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Drybar founder Alli Webb shares ‘The Messy Truth’ about her life and $255 million business sale

Eliana Berger and Alli Webb sitting on stage at WISE Summit.
Eliana Berger, Northeastern grad and WISE co-founder, chats with Alli Webb, Drybar founder and author, during the WISE summit kickoff event. Photo by Alyssa Stone/Northeastern University

Alli Webb said she was “such an underachiever” as a child.

She’s made up for it since — co-founding the blowout salon business Drybar; writing a book about the $255 million sale of the business in 2020; and starting a massage business, entrepreneurial support blog, and a “side hustle” of a jewelry business. 

But Webb told Northeastern members of the Women’s Interdisciplinary Society of Entrepreneurship that the biggest lesson she learned was “you’ve got to be able to roll with all of it.”

After all, Webb’s book is called “The Messy Truth: How I Sold my Business for Millions but Almost Lost Myself.”

“It’s not all roses and sunshine all the time,” Webb said at the WISE Pre-Summit Dinner on Friday evening. “It’s been amazing and it’s been so hard too: that is the truth of life — of all our lives.”

WISE is a student-led group that brings together women and underrepresented individuals to encourage entrepreneurial thinking in all fields and industries. The fifth annual WISE Summit was held last weekend on the Boston campus, and kicked off with a dinner Friday night at the EXP research complex.

“This summit is all about celebrating and learning and being energized by one another,” said Diane MacGillivray, senior vice president for university advancement and co-founder of Women Who Empower, in introducing Webb. “This year’s theme is embracing authenticity, and I can’t think of anyone better of talking about authenticity and an entrepreneurial journey than Alli Webb.”

Webb — interviewed by 2021 Northeastern graduate and WISE co-founder Eliana Berger — began her journey as a girl in South Florida whose “naturally curly hair was even bigger” than now due to the region’s humidity. 

But after beauty school, jobs in New York City high-end salons, and a stint as a stay-at-home mom in Los Angeles, Webb began a mobile blowout business — driving all over LA to blow out clients’ hair for $40.

With help from her now ex-husband (creative branding) and financing from her brother, she opened her first shop in February 2010.

It was an instant success. 

But Webb said “back then I didn’t know anything” about running a business.

“I knew hair and customer service and how a hair salon should be run,” Webb said. “But that was just the half of it.”

But Webb said she surrounded herself with people who knew things she didn’t, and advised “not letting perfect stand in the way of progress.”

“You start the thing, then you start figuring out the answers as you go,” Webb said. 

However, those answers didn’t necessarily come easily.

The second store she opened resulted in “crickets,” Webb said, as did the third.

But marketing and outreach, educating women that a blowout without the pressure of having a cut and/or color was an experience they could enjoy and need, and being resilient were all crucial to persevering as a new entrepreneur … as well as being a keen and critical observer.

“Welcome to my brain,” Webb joked. “I go into any place and I think ‘it could be so much better if…’”

The businesses soon turned into successes. And they became unique. Webb described how stylists were provided with all the same tools of the trade, rather than bringing in their own hair dryers and brushes. Mirrors were placed behind the chairs rather than in front, so that the customer could have a “reveal” after the blowout and they saw themselves for the first time. Services were provided at a bar, and styles were named after cocktails.  

In 2020, Webb sold the company for $255 million in cash.

But her life in the previous two years “nearly fell apart,” Webb said. She divorced and her son went into rehabilitation for addiction. 

“I was very open in this book about what my life looked like behind the scenes, because I wanted to show it’s not all glamorous and real life happens,” Webb said.

And while things have improved — for instance, Webb proudly reported her son is now in college on a football scholarship — Webb has learned crucial lessons that she passed along to the WISE students.

“Join as many communities as you can that are available to you for female entrepreneurship,” Webb said, touting her online community, “Messy Collective.” “Having that support is really everything.”

Mia Nguyen, 2021 graduate and co-founder of WISE, said that the story “resonated so well with what we do at WISE.”

“There were a lot of good sentiments shared, and we really do appreciate it,” Nguyen said. “We thank you.”