I was born in Madison, but we moved around a lot. I went to 13 different schools before I entered high school. My father was an alcoholic for a number of years, and he used to beat me and my mom when he was drinking. My father came from Nicaragua, and my mother’s family was from Norway. Her family settled in Iron Mountain, Michigan, on a rural farm that was just on the border of Wisconsin.

Roberto Rivera | Madison, WI
“I’ve lived in places like La Crosse, Wisconsin, and I’ve lived in Colorado. I’ve lived in Miami. I’ve lived in California for a stretch, Texas for a long stretch. When I was a kid, people asked me, ‘Where you from?’ and I’d say, ‘Man, I’m from everywhere,’ and they’d laugh, but I was serious.
I’m from everywhere, and so I feel that all of that has prepared me for the work that I’m doing today, whether I’m in a rural space or a suburban space or an urban space, I feel at home, for the most part.
In second grade, when I went to Madison Public Schools, I was formally assessed and labeled as LD. I had to take a test with the therapist and everything, and the conclusion from that was that I was LD, learning disabled, and I didn’t really know what that meant. No one thought to ask if we were speaking different languages at home, and so they said, ‘Well, we did this assessment, and your language acquisition is a little bit delayed, and therefore, you’re learning disabled.’
To a kid, that just means that you’re dumb. You’re stupid. You’re delayed. I remember this was a very clear and kind of traumatizing experience. That label really stuck with me, and so even when I moved to Texas several years later, I always self-selected to be in the slowest and most remedial classes, and I never planned to go to college.
When you’re a kid and you feel like you don’t have a lot of value, there’s a lot of influence that someone can have on your life, if they see value in you. For me, this took the shape of some of the older kids in the neighborhood approaching me and saying, ‘Well, hey, you have some good people skills. You seem like a smart kid. Here’s some weed. Why don’t you start hustling for us?’
In middle school, when we lived in Texas, I started hustling and selling marijuana. I got caught by my mom when I was in eighth grade. I was selling a kid some weed, and she overheard the conversation and busted into my room, and she’s like, ‘What are you selling?’
She wanted to search my room, and I just left. I ran away. I stayed with a friend, and when I came back, my parents had already filled out a report with the police, so as soon as I got home, the police came and hauled me down to the police station. I remember being handcuffed. The whole neighborhood saw me driven away in the cop car. Another humiliating thing, but you know, I started kind of building this kind of reputation. I’m an outlaw. I’m a thug. I’m a rebel, right?
In that period of my life, my parents were, I think, scared to death. They just cracked down so hard, they didn’t allow me to see any friends and they sent me to rehab.
In rehab, I had to do an assessment to measure my grief and emotional distress. I remember a woman asking me, ‘Have you moved anywhere in the last year?’ ‘Yeah.’ ‘Have you lost anybody close?’ At that time, yeah. All the questions, almost everything was a ‘yes.’ Until then I hadn’t realized all of the stress that was in my life, or acknowledged how that might be affecting me. But the reality was that I was so overwhelmed, so depressed.
That would plant a seed in me, later on in life, to wanna be an educator that could be paying attention to the social and emotional realities of students.
We can’t give up on the kids who are labeled unreachable or at-risk. We have to help them to manage and be aware of the very real challenges that they are facing.”
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“A critical point in my life was when my brother, Gabriel, was born. My mom had him when she was 43, and he was born with Down syndrome. Later on, he was diagnosed with having autism, as well. He was born down in Texas, concurrent with me doing all this rebellious stuff in middle school.
This was also the point in time when my father finally got sober, after my mom threatened to leave and never come back. So my dad went to AA and went to church, and he stopped drinking, but he became this dry alcoholic, where he just was real grouchy, real mean, worked all the time. His alcoholism evolved into workaholism.
Not long after Gabriel was born, my father was starting to verbally abuse and physically threaten my mom again. And with him not being sensitive to the therapies that my brother would need, it just was the last straw. So my parents separated forever.
For a young boy trying to understand how to become a young man, not having your father there, not having that consistent support, it just makes that young person more susceptible to other forms of masculinity that, at that time, were very stereotypical, violent, and materialistic—what the media was portraying.
