Baratunde Thurston on Humility as a Path to Wisdom
For Baratunde Thurston, humility is a tool to connect with people, and to bring them together around some collective sense of truth. The writer, comedian, and podcaster serves as an ambassador to his audiences, always considering what they’re going through and the questions they might ask. A Harvard graduate, Thurston has advised the Obama White House, worked as a producer on The Daily Show, and is author of the best-selling memoir How To Be Black. Across his work, he takes on nuanced discussions about race, technology, and democracy—and in the hopes of galvanizing his readers, listeners, and viewers, uses compassion and humor to make these subjects more accessible and approachable. “It’s okay not to know. It’s okay to be afraid,” he says on this episode of Time Sensitive, leading up to a pivotal question: “What do you do with the fear?”
A dogged dedication to transparency shines through all that Thurston does. An early adopter of technology—he bought the domain for his baratunde.com website in 1999, and worked in Harvard’s computer-support lab to help offset his tuition—Thurston seeks out accessible, inclusive ways of using digital tools for good. In a 2018 article he wrote for Medium about the fight for data privacy, he shared a public, read-only Google Doc that tracked his real-time reactions to Big Tech’s terms of service agreements. For his viral 2019 TED Talk, “How to Deconstruct Racism, One Headline at a Time,” he kept tabs of every news source referenced in the presentation on Airtable, and published it for viewers to download. In January 2020, he announced a public phone number for anyone to text him about anything on their minds (and for him to send them messages, such as timely reminders to vote).
In his quest to understand the big picture, Thurston also believes in the value of details. On his We’re Having a Moment podcast, he has broken down phrases such as “defund the police” and “George Floyd got killed” in an effort to illustrate the consequences of syntax. For the launch of his How to Citizen podcast, he laid out four founding principles—central facets of how he defines the word “citizen”—on the show’s website, giving listeners context and a framework for the conversations to come. Thurston’s other projects—whether writing about Will Smith’s Oscars slap or the metaverse for the media company Puck (of which he is a founding partner) or hosting the new PBS travel series America Outdoors With Baratunde Thurston—further extend the reach of his message: When it comes to navigating the world today, self-awareness, curiosity, and an open mind are key.
On this episode, Thurston speaks with Andrew about storytelling as a collaborative process, the value of open-source technology, and the word “citizen” as a verb.
Thurston speaks about his experience as the 2022 commencement speaker at Washington, D.C.’s Sidwell Friends School, his alma mater. He also reflects on his experience during the pandemic, and the importance of representing his audiences in his work.
Thurston discusses the consequences of syntax, including phrases such as “defund the police” and “George Floyd got killed.”
Thurston explains the four principles of “citizen” as a verb and the conversations he’s had via his public community phone number. He also shares his thoughts on the status of progress in America.
Thurston recalls his family history and his childhood in Washington, D.C. He also talks about the origins of his interest in technology and comedy.
Thurston expands on his early days as a stand-up comedian. He also remembers the death of his mother, and how her loss impacted him.
Thurston talks about the need for more inclusivity in technology. He also discusses why he joined the news platform Puck, and his new PBS series, America Outdoors With Baratunde Thurston.
ANDREW ZUCKERMAN: Baratunde Rafiq Thurston.
BARATUNDE THURSTON: Yes.
AZ: Welcome to Time Sensitive. Thanks so much for making time for us today.
BT: Thank you for making time for me.
BT: Yeah, I did.
AZ: When I found that out, when I was researching this, I just thought, That’s really interesting. That’s a bookend. That’s twenty-five-plus years later? Twenty-six?
BT: Twenty-seven years later. I graduated high school in 1995, and I spoke to the class of 2022.
AZ: How did it make you feel?
BT: Like I finally graduated high school. Like I’m done with that chapter. It made me feel more than I expected to feel. I do a lot of public speaking. I do a lot of gigs. I rarely get nervous. I rarely supremely prepare, because I generally know what I’m going into. My wife [Elizabeth Stewart] noticed this. She’s like, “You’re really preparing for this.” I wasn’t really talking to her on the flight or in the days before, just kind of heads down.
So it made me feel nervous, in anticipation of it. In the moment it made me feel humble, grateful, and in awe—a bunch of emotions. And sad, all at once, because the last time I was at commencement at that school, my mother was there. My sister was there. A good family friend was there. My mother has since passed. My sister’s in Michigan. I wasn’t surrounded by the friends that I graduated with, but I could see them in the kids who were graduating. It was all kinds of emotions, man.
AZ: I imagine. I was thinking about this idea of when we travel in physical space, especially to a space that held a formative time, what comes up in completely unexpected ways, and what kind of meaning you find in that space. Because it’s like integration, closure—
BT: It’s reintegration. Exactly. I mean, Sidwell is a school that was founded in 1883, a long-ass time ago.
BT: [Laughs] A handful of presidents’ kids. You send a couple of presidents’ kids to your school and all of a sudden, you’re the school of the kids of the president.
There’s this little schoolhouse. It’s called Zartman House. That was the original building, and that’s where the administration is. That’s where I went first when I arrived on campus. I was in that building a lot as a kid. I was having political-type meetings with the headmaster, agitating for change on behalf of the Black Student Union and other progressive issues of the time.
I was in that building lobbying for my own financial aid. I reached this critical point in high school, where we basically ran out of money. It’s an expensive school. I was there because of grants, and loans, and luck. I ran out of all those. My mom was like, “We got to take you out of there. Go to the public school that we’re already paying for.” I was like, “No, mommy, but friends….” I already had been there three years. I had a place. So I just went to the administrative building. I booked a meeting with the development office, and I said, “Look, we’re good for each other. You make me look good. I make you look good. You’re going to want to take credit for me later in life if I keep on this path. So can you just like—”
AZ: You made good on that promise.
BT: I did. I was, “Can you up the aid package?” So returning to that building, I was returning to contentiousness, and the angst of a teenager upset with authority. I was returning to gratitude. I was returning to this marvelous moment in my own life, where I was like, “That was a ballsy move for a kid to just, ‘Give me more money.’” They had changed. They have a head of diversity and inclusion, who was in school when I was there, Natalie [Randolph]. Her office is right where enslaved people used to work on the property, and so she’s channeling these ancestral spirits. When we stand where we used to stand, across a great distance of time, we’re sharing the same space with our former selves. It’s quite a reflective moment. Then if we include people who are a part of us, but not literally us, like the ancestors, it gets even more intense.
I felt a lot of that. I was reliving moments. I was remembering stuff I’d forgotten, just walking through the halls of the school: Oh, that’s where I pulled that prank. Oh, that’s where I got really sad one day. Or, Oh, that’s where I stashed those toys to sell illegally. Or whatever. I used to sell these illegal water guns shaped like elephants. It was a great racket.
BT: But I never kept them on my person. I stashed them in the classroom, and I told people where to pick them up.
AZ: You advise kids in your talk to author fearlessly and truthfully. You said, “Let’s write a better story, one that’s big enough to include us all.”
AZ: I was thinking about that in the context of the work you’ve done the last three years during Covid, which is just an insane amount of productivity. I know you may not feel that way, but it’s pretty extraordinary.
BT: Yeah. There’s more I want to do, but it helps me to hear that, honestly.
AZ: So, taking a long view, which you generally tend to do, in this big-picture perspective on things, outside of the micro moment we’re in, do you think we’re in a better place in America? Do you think that we are writing a better story? Do you think that we’re on our way?
BT: We’re definitely on our way somewhere. Where, is up in the air. I feel like we’re on a knife’s edge, and I am certain that everything is falling apart. Every institution we have had faith in, or pretended enough to have faith in, that we acted like we had faith in them, it’s coming down. Banks, churches, political parties, financial systems, the whole thing. I’m less clear on what we are creating in its place. So I’ve gotten increasingly certain, like, I don’t think we’re going to stop the disaggregation, the deconstruction, that’s already underway. I don’t think I’m here to stop that. I know I’m not here to stop that.
I still believe that we can create that bigger story. I’m very hopeful, but very uncertain, that we could use this moment of falling over the edge to fly. It’s scary as hell, because the abyss is there, and that abyss has a name. It’s racial violence, political violence, civil war, the whole thing. You feel it online. You feel it offline, now. Parent-teacher meetings and school boards are getting violent. That is not normal. But it’s also a sign that we might be able to create a different sort of normal as everything we’ve known, we stop knowing.
AZ: The pharmakon, the poison that’s healing us.
BT: Yeah. So I want that very badly. I think I need to believe that we’re not just destroying, but that we’re creating. I know enough people are. That keeps me motivated, but I’m not here to guarantee it’s getting better.
AZ: Right. But you worked hard on it. I want to go back to March 11, 2020.
BT: March 11, 2020.
AZ: The last flight before lockdown.
BT: Yeah. Wednesday.
