Class Action
Tyrone Boucher, radical philanthropist, Philadelphia

I wait by the Mahatma Gandhi statue in Union Square as the sounds of an urban farmers’ market buzz around me—crates of vegetables being lifted from truck beds, a guy hawking newspapers by the subway entrance, a conversation between two organic farmers. It seems an apt place to meet Tyrone Boucher for the first time. He’s the cofounder, with activist lawyer Dean Spade, of a blog called Enough, “a space for conversations about how a commitment to wealth redistribution plays out in our lives,” and he’s currently investing time and energy in food politics—working at a small-scale cooperative called Mariposa, in West Philadelphia.

I stumbled on his blog months earlier and was shocked at how transparent Tyrone, age twenty-six, was—he posted his entire giving plan and a thoughtful letter to his father about his reasoning for giving away the $400,000 he inherited. He’s part of a larger movement of young people from wealthy families who are questioning the morality of wealth accumulation and pioneering new ways of what they call “social justice philanthropy.”

The timing couldn’t be better: the United States is currently experiencing the biggest intergenerational transfer of wealth in its history. The Social Welfare Research Institute at Boston College estimates that even with the recent economic recession, $41 trillion will be inherited during the fifty-five-year period from 1998 through 2052. But the huge amount of wealth being passed down is concentrated in very few hands. According to the Christian Science Monitor, only 24 percent of adult Americans expect to get an inheritance, and those who do can expect to receive an average of only $37,700. Tyrone’s experience is rare, but it also means that what he does with his inheritance—and what other young people like him do—can have a significant impact on all of us.

After e-mailing back and forth a bit, Tyrone and I found a time when he would be in New York to see his partner. We didn’t bother exchanging phone numbers or physical descriptions. I put two and two together and figured Tyrone was probably a black gay guy in his twenties.

When a white trans kid, wearing black jeans cuffed at the ankle and a short-sleeved button-down shirt, walks up and says shyly, sweetly, “Courtney?” I am totally stunned—confronted with my own taken-for-granted assumption. In fact, it takes me a minute to even become conscious of how stunned I look. Tyrone has a punk rock aesthetic, his playfully curving eyebrows erupting into little unruly tufts at both centers, and tattooed lines on two fingers of his hands. He emanates gentleness.

“Hi,” I say, eventually replacing my shock with a smile. “So good to meet you.”

TYRONE DOESN’T MIND surprising people. In fact, his young life has been composed of a series of experiments in not meeting people’s expectations. Unlike so many privileged kids of our generation—known for its dutifulness—Tyrone has consistently rejected the rules put on him by a society that he diagnoses as oppressive and unjust. School? Couldn’t stand it. Even though he attended the Putney School in Vermont, a place he describes as an “artsy farm high school,” he spent most of those years frustrated that he wasn’t allowed to do his own thing. He zealously thumbed through the pages of The Teenage Liberation Handbook: How to Quit School and Get a Real Life and Education, fantasizing about all of the exciting projects he could undertake if he wasn’t stuck in high school. He loved learning and felt grateful for the amazing art program and nontraditional after-school activities (blacksmithing, gardening, knitting, farming) that his progressive private high school had to offer, but he resented being asked to pour energy into classes he wasn’t interested in.

He remembers his state of mind at the time: “I know deep down in the depths of my being that I just don’t give a shit about school. And that’s fine with me.”

What he did give a shit about was the DIY (do it yourself) punk subculture that he became immersed in during high school—a culture that nurtured independent production of music, zines, and art and encouraged independent thinking and creativity. This community was where he felt most at home. “My early understanding was ‘I’m a freak,’” Tyrone says. “I’m not like other kids. I’m queer and a weirdo and I don’t fit in.” He spent much of his time at shows of obscure punk bands, rocking out alongside friends covered in tattoos, wearing threadbare T-shirts and weathered Carhartts. But it wasn’t just about the music; it was about a whole philosophy of life that challenged mainstream norms and strove to build community and culture based on independence from the status quo.

But everything was not as it seemed. Though Tyrone was internally rejecting traditional education, he was also filling out applications for a long list of mostly elite colleges and scoring in the top 1 percent on his SATs. When I ask him about the contradiction—typing out college admissions applications while adoring The Teenage Liberation Handbook—he replies, “I was just on autopilot.”

