Alli Webb on Building and Selling Drybar for $225M, Founder Evolution, and Building a Second Business

On today’s episode, I’m joined by Alli Webb for an honest, behind-the-scenes conversation about building Drybar from a single storefront into a $255M brand — and what it really takes to evolve as a founder. We break down how Alli identified a white space in the beauty industry, scaled a service-based business at lightning speed, expanded into product, and ultimately made the decision to raise private equity and bring in a CEO. She shares candid insights on fundraising, delegation, leadership growth, and the hard lessons that come with scaling fast. We also explore the emotional side of entrepreneurship — navigating divorce, loss, and personal upheaval while leading a company, the identity crisis that can follow selling your business, and how self-awareness becomes a founder’s greatest superpower. Finally, Alli opens up about starting over with her new brand, embracing natural curls after years as the “blowout queen,” and what she’s doing differently the second time around. Whether you’re building, scaling, fundraising, or redefining yourself after success, this episode is packed with real-world wisdom and founder truth. Enjoy!

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This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

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