I moved back to Madison, Wisconsin when I was 18 years old and I went to a Catholic high school on a baseball scholarship, because the public schools didn’t want me back. I moved in with my grandparents, and brought a lot of emotional and physical baggage with me.
I was still angry and trying to find my way, but my grandfather had this huge impact in my life. No matter what school I was getting kicked out of, no matter what label was being slapped on me, he would always treat me as if I was gonna be somebody one day. I stayed sober for most, if not all, of those years, because I wanted to prove to my grandfather that he was right. I started selling weed again, but I wasn’t using it.
I never really understood what my grandfather saw in me. When I looked in the mirror I just saw pain and failure. But I realized later he had a Michelangelo vision, in that he didn’t just see the stone. He could see the sculpture in the stone, and I wouldn’t understand what he saw until my grandfather had a sudden heart attack and passed.
I remember going to his funeral not knowing if this would to lead me into falling down an abyss of despair or if there would be some redemption from it. I remember being in the audience and hearing my grandfather’s story for the first time.
The whole sanctuary was packed, and I realized that my grandfather had lived this second life of doing good deeds, of volunteering at different not-for-profits, of helping others. I also learned more about what it was like for him growing up.
On his family’s farm in Iron Mountain, education was not really an option. Neither of his parents and none of his siblings went to school beyond primary school. When he started sharing that he had a dream of going to college, folks in his community made fun of him. ‘Hey, you ain’t going to college. Why don’t you go work in the mines, or go do some work on the farm? You need to work harder.’
I inherited a journal that he had written in as a teen where he said, ‘I can't share my dreams with anybody, so I'm just gonna write my dream down in here.’ He kept that dream of getting an education incubated, and eventually saved up enough money to leave the farm to confront his destiny.
He got into school at UW-Madison and had to work two or three jobs, concurrently, while he was studying and selling cigarettes on the side, just hustling. It’s in the blood. He ended up graduating and eventually going to grad school, and he got a job, and it was more than a job—it was a career, a calling. He became a lawyer and eventually became a partner of a law firm.
He sent money back to his brothers and sisters, so they could attend college. I found out he had even given small, partial scholarships to kids who were the grandchildren of the people from his same community that made fun of him for wanting to get an education.
I realized that my grandfather also came from some pain and feeling boxed-in, and people seeing the stone instead of the sculpture, but he was able to channel that pain into fuel to keep going after his dreams and living and leaving a positive legacy.
At that moment, I realized that it wasn’t that my grandfather didn’t see the pain in my life. He did, but he knew that I could convert the pain into propane, and that I could do something special with it.
At the funeral that day, I decided I was never gonna sell drugs again. I wanted to continue the positive legacy of my grandfather. Following that, a friend of mine says, ‘Hey, man, you’re a hustler. Why don’t you hustle something legitimate?’ I thought, ‘Okay, well that’s a good idea. Huh. No one’s ever challenged me like that.’”

“After my grandfather’s funeral, I made a promise to myself to never sell drugs again. I was ready to ‘hustle something legitimate.’ I realized that I knew a bunch of great artists, visual artists, and I knew someone who made clothing and printed up clothing. I put it all together, and I designed my own urban line of clothing. I wanted this company to have a meaning behind it. I want it to be a positive cultural movement.
Hip-hop culture that started in the early ’70s is really about building community, about creating a common ground between different folks from different backgrounds and cultures. It was about giving folks a voice who felt voiceless. It was about taking what little resources you had and utilizing them to the utmost, and writing a new narrative for yourself and for your community.
When I began to start getting into the real history of hip-hop, I said, ‘Man. We don’t see enough of what real hip hop is,’ so that’s what my company’s gonna be, and I’m gonna call it Good Life.
I remember the first night at a hip-hop show, I had all the shirts there, and I wasn’t selling any, but the DJ had my shirt on, and midway through the night, he said, ‘Man, you all need to check out my man Roberto with the Good Life, representing that real hip-hop. Pick up a shirt before you leave here.’
After that announcement, people came up and I sold every single shirt. So here I was with cash in my pocket, and I realized that I didn’t have to worry about the police pulling me over or about going to jail. It was a good feeling, I liked not having that stress anymore.
