Drybar Founder Alli Webb Built a Blowout Empire—But Felt "Very Insecure" About Her Own Hair

With her company Drybar, Alli Webb built an empire around the idea of "perfect" hair. The chain of salons—which she sold in 2019 for $255 million—offered no cuts or color, only blowouts in a range of styles. As the founder and face of a brand devoted to sleek hair, Webb felt she had to embody that perfection herself—or at least look like it. Yet at the height of her success, she was deeply insecure about her own hair.

"I wanted my hair to look a certain way, so then I wore extensions forever. And I was so insecure when I would wear extensions, because as someone who's, like, very obsessed about their hair, I was always nervous you could see [them]," Webb tells editor-in-chief Nikki Ogunnaike on the latest episode of the Marie Claire podcast "Nice Talk".

"I never went anywhere without a handheld mirror. Every time I went to a bathroom, I would look at the back of my hair, make sure nothing was fucking showing," Webb continues. "I felt this pressure that I had to have this long, beautiful, perfect hair, and my hair wasn't. It was broken and damaged."

Webb says she felt "so blessed" to be featured in magazines, do photoshoots, and appear on Shark Tank—but admits she was wearing extensions during "all these very big moments in my life."

"I can't tell you how many times they were like, 'Will she put extensions in?' Because it was just, like, I was supposed to have this perfect, beautiful hair." But rather than boosting her confidence, the extensions made her feel "terrible."

"I felt almost, like, not enough. It's funny, I've never actually talked about this, but I remember that made me feel very insecure."

Webb says the pressure to project perfection went far beyond her hair.

"I really felt like I had to be perfect, and I had to have the perfect hair, and—I was married to my co-founder—this perfect marriage, and these perfect kids ... And it just was a little hollow, you know, and a little unrealistic, and I kind of kept up that facade."

Still, she adds, "I loved what we were doing, and I loved the fact that we were giving women confidence. And at that time, 15 years ago, it felt like the world needed it, and it was the right thing at the right time."

These days, Webb says the “pendulum has swung” in the opposite direction. Her new brand of haircare products, called Messy, is all about embracing ease—using low heat or letting hair air dry. Even the products’ names are affirmations: the styling cream, for instance, is called is called "I Am Enough." (And now, Webb says she feels “giddy” about her hair.)

"I was 35 when I started Drybar, and our tagline was 'crafted for the perfect blowout.' But, you know, as my own personal evolution and journey, I'm like, I just don't subscribe to that anymore," the now 50-year-old shares. "It's like, yeah, I did start Drybar, and it was a huge success, and I'm so incredibly proud of it, and I always will be. And now I'm just in a different place. You can be, too. We don't have to be who we were yesterday."

For more from Webb—including how she started Drybar, the best career advice she's received, and how the pandemic inspired Messy—check out this week's installment of "Nice Talk". The episode is available everywhere you listen to podcasts.