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.

Chapters:

01:17 Meet Kristy Caylor: Fashion Industry Innovator
01:52 Kristy's Journey with Maiyet
13:19 The Decision to Leave Maiyet
16:48 Building a New Business with Integrity
25:02 The What-If Mindset and Consumer Behavior
32:27 Introducing Trashy: A Circular Economy Solution
36:41 Proposing Partnerships to Brands
37:49 Marketing and Storytelling in Sustainable Fashion
41:16 Building a Community and Measuring Impact
42:11 Staying Resilient Amidst Fast Fashion
44:58 The Journey of Shifting Business Models
51:05 Balancing Startup Demands and Family Life
54:03 Defining Success and Personal Values
55:26 Tools and Practices for Transformation

Links:

Tim Ferriss x Diana Chapman Podcast Episode

Diana Chapman’s Full Body Yes meditation

Ashley Links:

Finding The Current Within Retreat: https://peggymarkel.com/adventures/finding-the-current-within/

Ashley Wick Instagram: https://www.instagram.com/ashleywick

The Ingenius Life Workshop: https://www.ingenius.life

Take The Leap Course: https://www.taketheleapwomen.com/

Sign up for Ashley’s newsletter for free coaching reflections, tools and news: https://view.flodesk.com/pages/643399411150f24bd562b5f5

Podcast artwork by George Bangs. Photography by Cary Jobe

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