The answer doesn’t satisfy me. After all, this was a kid hell-bent on redefining education, creating his own path, and stepping off the mainstream trajectory defined for him by his family and class upbringing. When I push him on it, he relents. “I think I just sort of thought that if I filled out the applications, then I could keep my dad off my back. I never thought I would actually go to any of the schools I was applying to.”

“I WASN’T SUPPOSED TO TELL you this,” Tyrone’s mom said. Tyrone was flopped on the couch in their airy Vermont farmhouse, thumbing through some zines and chatting with his mom about the future. Graduation was approaching, and Tyrone’s dad—divorced from his mom by this time—was hoping that Tyrone would go to one of the colleges that had accepted him. The fat envelopes weighed heavily in Tyrone’s mind. He wanted to be free, unencumbered, not sit in more classrooms.

His mom went on, “You have a trust fund. You’re going to inherit four hundred thousand dollars when you turn twenty-one.”

Tyrone wasn’t surprised, exactly—he knew that his father, who lived in a fancy new condo in Austin, was wealthy and generous. It wasn’t old money; Tyrone’s father made his fortune by cofounding a software company in the family’s basement when Tyrone was a baby. So no, it wasn’t surprising; but hearing the number out loud, the concrete nature of the tall, proud four and those zeroes, overwhelmed Tyrone. (Of course $400,000, as significant a sum as it is, pales in comparison to the amount of money some kids from wealthy families inherit.)

“The minute I get it, I’m going to give it away,” he told his mom.

THAT WAS ACTUALLY THE LAST conversation that Tyrone had about his trust fund for years. He says, “I filed it away.”

“Did you file it away effectively?” I ask, imagining Tyrone among a little crew of pierced punks eating pizza from a Domino’s dumpster, reveling in their rejection of capitalism and napkins. It seems as if it would have been really hard to compartmentalize.

“I didn’t tell people. I didn’t talk about it. Nobody talked about their class background—at least not about having privilege,” he says.

“It’s interesting to me that in a culture built on the idea of not conforming and being deeply vulnerable and honest, it wouldn’t come up,” I tell him.

“Hence the problem of so much of that subculture,” Tyrone admits. “It was cool to act poor. There’s no analysis of what it means to actually be poor.”

After graduating high school, Tyrone took a year off, during which he got a premier education in adventure. He lived the life of a true vagabond—hitchhiking wherever the wind or a new friend took him, scrounging for food, sleeping outside—until he finally relented and went to Stanford.

“Stanford?” I ask in disbelief. “Of all the schools, Stanford seems like one of the least likely fits for you.”

“Exactly,” says Tyrone. “I thought it would be a unique experience. Already, in high school, I was so entrenched in my counterculture that I was bored with it. I figured that if I went to a counterculture college, I might be tempted to pretend it was real life.” Stanford—with its palm trees bending gracefully beside California mission-style buildings and its sun-kissed lacrosse players laughing on the quad—was a symbol of elitism so pronounced, so obvious, that it didn’t feel dangerous to Tyrone. There would be no chance of slipping into conformity when it manifested as keg parties and classes in free-market economics.

Indeed. After just two months, Tyrone left Stanford, never to return.

For the next four years (2001–2005), instead of sitting in the hallowed halls of Stanford, Tyrone continued to travel with his motley community of hitchhiking, train-hopping punks and queers. It was a beautiful, liberating time. Tyrone felt truly independent, while simultaneously surrounded by a loyal community of DIY mavens, anarchists, and dropouts. He felt like the breach that had always gaped uncomfortably large between his values and his lifestyle was being lovingly sewn shut.

But it wasn’t utopia. Looking back, Tyrone feels conflicted. “There’s part of me that has this reaction—‘Oh God, I was so oblivious.’ There were so many problematic things about that time,” he says, referring to the lack of race and class awareness among many of the punk kids. Indeed, some critics call the white kids that hang out on park benches in San Francisco’s Haight neighborhood or play bad music in Washington Square Park “trustafarians”—referring to their unconscious parody of those who come from poorer, darker cultures.

Tyrone staves off the embarrassment by seeing that season of his life for what it really was. “For me, that moment in time, personally, was more about my own liberation from alienation and isolation than about a political awakening.”

