but we all want to live in a world where the water’s not toxic like it is in Flint. And I do think the question of coalition building is an important next step in the movement space. Challenging from the outside is always really important. But then I think that we will see people run for office, we’ll see people be on boards and commissions, fighting for justice and equity on the inside as well.
DORSEY: What’s been the most unexpected thing that you’ve come across in the past two years building the movement?
MCKESSON: I met @Jack! [both laugh] There are so many people who are waiting for an invitation. There are so many people who want to do something and just don’t know what to do. I think that is probably the single biggest thing—people want to be in this work. They want to fight. They don’t often know how to do it, and they’re waiting for people to invite them in. People bring up Beyoncé and how she follows me on Twitter, like, I get introduced as the person who Beyoncé follows. I didn’t expect that.
DORSEY: I think there’s been a critique in the past around online activism versus on-the-street activism. But what have you found that really gets people to act, whether that be online action or on the street?
MCKESSON: I think initially the videos—people seeing it so viscerally—got them to act. It is actually really simple. People knowing that they’re not alone is a big motivator. Social media helps people see that there are likeminded people close to them, and all across the country, who are ready and willing to challenge systems and structures. So they feel like they can come out and say it in the street because they know other people are there, too, that other people believe in this with them. And if they don’t have other people with them immediately, they know that they have a mechanism to invite other people to join. These issues were issues way before August of 2014, obviously. What changed is that we have tools that help us to build a community differently.
DORSEY: There’s something you tweet every day, and I just saw it on a T-shirt: “I love my blackness. And yours.” What does that mean to you?
MCKESSON: When I wrote it the first time, it was an affirmation. Like, I’m proud to be black, and I’m also proud of community in blackness. It’s important to me to publicly acknowledge that, to highlight my pride in black culture and how that culture has functioned in America, in all of its complicated ways.
DORSEY: Before you go to sleep, you tweet another thing, which is, “Sleep well, y’all. Remember to dream.” What’s that?
MCKESSON: I love it! It’s, like, my “goodnight.”
DORSEY: And do people respond to that?
MCKESSON: I don’t know. I go to sleep after I tweet it. [both laugh] But I think people respond since you know what it is. It also forces me off Twitter. Because when I tweet it, it’s like, “I’m not going to tweet anymore. I’m not going to roll over and tweet.” It is, “I’m going to sleep.” And if I didn’t have a thing like that, I would actually probably just tweet all night long.
DORSEY: I’m not mad about that.
MCKESSON: I need boundaries! Boundaries, Jack! [Dorsey laughs] Didn’t you write the first tweet?
DORSEY: Yeah. When we first wrote Twitter—and we’re about to be ten years old on the 21st of March—our system would tweet for you automatically as a way to teach you Twitter. So as soon as you created your account, it would tweet for you. And the tweet would read, “just setting up my twttr.” So that was the first official tweet. But that was actually written by the program. The first tweet that was written by a human was by me, and it was just two words: “inviting coworkers.” And what that meant was I was about to send the invites to all my Odeo co-workers. Odeo was the company, focused on podcasting, that we built Twitter out of. So after you see that “inviting coworkers” tweet, you’ll see a bunch of folks from the early days, like Ev and Biz and Noah and Florian, Adam and Crystal and all these people. And then they started getting into it, too. But, one last question, DeRay—what inspires you? What keeps you going every single day?
MCKESSON: I’m a big reader. I read less now just because I don’t have as much time to read fiction. I read differently now. I read newspapers and magazine articles, but I like fiction. I read a lot of books, and over time, they have been great sources of inspiration because they remind me that we can make the world a different place. I think about what it means to make a better world every day for the students I taught. They deserve to be in a better world. And as an adult, I’m implicated in that. And that pushes me to do what I can to make the world better. I have a niece and nephew, Selah and Isaac. Selah’s 3 and Isaac’s 5. I think about them every day when I think about this work. I think about all the people that I stood next to all across the country who are ready and willing and are doing incredible work. Who inspires you, Jack?
DORSEY: I love those moments of serendipity where you just come across something you weren’t expecting, and it changes your whole mind-set. And one of the things I love about what I find on Twitter is you just never know what you’re going to see. You learn so much. As you said, it’s not just about information. It’s somewhat disarming, because you just weren’t expecting to see that person and how they were communicating and thinking or showing off their world. That to me is inspiring, being able to go around the world and see it through other people’s eyes, to feel that connection and how small the world can feel in those moments. And anyone who changes my mind-set, anyone who gets me thinking differently is someone that inspires me. I look for more and more of that in my life.
JACK DORSEY IS THE CO-FOUNDER AND CEO OF TWITTER AND CO-FOUNDER, CEO, AND CHAIRMAN OF SQUARE.