BT: Wednesday, March 11, 2020. [Laughs] A day that will live in infamy in my mind. Go for that. Wow.
AZ: How did you process that moment? How were you thinking about time? How did you go in your life from sixty to zero?
BT: I was here in New York to do too many events in too little time, and ultimately engage in super-spreading activities, in hindsight. Tightly packed bars, conferences, extraordinarily loud talk, which means a lot of respiratory droplets. The escape from New York, which is what my wife and I think of it as, time got weird. We got to J.F.K. Airport and we were at the gate. I saw a friend, a great poet, IN-Q, he goes by. He said, “Have you listened to the latest Joe Rogan podcast?” I said, “No, I don’t listen to Joe Rogan.” He’s like, “You got to check this one out. There’s this epidemiologist on there, Dr. Michael Osterholm. I think you really want to hear this.” So we downloaded both versions of the podcast. There’s a short version and a long one, because these podcasts go three-and-a-half hours.
AZ: Three-and-a-half. Yeah.
BT: My wife and I listened to this podcast on our flight home. Now she showed up to the airport, ready for biological warfare.
AZ: She wasn’t your wife yet?
BT: She was my fiancée, but not yet my wife. She was bundled in a big coat. She had an N95 mask on, which the surgeon general said, “Don’t do that. What, are you crazy? Why would you do….?” We’re like, “But Asia, they seem to know.” So we’re on this flight, getting increasingly agitated by what this doctor is describing. Ultimately, his alarmist warnings were not alarmist enough. We blew through his projections. By the time we landed, I had ordered stuff from the grocery store on the inflight Wi-Fi—supplies, a freezer. We landed very changed. The flight represented a bigger transition than just New York to L.A. It was a very extreme mode of survival. Then the curtain kept closing and we got all these creepy….
AZ: But you opened up a curtain. You made Live on Lockdown—
BT: I did. Yeah.
AZ: —pretty quickly. Then the thing that really touched me the most was the We’re Having a Moment podcast.
BT: Oh. Wow.
AZ: So two podcasts, and you got married. All in 2020, which I think is evidence that you found some beauty in a moment of despair. You’re a hopeful person.
BT: Well, there’s something you asked. I realize I didn’t address it all, but going from sixty to zero.
BT: That was abnormal.
AZ: Because you went sixty to zero, and then zero to sixty.
BT: Yeah, that’s right. That’s right. I swapped out the engine in between.
BT: I think I rebuilt the vehicle during Covid because my sixty now is much healthier than my pre-Covid sixty. I’m running on an EV platform now, instead of the combustion engine. So it’s a cleaner sixty miles per hour.
Going to zero was alarming and initially terrifying, because my livelihood depended on gatherings of people, events, and flights, and trains. All that stopped. So like a lot of people in this sort of position, I was like, “Am I going to survive financially?” Then that fear ebbed, in part, because I created a project. I created this web series, Live on Lockdown, which was my way of collectively processing what we were going through, and using what I knew how to do. That was a big breakthrough, because I had spent a lot of time asking permission to make shows. I made pilots for MSNBC, I made pilots for TBS, produced shows. There’s just layers and layers and layers of people and bureaucracy and rejection. In Covid, we were all rejected. Everything was no. So I said yes to myself, and no one could stop me. I had no boss. I had no team. There was just me and my webcam. It was like that Tupac song “Me and My Girlfriend—”
BT: —and he is talking about his Glock, or I’m talking about my web, because, [sings to the tune of Tupac’s “Me and My Girlfriend”] me and my webcam. That’s all I needed.
BT: I had Elizabeth. We had each other, and I was very, very lucky that I wasn’t completely alone during this. I mean, there’s tension in being with just one person, but it’s better than being with no person. Then I found this community making this series, and that begat so much. The thing I did with little external support and zero permission—that gave me permission to make We’re Having a Moment, and ultimately, How to Citizen. Then once the moment of Derek Chauvin and the killing of George Floyd happens, I’m ready for it in a different way.
The other part of the zero for me, though, was, my life I constructed kept me busy enough to focus externally. I’m an analyst. I’m a political, cultural critic. There’s like a lot of phrases to describe…. Like, I talk shit about the world. So I’m focused outward, and looking at the hypocrisies of the politicians and the economic structures. And I rarely use those tools for an internal look. There were not so many places to look during Covid because I was seeing the same walls.
Covid gave me the time, and I used it to dive internal, as well, and that gave me a way to deconstruct some pieces of myself.
AZ: I’m sure. And that clearly benefited how you were seeing the world outside.
BT: Oh, yeah.
AZ: One of the things that I was so struck with was how you were processing events and synthesizing, overlapping—like, on one hand, the Amy Cooper moment, and Derek Chauvin murdering George Floyd, happening in the same moment. But you began to get into this idea of humility as a tool, which I found really refreshing in that moment, which is another thing that Covid may have brought all of us.
AZ: Because you were very clear in your show about what you didn’t know, and you were like, “Come on, let’s learn this together.” I think that’s part of the reason people really responded to the show, because they weren’t being barked at like they were, all day long and all night, on the news. I was curious about this idea of epistemic humility, what I don’t know. Was that something that came with that moment? Were you conscious of that? Were you seeing it as a tool, as a way to bring people along?
BT: [Exhales] The short answer is yes. I had my own moment that showed me that I approached public platforms and media influence differently than some of the gatekeepers I was trying to please. I was working with this cable news network. I made three pilots for them in the course of a few months. We did this sample show, where I’m at the shiny glass desk, doing my thing. I have some expert journalist on, who covered this beat, that beat. But this was a one-on-one moment between me and a woman who really understood national security matters that I don’t spend full-time thinking about.
She offered up some nugget, and I said, “Oh, I didn’t know that. Tell me more. Can you break that down a little bit?” She did. On set, everybody felt good—the producers, the camera people, even the interns and whatnot. They were like, “We need this show. That was so different from what we normally put on.”
AZ: That very simple idea of “I don’t know.”
BT: “I don’t know. Tell me more.” I basically get called into the principal’s office, by this head person of this network, who has a bunch of screens on the wall. He’s always watching and taking notes and he freeze-frames this moment. He’s like, “I want to show you something. You see that right there? You said, ‘I don’t know.’ You can’t do that. Our audience expects you to know. You got to tell them what to think.” It was the opposite of humility. It was pretense of omniscience. It’s dangerous. It was stupid.
I intuitively understood because I’ve been on stage a lot, in the room with the energy of the people I’m around. I think some of that can translate through the dead lens of a camera, if you’ve done it enough. And I know what I like. When I don’t know something, especially when I’m in a position of authority, I think it’s important to acknowledge that. I don’t always do it. Ask my wife, all right? It’s not like I’m always this gracious, graceful person. But in that moment, it was simple. You’re the expert. I’m not. I’m here to elicit more from you. Our audience probably doesn’t know, either, so by admitting I don’t know, I’m relating.
AZ: Yeah. You’re also representing the audience.
BT: Exactly. I’m the ambassador for the viewer.
BT: I’m always down for the user, for the people. Even when I’m making money, or in these powerful little rooms, or what have you, I still think about, What’s the person really going through here, and what do they not know?
So when this executive said that, I was like, “Okay. You’re wrong, and I’m sorry that.…” I didn’t get into an argument with him. We just never ended up working together, and that was for the best, ultimately, and it was their choice. But they made the right choice for me. Because I don’t want to have to fight that every day, when I know the truth. I’m connecting with this audience in a way that you don’t think is possible or worthwhile.
BT: So we’re just going to have to not agree on that.
AZ: It’s sort of fear-based.
BT: Yeah. So that humility—
BT: —is something that I have tried to bring to some media projects I’ve done. Even there was another show I was building, and my producing partner and I were like, “Let’s share our docket, and run-of-show live, in an open Google doc. And let people edit, and fact-check us, and have a segment of, Shit We Didn’t Know, What We Got Wrong.”
BT: Yes. That’s exactly it. Open source the thing. I wrote a data detox article for Medium, years ago. I was ringing the alarm about these big tech companies owning us, trading in human futures, which as a descendant of enslaved people, I really don’t like. I went through this process of reading the terms of service, and understanding all this, and having a call to action: “Here’s six things I think we can do better.” I put a Google doc version of that out there, and I let it be editable, and “add more examples if you want.” So that has been a part of how I approach media and storytelling as a collaborative instinct.
AZ: Also decoding, making it visible.
AZ: What was so amazing about the podcast We’re Having A Moment is you looked at grammar. I should just start with, what can the study of decoding grammar reveal from a systems perspective?
BT: Oooh. I think there’s value in understanding the structure of small things, because it helps us understand the structure of big things. We can wrap our minds around the small thing. So I can use my relationship with one person, or one object, to reflect on my relationship with a collective entity. My relationship with my mother relates to my relationship with the United States of America. But I can grok the mom thing more easily when I communicate the mom thing. It stands in for some of these other relationships and audiences and communities around me can see that. I learned that instinctively through stand-up comedy. I used to come at structural commentary from the top down, commenting on news headlines and political machinations. A lot of my audience is like, “We don’t read the news. What are you talking about?” So then I started doing this bottoms-up approach.