His awakening unfolded more like a sleepy morning than a burst of sunlight—a radical-women-of-color zine here, a disillusioning conversation there. Every time he would stop at his dad’s condo, he would spend hours printing out readings on white supremacy. Peggy McIntosh’s essay “White Privilege: Unpacking the Invisible Knapsack”—in which she encourages the reader to examine unearned privileges as minute as easily finding Band-Aids to match your skin tone—had a big impact on Tyrone. He devoured bell hooks and Angela Davis, examining the bibliographies in the back of each of their tomes to determine his next assignment. Tyrone, though not a fan of formal schooling, is a voracious reader and self-motivated learner. More than any other person I profiled for this book, he was constantly recommending books to me.

The readings helped him see his adventures on the road in a harsher light. For several years, Tyrone attended Camp Trans, a big festival in the middle of the woods that was created to challenge the transphobic policy of the Michigan Womyn’s Music Festival, a large annual feminist gathering that excludes transgender women. Tyrone reveled in the gender diversity of the participants, but remembers taking a good look around and realizing, “Huh, I hang out with mostly white people, and I always have.”

He was also growing increasingly uncomfortable with hiding his wealth. When opportunities came up for new friends to come and stay at his parents’ houses, he felt tense. What would they make of his father’s aesthetic—all modern, sharp edges, brushed steel, and dark hardwood? What would they think about his mother, just one lone woman, living in such a big farmhouse? “The dissonance between my politics and my class privilege was getting louder and louder in my own head,” Tyrone reflects. He had been through the process of coming to terms with his racial privilege. It seemed well past time to do the same with regard to his class privilege.

His motivation was solidified by one particularly difficult conversation that he had with a friend who grew up poor. “How could you turn your back on an opportunity like going to Stanford?” she asked. “Nobody gets that. How can you act like you’re above it?”

Tyrone felt like he’d been slapped in the face. He didn’t regret leaving Stanford. He knew that he would have been miserable there, that the place would have crushed his spirit, but he did have regrets. “What I find really embarrassing to think about in retrospect,” Tyrone says, “was my own arrogance.”

THE NEXT TIME WE MEET, Tyrone is talking a mile a minute, bubbling over with excitement about his recent trip to upstate New York to meet “movement elders” David Gilbert and Naomi Jaffe, two key figures from the Weather Underground Organization (WUO)—the militant faction of Students for a Democratic Society. SDS, as it was referred to, was the organizational center of student activism in the sixties. Its methods were disruptive, but generally peaceful—hosting teach-ins against the Vietnam War, protesting corporate recruiting and paternalistic rules on campuses, and coordinating the largest student strike in U.S. history, involving campuses all over the nation, on April 26, 1968.

The WUO, also called the Weathermen, was founded in 1969 by a mostly white faction of SDS members who wanted to develop more militant, underground resistance to U.S. imperialism in solidarity with people of color. In their founding document, You Don’t Need a Weatherman to Know Which Way the Wind Blows, they established their philosophy: “the main struggle going on in the world today is between U.S. imperialism and the national liberation struggles against it.”

Over the next five years or so, the WUO would conduct a campaign of bombings, usually targeted at government buildings; help writer and drug enthusiast Timothy Leary get out of jail; and even issue a “Declaration of a State of War” against the United States government. Naomi Jaffe says, “We felt that doing nothing in a period of repressive violence is itself a form of violence.”

The WUO and militant groups like it aimed to protect human life, but in the heat of their militancy, they sometimes failed. On March 6, 1970, three WUO members died in an accidental explosion at their pad in Greenwich Village. And Gilbert is currently serving a sentence of seventy-five years to life for his role in an attempted robbery that ended in the death of two police officers and a security guard in 1981. Tyrone visited Gilbert at the Clinton Correctional Facility, where he’s incarcerated. Jaffe, who was never incarcerated, lives in Troy, New York, and is involved with antiracist and feminist organizing. Tyrone was introduced to both of them through a friend.

“It must have been incredible to exist in that political moment, to feel that liberation movements were on the verge of defeating imperialism,” he exclaims, referring to the explosive moment in the late sixties and early seventies when the WUO was most active. It’s not just the idealism of the day that seems to inspire Tyrone, but the deep commitment of those privileged young people who believed in revolutionary struggle. He often talks about various clandestine activists from the sixties and seventies who supported nationalist liberation movements, both in the United States and globally, risking safety and security because of a deep belief in justice.

