Earn Entrepreneurship

The Messy Truth Behind Building A Multi-Million Dollar Business

Haley Paskalides  |  June 26, 2024

Drybar made Alli Webb an overnight sensation, but focusing on her business above all else ended up costing her everything.

When we talk about the question of whether women can have it “all,” successful careers, thriving marriages, and families, the messy truth is pretty much always, no, at least not all at the same time. 

That’s a lesson that Alli Webb, founder of Drybar experienced firsthand when her business blew up seemingly overnight. In her new bestselling book, The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself she shares what fame, attention, and obsession with building a brand cost her. 

This burden falls especially hard on female entrepreneurs —- a new study found that 75 percent of small business owners are concerned about their mental health, and 56 percent have been diagnosed with anxiety, depression, or stress-related problems by a doctor or mental health professional.

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“I had my first son a year after I got married to my first husband and then my second son two-and-a half years later and then a year-and-a-half after that we started Drybar. So, it was like baby, after baby, after baby,” she says. 

Her expectations about what it would take to sustain that sort of a roller coaster were completely out of whack with reality.  “I thought I’d opened the shop at 9, we’d close it around five or six, and I’d pick up my kids,” Alli Webb says. “But we had to start opening the shop at seven because of the demand. And it just became this massive thing, we were so underprepared and understaffed.”

When A Business Booms

In fact, the Drybar you know today bears little resemblance to the one Webb started.  Initially, Drybar was a mobile business where she would go to women’s houses and give them a $40 blowout. Not surprisingly, the women of LA — where Webb launched — took quickly to the idea.  She immediately had more demand than she was prepared to take on and opened the first location of Drybar in Brentwood.   A second location followed not too long after.  And the buzz came right on its heels.

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Webb immediately started getting interviews and invited to events where she was surrounded by celebrities. Initially, the fame was “intoxicating and amazing.”  A half-decade later, it had become a pressure cooker. “We raised a bunch of money and we brought in a professional CEO, so I was able to take a little bit of a step back,” Webb says. “Because of that, I realized that the business was my life, I wasn’t happy, and my marriage was struggling and really in trouble.”  

As she explained on the HerMoney Podcast, Webb decided it was time to go. “We had opened 150 stores and it was like we were doing the same thing over and over again,” Webb says. “While I loved it, I was just starting to kind of itch to move on, to do something else  and I had a lot of interesting opportunities coming my way.”

The View From The Other Side

Now twice divorced and on the other side of selling Drybar, Alli Webb has found that it’s important for her to share the messy truth behind what could be perceived as a woman who “had it all,” a thriving career, a glamorous life, and a gorgeous family.  The notes that I was getting from women were so inspiring to me that I decided to use my platform for good to talk about these things,” Webb says. “Which is why I’ve chosen to kind of let it all hang out.”


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All advisory services offered through Financial Engines Advisors L.L.C. (FEA), a federally registered investment advisor. Results are not guaranteed. AM1969416

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