AZ: Intimacy to universality.
BT: Yeah. The micro is the macro. We all have micro experiences, and we can then infer things.
So grammar, and the structure of language, and the structure of sentences, is something I have appreciated. I remember learning Spanish in high school. I learned more about English grammar through my study of Spanish than I did as a native speaker of English, because I’m coming at it—I’m a student again of something I thought I knew. So when we think we know, we still have more to learn. Like the humility thing, as well. Then I studied French in college and I was like, “Another twist! A new twist on an old favorite: words.”
The phenomenon of white people calling the cops on Black people, where we had the birth of the Karen caricature—
BT: It was Becky, initially.
AZ: Oh, right.
BT: Barbecue Becky was like the patient zero. This was the white woman who called the police on Black folks at Lake Merritt in Oakland, for barbecuing at a public park because she felt threatened—by seasoning. I don’t know what her deal was. Amy Cooper is in that spirit. She was on tape and the invention of a lie to call in state power to potentially murder someone.
So the repetition of the headline struck me as having a rhythm, and I kept reading these. First, not on purpose. They just showed up in the feeds. Then on purpose. Then I’m like, Oh, there’s a pattern here. Let me make a game. The pattern was, white person calls cops on Black person for doing non-threatening thing.
There were dozens and scores and probably hundreds of these headlines. I started assembling them. That structure, of a white person calling the cops on a Black person for X, felt like it was important. It was like, “Why does this feel familiar across time and across history?” So that scaled up to a TED Talk about that subject.
But the grammatical structure—getting back to your question—it helped me see structural abusive power, applied to race, but also applied to gender, and all kinds of other dynamics. Then the writer in me was like, “But we don’t have to do it that way.” The point of grammar, and the point of language beyond grammar, is to communicate—
AZ: With precision.
BT: —with precision, and it’s to create. I think it’s not just to describe; it’s to conjure, and call forth. If we get stuck in the analysis, and the description phase, and miss the proscription phase [laughs], then we’re missing an opportunity to realize our full humanness. Which is, we don’t just have to accept this. We don’t have to play by these rules, either. We can change meanings of words. We can create new words, and we can certainly rearrange sentences. Speak like Yoda, we can. Flip it and reverse it. So that made the game more fun. There’s the game of spotting. Then there’s the game of making. I’m down for the game of making, which comes back to something we started talking about with this moment that we are in. I could spend a lot of my energy describing the destruction, and the deconstruction, and the dissolution. But those moments are also moments of creation. Words and grammar. Diagramming sentences versus creating sentences. Same tools, different set of intentions, different possibilities. Are you looking at a page full of words? Or are you looking at a blank page and creating them?
AZ: What you created was an understanding, at least for me when I listened to it, about the consequence of meaning, and misusing words, and the order in which we use our words. How you can almost create…. You can mitigate culpability by using a passive voice.
BT: Yahdon Israel came into my life. He’s now an editor at one of these major publishing houses, but he created this Brooklyn-based literary society. I think it was called Literaryswag [Book] Club, something hip and literary. I had him on the We’re Having a Moment podcast, and he does a deep dive into the power of grammar and particularly the passive voice. The example was just around George Floyd and the headline of, “George Floyd Was Killed.” “George Floyd Got Killed.” So when you make George Floyd the protagonist, and you put him in the driver’s seat of his own murder, essentially. You ignore who’s truly culpable. So because of Yahdon, I was intentional about saying, ‘Derek Chauvin killed George Floyd.’ In fact, I would say, ‘Derek Chauvin slowly murdered George Floyd—’”
AZ: In front of people.
BT: “‘—in front of all of us.’” That was my refrain. Because otherwise you’re putting too much weight on George Floyd, as if he chose his own death.
AZ: Then directly afterwards you broke down the “defund the police” [phrase], which was so important, because this was one of these moments where language really was misunderstood and caused a lot of issues. So how did you go about deconstructing this concept of “defund the police”? Because you were one of the few in that moment, in a very short period of time, after we heard it for the first time, who was able to articulate it with clarity.
BT: Can you tell me what resonated with you?
AZ: Yeah. It was about this idea that you looked at the budget from a bigger-picture perspective. You were like, “Defunding lives in an economic sphere. So let’s look at what’s funded.” I think you were saying that something like, in L.A., again, intimate, used your own world, and it was sixty percent or something.
BT: Yeah. All right. Thank you for jogging that [memory]. But the intimacy is a good way in. So I think there’s this implicit spirit of a lot of the stories I tell on the media I make of learning in public. It’s old conflict-resolution skills that I learned as a kid through a lot of workshops, because I was a kid who did a lot of workshops. One of them was saying “I,” just using “I” statements. Instead of like, “You’re wrong about this,” [say,] “I feel,” “I worry about,” “I think,” “I experience.” Much harder to deny than categorical statements about the nature of the human condition, or some political party that I’m not a member of.
So as a new resident of Los Angeles, I decided to look up how much money my city was spending on everything. I learned that we’re spending fifty-[one] percent of our budget on the L.A.P.D. I had no idea. What?! I bet a lot of other people don’t know. Who goes and looks up their city budget? Journalists. Researchers. Students on assignment. The average citizen doesn’t do that. I’m confident. That got me thinking, Man, we’re kind of living in a police state. So I get to use the phrase “police state” from an economically sound perspective, from data-based use of terms. What else are we doing with our money? Oh, this is what we’re spending on parks, this is what we’re spending on this and that. Did we choose that?
I was looking at the trend lines, I remember, and saying, “Okay. They’re talking about, we’ve had this record decline in crime from the nineties to now.” Twenty years of just things getting better. What’s happened to police budgets during that time? They’ve gone up. So when crime goes up, we spend more money on police. I get that. When crime goes down, we spend more money on police. So now there’s no relationship between the job police are supposed to be doing and how much resource we apply to that.
AZ: And the underfunded social services.
BT: Then the other thing I brought to some of that argument was just thinking about trying to empathize with police, which was also not a popular perspective in that moment. It was just, a lot of people who knew nothing were just like, “Fuck the police!”
AZ: Run the Jewels had their new record. It was like the moment was not that.
BT: No. We were ready to blow. We had no distractions. We had no basketball. We had no brunch. We had no mimosas made by other people. We were just alone with our screens and our anger, and in some cases, generations of pent-up rage. Then people who were new to the struggle were just like, “Yeah. Burn it all down! I’ve done no analysis, but I like this feeling.” Sometimes hurting the cause that they were down for, with their rambunctiousness. But police—
AZ: But wait, I just want to take a quick pause, because I’m remembering your thing about looting at that time. You were like, “Helicopter view on looting.” Let’s look at looting over the perspective of time. You were like, “Let’s look at looting, again, grammar, context, and big-picture view.” You converge these things, always, to present this sense of clarity. The looting thing, how did you not immediately go to the, “Fuck you. They deserve to do whatever they want?”
BT: [Laughs] Here’s what I remember, and then you’ll tell me what you remember. I remember being frustrated at basically, young white kids showing up super excited to fight for Black people they actually don’t know. But it’s a moment to stand up and do what you think the right thing is. Basically, over-exuberant puppies out here just humping the leg of justice, and they think you do it by smashing a store window.
I also remember thinking, and I hope I communicated this, too, like, Who gets accused of looting, and from what resource? These banks looted the global economy, and nobody went to jail. They destroyed more Black wealth than has ever been created. The housing crisis destroyed trillions of dollars of Black wealth. I think that number’s accurate, but I know it’s the largest destruction of Black wealth in the history of this country. Probably other than the original destruction through the forced labor camps. Very little accountability for that.
BT: But these little moments of, ultimately, a couple of store fronts, a couple of downtowns, some fire damage, I’m not pro-that. I think there’s a fear and terror that can be associated with that. But there’s also fear and terror when you don’t have enough food, and you don’t have enough educational resources, and your whole community’s been divested of, or turned into a toxic waste dump, for environmental racism. We have not approached that looting with the same vim and vigor, as some of these more literally inflammatory moments.
Also, there was a particular story with our former president and his looting capabilities, which are just, he is the best at looting from us. The transfer of wealth through abuse of the tax system, the stealing from your own tenants, the falsification of documents with the government to claim your properties are worth this to raise the money, claim they’re worth that to not pay the money. That’s looting.
AZ: Looting from his own people. Sixty grand for [Kimberly Guilfoyle] to introduce her fiancé, Donald Trump Jr., on January 6.
BT: Yeah. As we sit here now, just learning about the grift, the profitable insurrection, the two-hundred-fifty million dollars raised by peddling this story to fund your hotels. That’s looting. That is grand larceny.
