The Woman Behind Drybar and Squeeze: Alli Webb

“Real Women, Real Work” is a Darling series about everyday women who work in various fields including business, entertainment, science and education. We want to get to know the WHY behind their WHAT and get an inside look into different industries.

When things don’t go according to plan, in business or in relationships, it can throw a metaphorical wrench in the vision you created for your life. Yet, uncertainties and disappointments do not signify failure, but instead, they often are the things that shape and redirect us.

Alli Webb, Drybar Founder, proves this to be true. Darling got to chat with the leading lady in business as she shared about her recent divorce from former husband Cameron Webb. She delves into self-care practices she used to help navigate through the huge life change. She also opened up about how she balances her career with being a mom to her two kids, as well as with starting her latest venture, Squeeze.

Here’s what Webb had to say about navigating personal and professional obstacles while still living a life of passion:

What obstacles did you face in the early days of Drybar?

There are so many obstacles in the early days of starting a business. It’s a time full of unknowns. Drybar resonated with women in a way we didn’t anticipate. We severely underestimated the demand. We were pretty understaffed and unprepared, but we figured it out as we went and learned day by day how to make it all work.

Drybar started off as a small salon in Brentwood where you did blowouts. When did the plan change to something on a larger scale?

Once we realized how popular affordable blowouts were, we knew we had to open more locations to serve more women. We opened our second shop in Studio City six months after Brentwood, which felt like an eternity. Our Brentwood business was booming so we couldn’t open more locations fast enough. I’m so proud to say that today we have more than 135 locations and a robust product line.

How have you navigated your professional and personal life in the midst of divorce?

It’s also a learn-as-you-go situation that no one can really prepare you for. I think the most important part for me was to take the time and space I needed to process the loss instead of just pushing through. I did a little of both, including a lot of meditation, reading a ton of books, therapy, healers, retreats and everything in-between.

What practical tips/self-care practices did you instill during that time?

For me, it was a lot of reading, hiking and being in nature. Doing Transcendental Meditation was a game changer for me. I believe any type of meditation is a really valuable tool for finding inner calm and peace.

What have you learned personally about navigating hardship and unexpected struggles?

Everything changes, the good and the bad. As hard as the unexpected and hardships feel in the moment, it’s how we learn and grow. Those hard times are really what shape us and help us grow.

What was the vision when you created Squeeze? How is it different from other massage boutiques?

For years, me and my business partner and brother, Michael Landau, lamented to each other about how we wished there was a better massage experience. We didn’t like the ambience and clunky booking process at the discount chains or the exorbitant prices at high end spas and hotels. Neither of us really liked having a stranger come into our home.

We had a vision for our ideal massage experience, starting with a super intuitive and seamless online booking platform combined with a beautifully designed space and incredibly talented and friendly therapists.

We finally decided to partner with our former VP of Marketing at Drybar, Brittany Driscoll, and our architect Josh Heitler, who both shared our passion for the idea. We’ve been developing the Squeeze concept and brand for more than two years now, and we couldn’t be more proud and excited about how it has come to life!

As the founder of two businesses, what advice do you have for other women interested in starting a business?

It’s a lot of perseverance and not fearing the unknown. I think it’s easy to get caught up in feeling like you don’t know enough to get started, but it’s an ongoing learning experience.

What are some short term goals you have for your businesses? And for yourself?

Drybar is continuing to grow its footprint and expand both in the United States and internationally. I personally have a lot of projects in the works that I’m really excited about. Michael and I host our own entrepreneur podcast, Raising The Bar. We have a lot of fun giving budding entrepreneurs advice, hearing their origin stories and talking all things business.

What obstacles have you faced along your career journey? What advice can you take from Alli’s story?

Feature Image via Kat Borchart