Drybar Founder Alli Webb Never Let The Fear Of Failing Get To Her

While most founders are quick to describe the happiest, most aspirational scene when asked about their most memorable day on the job, Drybar founder Alli Webb immediately tells me a story from her business' very early days that, honestly, sounds like a business owner's worst nightmare. "This one particular day, the shop was slammed. Every single chair was full, and I noticed there was like a little bit of a black drip coming from our ceilings," she says. "I'm looking at it and starting to get nervous ... Within a couple seconds of me noticing that first drop, the whole f*cking roof caved in with black goop on the floor."

Thankfully, Webb, 45, says, no one was hurt — and by some miracle, no one was covered in black mystery goop, either. "It was one of the scariest moments," she says. "The best part of that story is the stylists and the clients who were sitting in the chairs that were near it moved the chairs over a little, looked at it, and were like, 'Oh, yeah, look at that,' and then went back to blow-drying hair."

Of course, Webb is quick to follow this moment up with a classically triumphant one: the day in 2010 when she learned Vogue knew of Drybar, the swiftly successful chain of blow-dry bars that now has over 100 locations and counting across the U.S. — and will be going global in the near future. "I remember that moment thinking, ['holy sh*t. We're on Vogue's radar.'" Overall, the takeaway from both moments is clear: When starting your own business, there will be amazing days, and there will be god-awful days. And for Webb, no two are ever the same.

As Drybar's CEO, Webb's days are normally what she calls an "office situation," as she juggles meetings, strategy, publicity, mentoring, and other top-level daily operations, although the current coronavirus pandemic has turned her usual office routine into a virtual one. In addition to virtual appearances and mentoring, some of Webb's quarantine work duties have involved her going back to physically styling hair — the arena she started in — by doing more hair tutorials and sharing them on social media. "I don't spend time really in the shops doing work [now], but I still love doing hair," she says. "It's still a deep passion of mine."

When she opened her first Drybar shop in Brentwood, California, in 2010, Webb's days were a far cry from the office situation she navigates now. Naturally, her days involved doing a ton of blowouts, but they also involved running point on all the behind-the-scenes work, too. This meant spending one minute working behind the reception desk, then doing payroll and making schedules, and then squeezing in several blowouts, all while attempting to "manage" the salons and so much more. If you're exhausted just reading that, know that wasn't even the half of it. Spending hours dealing with the minutiae of her business — the parts you probably wouldn't even give a second thought while getting a blowout — began long before Webb even opened her first shop.

I cleaned many a bathroom in Drybar.

"I can't tell you how many hours I spent on the phone with the cosmetology board trying to understand what licensing we needed, because we weren't cutting hair, we weren't coloring hair, we weren't doing anything permanently different to people ... not to mention spending hours on the phone with the phone company, getting our WiFi set up, and getting our towel services," she says. "I also spent hours and hours and hours on the floor cleaning floorboards, and I cleaned many a bathroom in Drybar."

Webb didn't spend her childhood and young-adult years dreaming of cleaning her business' bathrooms. In fact, she wasn't even completely sure what her dream was, career-wise, until after she spent about a year studying fashion marketing in college and decided it just wasn't right for her. "The only thing I can remember wanting to be was a fashion stylist. I always loved clothes," she says. "I just didn't love [college] ... All I really cared about was hair."

After deciding to leave college, Webb didn't immediately enter the beauty industry. Rather, she teamed up with her brother Michael Landau, who's still her business partner to this day, to open some Nicole Miller fashion boutiques in New York City. Soon enough, though, Webb succumbed to the "nagging in the back of [her] mind" and trained to become a hairstylist under renowned celebrity hairstylist John Sahag. And even then, becoming a hairstylist still wasn't Webb's one-way ticket to founding Drybar.

She remembers vividly the moment in 2008 that would eventually lead to Drybar's conception. She'd taken a break from hair, and had been a stay-at-home mom for the previous five years. "I was sitting in my living room with my best friend, and I was like, 'You know, I feel like I kind of want to start doing something again.' I didn't want to go back to a salon full time or back to work in a full-time capacity, but I was like, 'Maybe I should start a little mobile blow-dry business where I basically run over to our friends' houses that have babies while the babies are sleeping and blow out their hair,'" says Webb. "She thought it was a great idea ... so I started this mobile business."

Webb's affordable, convenient mobile blow-dry business, called Straight At Home, quickly took off, and after many conversations with clients, she learned why. "While I was operating this business, I realized there [was] no place for women to go for a great blowout at an affordable price." she says. "That's when I started kind of percolating the idea of Drybar." With her husband and her (oddly enough, bald) brother on board with the idea, the three of them began the instantly successful business. "It was a big gamble and risk, but we decided to go for it, and thank God we did," says Webb, who was named one of Fortune's "40 Under 40" in 2013 and one of Fast Company's "100 Most Creative People in Business” in 2013 following Drybar's launch.

For me and all of the hairstylists I know that have 'made it' ... they have really paid their dues.

While Webb naturally dealt with some harsh realities as Drybar began — from having to be the person everyone goes to when sh*t hits the fan to accidentally signing a terrible contract for towel services — the fear of failing, not only didn't stop her, but it didn't really faze her at all. "My mentality was, the world's not going to fall apart if this doesn't work out," she says. That was what made me be able to squash the nerves ... and not to mention, I just really believed in this idea so wholeheartedly."

Webb is quick to advise that measurable success doesn't happen overnight. Rather, taking the time to learn and pay your dues, as well as having "thick skin" in regard to constant feedback, are crucial steps for anyone hoping to start a business in the beauty industry. "For me and all of the hairstylists I know that have 'made it,' like the Jenna Atkins of the world and Chris McMillan ... they have really paid their dues and had to be somebody's assistant, doing the not-fun stuff — just washing hair all day long and standing and watching and learning." Learning, Webb says, is key to being successful in the beauty industry, or in business in general. "Getting too caught up in thinking you're so great and you can't learn anything else — that's a good recipe for disaster."

But if you're desperately waiting for a 100% original idea for a cooler career or business to fall in your lap, well, don't hold your breath. Great ideas rarely just come out of thin air, and Webb is the first to admit this. "[Drybar] didn't invent blowouts, clearly. We invented a better experience around it," she says. Her advice to aspiring founders is to take a hard look at the services, products, or experiences you're interested in, and examine if and how an idea can fill in the gaps. "Look for what's missing, even if it's something that you love or something that exists, but that you don't love the experience of," she says. "Whatever that is, how can you make this thing better?"

Especially now, as everyone sits in quarantine, forced to rethink what their lives look like anyway, if you have an itch to revamp your career, and potentially even venture off on your own, Webb says to do it fast. "Life is so short, and I think that we're all living in that reality more than ever right now," she says. "If you're not doing something that makes you excited and happy to get out of bed in the morning, go find that thing that does."