Drybar propelled Alli Webb to fame, but her intense focus on the business led to significant personal sacrifices.
When considering whether women can balance successful careers, family, and personal lives, the harsh reality often says no, at least not simultaneously.
Alli Webb, the mind behind Drybar, learned this lesson firsthand as her business rapidly gained traction. In her recent bestselling book, The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself, she candidly discusses the price of fame and the obsession with brand building.
This challenge is particularly pronounced for female entrepreneurs. A recent study showed that 75% of small business owners worry about their mental health, with 56% having been diagnosed with anxiety, depression, or stress-related issues.
“I had my first child a year after marrying my first husband, followed by a second two-and-a-half years later, and then we launched Drybar a year and a half afterward. It was like baby after baby,” she shares.
Alli's expectations of managing this whirlwind were misaligned with reality. “I thought we’d open the shop at 9, close by five or six, and I’d pick up my kids,” she recalls. “But we had to start opening at seven due to demand. It turned into a massive operation, and we were ill-prepared and understaffed.”
When Business Takes Off
Today’s Drybar is a far cry from its origins. Initially, Webb offered mobile services, delivering $40 blowouts right at women’s homes. Unsurprisingly, the concept resonated with LA women, leading to more demand than she could handle. This prompted the opening of the first Drybar location in Brentwood, followed by a second shortly after. The buzz was instantaneous.
LISTEN: When Ambition Goes Too Far
Webb quickly found herself in interviews and events alongside celebrities. Initially, the fame was “exciting and wonderful.” Five years later, it transformed into an overwhelming pressure cooker. “We raised significant funds and hired a professional CEO, allowing me to step back,” Webb explains. “That’s when I realized my business had consumed my life, I was unhappy, and my marriage was deteriorating.”
As she mentioned on the Podcast, Webb recognized it was time to move on. “After opening 150 stores, it felt repetitive. While I loved it, I was itching for something new, with interesting opportunities on the horizon.”
Reflections After the Storm
Now twice divorced and reflecting on her journey post-Drybar, Alli Webb emphasizes the importance of sharing the untold struggles behind what may appear as a woman with it all: a successful career, luxurious lifestyle, and a beautiful family. “The messages I received from women were so uplifting that I decided to use my platform to discuss these realities,” Webb shares. “That’s why I’m committed to being open about my experiences.”