Back to this defund thing, I think I felt some empathy for police, who, like public school teachers, we ask to do things that collectively we have failed to do. I’m somebody who policed technology in college. I was a computer support person. I worked the help desk. I worked the hotlines. I ended up being—
AZ: You went to underfunded schools, and taught computer literacy.
BT: Yeah, I did. While I was at Harvard, I worked in the Section 8 housing, teaching computer skills to basically new immigrants, mostly from Haiti. But when you’re in that problem-solving crisis mode—doctors feel it, teachers feel it, police feel it, tech support feels it—there’s a bunch of stuff that’s gone wrong before the problem gets to you. Police are at the bottom of a hill that has snowballed problems. Kids weren’t fed right, lead in the water, influx of guns, bad media narratives, low expectations, fear-based expectations. So they got to do cleanup. They’re janitors for our wasteful social systems, or absent social systems. They’re trying to solve homelessness with a gun and a badge? That’s the thing. We give them a gun and a badge, very little training. Especially versus other nations.
So I’m like, “How are you going to ask this cop to do seven jobs?” Very little of it is about solving crime. A lot of it’s about fixing some other part of society’s failure to do their job. And we’re just going to give them more bullets, more tanks, more armored personnel carriers, more riot gear, more weapons, and more license to not be accountable for any mistakes they make?
I also remember this, man. I remember thinking about our amazingly complicated and wonderful founders, whose driving fire was probably about profiteering, but also was about checking power. We set up this system of checks and balances, because we’re always suspicious of concentrating too much power in the hands of the state. And here we go with qualified immunity, and these very strong unions, not holding people with the power of life and death accountable. Isn’t that the problem we have with King George? Didn’t we take all his shit and dump it in a harbor? Didn’t we start a revolution over this? How are we just—
AZ: That was so great how you brought it back to the Boston Tea Party and just the whole idea of like, “We were Brits. We drank a lot of tea.”
BT: “We loved that!” We were addicts! There was probably a little cocaine in that tea. There’s cocaine in everything back in the day. That was like sugar. So, we have forgotten some of our own story, some of our own values.
Basically, I was just trying to…. “Defund the police” is a simple phrase. I don’t know that “Consciously reallocate resources in a more balanced way” would’ve worked better. But it lent itself to intentional misinterpretation. It was weaponized by people who claim to hold the flag exclusively, who claim to love the country exclusively.
AZ: So in late July, you wrapped up the series with a final episode called, What Happens Next. You talk about your fatigue. You felt disempowered in a way. You decided to start something new, How to Citizen, which leveled up the whole situation. You and your wife, Elizabeth, joined forces to do this. So for those who haven’t listened, you have this fantastic premise I wanted you to share with our audience.
BT: The premise is that “citizen” is a verb. That we know the noun meaning. It’s back to grammar, right [laughs], and remixing, and intentionally changing. “Citizen” as noun is something that we have very viciously weaponized against people born on the wrong side of imaginary lines, to our detriment. I think we’ve discarded people who have done things citizens should do—serving their communities, thinking about more than just themselves, becoming assets rather than liabilities. But because they don’t have the right paperwork, because of bureaucracy, we are willing to lose out on their contributions.
“Citizen” as a verb says, “There’s something we can do.” At the end of the We’re Having a Moment, it’s really nice that this somewhat linear flow from Live on Lockdown and these little productions, to a We’re Having a Moment kind of argument, to like, “Okay, now that we’ve described the moment. What are we going to do about it?” We’re going to citizen. What does that mean?
So Elizabeth and I developed these principles and in collaboration with our guests, our early guests, to say, “These are the four founding principles of ‘citizen’ as a verb.” Then we built a show around those principles.
AZ: Which are?
BT: Number one: To citizen is to show up and participate. We just assume there’s something we’re supposed to do. We may not know what it is, but it’s a mindset shift to, “Put me in, coach.” This is an active and participatory sport. A lot of the news is very passive in terms of our role. Watch more news.
Number two: To citizen is to invest in relationships—with ourselves, with others, and with the planet around us. That first one is really important, because a lot in moments like the ones we’re in, we’re expected to have these press secretary–ready statements about really complex issues we don’t understand. We’re afraid to say, “I don’t know.” It’s like we’re comms directors for a major corporation or our government. We’re just people. A lot of us are new to some element of whatever the crisis is. What do we feel? What’s going on inside?
So the relationship with self is very important. Relationship with others—we don’t citizen alone. And relationship with the planet, because there’s no separation between us and these other life forms. We need them. They need us.
So relationships being the second pillar, understanding power is the third. To citizen is to understand power. This is all about self-government and democracy. I try not to use those words. They don’t really resonate with people. “Power” does, and we’re in a system of people power, power for the people, power to the people. But we’re not trained in that. We’re not literate in power, as Eric Liu, one of our early guests, described. So we need to understand power if we’re going to wield it in service to the people. There’s a lot of different ways to do that, and it’s not a dirty thing. It’s just getting people to do what you want them to do.
And number four: To citizen is to do all these things—to serve the many, not the few; to serve the collective self, not just the individual self. We had this great, our very first guest, such a—
AZ: Valarie Kaur.
BT: —conscious choice. Man, of all the choices I’ve made in my media life, making Valarie Kaur, K-A-U-R, the first guest on How to Citizen, may be my best.
AZ: It got the show going because of one simple idea.
BT: Valarie wrote this book called See No Stranger. The idea is that a stranger is a part of me I do not yet know. That’s the relationship piece. If you are thinking about serving the collective, not just the individual self, a lot of us are wired to fear that. Because we fear we’re giving something away to people who don’t deserve it. That’s the basis of a lot of the racial arguments, the class arguments, people who are addicted. “Well, they’re just immoral. They didn’t work hard enough. I have money because I deserve to have money. And my having money is a reflection of the fact that I deserve good things in life. You don’t have money, that means you didn’t work hard, and you don’t deserve.” We add God to the mix, and all this stuff, because we’re afraid that someone else winning means we are going to lose, as Heather McGhee argues beautifully in her book The Sum of Us, S-U-M.
But Valarie put a pin in it when she said, “A stranger is a part of me I do not yet know.” So if that’s true, then serving the collective is also serving the self, individually, because we’re part of that. Vaccines prove it, sports teams prove it, military cohesiveness proves it. The whole premise of living in a society proves it. If I’m going to do everything by my damn self, what’s the point? I got to build my own buildings now? I got to inspect my own meat? It comes back to that weird data detox, from 2017. I remember being so frustrated by the fact that I don’t know what these companies are doing with our data, I don’t know how they’re sitting on it. I’m like, “When I go to the grocery store, I don’t bring a chemistry set with me and individually test every item before I purchase it, understanding its chemical makeup, and the nutrient quotients, and the calorie counts.”
AZ: Part of what a society does.
BT: Yeah. The F.D.A. does that. Industries are regulating themselves to help do that so that we have a shared trust. Otherwise, we’re just alone and exhausted all the time.
BT: [Laughs] Yes!
AZ: I was always curious if people did reach out, and if unexpected things happen in that space, and how that made actionable, or visible, this “we.” You were like, “This is my number. Text me.” What happened? Did you have interesting conversations there? Was it safer than a social media public platform?
BT: I still run the text number, and I’ll share it happily with your crew here at Time Sensitive. I got a lot of people just sharing positive feedback in a deeper way. I got folks sharing personal relevance of some of what they’re hearing in these stories with what’s going on in their lives. I got people asking follow-up questions that they didn’t have time for—I did a lot of virtual speaking during this time. Obviously making the podcast is not always in front of a live audience. Even when it is, only a handful of people get to raise their hands, and get called on and get heard in the final edit. So this was like, overtime, and a space for that.
Also, I use it as—the image of choreography comes to mind. There’s a dance with it, where social media, as we experience it, is very public, and thus very performative. We’re all performing when we post a comment on a newspaper website, when we tweet something. For the most part—
AZ: We’re publishing it.
BT: Yeah. We’re all publishers. Again, we’re comms directors, we’re PR specialists, we’re managing our brands. When you text someone, you’re not doing that. I’m the only one who sees it. So you are wasting your energy if you think you’re going to rile up other people by showing folks how you stick it to me. Just tell me what you think. So I think I get a lot of honest criticism, and a more useful criticism, through this medium. Then I get, because of the way the technology is set up, I can address subsets of folk in a way that Twitter, Instagram, Facebook, TikTok, whatever new thing gets invented.
AZ: You can speak to them in their language and meet them where they’re at.
