Podcast #5: Reflect Yourself with Jay Z & Tracy Chapman

Podcast #5: Reflect Yourself with Jay Z & Tracy Chapman

“Songwriting is a very mysterious process. It feels like creating something from nothing. It’s something I don’t feel like I really control.”
- Tracy Chapman, songwriter


Tracy Chapman was born in Cleveland, Ohio. Deserted by her father, she and her sister were raised by her mother, Hazel. She was a quiet child and liked to be by herself. It was her mother who recognized her love of music and cultivated it from a young age. At the age of eight the future songwriter became captivated by a country music television show, which led her to ask her mother for a guitar. The instrument harmonized with her soul. Quickly developing her strumming and composition skills, Chapman has been writing her own songs on guitar ever since, expressing herself through lyrics and chords. She grew up in a rough neighborhood. “At times,” Chapman remembers, “it was a terrifying place to be.” When she was thirteen, her Ohio school system began integrating black and white students. One day, she was attacked, beaten, and almost killed by a group of white students. As she recalls: “They shouted racial slurs at me. I responded to them and they got really pissed off. They turned around and started beating me up. One guy in particular. It was snowing and he knocked my books to the ground.” It would get worse. After her own friends had taken off, terrified, Chapman’s main assailant reached into his boot and pulled out a gun. “He told me to run,” Chapman recalls, “otherwise he was going to shoot me. I don’t know why he didn’t.” Deeply traumatized by the incident, she would later recount that painful day in her music. The event gave her a determination to escape her surroundings. She pursued a scholarship to a Connecticut boarding school, and secured it. Looking back at this critical juncture early in her journey, Tracy Chapman said the move saved her life.

After relocating east, her love for music continued to grow. Following her graduation from the boarding school, she attended Boston’s Tufts University and developed a strong local following for her solo shows. Eventually, fellow Tufts student Brian Koppelman, future screenwriter of films and TV shows such as Rounders, Ocean’s Eleven, and Billions, discovered Chapman. It was 1987. The son of a man in the music business, Koppelman was “helping organize a boycott protest against apartheid at school, and someone told me there was this great protest singer I should get to play at the rally.” He went to see Chapman perform at a coffeehouse. From that moment on, their lives would never be the same. “Tracy walked onstage, and it was like an epiphany,” Koppelman remembers. “Her presence, her voice, her songs, her sincerity—it all came across. It was immediately clear to me that she was among the most gifted people walking the earth.”

Koppelman connected with the songwriter after her show and told her, “I have been managing bands since I was thirteen, and producing demos, and working in record companies every summer. And I really have worked to be my own person, but you’re so extraordinary. I think my dad can help you, and we should find a way to do something together.” Chapman responded by saying she would play the rally but wasn’t really interested in anything else. She performed at the protest, and when Koppelman heard her, he realized she was even better than he’d thought the night before. He was intoxicated by the honesty of her songwriting—every time she performed people would leave in tears, moved by the music’s beauty and emotion.

Koppelman continued attending Chapman’s shows wherever she went, finding himself in coffeehouses, lesbian bars, anywhere and everywhere she performed. Chapman kept talking with him, but declined to cut any demos. So Koppelman hatched a plan; he found out that Chapman had recorded some demos at the university radio station for copyright purposes, so he snuck into the broadcast booth and, while his friend distracted the DJ, grabbed a demo and copied it onto a cassette. It contained only one song—“Talkin’ Bout a Revolution.” Koppelman sent the tape to his dad, co-owner of a large music publishing company, and the older Koppelman immediately flew up to Boston to see Chapman perform. In short order, he signed her to a contract.


Every record label took a pass on Tracy Chapman except one: Elektra Records. They signed her, but had little expectation that her music and image could make her a commercial success. The signing itself surprised Chapman. “I have to say that I never thought I would get a contract with a major record label,” she remarked back in 1988. “I didn’t think [record] people would find the kind of music that I did marketable. Especially when I was singing songs like ‘Talkin’ Bout a Revolution’ during the eighties…. I didn’t see a place for me there.” Most of the industry agreed with her assessment. Even once Chapman was signed, more than a dozen producers declined to work on her album.

Eventually producer David Kershenbaum accepted the project. Chapman’s greatest concern was that the integrity of her songs remain intact. “She said right off the bat that she wanted the record to be real simple,” says Kershenbaum. “I wanted to make sure that she was in front, vocally and thematically, and that everything was built around her.” Every song on the eventual album, with the exception of “Fast Car,” was on the original, full-sized demo. Chapman played “Fast Car” during her first meeting with Kershenbaum, and he loved it the minute he heard it, later saying, “It was the most heartfelt song on the album.”