One night I went to a concert and was networking with folks and selling some shirts and hoodies. I met a guy named Arthur Richardson, who was the director of the Lussier Loft Teen Center in Madison. We connected, and he said, ‘Man, I got a lot of kids who are trying to learn about hip-hop at the center, but there’s really no one to guide them. What if you could come through and just check it out?’
When I went to the teen center, it felt like a scene out of a movie. There was big, beautiful aerosol art on the wall. There were kids who were dancing in one corner. There’s music playing. Kids who were doing impromptu rhythm and poetry, also known as rap.
I started connecting with the kids, and they were very talented and had a lot of dreams, but they were lacking the support, so I said, ‘Well, I have this line of clothing. I have people that I’ve sponsored, who are the best at dancing and music and rhythm poetry and art. I’m gonna have them come down, and we’re gonna start doing workshops with you guys.’
That’s how it all started, the workshops evolved into doing concerts, evolved into doing festivals, evolved into full-blown, hip-hop theatrical productions. I was just out of high school when I started working at the teen center with Arthur. I was hired on full-time from there, and we just kept elevating the work. We were on the front page of local papers, we were getting noticed at the national level. One of the hip-hop plays that I co-wrote was even selected to be performed at the Kennedy Center in Washington, DC.
This work at the teen center was having what I would call ‘reciprocally transformative impact,’ in that some of the kids who were doing negative stuff in the community were starting to be more positive and more open to education and learning, but it also was transformative for us, who were the mentors and leaders, particularly myself.
Just as we were getting attention for our work with teens, the center was forced to close due to an incoming arts center that bought out the space. It was a really difficult time, as we tried to figure out how to move forward for ourselves and for the students.
I began to think about my grandfather and his passion for education, and he had encouraged me to not give up on college. I had been taking classes at the local community college. I was getting all A’s in school and winning community service awards, and I thought, ‘Man. I wish I would have known education could be this meaningful and transformative earlier.’
Eventually, with the help of many hands, the teen center found a new and permanent home at the Goodman Center over on the East Side of Madison.
Seeing the need for spaces like the teen center, the struggle we went through to keep the doors open, and the change it made in people’s lives put me in a different mindset. I decided to transfer to UW-Madison to continue my education so I could do even more. I thought, ‘Okay, I’m not here to be schooled. I’m here to get an education. I’m here to be empowered to better serve my community.’”

“I was coming to UW-Madison as a junior, so I had to declare a major. I’m trying to figure out what that’s gonna be, but I couldn’t decide. I love theater. I love Communication Arts. I love African-American Studies, Latin-American Studies, Community Development. I was looking through the course book and I saw a little paragraph in the middle of the book that talked about an individualized major, and I thought, ‘This is it!’
But then I found out that in order to make my own major, I had to get a faculty advisor to support me, and I needed to find a similar major at other major universities and look at all their breadth and depth requirements. Then I needed to develop a proposal and defend the proposal in front of a board of professors and deans. My advisor told me, ‘Look. I’ve been a counselor here for over 20 years, and I can count on one hand the number of students who’ve been successful at creating their own major.’
I took some time to just go pray and meditate and do some soul-searching. What I felt like the Creator was prompting me to do was to lean into the dream.
After a long battle, I got my major approved, but they said that I would need to take more advanced courses with people getting their Masters and PhDs. I’m a kid who was told he was LD, so I have this tape playing in my mind, and I’m thinking, ‘Okay. I’m not smart enough to do this. Who do I think I am?’
Then I had another tape play of my grandfather, saying, ‘This is your opportunity. Take it.’ And I’m thinking about the kids that I mentored saying, ‘Big bro, this is it. Don’t back down.’ I was able to reject the fear I had in my heart about not being smart enough, and I looked at the board and said, ‘Look. If this is the only way you’ll accept my major, I will accept your terms, and let’s do it.’
So I had to work my tail off. It was interesting, though. I’d have a course on community development, and right after, would have a course on directing theater plays, and I started seeing the connections between the two, and started writing papers where I would talk about how policymakers are like playwrights, trying to get the normal citizens to be actors in their plays.