BT: And literally where they’re at, geographically. So I will send messages to different states on their primary voting days, or their voter registration deadlines. I just love asking, “Did you vote today? If so, send me a picture. How was the experience?” Folks will send me their selfies with their kids, or they talk about the long line, or they’ll share some messed-up incident that’s happening. It’s a relationship. It’s hard to have deep relationships with thousands of people. But we can at least have moments of relationship that are a little more grounded than “hashtag this” on a massively public space that someone with bad intentions might try to weaponize, and use against you, and publish in their thing, that has an agenda. People are trusting that I won’t do that with what they’re sending me, and so far, I haven’t.
AZ: When you did your TED talk, right after, they asked you this surprise question. This woman came on stage, and she basically said, “Amidst the ugliness of everything, do you have hope that we can face the ugliness of our own history?” And now, a few years later, you’ve put so much effort into trying to reveal this truth, and try and break down these kinds of spaces between people, the text messages, all of the things you’ve done. Have we been making progress and are we facing the lies that we’ve been living with?
BT: Yeah. Many of us are. I don’t quote Joe Biden very often, but his inaugural address had a powerful line in it on this theme of unity. He said, “Unity doesn’t mean everybody agreeing on everything.” I’m paraphrasing. It just means enough people have come together to move all of us forward. If we’re honest about our history, we have to acknowledge many things. One, is that it is very imperfect and full of heinous crimes. Another is that it is incredibly inspiring and full of glorious achievements.
When we are thinking about the positive progress we’ve made, some of us can get very simple about, “What was better back then?” Everybody agreed. Everybody knew Reverend Dr. Martin Luther King Jr. was a prophet amongst us, a veritable Founding Father. No. He was an enemy of the state. J. Edgar Hoover had it in for this guy. The government was trying to undermine him at every moment. And most Black people did not march with him. Most, but enough did, to move all people, not just Black people, forward. So in this moment, it is easy for us to be, and us, really, including me, really easy to be like, “I can’t believe people don’t believe.” But I see signs that many people do.”
The conversation that we are having about masculinity is such a powerful example of this. Liz Plank, an old friend of mine, I think her podcast is called Man Enough. She wrote a book called For the Love of Men. She’s having these beautiful conversations about what it is to be a man. I’m having beautiful conversations with my fellow men that I had never had five years ago—much less fifteen, and definitely not in those locker rooms in high school—and challenging what we were taught, rediscovering our vulnerability, our femininity, our inner child, crying with other men. Trying to shed some of the stuff that we’ve been performing, so that we can become more human ourselves. Invest in that relationship with ourselves so that we can relate with others in a more healthy term. That’s a wrenching experiment and experience.
There is a backlash to it. The Proud Boys is kind of the opposite of that. They’re ratcheting up the masculine performance. Every man needs a gun, and body armor, and being proud of a Western chauvinistic history, because they haven’t gotten past the fear of loss that will come with acknowledging the weight of what we’re carrying that doesn’t serve us anymore.
It’s okay to not know. It’s okay to be afraid. What do you do with the fear? I’m a man, I get the fear. There’s a lot to worry about. Women are coming, and they’re demanding money, and equal rights. And that might mean I get less money. Does that mean I get less rights? Nobody wants less of anything that’s good. Well, what’s really going to happen here? Do I have to worry? Are there things in my closet? Are there things in my past that I’m worried might come to the fore? Or just worried that I’ll get caught up in something without any justification? That’s not even true?
Okay, so I’m acknowledging I’m afraid. [Exhales] I just wish more men could do that. And for those who choose to acknowledge that, and then process it in a healthy way and move through it, we realize like, “Oh, a woman gets paid more, then our households have more money and resources because it’s, ‘we,’ not just ‘me.’”
AZ: And they just might be better at communicating, taking care of others. There’s another—
BT: Yeah. There’s a scarcity mindset around power, which is so frustratingly limited. I want those of us who hold any kind of power to just practice considering the “other”—the trans kid, the immigrant, the poor person, the addict—might have something to offer, might be here to relieve us of a part of our burden. It’s a burden to carry a whole society. If you’re a white dude, you’re like, “We’ve been running this civilization for a millenia.” Take a break!
AZ: So I want to turn a little bit to your childhood, you grew up in D.C.
BT: Yes. Chocolate City, more caramel now.
AZ: I read somewhere, you said, “I grew up in a house full of [fun] contradictions rather than stereotypes,” which I love.
BT: Ooh, I said that? That sounds cool.
AZ: It’s a beautiful line. I thought I knew what that meant, but I was curious, from you, what that really meant. You used the example, and I think it goes deeper than that, of just like, “I had a computer in the house.”
BT: I’m born in 1977. I was raised on Newton Street in Columbia Heights, Mount Pleasant neighborhood, between 14th and 16th Street—people can look that up—up until 1990. Then we moved to Takoma Park on the Maryland side of that neighborhood. In another Black neighborhood, but one with yards and driveways, and it was much quieter and less police action. On our block, down the hill, Maple Avenue—housing projects, more drug dealing, more police activity. You’re never too far from that in the District.
But the contradictions are that I experienced a version of the highly marketed tale of ghetto woe in America. Single-parent household. My father was shot and murdered when I was young. I witnessed a lot of drug activity—local economic entrepreneurship, as I sometimes refer to it. I saw police raise their weapons. I found weapons in the bushes, as a kid. I experienced the crumbling infrastructure, the potholes, and the lack of investment. That’s all true. I didn’t have cable TV until after I graduated college. But I had a computer in my house, and I went camping regularly. My mother was a member of the Sierra Club and had a membership to REI.
I went to two different churches, a Catholic church and an Episcopal church, because the Episcopal church was closer. But they both had incense, and really boring singing. I went to public school, and I went to private school. I was a majority member of the population; I was a minority member of the population. I had nothing, according to some statistics and interpretations. I had everything. I had one parent who played the role of five.
There’s just this version of my life which is a sob story. I remember going on Mark Maron’s podcast, real long time ago. He was really hammering home this, “Man, what was it like? Just your mom, your father’s killed, blah, blah, blah. Drug deals.” He kept digging for the angst, and the torture, and the pain. And I was like, “Yeah, but I was in the Boy Scouts.” I had friends. We played bike tag, which is super-hella dangerous. We played tackle football on our concrete playground, but we played. I had a great community.
AZ: You talk about spending a lot of time in the car.
BT: Road trips up and down the East Coast.
BT: [Laughs] Yes. I would race home to watch the NBC Nightly News.
AZ: Ms. Arnita Thurston—
BT: Yes, my mama.
AZ: —was a product of a condition of lineage that was also challenging, but also extraordinary, and filled with contradiction. I did want to hear a bit about your grandmother, and the thread backwards through the American story.
BT: I like to joke that you can’t be more American than being owned by America. So, us descendants, the slaves, are the ultimate Americans and patriots for sticking around and not constantly burning the place down.
On my mother’s side, her grandparents are products of the end of slavery. Lonesome was her grandfather’s name, Benjamin Lonesome. He was born, I believe in Caroline County, Virginia. We were told he was born a slave.
AZ: But in 1870.
BT: Yes, but the public records suggest that that was impossible and illegal. I don’t know if it’s a folktale or if the Emancipation Proclamation wasn’t universally enforced at the same time.
AZ: It took a long time.
BT: And clearly, Juneteenth is because—
AZ: We didn’t have social media then.
BT: —horses move real slow. I’ll put it down to the horses.
Anyway, my mother’s grandparents were D.C. people. They migrated to D.C. Her grandfather, Benjamin Lonesome, worked for the city of the District. He was like a surveyor or some kind of infrastructure worker. I don’t know what his wife did professionally, if anything. She might have just been in the time of running the household during this. They gave birth to my mother’s mother, Lorraine Martin, who…. That’s a contradictory, interesting figure. I learned more about her after my mother’s death than I did during her life.
AZ: You didn’t know her history when you were growing up?
BT: No. I knew her a little bit. I remember her smell—cigarettes, a hint of vodka, orange juice. She loved a screwdriver. I remember her house was dark, and had stairs that went up and creaked. My mother and her mother had a massive falling out, in part over my mother’s childhood. My mother was abused in the household by her father. Her mother, Lorraine Martin, sided with her husband instead of her child. Verbally abusive, psychologically abusive herself. Told my mother she was dumb, too dark, all these things. My mother was not dumb. And there’s no such thing as too dark. She was a brilliant woman. She became a computer programmer. Didn’t even go to college. Didn’t finish college. No dummy does that.
AZ: This came from a woman who was the first Black employee—
BT: Black employee inside the Supreme Court building. Lorraine Martin, my mother’s mother, first Black employee inside the Supreme Court building. I learned this after my mother’s death, going through her files and finding newspaper clippings. Her mother, after her death—my sister who had a much deeper relationship with our grandmother on that side, being nine years older, found clippings that she kept. When my mom and me were featured in the Post about surviving D.C., her mother had that clip. They were still connected to each other’s stories, even though they weren’t connecting directly anymore.
