In this episode, host Ashley Wick sits down with Kristy Caylor, who is on a mission to change the way we think about fashion and waste. The industry produces a staggering 100 billion garments a year, and 85% of that ends up in landfills. It’s a cycle that feels impossible to break—but Kristy is proving otherwise.

As the CEO of Trashie, a company making textile recycling easy and even fun, she’s tackling the problem head-on. Her journey started in industrial engineering before she found her way to fashion, leading projects like Gap’s Product RED and later co-founding Maiyet, one of the first ethical luxury brands. At Maiyet, Kristy poured her heart into proving that high fashion and conscious business could go hand in hand.

But after six years, Kristy faced an excruciating decision. Some of Maiyet’s inner workings didn’t align with her values, and she had to ask herself: Was she willing to stay and compromise, or would she walk away from the company she loved? She chose integrity, letting go without a clear next step. What followed was a period of uncertainty, but also a powerful reset.

In this conversation, Kristy shares the question that stumped her and ultimately reshaped her approach to leadership. She talks about failure, the role of intuition in big decisions, and how asking “What if?” has fueled her most innovative ideas. They also explore behavior change—why guilt and shame don’t work, and how Kristy is using joy and ease to shift the way people think about recycling their stuff.