How Drybar's Alli Webb Went From Stay-at-Home Mom to Hair Mogul

After staying home to raise her sons, Alli Webb wanted a way to get out of the house, earn some money and do something for herself. Here's how that turned into the Drybar empire we know today.

By Samantha Schnurr May 03, 2021 2:00 PMTags
Alli Webb, Her Two Cents, CareersGetty Images/E! Illustration

Welcome to E!'s Tales From the Top, our series on women who are leaders in their fields and masters of their craft. Spanning industries and experiences, these powerhouse women answer all the questions you've ever had about how they got to where they are today—and what they overcame to get there. Read along as they bring their resumés to life. 

Just when you're trying to figure out your next step, life can blow you in the right direction. 

Given the subject of this story, it's only fitting that we work in an airy pun. After all, we're talking about none other than Alli Webb, the woman synonymous with an empire built on possibly the most beloved part of any hair appointment: the blowout. "Once the hair is blown out—it's obviously cut well and then styled well—that's when clients are really happy," she told E! News in an exclusive interview. "That's that kind of glorious moment."

But before the 11 years of Drybar business, more than 100 locations, a product line and devoted customers across the country, Alli was a thirtysomething stay-at-home mom of two with an "itch," as she put it, "to get back out there and do something for myself."

She was no stranger to the work force, having been raised by entrepreneur parents whose clothing store taught her the ropes in as a child. After more retail clothing experience as a teen, she shifted gears slightly as a receptionist in a local hair salon—"one of the seeds," she said, that planted her own eventual hair pursuits. After high school, Alli instead had her heart set on fashion with dreams of styling. With a move to New York City from her native Florida, she landed retail gigs with the likes of Cynthia Rowley and Nicole Miller. She and her brother, Michael Landau, brought some of Nicole Miller back home to Florida when they opened two boutiques together.  

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"At the ripe old age of, like, 21, maybe, I was basically managing two retail operations, Nicole Miller licensees that we bought," she recalled, "and realized I was deeply unhappy with it. My brother and I were fighting a lot. That's when I decided to go to beauty school."

Eventually, Alli was once again in Manhattan, but this time as a full-fledged hairstylist honing her skills under renowned celebrity hairstylist John Sahag. "I loved doing that until I didn't," she said. While it was a "great honor" to work for Sahag, "Just after a couple years," she said, "I was like, 'Ah, I think I want to do something else."

That 'something else' became developing her writing skills as a legal department assistant at a public relations firm. "I worked in a cubicle and I loved it," she said with a laugh. "I really got that experience that I had not gotten because I didn't go to traditional college."

Being in New York City was also a personal catalyst as she met her now-ex-husband, Cameron Webb, who she called the "creative mastermind" of Drybar. Together, they moved to California, where they welcomed two sons and, after about five years of raising them at home, a mobile blowout business proved to be the perfect fit for Alli's next stepping stone. 

"Obviously, that is what ultimately turned into Drybar," she recalled, "realizing there was this pretty massive hole in the marketplace, and there was nobody doing affordable blowouts in a cool space. It didn't exist back then."

But, she did not start with the buttercup yellow, cocktail-themed brick-and-mortar salons customers know today. Instead, Alli went to the clients first, offering her straightforward singular service for $40 without all the fussy equipment required of a cut or color. "I liked the ease and the fact that I could do blowouts in my sleep just felt like the perfect fit, so I loved the idea of it just being blowouts," she explained. "And then it was a great way for me to get out of the house and be on my own for a couple hours. That was it. It was never like, 'Oh, I'm going to now start this big business.'"

Still, big was where she was headed. Her mobile business took off and as the calls for appointments grew, Alli had to expand somehow. "I realized I'm either going to have to bring on other stylists and turn this into a mobile business which, I was like, if I bring on other stylists, I can't really control it and then they'll become their clients," she explained. "In terms of growth, that doesn't really work." Instead, she had the customers come to her and, with Michael, Cameron and architect Josh Heitler on board, the first Drybar, in the Brentwood neighborhood of Los Angeles, was born. For Alli, it was a culmination of, as she put it, "the only thing I knew."

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"I really believe that part of why it works so well for us is because of my background," she said. "I spent most of my life figuring out how to blow out my own curly hair. And then once I learned, styling other people, I have so much experience in that particular very niche area and I've worked at so many hair salons and I worked under so many owners, so I knew so much about the space...That was what I had spent my life doing."