My father’s family, the Robinson family, I had a late reconnection with them. My father was shot when I was 7, 8 years old, in D.C. Never solved, not even sure it was investigated. I did not go to his funeral. I found out later he was on life support for a very long time, in a coma. My mother didn’t want me to see him in that state. She gave me a choice, “Do you want to go to this funeral?” I was like, “I don’t want to look at a dead body.” I lost touch with his family from that moment on, until Facebook. In a moment of not just destroying democracy and wholesale trafficking in human misery and desire, a cousin messaged me. She saw me on television, saw me on CNN. “I’m your cousin!” Every Black person’s my cousin when I’m on TV. I didn’t take it seriously. It took me years to find it, because it was in the spam folder.
Long story short, I have, since writing my book, How to Be Black, connected with my father’s brothers. There were two. One survives now, but I met both of them when they were alive. And his mother, my grandmother on my father’s side. I’ve spent hours with her, and I’ve learned some of her story. She’s from South Carolina, Orangeburg, South Carolina, and her husband. She came up to D.C. in 1944. Couldn’t get out of the South fast enough. Her daddy owned his own land, had six kids. Owned his land, big deal. But there’s a twist in her story that’s really wild. She had to drop out of school every year, seasonally, to “gather the farm,” as my grandmother puts it, to harvest the crops. But not just for their land, for the white families as well, in order to have her father get extended credit by those same white shop owners. So slavery was still happening. She’s like, “I don’t want any of that.” She came up North. She worked for the Government Accountability Office. She worked for the U.S. Information Agency.
Her husband worked for Amtrak. This is beautiful to me, because I didn’t know this at this time. I grew up on Amtrak. These trips I took with my mother, Amtrak power trips. The greatest trip of my childhood was a two-and-a-half-week trip around the lower forty-eight by Amtrak, and into Mexico on the Mexican train. I always loved trains. Acela member for life. And to know that that was in my blood, that I could have been riding for free had I known—because family gets free rides—I was excited and a little annoyed about that. So there’s a D.C. legacy, a government legacy, a bit of a pioneering information systems, information technology legacy, in terms of my grandmother working in the Information Agency, on my father’s side. My mother working in the Treasury Department, doing this computer-science work.
AZ: Giving you a computer. I mean, get ready for it, because we’re about to go into some tech stuff.
AZ: Which is where we share a lot of philosophical foundation. Your mom, in the eighties, puts a personal computer in your house. This was not normal.
BT: No. For anybody.
AZ: I grew up like that, but none of my friends did.
BT: No. We were weird.
AZ: You tell this great story about your first act of subversion in high school, where your friend got expelled.
BT: Yes! [Laughs]
AZ: This is, to me, so powerful, because it’s this moment where you were like, Wait a minute, I know how to do something. I have access to information and information is power. I can create story and change out of this. I got to hear this story from you.
BT: This is a story of high school glory for me. Sidwell Friends is my high school. It had, and continues to have, great resources. One of those resources at the time is we had a then very fast, always on, T1 internet connection. T1 is about one point five megabits per second. It’s like DSL today. We had a computer in a lab that was always connected to the internet. I’m Mr. Computer Nerd, living in that lab, even beyond the classes I have to take there. A situation goes down where a good friend of mine gets expelled from school, in a way that didn’t feel just to many of us. There was a conflict of interest we saw between his prosecutor and his investigator, shall we say, who were kind of playing both sides of the deal.
There was a lot of expulsion of Black boys going on at the time. I think the school was feeling a lot of pressure having had the Clinton, having had Chelsea, in the school, and all this extra media scrutiny. They would invite these Black kids to the school, and then anything goes wrinkled, get rid of them—which happens with a lot of these institutions thinking they’re being progressive. My friend’s family sues the school. I get called in for a deposition, a lot of other students, about what we knew, when we knew it, what we heard, how things were communicated. No one in the school knows about this, unless you’re one of the few that’s been called or you’re very close to this student.
I was like, people need to know that there are great injustice that have happened. Court proceedings are public record. So I did two things. One thing I did is I found the court proceedings using LexisNexis at the American University Library. I printed that out, and I delivered them to the children of the members of the school board, just hoping one of these kids would bring this home and let these influential parents know something’s not right here. Because there was a lot of stuff that came out in discovery about the ways the administration acted that was not very Quakerly, and this is a Quaker institution, Society of Friends.
The other thing I did is, I gotta let the newspaper know. I was on the newspaper staff at the time. Of course, I could have just called a meeting and, “Hey, everybody, this is happening., My friend is going through this thing.” But I had this odd sense of ethics around it, where I was willing to break some rules, but not others. I basically was like, I just want them to know, and decide on their own how to proceed. I don’t want my fingerprints on it, because they might do it for me, or they might not do it, because I’m close to it. So, how do I get information to them secretly? I’m in my Watergate phase at the time. I’ve been studying, we watched All The President’s Men.
AZ: Interning at the Washington Post.
BT: I was literally working at the Washington Post at night.
AZ: Watching All the President’s Men—
BT: I emailed the newspaper, but through a series of…. I covered my tracks, and I hacked into a computer. I committed computer crime, and I used Yale’s computer system to do it. It was very insecure at the time. Essentially what I did, for the nerds listening, this is all command-line Unix work. There’s really no graphical interfaces on the internet much at the time. I pretended to be a mail client myself, and I communicated with the mail server in the same language of the machines, and created a legitimate header, crafted a message, and invented an email address, “the firstname.lastname@example.org.” I was like, this is my Deep Throat moment. I alerted them to this lawsuit: “Here’s the case number. You can find more information.” They started digging on their own. There was this moment of buzz in the newsroom, and I had to keep my mouth shut and just act surprised like, “Oh my God, this is really fascinating. What’s going on here?”
Then the last thing I did, and I don’t know if I’ve shared this very much publicly, or if you heard this story, I used my power at the Washington Post—not to get them to cover anything; I just needed their copy machine. Again, I’m very much in my, like, skeptical of American power mode. I had been researching how the U.S. government dealt with people—wire taps, and prosecution on other charges, such as mail fraud. That’s how they got Capone.
I created a “wanted” poster for the principal and the dean of students, who I saw as the corrupt members abusing their power in expelling my friend. I put their faces on it and a list of accused crimes, and I printed out posters. But I used the copy machines at the Washington Post to print out Washington Post–sized broadsheet posters. I got to school early one day, and I put these posters up all over the school, on the day of the week where we do our meeting for worship. It’s like chapel, without the pastor. The whole school’s in one room and people just reflect on what’s on their mind, and spiritual stuff, and political stuff. I had the gym, where we did this, lined with these posters. I was just provoking these kids. The kids were fired up,and they were just making testimonies about abuse of power, and how the hypocrisy…. I didn’t have to do that. I just created a space where people could do that.
There was a moment when I was putting these posters up—I mean, I put them up in the teacher’s lounge. Balls. I went into the teacher’s lounge and I got there very, very early. I was inspired by kids who had done pranks years prior, and they deconstructed the entrance to the school, and parked a Jeep inside the school, and then put the doors back on. I was like, I could do something like that, for totally different reasons. A teacher came in when I was putting this poster up, and it was one of these moments of, Am I going to pay the price for my activism now? Is this where it all ends? The teacher just looked the other way, and let me finish doing what I was doing. [Laughs]
BT: I kept those secrets for years and I didn’t tell anybody. I got my diploma. I went off to college. I told two kids who were still at the school at the time, and they kept the secret. I went back to the school some years later. My prediction played out. They were proud of me, wanted me to come back and talk to the students and inspire them, and I showed the poster I made. And the principal was still there! [Laughs] I was like, “Let me tell you about my time at Sidwell.”
AZ: Punk. Straight punk.
BT: [Laughs] The kids loved it. The teachers were like, “Eh.” The administration was… You can’t do nothing to me now, I got the paper.
AZ: You got to Harvard.
BT: I got to Harvard.
AZ: And shockingly, you studied philosophy.
BT: Yes. Which a Sidwell teacher inspired me to do. Erika Berry. I always give her credit for planting that seed.
AZ: Which I wasn’t surprised to learn, in that you basically challenge assumptions. You ask questions. You’re concerned with being. But, very quickly you got into comedy.
AZ: Which, I was surprised to know, you weren’t like, or you’ve said, you weren’t a comedian as a kid.
BT: I don’t think I was. I think people who say that I was funny as a kid are lying. I really do. My memory of myself is like, you would’ve called me, in today’s language, one of these super-woke kids. I was very conscious. I was very self-righteous. I was very earnest, and I still am in many ways. I just learned to put some layers on it, cover my tracks. Humor and jokes allowed me to do that.
AZ: Were you already seeing—and I know this is a hard question to answer—but were you kind of seeing tech, humor, news, convergent as a medium? Because it seems like it’s kind of what you do now.
BT: Everything I do now I did in high school. In some ways, I’ve made no progress. [Laughs]
AZ: You just got better at it.