In contrast, Tyrone and I sit discussing radical revolution in a place that, on the surface, seems distant from the radical struggle that is the topic of our conversation—the Resource Generation offices, located in the headquarters of the Mertz Gilmore Foundation, a luxury brownstone on East Eighteenth Street in Manhattan. Dan Berger, a young radical, wrote a painstaking history of the WUO, and in it he argues that “privilege was its raison d’être—the group set out to use its privilege in service of revolutionary change.” Resource Generation (RG)—the very center of the new movement of young radical Americans with privilege, and the organization responsible for Tyrone’s class consciousness—has an almost identical raison d’être, but its methodologies manifest very differently. RG organizes young people with wealth to leverage their class privilege for social justice. They don’t bomb buildings; they teach workshops, organize conferences, and support young people to have dialogues with their families and communities about class, wealth, and social change.

Tyrone facilitates workshops for RG from time to time, so we are welcome to use their space when we have our interviews. “Something that hits me really hard when I hear about political movements from a few decades ago,” Tyrone says, “was that the nonprofit system didn’t exist on the left at that time. Things are so different now—I’ve never known a world before the nonprofit industrial complex.”

The term “nonprofit industrial complex” was coined by an organization called INCITE! Women of Color Against Violence—a collective that was stripped of its Ford Foundation funding after publicly declaring support for Palestinians. INCITE! compiled a collection of essays, considered required reading among the more radical RG folks, called The Revolution Will Not Be Funded, published by South End Press in 2007. In it, the authors argue that the nonprofit model “replicates historical oppression by keeping funders in power over activists, emphasizing institution building and business practices over organizing and systemic change, and perhaps most egregious, forcing social justice activists to please their funders rather than their own communities.”

Though the rhetoric in the book can sometimes feel hyperbolic, the argument is profound. The development of the nonprofit sector—initiated largely because it would provide a tax haven for the superrich, while also allowing them to do some good—has historically been seen through rose-colored glasses. Philanthropists are routinely celebrated for “making the world a better place”; but if you actually examine where people donate their money, most often it would be more accurate to recognize them for making their world a better place. Giving to alma maters and elite cultural organizations, like the ballet or the opera, top most yearly philanthropy lists. The Giving USA Foundation found that dollars donated to groups working most directly with those in poverty dropped from 24 percent of annual philanthropy in 1955 to 8 percent in 2004; organizations that help America’s poor are particularly neglected.

The nonprofit sector also has an interesting impact on youth activism. Young people pumped up on altruistic visions log on to Idealist.org, clamoring for nonprofit jobs that seem to be the most direct route to do good. They are quickly assimilated into a system that, more often than not, maintains the status quo whereby wealthy, mostly white people hold institutional power—with the added psychological bonus of getting to feel smug about their charity work. As Tiffany Lethabo King and Ewuare Osayande ask in The Revolution Will Not Be Funded, “What are the implications of a social justice movement in which power and resources are transferred based on one’s ability to develop a relationship with the right white people?”

Tyrone was already convinced of this critique, but studying radical youth activism of the sixties and seventies seems to have only increased his investment in the idea that the nonprofit system is actually part of the problem. “During that era, there was so much social justice movement stuff happening, and no one who was truly working for fundamental change expected to be paid for their activism.”

“Right,” I respond. “But isn’t there also an inherent elitism in expecting people to be able to do activism without being paid? Wasn’t that part of the critique of the radical left movement in the sixties—that they weren’t aware of the luxury of protest?”

Tyrone is quick to counter: “The work people do to fight for liberation is different than the work we do to earn a living, and it always has been. There’s certainly overlap sometimes, but you have to wonder: why would the capitalist system pay you to fight it? If we’re trying to build a mass movement, we need to create social justice infrastructure that supports everyone, not just the handful of folks who are able to be paid to do the work.” He continues, “It doesn’t mean that people shouldn’t work for social justice nonprofits, but if that’s the main model we have for building movements, it limits us.”

Tyrone himself now lives on very little money each year—$17,119.16 in 2008, actually (he keeps an Excel spreadsheet with all of his expenses). He tries to make as many of his own meals as possible, with an intention to buy locally grown, organic produce from the co-op he helps run. He pays $275 a month in rent, always takes the bus when he comes to New York to visit Elspeth (his partner, the program coordinator at RG), and spends very little on clothing and entertainment. One manifestation of his political principles, in line with globalization experts like Naomi Klein (author of No Logo and The Shock Doctrine), is a commitment to conscious consumption. Tyrone makes a note of every single thing he buys.

