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July 19, 2025 17 mins

Note: This is the second in a series of episodes of The Way Up, a new video series from Square highlighting the real stories of grit, vision, growth, and heart behind some of America’s most innovative local businesses.

She opened a custom hat shop in Nashville… while eight months pregnant.

In this episode of The Way Up, Guy Raz sits down with Alex Samuels, founder of Rustler Hat Co., to talk about how a disappointing shopping experience turned into a thriving business rooted in storytelling, craft, and community.

Alex shares how she went from real estate deals to designing custom hats, balancing motherhood, managing explosive growth, and creating unforgettable experiences, one hat at a time.

Video Links:

  • Watch the full series here
  • Check out the episode page here
  • Watch this episode on Youtube
  • Watch all episodes of The Way Up, including the bonus panel episode 'Behind the Business: How 5 Entrepreneurs Beat the Odds'.


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