Episode Details

You don’t need permission to build what you’re here to build…

You need the courage to trust yourself.

In this episode of She Wears the Pants, Ashley Deland is joined by Alli Webb, New York Times bestselling author, beauty industry pioneer, Shark Tank guest and the founder who turned one simple idea, blowouts only, into Drybar, a category-defining brand. Together, they unpack what it really takes for a high-growth woman to build something iconic, lead at scale, and evolve without losing herself in the process.

This conversation goes beyond the highlights. Alli shares why she doesn’t operate from fear, what she had to change about her leadership as the company grew, and what it looks like to release a business when the startup season ends, especially as life gets heavy behind the scenes.

If you’re a woman building in real time, balancing ambition, identity, leadership, and the emotional cost of growth, this episode will help you refine your inner compass, strengthen your standards, and lead with more self-trust than noise.

In this episode, you’ll learn how to:

• Trust your instinct as your most reliable leadership tool, and move without needing permission
• Lead people with clarity and steadiness as your company scales
• Recognize when a season has ended, and exit with integrity rather than guilt
• Separate your identity from outcomes so success never becomes your only source of safety
• Build what’s next from self-knowledge, not external expectation

By the end, you’ll walk away with a clearer understanding of the woman you’re becoming, and the internal leadership required to build what lasts.

Meet Alli

Alli Webb is a serial entrepreneur, New York Times bestselling author, Shark Tank guest judge, and beauty industry pioneer. She is the founder of Drybar and the creator of Messy, a haircare line designed to support healthy, lived-in texture and a more freeing relationship with beauty.

Website: itsmessy.com

Instagram: @alliwebb

Continue the Work with Ashley

Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power.

→ https://ashleydeland.com/inquire

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→ https://ashleydeland.com/inquire

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→ https://www.instagram.com/ashleydeland/

She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.