When Alli Webb co-founded Drybar in 2010, she had no idea what the future would hold. She only had a gut instinct that women needed her service — and she set out to provide it. 

Today, Drybar has over 150 locations across the country, but not before Alli sold the business in 2020 to Helen of Troy for $255M. Now, she’s a serial entrepreneur as the co-founder of Squeeze and Becket and Quill, as well as president at Canopy. 

We recently had the privilege of chatting with Alli at Playbook 2022. And in this session, she shares seven critical lessons from scaling Drybar and her other businesses.

1. Failure is possible, but you have to try. 

Before founding Drybar, Alli worked as a hairstylist in Los Angeles. She often provided blowouts (and got them done herself) to help manage clients’ curly hair. But it wasn’t long until she realized a business opportunity and started a mobile service. 

“There was a hole in the marketplace for women to get a great blowout at an affordable price in a beautiful, luxurious space,” Alli explained. So, she quit her day job and started charging $40 to go into women's homes and blow out their hair. The service blew up, and she had to expand. 

“When I went to my brother [Michael Landau] and [told him about] turning my mobile business into [the first Drybar], he wondered why women couldn’t blow dry their own hair,” she told us. 

But despite his initial reluctance, they opened the first Drybar and took the risk together along with her ex-husband (and one of the creative forces behind Drybar) Cameron Webb. 

“There was no business plan,” Alli shared. “[Just a] strong gut feeling that there were enough women out there who felt the way I [did].” And luckily, her instinct was right and paid off well. “The first [store] was bananas, and we were so busy [it was] the hot club you couldn’t get into.”

Today, Alli reflects on that risk and recognizes that all leaders must take one like it. “As an entrepreneur, there’s [always] a chance it won’t work,” she told us. But you can’t know for sure unless you actually try and take a leap of faith.

“Failure is an option, but we're gonna try it anyway.” – Alli Webb, co-founder of Drybar, Squeeze, Becket and Quill, and president at Canopy

2. You won’t win every move, but it doesn’t mean you’re losing.

After the success of the first two locations, Alli opened another Drybar on Sunset Boulevard. But this one had a slow start. “It was so slow [at the third location] for the first six months,” Alli told us. But they didn’t give up and looked for solutions instead.

“We don’t talk about [the slow start] much, but it wasn’t a snap of our fingers,” she explained. “It was hard work.” And for business leaders, it’s a good reminder that all moves might not immediately take off — but that doesn’t mean your plan won’t work in the long run.

“You might look at Drybar 12 years later [and think] it’s this massive hit. But it wasn't a slam dunk; it took a lot of hard work.”

3. Hire leaders who complement your skills

Drybar eventually started franchising its business model to grow quickly. But Alli needed help with some of the financial operations, so they brought on leaders who understood systems.

“We quickly realized we had to hire people [with] more experience in growing and scaling a business,” she explained. “Because there was so much we didn't know.” As a result, they hired former Taco Bell CFO Liz Williams as their new CEO (with plenty of financial experience).

“[We finally had] all these systems, so things got much more organized,” Alli told us. But it might not have been possible without recognizing the need to hire relevant experts first. 

4. Hire fast and fire fast for best results. 

When a brand takes off, you must hire quickly to continue growing and fill any expertise voids. “You need to hire people [with the] experience that you don't have [in order to] grow,” she told us. But for Alli, that means you must also fire fast when someone doesn’t work out. 

“You must recognize when something's not working, move on, and keep networking [to find the next person],” she explained. And eventually, she says, you’ll stumble across the right person with the knowledge and background you need. “I leverage my network all the time,” she added. 

That said, you might not have enough capital to hire anyone yet. But that doesn’t mean you can’t find a way to bring on more people. You just have to get a little creative with your offering. “If you don't have the money to hire somebody, [give them] equity,” she explained.

5. Your manual and training could change everything.

When Alli looks back on building Drybar, she notes a particular moment when operations significantly improved. “One of the biggest innovations for [Drybar] was our stylist training process,” she explained. “We put a system in place and started making manuals.” 

Drybar also appointed certain stores as training shops — where managers or franchisees can shadow and train for their store. As a result, Drybar has a much more efficient process for training and sharing knowledge. And they ensure that all of the stores get the same training. 

“[Having a process and documentation] makes [training] so much easier to follow.”

6. Ask employees for their feedback and listen. 

Because Alli was a hair stylist before Drybar, she understood her employees’ needs and challenges. But that didn’t stop her from continually seeking feedback from her team. “Having that open dialogue with your team is crucial [to understanding their needs],” she explained. 

For example, Drybar gets to know its stylists by understanding their long-term goals. “There's got to be [an incentive] that gets them to the finish line,” Alli explained. And for Drybar stylists, it’s often a chance to grow and thrive in a non-competitive environment.

“It's time-consuming to [get feedback], but it also makes [employees] feel seen and appreciated,” Alli added. And that result alone will support your long-term retention.

“You'd be surprised at what information you’ll get back from [employees].”

7. Believe in yourself and your abilities.

When Drybar brought in investors, Alli often avoided asking questions in board meetings. “I would text [my brother] questions under the table [because] I was scared to [say them] out loud,” she told us. But her brother Michael always encouraged her to speak up and ask them. 

Now, Alli reminds other business owners to believe in themselves and use their voices. “If you've gotten yourself this far, you've done something right,” she said. But for others to believe that, you must believe it first. And for Alli, that means finding your confidence and owning it. 

“Believe in yourself in a very unapologetic way.”