Alli Webb Straightens Out The Tangled Hair Business

Who knew that having naturally curly hair could lead to business success? Not Alli Webb, who, in 2010, co-founded Drybar, a chain of salons that provided only blowouts — no cuts, no color — to women.

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It’s a success story that is as circuitous as the frizziest hair she hoped to resolve. The business, now based in Irvine, Calif., grew beyond her initially modest expectations, and she sold it in 2019 for roughly $255 million to Helen of Troy (HELE).

Webb was herself a victim of the frizz, a condition exacerbated growing up in Boca Raton, Fla., where her parents ran a small chain of what she calls “older-lady clothing stores.” In an interview with IBD she added: “They opened these clothing boutiques for older ladies adjacent to retirement communities.”

Form A Solid Team

Both she and her brother (and subsequent business partner) Michael Landau worked there. “We didn’t work very hard. But we were around my parents and kind of learning the business. I was getting an education that I don’t think I appreciated until much later,” she said.

In fact, she didn’t think about going into business for herself until years later when she came up with the idea for Drybar. The idea came after — as she describes in her memoir, “Messy Truth: How I Sold My Business for Millions but Almost Lost Myself” — an aha moment. “There was an unfilled need out there, a need I personally felt I could fulfill,” she said.

In between she went to beauty school, worked in salons and for designer Nicole Miller, got married and had two children. The closest she came to entrepreneurship at the time was a dog-walking business she briefly ran years earlier.

But when her sons were two and four years old, Webb began “to really miss something of myself. I felt like something was missing,” she said. “I wanted to do something I liked beyond just being home with the kids — though I was grateful for that opportunity.”

Follow Your Heart

Then inspiration struck. There must be other mothers at home with young children feeling they were missing out, too. Mothers, she felt, who would love the restorative powers of a professional blowout.

So she started a mobile blowout business that operated while her children were in preschool. It was a success virtually from the day she announced it on her Yahoo mom group. Her pitch: “I’m a stay-at-home mom and a longtime hair stylist. I’ll come over and blow out your hair for only $40 while your babies are sleeping.”

Business was so great, she started thinking about opening brick-and-mortar locations. Her brother was skeptical at first, but didn’t stand a chance to stop her. “Ever since she was a little kid, Alli has always had a level of determination that was off the charts,” Landau told IBD. “As soon as she sets her sights on something, for better or worse, she can’t stop thinking about it, and won’t give up until it’s accomplished.”

Ultimately, he also bought into her logic: “Most women can’t do their hair as well as a professional. When a pro does a blowout, for a woman, it’s like getting your makeup done or putting on a new outfit: She gets an extra layer of confidence.”

And there wasn’t much competition for that business. “Hair stylists at salons didn’t want to be doing just blowouts. They wanted to spend their time doing higher-priced services. There were discount places, but they didn’t provide the same experience,” he said.

Don’t Overthink Your Idea

She knew there’d be challenges, but this was “an idea that wouldn’t leave her alone. Her philosophy when starting a business was: Don’t overthink it. “Don’t get too far ahead of yourself. Start with a great idea. Don’t worry about all the other stuff. Worry about all the other stuff as you go,” she said.

She enlisted brother Landau, one of the first 100 Yahoo employees, who contributed the bulk of the early financing. Alli’s husband, Cameron Webb, worked in advertising and handled the marketing and branding.

That left her to set the standards for ambience, “to think what type of culture you want to create,” she said. This included not just the physical blowouts, but how “to greet clients with a different approach such as ‘Hey, Sally, nice to see you. Let me get you checked in. Would you like a mimosa or a glass of water?’ Not, ‘Do you have an appointment?'”

Make Customers Feel Special

Alli wanted every visit to be an event. Different cuts were named after cocktails. Mirrors were not placed in front of the chairs, but behind them so customers could have a reveal” when finished.

Bringing the concept to life, however, was easier said than done. “On opening day of Drybar, I had the overwhelming and wrong idea that I had to have all the answers. It took me time to realize I didn’t know everything,” she said.

Another early problem: “I always had the mentality that no job was too small for me to do. It took me a while to discover how to be a leader. I was very passionate about what we were doing, and that passion would often be mistaken for toughness. It took me a while to learn that every person who worked for me was different and motivated in different ways.”

She believes her experiences weren’t unique. “When you are in the early phase of building a business, you’re always in a state of trying to figure things out, learning by failing, asking questions, calling people, asking favors, leveraging your network and utilizing people around you,” she said.

Know That Struggle Often Follows Success

Ironically, Webb says, “Even when you have success, it’s followed by new struggles.”

For example, the company’s early rapid growth put a strain on personnel. “That was hard, because you couldn’t just hire anybody. You needed to get the right stylist. We were very discerning, and that was an occasional problem. There was a lot of pressure from (some), saying ‘we could do more blowouts. We could make more money.’ But for me it was reputational. I didn’t want to ruin what we had built, because if we started not delivering amazing blowouts the whole thing could collapse.”

Ultimately, though, there was strain on the personal, as well. Her fame was growing — and that included guest appearances on “Shark Tank” and cover articles in magazines — putting more pressure on her to be all things to all people. Ultimately, her marriage fell apart in this pressure-cooker environment. She solved that a bit by stepping back, recognizing “you can’t be everything to everyone. You have to make sure you fill the company seats with people who know what they’re doing.”

“Businesses don’t usually fail because their idea wasn’t good enough. More often they fail because the founder didn’t get that while they are a brilliant visionary, they are a poor executive,” she said. “It wasn’t until we raised our first round of private-equity financing that people started suggesting, ‘We think you’re going to need a professional CEO.’ In my mind, I was like, why? Michael is doing such a great job.”

Hire People Smarter Than You

She listened to the advice, though.

“But as we grew, managing that growth was completely outside of our scope of what we knew. It’s one of the best pieces of advice I give to entrepreneurs: Bring in people who are smarter than you,” Webb said.

Webb now applies the lessons she learned in a new venture, Squeeze. A chain of brick-and-mortar massage locations, Squeeze is based on the same principles as Drybar: Create a special experience for customers at a price point far below what exclusive spas charge.

The company was started in 2019, just before Covid brought the world to a halt. But it expects to have about 100 franchised locations open by the end of this year.

So, yes, lessons were learned one blowout at a time.

Alli Webb’s Keys

• Founded Drybar, a chain of salons that provide only blowouts.
• Overcame: Pressure to grow too fast.
• Lesson: “It can be intoxicating to grow fast, but it is easy to lose sight of what made you grow in the first place. It’s important to remember what made your business unique in the first place. Don’t lose authenticity in favor of the short-term goal of making more money.”