He also recognizes that living cheaply, ironically, is also a privilege of sorts. Tyrone wrote on his blog:

One great thing about giving away this money is that it’s made me think hard about living within my means. When I decided to give away most of my trust fund, I realized that I was going to have to get my act together financially and stop living like an irresponsible rich kid who could get bailed out by my parents whenever I over-drafted my bank account…. Of course, having class privilege means I get to see living on a really small budget as an exciting project rather than a stressful necessity. Truly being poor is expensive, and having had good healthcare my whole life, never having to go into debt, not having to take financial care of my family, and a million other things make it easy for me to live cheaply.

Tyrone is also opposed to ambition of the careerist sort, so emphasized for young Americans in today’s preprofessional college environment. In fact, the idea of being part of this book, of being recognized as unique or special in some way, was initially extremely off-putting to him. Tyrone spent much of our first meeting trying to convince me of all the other grassroots activists that I should choose rather than him. Like a lover playing hard to get, he only intrigued me more.

Tyrone is fired up now, talking about grassroots movements the world over. He jumps from the economist Milton Friedman to the Ford Foundation and neocolonialism in Latin America, to memoirs by clandestine radicals, to the problems with elite philanthropy—all in a matter of minutes. It’s hard not to be intimidated by the depth of Tyrone’s knowledge. Probably noticing that I’m beginning to look overwhelmed, he takes a deep breath and says, “I get really excited about this stuff. I was talking to Elspeth about this…. There are certain conversations that I’m interested in having, but I realize I should sort of start at step one.”

It’s the wisdom of an older, more patient Tyrone—one who realizes that not everyone is as steeped in movement histories and social change philosophies. I can imagine him early in his political awakening, operating on six cylinders of new learning and outrage, unintentionally steamrolling less informed people. “Bottom line,” he says, getting back to basics, “is that grassroots movements have always come from poor people, from disenfranchised people. They don’t come from academics and philanthropists. Someone commented on Enough after foundations started losing all this money in the stock market crash, asking how horrifying it is that our movement funders are literally more invested in the success of capitalism than they are in the success of grassroots movements.”

I want to believe—truth be told, I have to believe—that people sometimes do nothing to end suffering, or in the case of so much elite philanthropy, do inadequate or misguided things to end suffering, because they don’t know another way. It’s not that people don’t care, that the rich who give copious amounts of money to the opera or the ballet have stones for hearts. It’s not that they are superfans of free-market capitalism. (Okay, maybe some of them are, but they’re rarely the ones dishing out lots of money to support the arts.) More often, it’s that they have been socialized in a system where that is what people do with their money. They get psychological rewards—the beauty of the music, the recognition from their friends, the continuation of a family tradition. Most wealthy people simply haven’t been inspired to see another way—as Tyrone, blessed with a very rebellious, curious nature, has—or had a powerful experience of a different kind of giving.

David Gilbert himself said, “In learning from history, we need to break from the mainstream culture that defines people as either purely ‘good guys’ or purely ‘bad guys,’ which can lead to the self-delusion that getting certain basics down guarantees that everything else we do is right. The WUO made giant errors along with trailblazing advances. Hopefully both are rich in lessons for a new generation of activists.”

I can see Tyrone wrestling with this wisdom when he speaks about these issues, when he meets young people just being initiated into the community at RG and the idea that, in his words, “being rich is wrong.” It takes such patience, such conscientiousness, a constant return to empathy despite all the forces that make it easier to see certain people as the enemy. And as it turns out, sometimes the easiest people to vilify are those who remind us most of ourselves.

Tyrone wrote beautifully about his own challenges with this on his blog after a recent conference:

In doing economic justice work with other class-privileged folks, I struggle with what often feels like a fine balance: trying to constantly betray and oppose the oppressive systems that I benefit from, while also having real compassion for myself and other folks who are struggling to find their way out of those systems in lots of different ways. Each year [at RG’s national conference] we do an anonymous survey to collect data about how much money participants have and how much we’re giving away, and then present the results in a slideshow during one of the plenary sessions. It’s always shocking to see the results: millions and millions of dollars owned by the small group of people right there in the room (mostly inherited from wealthy families), and a minuscule percentage of it being given away. It’s pretty disturbing to sit in such a major locus of massive wealth accumulation—even more disturbing because we represent some of the very few rich people attempting to challenge economic injustice. It’s an incredible illustration of how deeply the messages of capitalism—to hoard, protect, and grow wealthy—penetrate. I spoke with several anti-capitalist … attendees after the survey about our shared inclination to shout, “People—what are we doing!?? We are the problem!”