I started using these metaphors in my Community Development class, and my professors were giving me A pluses and writing me notes like, ‘This is the most amazing paper in the class,’ and doing independent studies and connecting things to the community. I ended up graduating with Honors, with my major entitled Social Change, Youth Culture, and the Arts.
About a year after that, the university called me up, and they said, ‘Actually, we think your major was a good idea. Can we hire you to be a consultant? We think that other kids could benefit from the sort of coursework and ideas that you have. We wanna start a learning community, where kids who are into spoken-word poetry and hip-hop can do stuff in the community.’
So I ended up becoming a consultant for a program called First Wave, which is the first spoken-word and hip-hop learning community in any major university in the nation. Now, they’re in their tenth year of recruiting spoken-word poets and hip-hop artists from around the world and giving them this foundation to become great artists and change-makers.
In addition to the consulting work I was doing for the university, my full-time job was a ‘legitimate hustle,’ doing sales and marketing in the health club industry, which was a job offer that came out of an internship I’d had in school. I was able to make enough money to buy a house. My parents never owned a home. I got married and went on a trip around the world with my wife.
I thought I was living the good life, but then my little brother Gabriel got diagnosed with leukemia.”

“I was always really close to my little brother, Gabriel. We called him Gabe. He was born with Down syndrome and later diagnosed with autism, as well. Then, when he was only eight years old, he was diagnosed with leukemia.
We used to, every week, do a brother’s day together. We’d go and do stuff at the pool or go to Chuck E. Cheese or just hang out. When Gabe got sick, we started doing brother day in the hospital. He’s connected to this mechanical octopus, and a lot of his hair is falling out, and he’s puffy ’cause of all the chemo and stuff, but he’s got this ginormous smile in the midst of all that.
On February 26, 2005, my brother died in my arms. It was the biggest loss I’ve ever had. Beyond just being a big brother, my father was completely out of the picture, so I was like a father figure for him. I felt like I had lost a child. It was such a reality check for me because I realized that not only did I lose my little brother and a good friend, but I was losing this identity of being a big brother, which I had a lot of pride in being.
I’m grieving and going through what I would call a hurricane in my life. The only way I knew how to deal with the grief that society had taught me, that my own experience and my own history had taught me, is I needed to check out. So I felt this temptation to wanna party and drink and smoke, but I had also been growing spiritually, and I felt, okay, I came too far to go back to that.
I was part of a men's group at church, and I told the guys, ‘I need you to call me every day to check in on me because I'm just uncertain of what I might do.’ And they were really there for me. These guys called me every day, and held me accountable.
In May, I went to visit Gabe’s grave. When I got there, it felt like the earth was shaking. It felt like I was shaking, and if someone was walking by, they would have thought I was a madman, ’cause I was moaning and crying, and truly grieving my brother’s death.
After this experience at the cemetery, I started asking God, ‘My God, I know I’m not promised to be 85 years old, that I could be gone in six months. If I were to die in six months, am I doing what you want me to do? Am I walking in my purpose?’ And the answer that I got back from the Creator was, ‘Nope,’ and I was like, ‘Whoa,’ and I started soul-searching. Okay, when did I feel like I was walking in purpose? And that’s when I was doing all the stuff in the community. It’s when I was working with youth and doing hip-hop.
At this point in time, my wife Jennifer is a graduate student getting her MPA, Masters in Public Affairs. She’s taking a course in the business school on social entrepreneurship. As part of her class, she had to write a business plan, but she’s struck with grief as well. She was very close to my brother. She says, ‘You know, I think I’m gonna have to drop this class, ’cause I have no idea what I’m gonna even write,’ and I said, ‘Well, you know what? I have some ideas, maybe we can work on something together.’
I said, What if we could use hip-hop as a tool to engage young people and to begin to transform their experience with education?’ So we put a business plan together.
I remember going to Gabe’s funeral, and it was just kind of a blur, but I do remember a business guy who had a business that worked with kids with special needs, said, ‘You know, I have a few businesses. I hear you have a passion in education. At some point, we should connect.’ So I took his card. I’m like, ‘All right. Great. Whatever.’
