'I Almost Lost Myself': CEO Who Built $255M Hair Styling Empire Didn't Prioritise Mental Health

Alli Webb is an American businesswoman, entrepreneur, and writer best known for co-founding Drybar, a hairstyling service chain.

Webb worked for almost ten years, between 2010 and 2019, to transform her small business, a mobile hair styling side hustle, into a well-known chain of salons that developed into an empire comprising more than 160 locations across the globe.

After Helen of Troy Limited bought Drybar for roughly $255 million in 2019, Webb was recognised as a female founder and successful entrepreneur. Webb, who spoke to CNBC Make It, said she "knew my life was going to change forever."

However, Webb revealed that building a successful business is not always how it's built up to be. Just seven years after she founded Drybar, Webb claimed that "everything was starting to unravel for me personally."

During that time, Webb and her first spouse, Cameron Webb, also the co-founder of Drybar, got divorced after 16 years of marriage. Then, the entrepreneur lost her mother to cancer, and her teenage son sought addiction treatment.

Webb said that she buried herself in her work to avoid her personal issues until her problems became too big to ignore. The co-founder discussed this traumatic period in her book, "The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself," released in November 2023.

"I wish I had paid more attention while I was in it, so it didn't crash down the way it did," Webb said. "Sometimes our rock bottoms and everything crashing down is how we learn."
The co-founder claims that specifically, she learned how to identify and deal with burnout symptoms and prioritise her mental health without feeling like she had sacrificed her family or job.

The businesswoman, who would share words of wisdom in her Instagram account, shared two vital realizations she learned the hard way in the course of her stint in Drybar:

"I Didn't Address My Issues"

Before she sold Drybar in 2018, Webb revealed in her book that she experienced "great depression." The self-diagnosed depression included symptoms of physical and mental burnout and self-inflicted guilt - stemming from her decision to end her marriage and her son's substance abuse.

"Am I ruining my family? Our lives?" she wrote in her book.

Webb went on to note that her inability to address the issues in her personal life and how they affected her at the time only intensified her mental struggles. Instead of facing her problems head-on, Webb used Drybar to delay recognising the impact of her divorce on her two children or confronting her thoughts about her marriage deteriorating.

"I was very [much] on this fast track and not paying attention," said Webb, going on to explain: "We distract ourselves when we don't want to deal with s---. Every human does it. I had to look at some stuff that I was unwilling to look at for a long time and had just hoped it would go away. But it never did."

The co-founder revealed a conversation with Brené Brown, an American professor, social worker and author who spent two decades studying courage, vulnerability, shame, and empathy, ultimately improving Webb's mental health.

According to Webb, through Brown, she was made aware that she had not given enough thought to the pain caused by her divorce, the loss of her mother, and her guilt for her son's troubles. From then on, the co-founder started participating in activities to boost a person's well-being, such as journaling, meditation, regular exercise, and therapy.

Webb has since publicly shared that she favours journaling and therapy. "Writing down your thoughts and feelings can often help people process their emotions or manage their depression and anxiety. Talking it through with somebody is a big deal," she said. "It's like, get that stuff out of your head and onto paper. That, in and of itself, is so alleviating when you're dealing with something hard."

"I Didn't Prioritise My Mental Health"

Following Drybar, Webb co-founded many businesses, including the massage firm Squeeze. Webb is also the president of Canopy, a manufacturer of humidifiers.

As her career has developed, the co-founder said that having a solid support network and financial security makes it easier to prioritise her mental health, and she no longer lets her work get in the way.

Webb advised everyone, including her present employees, to stop approaching their work as she did at Drybar.

"As long as you're getting everything done, I don't care how many physical hours you work," Webb urged. "That's the mind shift that I hope to see in the world more. It's like, let's get our work done. But let's also enjoy our lives."

Since releasing her entrepreneur memoir, which has gained a four-star rating on Amazon, Webb has become a trusted ally to other entrepreneurs. One reader, Jeni Castro called Webb an inspiration, noting: "As a business owner and entrepreneur it's nice connecting with stories to remind us that we're not alone. I love her drive and vision and can't wait to see what she does next!"