I try to remember that my rage against these systems is not objective or theoretical, but is a lot about how much I hate being in a role that often makes me complicit with massive global exploitation and oppression. I think my indignation and tendency towards ranting can be ways to push the pain of this away—like if I just constantly articulate some really well thought out critique of capitalism, and write things dissecting the ways that privilege functions, and drag all the privileged people I know into these really complex critical conversations, then I can distract myself from how much it all hurts and is sad.

Many of the young people who end up “coming out” at RG have passed as middle class their entire lives, mastering tricks to appear less wealthy than they are around new friends. Having their parents drop them off blocks before their destination so no one sees the Lexus, wearing thrift-store clothing, and complaining about imaginary debt are some perennial favorites.

The language—“coming out,” “passing”—isn’t just coinci-dental. One of the first things that I noticed, once I started hanging out with Tyrone and some of the other RG staff, is that the majority of them are queer, trans-identified, or both. Tyrone talks excitedly about how he came out at fourteen, at the same time as his own mother: “It was awesome!”

He didn’t change his name to Tyrone or start asking that people use the masculine pronoun until his vagabond days. He describes coming of age in a queer community that was vibrantly redefining gender; he felt supported to claim the gender identity that felt most right for him, whether it was normative or not. Politically, his commitment to trans liberation is bound up in his commitment to broader economic justice; trans and gender-variant people are often the ones who are hardest hit by poverty, policing, and other forms of injustice.

Tyrone feels grateful today for the privilege of having had such a tight-knit queer community. “I don’t always realize how nurturing it is until I step outside of it into a space where I’m the only queer or trans person,” he says. “Now I work and organize a lot in spaces that aren’t explicitly queer, but queer community was the air I breathed for a while, and I am so grateful for that.”

So why the big crossover between the queer and radical giving communities? Tyrone ventures a theory about alienation: “If you’re queer, you’re more likely to have a negative experience of wealthy culture,” he says. “That pushes you to critique the culture at large.” Many of the kids who gravitate toward RG have been rejected by extended family members, harassed at school or on the streets, or experienced subtle judgment or a basic lack of understanding from parents and friends.

It makes a lot of sense. Wealthy people, children especially, tend to be insulated from the world of poverty. Tyrone explains, “Privileged people generally don’t have to challenge ourselves. We’re not the ones who are going to die. That’s what inspires me about white antiracist organizing and groups like Resource Generation that are challenging the invisibilized role that capitalism and white supremacy play in injustice. That’s what inspires me about solidarity movements of privileged people that make oppression our business and our responsibility. They’re saying, ‘We can’t continue to live our lives in a bubble. We can see that there’s a war against poor people and people of color, and that if we’re not working for liberation we’re a part of that oppression.’”

After wealthy queer kids experience discrimination, they’re more likely to see it all around them. They may not declare war, like their predecessors in the sixties, but they certainly can’t retreat back into their wealthy bunkers either.

TYRONE CLUTCHES A FAT MARKER in his hand and stands next to a big white flip chart. “When I first started coming up with my own giving plan,” he says, “I wanted it to be perfect—politically speaking. I wanted to do the research and create this totally perfect thing that would redistribute my inherited wealth in the most socially just way, and then be done with it.”

The ten young people seated in front of him in a U shape laugh a bit in relieved recognition. Guilt over the many complexities and hypocrisies inherent in being a left-leaning person with wealth is prevalent in this community. Karen Pittelman, whom Tyrone calls a “fabulous, radical philanthropist extraordinaire,” gave away $4 million upon inheriting it at twenty-one years old. She also wrote a book—considered the primer on the movement—titled Classified: How to Stop Hiding Your Privilege and Use It for Social Change. In it she jokes, “Based on dedicated attempts by many of us involved with Resource Generation, we can say definitely that punching ourselves in the face does not resolve any of these contradictions.”

One of the most interesting dynamics in the coming-out process for rich kids is rewriting some of the family mythology around how their wealth was earned in the first place. Many wealthy children are raised on very precious, and sometimes exaggerated, American Dream stories about the ways in which they came into wealth. These stories can mask the role of race and educational privilege, immigration status, exploitative practices (sweatshops, union busting), and other systemic factors that contribute to the process of wealth accumulation. Pittelman also writes, “Dealing with discrimination requires reclaiming individual identity. Understanding privilege, on the other hand, requires figuring out all the ways that we’re not unique individuals.”

