Unmasking the Toxicity of Racism: A Raw Conversation with The Contraband Wagon

In this episode of “Everyday Conversations on Race for Everyday People,” Simma Lieberman welcomes her guest Will Upland (also known as Contraband). He is the creator of the show on Twitch, The Contraband Wagon. Listen to this enlightening, personal and often humorous discussion of race, racism and disruptive conversations.

Will (aka Contraband) recounts times in his young life when he encountered people who tried to discourage his success, and were angry that he, the only young Black man in his class stood above everyone else for his talents and brilliance.

After feeling frustrated with the discussions on race in mainstream media Will decided to start his own show. Simma and  Will (aka Contraband) discuss their shared mission of disrupting the way people talk about race and how to bring people together across racial lines.

Will shares a powerful story from his childhood that made him conscious of stereotypes and internalized racism.

At the age of six, he had a conversation with another Black boy who believed that acting “Black” meant being disrespectful, getting bad grades, and being part of a gang. This experience opened his eyes to the impact of racial stereotypes and the struggles that come with them. Listen to this episode to find out what happened when he ran into that same “kid” 25 years later.

Both Simma and Will emphasize the importance of self-esteem and a strong sense of identity in navigating experiences of racism. You’ll hear examples from “The Contraband Wagon,” about other Black people with different perspectives on race. You’ll also hear stories of how several white people  became conscious of race and racism after being in denial.

Throughout the episode, Simma and Will highlight the need for open and honest conversations about race. They discuss the role of education and awareness in reducing the toxicity of our racial environment. They also emphasize the importance of empathy and understanding, using examples from their personal lives that encourage listeners to approach conversations about race with an open heart and an open mind.

To take action and engage in conversations about race, Simma The Inclusionist and  Contraband suggest the following:
Educate yourself: Take the time to learn about the history of racism, systemic oppression, and the experiences of marginalized communities. Read books, listen to podcasts, and engage with diverse perspectives.

Engage in dialogue: Seek out opportunities to have conversations about race with people from different backgrounds. Listen actively, ask questions, and be open to learning from others’ experiences.

Challenge your own biases: Reflect on your own beliefs and biases. Be willing to confront and unlearn any prejudices you may hold. Engage in self-reflection and actively work towards being anti-racist.

Join Simma The Inclusionist and Will Upland  (aka Contraband) on their mission to change the conversation on race and create a more inclusive and understanding society. Tune in to The Contraband Wagon on Twitch and engage in their monthly private racism discussion group and book club. Remember, every conversation counts in the fight against racism.


Guest Bio

Will Upland, also known as Contraband, is a community college professor and the creator of The Contraband Wagon, where he is changing the conversation on race. After years of frustration watching the conversations on race in media without seeing the kind of dialogue he finds valuable, Contraband decided to create his own platform. He has had over 100 live 2-hour conversations on race and continues to have them regularly on his Twitch channel. He also hosts a monthly private racism discussion group, a book club, and live events that inspire discussion on the subject of race. Contraband hopes to increase knowledge on and awareness of race to reduce the toxicity of our racial environment

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Host Bio

Simma Lieberman, The Inclusionist helps leaders create inclusive cultures. She is a consultant, speaker and facilitator. Simma is the creator and host of the podcast, “Everyday Conversations on Race for Everyday People.”

Contact Simma@SimmaLieberman.com to get more information, book her for your next DEIB  event, help you become a more inclusive leader, or facilitate dialogues across differences.

Go to www.simmalieberman.com and www.raceconvo.com for more information

Simma is a member of and inspired by the global organization IAC (Inclusion Allies Coalition) 


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Previous Episodes

Confronting the Lack of Diversity in Nonprofit Leadership

“From Apartheid to Forgiveness” a Conversation on Race

Race, Sentencing, and the Criminal Justice System: A Shocking Inside Perspective A Conversation on Race with Sean Wilson, Organizing Director of Dream.Org

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