While she felt in her gut that the shop would work, Alli had not anticipated the challenges that would come with swift success, too—and we mean swift. "When we opened that first shop, that first day, I had only six stylists on. I didn't hire a manager, because I was like, 'I'm going to run it,'" she recalled. "We were so slammed that I was doing blowouts in the first chair—only in the first chair, so I could see the cash register and I could also greet people. It was such chaos. I mean, beautiful chaos, but such chaos...And it was day one. I've worked in enough hair salons to know that you're not that busy the day you open, so it was just a crazy phenomenon." 

From that point forward, she learned on the job. The Drybar call center for example? It was born out of Alli's desire to have employees focused on the customers in front of them instead of a ringing phone. Of course, there were some gaffes, too. In hindsight, she learned even making the shops white inside wasn't the best idea. "The maintenance on it is really insane and very, very costly, frankly, to keep replacing things," she said. "But I wouldn't change it. It's just like, 'S--t, we didn't see that coming.'"

With every task that needed handling, Alli wasn't alone. "All the sudden, I was in charge and I was the boss of a lot of people, and payroll and all of those things that were like, 'Oh, s--t. How do I do this?' And that's where I was lucky enough to have my brother, who intuitively knew that better than I did,' she credited. "My brother and I used to share an office...I would hear him on phone calls. He would hear me on phone calls...If I had a quarter for every time I asked my brother, 'What does that mean?' and 'What does that word mean?' and 'What does this thing mean?' So I learned so much from my brother. I learned so much from on the job."

As for any similar businesses popping up, they would have to compete with family. "When we thought about competitors and other people encroaching on the space, it was like, 'There's no way they have what we have and cannot pay the people that we have,' because me, Michael, Cam, Josh—none of us paid ourselves forever, for years. So it was like, you'd have to go and hire all those people...We were family and we really cared about it at a level that only family can."

While they eventually hired executives as the company soared, the lessons only continued. "It was an incremental learn," she recalled. "Those first five to seven years were just so much coming at me and I loved it. I felt really fortunate. I feel like I got a business degree in entrepreneurship growing this thing and learning so much."

If you have a burgeoning business idea, but don't quite know the ropes, take it from Alli—someone you know might. "I think that there's a lot of people in our lives that have experience that we don't. And that's always my advice is seek out those people," she advised. "It's pretty amazing if you think about all the people in your network. Even if it's not somebody you intimately know, it's a friend of a friend. There's always somebody who has that kind of experience. I have found in my life, really in my career, that a lot of people are willing to get on the phone with you and walk you through something and explain it to you."

While Alli suggests seeking out a business partner if you're struggling with how to execute your idea, there's something that any budding entrepreneur should probably throw out the window first: inhibition. "It is in my nature to be like, 'I am going to figure this out one way or the other and nobody can stop me,'" Alli described herself. "I think that that kind of determination is kind of like a prerequisite to an entrepreneur. You have to have no inhibition to cold call somebody and just be ballsy and ask people favors. It's kind of the level you have to be at and it's not for everybody."

As for Alli, her resumé has continued to expand with the app-driven massage company Squeeze she co-founded in 2019 and, most recently, the jewelry line Becket + Quill, which she launched online with designer Meredith Quill in February after almost a year of the ongoing coronavirus pandemic.

"I actually enjoyed being forced to slow down. For me, I was on a plane every other week of my life and I was burnt out, and I was stressed and I was tired. I know it's like, 'Boo hoo, cry me a river,' but that was my personal frustration. I felt very lost and I didn't have the things that I always did, and I had to—I feel like the word pivot is the most overused word of 2020—but I did and I had to figure something else out and it took a while to figure out what was going to be the next thing for me," she shared. "I actually ended up starting a jewelry company in the midst of a pandemic because that was something that I could do from home."

Now, as people continue to grapple with the effects of the pandemic and anything else on their daily plate, Alli's answer to how she does it all resonates loudly. Simply put, there are always going to be good and bad days. "There are days where I'm flying high and everything's working out and things are great," she said, "and then, the very next day, you feel like you suck and you don't have anything under control and everything is falling apart and everybody's mad at you and nothing is working. It's that bipolar."

The solution? "I think it's, you hang onto the good days, knowing they're going to come again, and brace for the bad days, because you know they're coming, too."

"I think that's kind of how I've dealt with my life in general," she noted, "on the bad days, being like, 'I hate it. I wish it wasn't like this, but I know it's going to get better.' And on the good days, 'I know a bad day is probably around the corner, too. And I guess not being so thrown by either one and learning how to take it in stride and learning the things that calm you down or get you out of that mode."

Ultimately, she keeps this in mind: "I think I come back to—It's all part of the journey, which I know sounds like a postcard, but it really is."