Jackie Kruger: Black Milk. Fandom, Sharkies & Alternative Fashion

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From a kitchen table in Brisbane to a global online fashion movement — this is the story of Black Milk Clothing.

In this episode of What I Learned in Business (That Didn’t Kill Me!), host James H. Stewart sits down with Jackie Kruger, CEO of Black Milk Clothing, the cult Australian label known for its bold designs, product range diversity, and fiercely loyal community of Sharkies.

Jackie shares how she stepped into the CEO role following the tragic passing of founder James “jL” Lillis, and what it takes to balance creativity, commercial discipline, and community trust in a brand built on authenticity. Together, they unpack:

  • How Black Milk grew from James Lillis’s home sewing machine to an international e-commerce force

  • The emotional and operational realities of leading through grief and transition

  • How community and connection fuel long-term brand loyalty

  • The leadership, culture and resilience lessons that apply to founders, executives and team leaders alike

This conversation is a powerful look at creativity, courage, and the soul of a brand — and what it takes to carry that forward.

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