BT: Yeah. And then certainly everything I do now, I experimented with fully in college. Household, seeds were planted. High school, seeds were watered. College, they start to sprout. Then, the decade since, I’m cultivating, I’m pruning, I’m ripping up some of these things that don’t serve me anymore. I’ve obviously planted some new seeds as well. The spirit is really played out in college.
AZ: You bought baratunde.com in 1999.
BT: Yes, I did. June 1999.
AZ: Most people didn’t have an email address till, what, 2003?
BT: Absolutely, because I felt connected through this stuff. We had an email community of the Black kids in the class of ’99 at Harvard. It’s just social media. It was just our subreddit. It was our mailing list. It was our Mighty Networks community. It was our WhatsApp group, which is now a Signal group.
Here’s what’s happening in college: I am considering majoring in computer science and taking coding class. I am working to pay the bills at Harvard in the computer services department on campus. I am working as an IT admin off-campus at a software company on their Windows NT network. I am a member of the Harvard computer society, leading the publication of a book called, like, Computers at Harvard: The History. I am on the student newspaper, The Harvard Crimson, as its first online editor, with Jenny Lee, we were co-editors of this section, building the first website for The Harvard Crimson. I’ve got my own comedic email publication and a column in the paper about technology that’s comedic. So humor, Blackness and identity, income, creative power, journalism, is all coming together.
AZ: And you’re learning how to be a stand-up. Somehow you got to The Onion. You got to New York. In 2005, you were nominated for an award at the New York Underground Comedy Festival.
BT: The Bill Hicks [Spirit] Award for Thought Provoking Comedy.
AZ: What about that was unique for you? Because it was bittersweet.
BT: It was unique to be nominated for an award for doing stand-up.
BT: I was still a baby.
AZ: You were two, three years out.
BT: I was a baby in the game. It’s funny. Look at your life, at moments you think you’re the greatest thing ever. Then you live a little more and you’re like, I knew nothing. And so now, I know that I’m very good at some things. I look forward to humbling myself, or being humbled by life and looking at a moment like this. Like, I thought I knew how to interview. You know what I mean? I thought I knew how to have a conversation on a microphone in midtown Manhattan. So, I was nominated for this award, and I had to bail on going to the final performance because my mother was very sick.
In 2001, two things in my very personal life happened after 9/11, or right around 9/11. One, we’ve already talked about. I started studying stand-up comedy and that would change the trajectory of my life. The other is my mother was diagnosed with colon cancer, and that would change the trajectory of my life, and hers, and everybody connected to her.
So she’s living in Southern Massachusetts at the time, near the Rhode Island border. My 9/11 was spent with her, as she’s recovering from the removal of this tumor from her intestines. We were watching the news. We turned it off. It was not helping her healing. We went to a state park, and we spent the day with me riding a bike and her walking, and just taking in nature, and then refilling our cup from that connection. I would then dive back into my screens and news and emailing when I got back to Boston late that night and the next day.
Four years later, she had a relapse, and it came on very suddenly, in the summer of 2005. My sister had gone to visit her. She had moved to Portland, Oregon, where she always wanted to live on the west coast. She’s on Harrison Street, if anybody knows, these high-rise apartments right along the river, within the range of the Fareless Square–bus system—free public transit in Portland. Sounds so dope. My mom was made for Portland—it’s like the hippieist, crunchiest, outdoor friendly, wokest town in America. Previously, Takoma Park, Maryland, where we also lived for a while, and of course, D.C. She had wasted away when my sister saw her. I would visit the next week, and then, emergency mode, interventions, getting to Dana-Farber Cancer Institute in Boston, and she died there. She died at the Dana-Farber Cancer Institute with a giant tumor in her body. And I had to speak to this committee about the award from the hospital, and say like, “I can’t make it to this thing. My mom’s, I think, on her deathbed.” We were trying to figure out what to do, make arrangements. So they let me put it off to the next year.
AZ: How is your response to her death? How did you react to it?
BT: [Sighs] Eviscerated. Eviscerated. I’m very defensive of my mother, and a lot of us are. A lot of boys and men are. I was a mama’s boy. I was very transparently aware of everything she had done to make everything I could do possible. Financial sacrifice, emotional, health, physical sacrifice. Fierce, fierce woman. She was 65. This was way too soon.
We had the benefit of that first bout with cancer, four years prior, to kick into extra quality-time mode. Took her to Tina Turner concerts, and Joe Cocker, and Bill Cosby, before we knew he was a monster. I took her to see Oprah live in Chicago, courtesy of my friend Mawi Asgedom. So there was a bit of a bucket-list sprint going on. I just didn’t expect it to end so quickly. She was wrestling with a lot of her own shadow, and pain, and demons. She was finally rid of us as kids, and meeting us as fellow adults. I was just starting that journey with her.
AZ: You were young. From what I understand, putting things together, you were doing the management consulting thing, doing the comedy, still trying to figure it out, but kind of hedging.
BT: That’s a good way to put it.
AZ: It felt, to me, and I don’t want to project on to it, but it felt to me that after that moment, you gained a certain confidence of like, “You know what? I’m just going to do the stuff that matters.”
BT: That’s a nice interpretation.
AZ: I don’t know if it’s true. I’m just asking.
BT: I’m going to speak and feel out if it is. It’s true-ish, for sure. I had a sense of responsibility coming out of college that my mother reminded me of. We made a deal that, because she had so overextended herself to pay for Sidwell, I was responsible for Harvard financially. So I had these jobs that we’ve talked about and it still wasn’t enough. She still had loans. She is the parent. But I’m responsible for paying them off. I conveniently forgot that detail my first year out of college, when I took a job that paid well, so I could pay off loans. So she reminded me of this, which, you know, to her credit, she didn’t explode, but she was like, “Do you remember? We have a deal.” She wanted to live her life, too.
I’m working in corporate strategy consulting around tech and telecom, making more money my first year than she made in her best year, which is like $65,000. I think it was my first year starting salary, without any bonus attached, and paying off this government. I switched priorities to pay her first. I’m like, “The government can wait.” Especially when we got to [President George] W. [Bush] using this money to fund wars I didn’t believe in. I’m like, “The tax man can wait. I’m good for it.” But I didn’t feel like I could afford to just pursue art. That felt very irresponsible. I got loans to pay. I don’t have anything to fall back on.
So I just worked harder, because I wasn’t also willing to totally give up on my artistic, creative, and sort of political aspirations. I had the benefit of my wife at the time, my first wife, Mieka [Pauley], who was an artist herself, and really encouraged me. A lot of the story that you’re hearing right now, she inspired and provoked for me. She was a good challenge that I was living with, who was pursuing her art, all out. She’s like, “What are you going to do?” So that stand-up, taking that class, she encouraged that. Getting my newsletter going again after college, she encouraged that. She practiced what she preached, busking in Harvard Square with her guitar at the time. So I had that going, but I still wasn’t going all in.
When my mother passed, it destroyed me in the short term. I lost all sense of responsibility for things that are supposed to matter. I stopped paying bills. I stopped checking my mail. I just wept a lot. And Mieka picked up the slack, and she organized. I kept going to work. I came home from work one day, and she had organized all the mail into these prioritized piles with Post-its like, “Must do first, second, third, fourth.” Because I messed up my credit, just in mourning, not giving a shit. What does a credit score matter when your mom’s dead? I give much credit to her for helping me through that.
My comedy changed, in that her passing led to me transitioning to some of that internal analysis and reflection on stage. I started talking about myself on stage, not just about Dick Cheney and the shenanigans, which I was super comfortable doing. Always happy to point out. Now, I challenged myself to point in. I started talking about her more—talking about my mother, talking about how I was raised, talking about the absurdity of my childhood. That stuff became How to Be Black, my first book.
AZ: Which was a monster success.
BT: Yeah. I hit The New York Times Best Seller List.
AZ: The autobiographical guidebook.
BT: Yeah. So not having my mother to talk to, I talked to myself more. She was the subject of a lot of those conversations, and I pushed myself more. I felt, in those years, immense gratitude, almost exclusively. In more recent years, I’m finding another part of my mother’s story that I wasn’t willing to examine as the mama’s boy, who only saw the perfect, sacrificial, saintly Arnita. Now, in my forties, and with the time of Covid, I’m like, “Oh, there were some shortcomings, too.” So reckoning with the imperfect Arnita, and the mother who was very different with my sister than she was with me, talking to her friends about the type of person she was, and what she was into. Nothing criminal, but just not this model—
AZ: But she’s not an object anymore.
BT: No, she’s a human again. And so I objectified my mother in some ways, in the immediate aftermath of her passing, as a way to celebrate, honor, and memorialize her, and demonstrate my love for her. That practice has changed for me now, and I think, gotten better.
