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In this episode, we sit down with Yossi Chayo, the founder and creator behind the iconic Bellissimo hat brand—one of the leading names in custom fedoras worn by thousands around the world.

From selling hats to global celebrities like Snoop Dogg and Floyd Mayweather Jr., to building a respected name in the fashion industry, Yossi’s story is anything but ordinary.

He opens up about his early struggles—being a high school dropout, getting kicked out of multiple schools, and working small hustle jobs like sushi shops just to get by. With raw honesty, he shares how he and his brother found their way into the hat business and turned a simple idea into a thriving brand.
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Brooklyn, NY 11234
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