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July 23, 2025 53 mins

In this episode, Tanya and Jessica talk about one of their favorite places for Black joy and peace, Martha's Vineyard with someone who calls it home year-round. While they’re not there yet, a summer visit is in the works, and they wanted to shine a light on the island through the lens of a dynamic local leader.

Meet India Rose: Entrepreneur, Massachusetts Real Estate Agent, and Social Justice Activist. She’s the founder of Sideline Brand, the creator of the Black Owned MV directory, and the powerhouse behind several ventures that celebrate culture, community, and connection.

Together, they dive into the beauty and complexity of year-round island life, the history and legacy of Black presence on the Vineyard, and India’s experience opening a storefront during the pandemic. From housing challenges to pop culture moments, Black Fashion Weekend to building community through entrepreneurship, this episode is packed with insight, heart, and inspiration.

Explore more of India Rose’s work:

 

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