
Winner’s Circle
Winner’s Circle is a mobile show spotlighting thriving entrepreneurs, brands, and creatives who don’t always get the recognition they deserve. We go beyond the typical success stories — we interview the overlooked, the underdog, and the next big thing.
But we don’t just talk — we take action. Alongside our guests, we host community events that directly support youth and the unhoused, blending storytelling with real-world impact.
Our mission is simple: build a community where entrepreneurship meets purpose, and where rising together is the standard.
Winner’s Circle
The People of Boston
Winner’s Circle connects with Matthew from The People of Boston Podcast. Matthew is an entrepreneur and podcast host based in Boston. His podcast takes place on the streets of Boston, where they ask funny, interesting and thought provoking questions while aiming to highlight Bostonian's uniqueness, opinions, and stories first hand.
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Thanks for tuning in to the Winner’s Circle Podcast — the potluck of entrepreneurship.
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Your support helps fund:
• Podcast editing and production
• Community outreach for youth
• Care initiatives for the unhoused
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Inside, you’ll get early access, business tools, networking, and more.