Eventually, I call his secretary and she asks if I can come in to meet with him on April 12th. Well, she doesn’t know it, but I know it: April 12th is my brother Gabe’s birthday. His first birthday he’s not alive. I go to his office April 12th. Spring day. Big office. He’s like, ‘Well, tell me what’s on your heart,’ and I started sharing my heart.
I said, ‘Well, I think kids that are told that they’re LD and ‘at-risk’, actually I think they learn differently, and if we re-framed it, they could be ‘at-promise.’ I think if we can engage them in a way that’s holistic and culturally relevant and then can show them that education can be tied to empowerment and community change, we can engage all these kids, and I have an idea for a hip-hop based curriculum.’
He started to light up and he said, ‘Well, this is all interesting. Do you have anything written down?’ I reached into my bag and pulled out the 67-page business plan that my wife and I wrote and handed it to him. He put on his reading glasses, and for 20 minutes, didn’t say a word to me.
Then he put down his glasses and put down the plan. He said, ‘You know what? I’m gonna help you start this business, and we’re gonna do this to honor your brother.’”
“30 days after pitching my business, I had an office. I had a full staff, and I realized that my purpose was to be a big brother to a generation. Everything that we created was not just trying to help kids do something that was good, but to help kids do something great and profound and deeply meaningful.
We piloted the curriculum in Madison. There was one school in particular that was getting a lot of negative press. Police being called every day, kids were being caught smoking weed at the school, there was gang recruitment.
We brought the idea of doing an innovative hip-hop curriculum to the school’s superintendent and he said, ‘Well, we’ve tried everything under the sun. Might as well try this hip-hoppity stuff.’
They connect us with these four classes that are creating 90% of the issues, and we decide that they’ve already had too many things trying to fix them. We wanna come in in a different light, so we did an all school assembly, Rock the Hip Hop show, but also I shared a little bit of my testimony and story. We said, ‘We’re looking for a few good young men and women to be a part of this leadership program,’ and all the kids signed up, the whole school.
Then we went to the four classes that were the most underperforming. We said, ‘We choose you guys. We think that you have a lot of influence and that you can use the influence for good. You have passion and sparks that have been overlooked. We’re gonna help you find those. You have a voice that needs to be heard. We’re gonna help you tell your story and write a new narrative for the school.’
They could not believe that we chose them. They truly were in shock that they had been invited to step into a leadership role with us. We worked with these students over the course of ten weeks to think critically about their role in the community through the lens of hip-hop and embrace their different types of intelligences. Their project was to lead a school-wide talent show, and to MC the event. We opened it up to the community. The students performed poems and raps and dances and monologues, created a platform for their peers. They got standing ovations for that, and the data showed that students’ GPAs in all four classes we worked with went up half a percentile point, so 0.5 on a 4.0 GPA scale. The kids who were the most disengaged, their GPAs went up a full point, and attendance improved. Behavior issues in the school went down.
The superintendent held a town hall meeting where the kids could share their testimonials. One student said, ‘Hey, man, I used to smoke weed every day. I don’t do that anymore.’ Another was like, ‘Hey. I was gonna join a gang, but now I realize I have a dream. I wanna be a music engineer, and so I’m gonna do well in school so I can follow my dream.’ We started to expand to other schools in the district. But then just as we were getting things off the ground, the superintendent, chief of staff, and lead grant writer for the district all retired in the same year. Our plans to scale in Madison fell flat.
During this time, the learning community that I helped to design, First Wave, was starting to launch at UW-Madison, and Madison is my whole world. But my wife got offered her dream job in Chicago. She had supported my dreams all along, and I realized that the most important thing that I could do is support hers. So we moved to Chicago. The move created a strain with my business partner and on our business. It was hard to manage the business remotely. It was a very difficult time, and in the end we parted ways.
But I continued on. I started a new business, wrote curriculum, would speak at education conferences and do community engagement work across the country.
For me, I’m so tied to this idea that we can’t give up on these kids who are deemed unreachable, who are deemed at-risk. I believe that they can become scholars and innovators and folks who could even give birth to a new industry. I often tell our students, I was just an average kid. If I could do it, then YOU can definitely do it. I believe in them as my grandfather believed in me. I don’t see a stone, I see Michelangelo sculptures inside the stone. That belief in kids motivates me to do this work every single day.”