AZ: In 2016, you wrote this Fast Company column that struck me because it was the very beginning of the techlash. I was obsessed with it. I was getting super deep in it. You said, “Tech has no inherent truth or goodness. It is what we do with it that matters.” And you go on to say, “We must humanize technology (and the businesses driving it) by bringing humanities back into the picture.”
This is one of the main issues that I’m going to choose today before we finish, to talk about, “Where we go from here?” I mean, we were both in a conversation with someone recently who’s very powerful in tech. We were both saying, “Is there a philosopher at the table?” So for us to move forward, what thoughts do you have regarding the lack of humanities at the table right now? Where’s it gotten us? And how are we going to build a better future with technology?
BT: There were many moments, I started to realize, that the people building these social spaces with technology, only knew the technology part. I remarked on it in a very early TEDx talk of mine, and said, “Just because you’re a good software engineer, doesn’t make you a good social engineer.” But we have very limited minds trying to cover all types of mindsets, and all types of behavior: government, romance, spirit, sports team. We’ve usually had specialists. People who are good at bridges, build bridges. People who are good at teaching design schools. So we’re just having people who are good at like JSON, build everything. That doesn’t feel right. And the consequences, we’re living through them.
So to me, it’s obvious we need more types of minds shaping this. We need essentially a more democratic—small “d” democratic process—a more participatory process, because it’s not technology that we’re building. It’s society, it’s business, it’s our pleasure zones. It’s everything we actually care about, but very few types of people are at the table building it.
Also, the money that has driven the incentives to build the way we’ve built, what we’ve built, is a problem to me. Money’s always been around in economics, this behavioral economics. There’s reasons to create financial incentives, but not for every single thing that we do.
BT: Yes! And so we’ve monetized attention. We’ve put everything inside of a mall, basically, all of our interactions of any kind, and that has perverted how we show up. Not just online, but IRL, too.
This word “community,” to me, it dovetails with the idea of free speech. We’re having very simplistic and absolutist interpretations of these terms. Simplistic on community. A bunch of people in the same space is a community.
AZ: It’s not a town square. And there’s not one town square.
BT: And free speech, where I get to say what I want. When I think about the communities I’ve been a part of, in meet space, in real life, they feel very different from what we’re doing online. They move more slowly. There’s implicit mentorship involved. There’s a period of observation and learning before mass communication, and influencing, and dominating. Your first day on a new job, you don’t hijack the P.A. system and start mouthing off on your feelings about eugenics.
BT: Esra’a work with majal.org, Eli Pariser with New Public—there are many people who’ve reminded me that we could build things differently. What we’ve chosen instead, we’ve been very unimaginative. Again, a lot of my critique comes down to a lack of imagination—on business model and on mind type—to create these platforms. So we’re just up into the right as fast as possible, and we break all the stuff that matters, including the fabric of society, to some degree, and a hold on shared reality, even if it’s not actual reality. The absence of sharing is making it really untenable.
So what do we do? I mean, we build our own stuff. We move slower. We preserve spaces to not be monetized in the only way we’ve discovered, which is advertising and attention mining. We ask ourselves, How do we want to feel in a space?, and design for that. I don’t remember being asked, and I was very early to all these platforms, “How do you want to feel on Twitter?” I know how Twitter makes me feel, and I know it’s not how I want to, but there was no conversation early on about, “What am I looking for here? What am I trying to get out of this?” There’s just this assumption that I will do what the platform encourages me to do. That’s been a safe assumption, because they can hack our brains now. They know the psychology. They have applied math on their side. They have infinite resources relative to our sole resistance to that kind of button-pushing.
AZ: But things are changing. I mean, you joined Puck. I’ve been reading all your pieces in Puck, and you’ve been using this platform, it seems, to take a little more time. I wanted to ask you why you joined Puck, and what the opportunity there is affording you, in terms of time and digital media.
BT: I’d been giving away a lot of my thoughts to platforms that were happy to take them, and not offer me very much in return. I am Instagram-captioning my essays. I am atomizing my coherent thoughts into tweets to serve their design construct. I am making ephemeral disappearing things for TikTok, because that’s what you do to get attention. And I am not above incentive structures.
I like Puck because it’s a bit of a collective. This is a subscription media startup covering Washington, Wall Street, Silicon Valley, and Hollywood, with some of the best reporters in the game, from Bloomberg, Politico, and Vanity Fair, and me. I’m not a reporter. I don’t have sources. I don’t go to press conferences. I don’t have people on background. I’m there to analyze, sometimes myself, sometimes parts of our larger society, and to explore race, technology, democracy.
I liked that this is a journalist-owned platform. I liked that, unlike something like a Substack, which is running a MailChimp—which I’ve done in some form since 1996—I’ve got colleagues again. I’ve got an editor again. I’ve got some level of accountability and support, and those really work hand in hand. There’s a team. So, just doing things on my own, I can, when a pandemic forces me to, and I can be my own editor, and producer, and shooter, and writer, but deadlines are nice.
AZ: You’re with a crew.
BT: Yeah. I get to shout-out Julia Ioffe’s Ukraine/Russia coverage, what Bill Cohan is covering and revealing on what’s happening in Wall Street, and Tina Nguyen, who’s deep into the alt-right MAGA universe where I will never go, because I love my sanity at a certain minimum level. But she’s doing it, so I can just shout out her stuff. So I get to learn from other people. That’s exciting. And most selfishly for me, the Puck audience isn’t my audience. There’s some overlap, but it’s unique. It’s like the power-broker set. People who run these massive media companies and financial institutions—
AZ: It’s definitely the who, not how many.
BT: The people who are covered by Puck pay to read Puck. They weren’t following me on Instagram. They weren’t reading my tweets, but they are getting to read my longer thoughts about this intersection of race, tech, democracy, and increasingly, climate. That’s attractive to me, to have an additional set of folks to be in dialogue with, to hopefully provoke—
AZ: And you stand out in that crew because of that. Before we wrap up, I do want to talk about a new show you have coming out in a few weeks that brings you throughout America, telling stories about America, through the outdoors that we all share.
BT: Thank you.
AZ: Has your relationship to the outdoors changed from doing the show?
AZ: We want people to see it.
BT: We do want people to see it. And you can watch it for free, on the [peoples’ streaming network, pbs.org/americaoutdoors.
AZ: Which I think is such an important network.
BT: Man, I’ve underestimated, at every stage, what this project would mean. I thought, This would be a nice way for me to reconnect with some of my childhood. That bike-riding kid, that camping kid, the kid who went on these long rides with his mom when he was, like, 10 years old, because no other moms would take their kids out in Rock Creek Park, and toward Monticello, and all this beautiful stuff in the D.C. area, out to the Blue Ridge Mountains.
AZ: The Billy Goat Trail.
BT: The Billy Goat Trail. So this show gave me that. It gave me an exit from my zip code during the summer of 2021, which wasn’t the “hot vax” summer we were promised because of the Delta variant. My wife is still jealous that I got this adult summer camp experience while she stayed home.
But I got more. I got to connect with people who are connected to the outdoors that don’t look like the people I expect to see. With all of my diversified experiences and coming from Mount Pleasant, I still am triggered to think about the outdoors as like a white dude with a beard, and a rod of some kind, conquering a hill of some size. And that is not the exclusive case with this show.
I got to surf with large numbers of Black people at the same time. We were Wakanda on the waves, man. It was so cool. I got to spend time with these Indigenous communities in their rice harvest in Northern Minnesota, and they let me knock the Manoomin, as it’s called. They don’t call it wild rice, the name is Manoomin. I’m in these canoes with them bringing in these rice grains in a tradition they have been practicing since time immemorial. That’s not typical outdoor show material. I whitewater rafted with this paralyzed dude down the New River in Appalachia. That was great. I got to hang out in the Chesapeake Bay with the most conservative mayor in America, by some measures, because his island town is disappearing due to rising sea levels. So it’s a climate show. It’s a race show. It’s a history show. It’s a financial economic show. And it’s a just, like, nature show. But all of it makes it a people show.
So I think of the show as America, comma, outdoors. It’s in deep contrast to that story I shared earlier, about making this cable news pilot in this city, on a high tower with a glass desk, reflecting on America from far above America. This is a conversation with America, on American soil and waterways. Like, when your studio is a trail, or a sand dune, or a surf break, you can get at people differently—and be gotten differently.
We talk about all the stuff I want to write about at Puck and I’m writing about. We talk about stuff that’s been in my stand-up when I did stand up a lot. We talk about stuff that’s in my Fast Company column. But it’s conversation, it’s active, and it’s fun. It’s also very sweaty.
AZ: Amazing. Well, I can’t wait to see it, and I look forward to all the new things you make. Thank you for coming in today.
BT: Thank you for this beautiful use of time.
This interview was recorded in The Slowdown’s New York City studio on June 16, 2022. The episode was produced by Emily Jiang, Tiffany Jow, and Johnny Simon.