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!To connect with Siff on Instagram, click HERE.To connect with Siff on Tiktok, click HERE.To learn more about Arrae, click HERE. To check out Siff’s LTK, click HERE.To check out Siff’s Amazon StoreFront, click HERE. To connect with Alli on Instagram, click HERE.To connect with Messy on Instagram, click HERE.To shop Messy at Sephora, click HERE.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.This FREE powerful manifestation guided audio will shift your energy FAST. Get a 14 day free trial and over 60% off for a limited time at www.activations.com/dreambigger. Discount only available through the website, not the app store.Refresh your wardrobe with Quince. Go to Quince.com/dreambigger for free shipping on your order and 365-day returns. Now available in Canada, too. That’s Quince.com/dreambigger to get free shipping and 365-day returns. Caraway’s cookware set is a favorite for a reason, it can save you up to $190 versus buying the items individually. Plus, if you visit Carawayhome.com/BIGGER you can take an additional 10% off your next purchase. This deal is exclusive for our listeners, so visit Carawayhome.com/BIGGER or use code BIGGER at checkout. Caraway. Non-Toxic kitchenware made modern.Get started with the Experian App now!Text DREAM to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply.Use code DREAMBIGGER15 for $15 off first purchase at thirdlove.comProduced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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