Alli Webb on Building and Selling Drybar for $225M, Founder Evolution, and Building a Second Business
The Dream Bigger Podcast
Siffat Haider
4.7 • 659 Ratings
🗓️ 18 February 2026
⏱️ 54 minutes
🧾️ Download transcript
Summary
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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Transcript
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| 0:00.0 | The following podcast is a dear media production. |
| 0:04.9 | Hi, I'm Sif Heider, the founder of Hire. |
| 0:08.1 | I'm a wellness entrepreneur and digital creator, and this is my show, The Dream Bigger |
| 0:12.4 | podcast. Listen, I love dreaming big, but you know what I love more? |
| 0:17.3 | Actually having the resources to make those big dreams happen. |
| 0:22.7 | And hey, dreams can sometimes be private jets, but other times, they can look a little something like having the best |
| 0:27.4 | skin of your damn life, or starting a successful business, or delving into spirituality. So on this |
| 0:34.4 | podcast, I chat with experts and thought leaders from different fields about their tips and tricks on doing exactly that. |
| 0:40.7 | So let's get right into it. |
| 0:46.5 | Hello, hello, friends, and welcome back to another episode of the Dream Bigger podcast. |
| 0:50.6 | Now, I apologize for how I sound. |
| 0:52.3 | I am still a little bit congested, but I am on the other |
| 0:55.7 | side of whatever I have picked up, but I do apologize. Just bear with me for the intro. I know |
| 1:01.5 | I sound a little bit rusty, but on the bright side, I am feeling so much better. So I am so |
| 1:07.7 | excited to bring you today's episode. It is with Ali Webb, who is an absolutely iconic founder. |
| 1:14.5 | So she first started Dry Bar, and now she is the founder of a new hair care brand called |
| 1:20.4 | Messy. |
| 1:21.3 | I have looked up to Ali for God knows even how long. |
| 1:25.8 | I became a Dry Bar customer years and years ago. |
| 1:29.3 | I have so many of their hair tools that I use right now because they're phenomenal. |
| 1:34.7 | And, you know, Ali started one of the most iconic CPG businesses, which is, of course, |
| 1:40.3 | Dry Bar. |
... |
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