The album took eight weeks to record. When they played it for the executives at Elektra, everyone in the room said they loved it. Everyone also thought it wouldn’t sell more than 50,000 copies. They couldn’t have been more wrong. Tracy Chapman was released on April 15, 1988, and went on to sell thirteen million copies. It’s ranked No. 10 on Rolling Stone’s one hundred best albums of the eighties, and that year Chapman won the Grammy for Best New Artist and Best Female Pop Vocal Performance, among countless other accolades.

The beauty, quality, and deeply personal nature of Chapman’s music, which had clearly resonated with so many early listeners in Boston, did so in exactly the same way with a large national audience. While she didn’t fit into any clear category, the fact that she was different and had manifested a deeply personal message resonated powerfully with the world. Chapman was recently asked what advice she might have given herself when she was starting out, and she responded, “It really is okay to be yourself…. If you are living a life that feels right to you, if you’re willing to take creative chances or a creative path that feels like it’s mostly in keeping with your sensibilities, you know, aesthetic and artistic, then that’s what matters.”

Reflect Yourself

Tracy Chapman’s music is a reflection of her life experiences, her purpose. Ian Schrager’s hotels are a reflection of his life experiences, his purpose. And Supreme’s hats and skate decks are a reflection of James Jebbia’s dreams and desires. Each of them took their own experiences—the ups, the downs, the good and the bad—and turned them into something sharable, a real-world reflection of themselves. And because it combined their purpose with their singular talent, it flourished.


Jay-Z tells a similar story when describing the journey he took to share his purpose:

My first album [was] called Reasonable Doubt…. It didn’t sell massive numbers worldwide. It was still very niche. In my second album [I] tried to make [something that was] bigger and would be more popular, which was a failure. Going for that success really messed up that project and set a bad tone. It was a huge learning lesson for me—that if I was going to be successful I had to be successful at myself…. I had to do what I believed in and what felt real to me and felt true to me. Because the worst thing to be is to be successful as someone else.

Jay-Z went on to say:

I feel sorry for someone who has to walk out the house every day as someone else to make this art and to make something that people connect to. And whatever you have made is not you, you’re not happy about it, but it’s successful. Just to maintain that level of success has to be very draining and you know a very sad existence because at some point you have to go home. And when you go home all the lights are off and everything is off and you have to look in the mirror and look at yourself and say I like who I am or I am not very happy with who I am. By my third album I had the combination of failing with those pop records and the true and real music I wanted to make. And I blended those two together to make a song called “Hard Knock Life.” And that album is when I knew I could do it.

Just like Tracy Chapman, Jay-Z eventually reflected himself in his music. And it worked, both personally and in terms of listener response. As for Chapman’s amazing journey, it’s worth underscoring again what it illustrates.

Whether it was the kids in Cleveland or record executives in New York, she never allowed them to convince her to be something she wasn’t. That fierce commitment to her true self and vision made the music deeply resonate with her audience. She didn’t go out and say, I want to be a star; I want sell a million albums, and make money. Her aim was to make music that meant something to her, that represented her life experience, and this authentic spirit eventually spoke to millions. In the process, she fulfilled both her internal need to create, and her external need to support her art by selling records.

This core idea of reflecting oneself also applies to the audience. People choose products, services, and, ultimately, brands because they see a reflection of who they are or who they want to be in them. We encountered this with Supreme. Yes, it reflected James Jebbia and the original skaters who worked in his store. But it just so happened there were numerous people with similar values and aspirations who grew up enjoying street style and skate culture. And they chose Supreme because they saw parts of who they were or who they wanted to be in the brand, what it stood for, and how it felt. The more people identify with that energy, the more the energy expands. When a product is a pure reflection of a founder’s core values and the customer feels that energy, they’re attracted to that product.


We’re tribal beings. We build our identities through the people and communities we choose to associate with. There’s no difference between an ancient tribe tattooing its members with unique symbols and a young person wearing a Supreme T-shirt to associate with the tribes of street style and skate culture. It all comes from the same place, and it’s critical that we recognize this behavior so we can apply it to the sharing of our own creations.

Your highest calling is to manifest a reflection of what makes you special. And then share that reflection, be it a product, a service, a brand, or a work of art, with people who aspire to similar wants, needs, and desires. You reflect yourself in your creations, and they reflect themselves in their consumption and self-expression. The combination leaves both sides fulfilled. In a world where human creativity is the last remaining sustainable, competitive advantage and the principle driver of value creation, your most potent weapon is you. Or, as Oprah explains, “There is no greater gift you can give or receive than to honor your calling. It’s why you were born. And how you become most truly alive.”


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