Rich kids have to get sober about their family history, but also start to dissect their own lives in order to see the ways in which class privilege, not some special gift or mysterious divinity, has led to many of their opportunities. This is especially critical for privileged young people born in the eighties and nineties, many of whom were raised to believe they were rarified human beings destined for greatness, thanks to trends in affirmative parenting and self-esteem education run amuck. Many privileged children have actually been done a disservice by being pumped up on unrealistic expectations for their lives and shielded from the kinds of opportunities to fail and recover that create resilience.

Coming to terms with privilege is about not only rewriting family mythology but erasing family hubris. Many wealthy kids are raised to see their parents and other high earners or big inheritors as expert in a way the rest of the philistine world simply is not. In this worldview, it seems natural that rich people—who, again, deserve their excess wealth—are positioned to make the smartest decisions about how their donations might be spent to better humanity. The social justice philanthropy framework, in contrast, pushes privileged people to not only give away money, but also let go of a sense of superiority.

Tyrone has written the elements of this small but growing type of giving on the flip chart at the front of the room:

“Social justice philanthropy grew out of the sixties and seventies liberation and community self-determination movements,” Tyrone says in a patient, excited voice. “It’s about actually changing systems, rather than providing Band-Aids.”

One example that Tyrone often cites is a collaboration he engaged in with other RG-related young people, called Gulf South Allied Funders (GSAF). In the immediate aftermath of hurricanes Katrina and Rita, this small group of young people got together to brainstorm how they might leverage their own wealth, and the wealth of their networks, to get the people affected by the storms the resources they needed. They decided that they would give and raise one million dollars a year for three years to support grassroots rebuilding and social justice work in the Gulf Coast region—and rather than choosing whom to give the money to themselves, they would find a grant-making organization with strong ties in the region that could distribute the money to effective grassroots organizations.

Tyrone doesn’t have as much access to old money as many of the other young people in RG. He didn’t, however, use that as an excuse to avoid fund-raising from his extended network. “Despite the fact that my money hasn’t been passed down for generations, I went to private school. I went to summer camp. We don’t always admit that our socioeconomic circles include a lot of people with money, but if we’re coming from a place of class privilege, they often do.”

In March 2008, Tyrone brought his dad to New Orleans for a donor tour with the Twenty-first Century Foundation (the New York City–based black social justice foundation that GSAF partnered with). It was a moving experience for both of them. One night, after meeting with various grassroots leaders in rural Mississippi and Louisiana—mostly based in small local churches—Tyrone’s dad turned to him and said, “This funding model makes so much sense—as an outside donor, you can’t just look in the Yellow Pages under ‘powerful community leader’ and know who’s doing this work. The relationship building [that Twenty-first Century is doing] is really important.”

The next year, Tyrone returned to New Orleans for a month as a volunteer, working with grassroots groups like Safe Streets, Strong Communities, which is fighting police brutality and incarceration conditions in the New Orleans area—both huge problems post-Katrina. “What’s happening in New Orleans in the aftermath of the storms is a really brutal example of the type of systemic violence that happens everywhere because of capitalism and white supremacy,” Tyrone says. “Many of the people who have been doing the grassroots rebuilding work were fighting the same problems before Katrina. They’re the problems poor people and people of color face everywhere—lack of affordable housing, lack of quality education, police violence, incarceration, racial profiling…. People started paying a lot of attention to these things after Katrina, but they aren’t new.”

The project Tyrone worked on had all the elements of social justice philanthropy. Rather than handpicking organizations worthy of their charity, as so many donors do, even in regions and fields they know next to nothing about, the Gulf South Allied Funders recognized what they did know—organizing rich people to support social justice—and what they didn’t know—what folks in New Orleans needed and how they needed to get it. This approach requires humility and trust—two qualities rarely associated with the superrich.

AFTER THE WORKSHOP, Tyrone and I sit and catch up. His paternal grandmother has fallen sick, and Tyrone’s dad and his dad’s siblings had to relocate her to an assisted living home. The experience has shaken the whole family. “I think it tapped into some existential fear in my dad,” Tyrone tells me. “He was really dealing with how much money it cost for my grandmother to have round-the-clock care. It brought up a lot of stuff about money and security and his desire for me to be okay and to be taken care of.”