“I had success developing a program in LA and then returned to do some community engagement in Chicago, where I was running my curriculum in a pretty selective school…selective because the students had to be kicked out of two other schools before they could get in. It was fall, the school year had just started, and I was just doing everything I could think of to get the kids engaged but it was really difficult. Then Christmas break happened, and then I came back, and the kids were like, ‘Wait. You came back?’ After that, they were all engaged, because they could trust that I wasn’t going anywhere.
They ended up doing an event for their class project. They got a major radio station to cover it. They said, ‘We’re gonna rebrand our community. Lawndale has been known as being the most violent, negative spot. There’s a lot of beauty here. There’s a lot of talent here, and we wanna put that on display for the whole city to see.’
One of our superstars from that program, David, got a scholarship to go to college wherever he wanted. He had a 4.0 GPA, hundreds of hours of community service, Chicago Boys and Girls Club, Student of the Year. When he graduated from high school I took him to have dinner downtown at a nice Italian spot with good steaks. He had never been downtown to have a meal before, ’cause he was living in the bubble, being in the ‘hood.
He told me he wanted to go to an Ivy League school out east, but he was nervous about it as a person of color, being in the minority for the first time in his life.
I shared a quote with him that I learned along the way. I said, ‘Well, all right. You feel a little nervous? That’s good. Man, that is just an opportunity to be courageous. Courage is not the absence of fear, but action in the face of fear,’ so I said, ‘Go be courageous, man!’ And he did.
He not only punched the clown of fear…you know, those little punch clowns that you blow up and knock them? He hit it so hard, it didn’t even wanna come back up. He ended up graduating from this Ivy League School, going abroad, studying in Spain and Morocco, and his action in the face of fear…it impacted me.
I looked at what David did, and I realized that I had some areas of fear in my own life. At that point in time, I had graduated with my Masters in Education. I had a 4.0, but I thought only in my craziest dream would I ever go on to get a PhD. I did always think about it, but I felt too afraid to go after it. I decided I owed it to David, and I owed it to myself to at least take the GRE.
If I was going to get my PhD, I was going to need financial help. I found a way to get full tuition and a stipend for living expenses.
I got the fellowship, and I’m currently wrapping up my PhD at the University of Illinois Chicago in Educational Psychology. I’m really excited and passionate about the idea of engaging youth in a holistic and a culturally relevant way, particularly those youth who are deemed unreachable. Particularly youth who have gone through a lot of hardship, heartbreak, grief, and trauma.
I think part of what I’ve been excited about is this whole idea of ‘post-traumatic growth.’ We’ve heard a lot about post-traumatic stress disorder. It’s this idea that you’ve gone through a trauma, and you’re sort of inhibited from your well-being, from being able to thrive.
Resiliency is the ability to recoup and to bounce back to baseline. Post-traumatic growth is the phenomenon by which people grow from the pain and trauma they have experienced, and end up with an enhanced sense of empowerment, a clarity of purpose, and more intimate and close relationships with those around them.
For me, post-traumatic growth becomes a lens that I can use to work with youth, who, from the inner city of Chicago, had 48 people get shot this past July 4th weekend. They’re living in this war zone. Typically, the literature about post-traumatic growth is tied to people in war in Afghanistan and Iraq and everything else, but it’s right here, too.
With young people engaged in this way, we’ve seen young people go from attending school 50% of the time to 96% of the time. We’ve seen these students go on and become community leaders. They’re engaged as being these agents of change in solutions instead of the problem.
What it does is it allows us to reach these young people, not as these objects that need to be changed, but to engage them as agents of change themselves. If the trauma and the pain can be converted into propane, then they can be empowered to provide solutions to different problems going on in their schools and their communities and in the nation.
My dream now is to transform public education in my lifetime. I sold my business on March 1st, 2017, and now I’m an executive with the company, an equity partner, and I’m digitizing the curriculum. Now we’re moving towards reaching millions of kids.
I had someone like my grandfather who had Michelangelo vision, seeing the sculpture inside the stone, and believed that pain could become propane. I see that for these students, and I want to let them know they should never give up.”
-Roberto Rivera | Madison, WI