Drybar cofounder built a $255 million dollar hair business while her personal life ‘imploded.’ She has a warning for success-hungry entrepreneurs
When Alli Webb founded Drybar in 2010, she couldn’t have anticipated her passion for hair styling would transcend into a multi-million dollar beauty empire with over 150 storefronts nationwide. With its notable yellow and gray logo and brightly branded products, the company capitalized on an unmet consumer interest—a simple blowout, no cuts nor colors.
“We were on such a rocket ship with Drybar, and the trajectory of the business was so fast and amazing,” Webb, who sold the $255 million blowout company in 2019, tells Fortune. But, there was a harsher reality to Webb’s story, which she reveals in her newly released memoir The Messy Truth. “I am a living, breathing example of just how high one can climb and how fast one can fall,” she writes in her book.
Webb didn’t have a traditional business background but recalls feeling celebrated in what she describes as a time of entrepreneurial popularity for female founders. “I was kind of your unexpected, scrappier entrepreneur,” says Webb. But with her rapid rise to success came the spotlight—and then the pressure to keep her place in it. Coupled with challenges at home, she faced burnout and depression and now shares her story as a message for other founders.
Burnout and depression as an entrepreneur
Webb always loved styling hair. After attending beauty school, getting married, and having two kids, she began offering moms a simple $40 blowout in the comfort of their homes as their newborns slept. Her services became highly sought after, particularly for working moms, she details in the book. As word of mouth propelled her at-home service business, she laid the groundwork for her next venture. When her sons were about three and five, she founded Drybar alongside her brother and then-husband to bring blow-drying services to the masses.
But as the business took off, Webb suffered a series of emotional difficulties—a failed marriage with the husband whom she worked alongside, and her mother’s death after a cancer diagnosis—that left her with depression.
Webb masked her feelings by hustling more at work—so much so she was featured on the cover of Inc. magazine and appeared as a guest judge on Shark Tank. Webb recalls feeling successful in one realm of her life, but a failure in another. She hated that she no longer had the picture-perfect image she had of herself and her family, she says. But Webb refused to slow down, which eventually led to burnout.
“You’re giving so much of yourself to the cause, and you can easily lose yourself,” she says. “My life kind of imploded along the way.”
Eventually, numbing didn’t work, especially when her son needed help. By year seven of the company, her eldest began to struggle with his own mental health and spent some time in rehab. She regrets not seeing the extent of his suffering earlier, she writes in her book. Feeling like she failed her family, Webb, for the first time in her life, had lost the motivation that propelled her professionally. She didn’t feel like herself, wasn’t caring for her body physically or mentally, and couldn’t get out of bed.
Alli Webb
Looking back, Webb tells Fortune her inability to delegate at work and, later, her lack of self-care was “very small thinking.” Webb, who has since gone to therapy, says she’s learned to take care of herself by admitting when things aren’t as glamorous as they seem instead of using working to avoid challenges.
She has a message for entrepreneurs: Don’t be afraid to be vulnerable, take a back seat when you need to, and check in with your ego.
How entrepreneurs can combat the dark side of success
Webb admits she began to crave praise and accolades: “Drybar was all the rage, and it was intoxicating. I loved it,” she says. “It’s a little bit of a drug. It’s like an addiction.”
Finding contentment beyond the brand was critical. “At some point, [things] will start to implode because you’re not taking care of yourself,” she says.
Learning to delegate and trust others served the company and allowed her to take care of herself. Webb, who is acts as more of a creative consultant now, feels lucky for her business’ far reach and the opportunities it’s provided.
She also hopes her memoir serves as a reminder to take a more balanced approach to ambition and success: “You’re not letting the great things that happen be this crazy high, and not allowing the bad things that happen take you down,” she says.