The experience prompted an intense conversation between Tyrone and his dad about the remaining money in his trust. Tyrone had planned on giving away his entire inheritance in a short period of time, and his dad had repeatedly urged him to reconsider. In previous conversations with his father, when Tyrone would talk about his projected giving plan, things sometimes devolved quickly. He says, “Eventually he would get scared and I would get indignant, and then he’d end up saying, ‘You’re young and idealistic.’ And I’d say, ‘You’re a pawn of capitalism.’ And the conversation would pretty much stop there.”

But this time was markedly different. “We had a really deep interaction,” Tyrone says. “For maybe the very first time, I really got that the money he’d set aside for me and my brother was so deeply based in love and wanting us to be taken care of. It doesn’t change the fact that I don’t believe in inheritance, but it’s important for me to respect and appreciate that gift he gave me. People like my dad are particularly positioned to accumulate wealth with the help of a lot of race, class, and gender privilege, but of course it’s also true that he worked really hard to support us. I’m trying to hold both pieces—the critique and the love.”

When Tyrone thinks about planning for his future, he imagines investing in justice and community rather than in a big retirement fund. He wants to help build a world in which all people are taken care of, no matter how much or how little money they have. “The future’s totally scary,” he says. “Social Security doesn’t take care of people, our resources are increasingly privatized, the U.S. is the only industrialized country without universal health care…. All you have to do is read an article about climate change to get totally freaked out about the future. But that’s the psychology of capitalism, right? Make everyone feel so insecure that we hoard all the resources we can and forget how to share or take care of each other. I’ve noticed that often, the more money people have, the more scared and alone they feel. Real safety requires interdependence; wealth so often takes that away from us.

“We talked about how money doesn’t make you safe, which, on one level, he agrees with. But on this other level, he just really needs me to hear him,” Tyrone says. They talked about the possibility of Tyrone slowing down the process of giving away his trust fund. “I finally asked him, ‘Dad, what are you going to be comfortable with?’”

Tyrone is compromising for now. He’ll still give away half of the $400,000 in his trust fund by 2010, but the rest he agreed to leave untouched for a while, pending further conversation with his dad. He still plans to give most of it away, but he’s willing to wait for a while and keep engaging his dad in the conversation. For him, it feels like maintaining a balance between his political ideals and the understanding that decisions like this are bound up in the complexity of human relationships and family.

“I think of giving money,” he once wrote, “as one small facet of my social justice work that reflects my broader commitment to wealth redistribution, anti-oppression, and grassroots organizing.” For now, he will continue his economic justice organizing and his food justice work with the Philly co-op. He gets excited about building bridges between radical philanthropists and the grassroots organizations that are leading liberation movements. He would like to continue to do workshops on radical giving and work toward creating an even more liberatory conception of social justice philanthropy. Tyrone would like to keep the WUO’s intention, as described by Bill Ayers—“to show that ‘the man’ is penetrable”—alive and kicking in the twenty-first century.

Meanwhile, he will continue to wrestle with his own nature—the passion that leads him to inspired action but can also tempt him to fall into polarized thinking. Ultimately, what is most impressive about Tyrone Boucher is not his willingness to part with his trust fund—unusual as it is. Nor is it his intelligence or his penchant for adventure. What is most impressive about Tyrone is his courage to consistently examine himself. On his blog he writes:

I’ve sometimes been encouraged by fellow organizers to take my political intensity down a notch because it can alienate people. It’s important for me to hear this, because it reminds me how important it is to meet people where they’re at, be compassionate and humble in my relationships with other radical or progressive folks who share my privilege, and work in my own communities to help build a strong multiracial, cross-class movement. I appreciate being challenged about this stuff, and it often serves as a much-needed check on my tendency towards stubborn indignation.

But this conversation touches on something that I ponder a lot, something about militancy and ideology and the balance between being gentle enough to be accessible and having a political critique that is strong and uncompromising.

Reading Tyrone’s words, I was reminded of Plato’s old edict: “The unexamined life is not worth living.” Suffering is hell. We must do everything we can to eradicate it. But in the meantime, we must also suffer the absolute terror of being honest about our own tendencies, our own gifts, our own limitations. We must see the ways in which we ourselves are the problem and—sometimes even more difficult—the ways in which everybody else, even the most unconscious of people, could be part of the solution.