Success looks great on Instagram. We see the blowout, the yellow branding, the $255 million exit, and the "Forbes" covers. But Alli Webb’s memoir, Messy by Alli Webb, feels like a long, deep breath from someone who spent years holding her stomach in for the camera. It’s not a business manual. If you’re looking for a step-by-step guide on how to scale a franchise, you’re going to be disappointed. This is about the cost of that scaling.
It’s about the divorce. The parenting guilt. The reckoning with a son's sobriety journey.
Honestly, it's about the stuff that happens when the blow dryer turns off and the room goes quiet. Webb has been the face of "having it all" for over a decade, but this book is a deliberate attempt to dismantle that specific, exhausting pedestal.
Why Messy by Alli Webb is Rattling the "Girlboss" Narrative
The timing of this book matters. We’ve seen the rise and fall of the "Girlboss" era—that mid-2010s aesthetic of pink power suits and relentless productivity. Webb was at the epicenter of it. She didn't just start a business; she created a category. But while she was building an empire that focused on making women feel "pretty," her personal life was often in a state of absolute, crushing chaos.
Messy by Alli Webb doesn't shy away from the irony. It’s weird, right? You’re the queen of aesthetics, yet your world is falling apart. She writes about the 2018-2019 period with a level of grit that feels startlingly real for a celebrity entrepreneur. People usually wait twenty years to talk about their "dark period." Webb did it while the paint was still drying.
She talks about her divorce from Cameron Webb. They weren't just a couple; they were business partners. When that dissolved, it wasn't just a legal filing; it was a systemic shock to the brand they built together. Most business books gloss over the "personal stuff" as a footnote. Webb makes it the lead.
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The Reality of "The Exit"
Everyone wants the big exit. In 2019, Helen of Troy acquired Drybar’s products division for $255 million. On paper, that’s the dream. It’s the finish line.
But in the book, Webb describes the aftermath as a confusing void. There’s this misconception that money fixes the internal static. It doesn't. It just gives you a more expensive place to sit while you deal with it. She’s very open about the fact that her identity was so wrapped up in being "The Drybar Lady" that she didn't know who she was without the constant noise of growth.
Parenting in the Public Eye
The most visceral parts of the book deal with her son, Ren. It’s heavy. She discusses his struggles with addiction and the harrowing experience of being a "successful" person who feels like a total failure at home. This isn't just "mom guilt." This is the kind of trauma that makes a business meeting about Q4 projections feel utterly meaningless.
She recalls moments of sitting in board meetings while her mind was at a rehab facility. That’s the "messy" she’s talking about. It’s the cognitive dissonance of being a professional icon while being a grieving, terrified parent in private.
The Business Lessons Nobody Wants to Teach
Usually, when people talk about Messy by Alli Webb, they focus on the drama. But there is a massive business lesson hidden in the vulnerability: the danger of the "Face of the Brand" trap.
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When you are the brand, you don't get to have a bad day. You don't get to look "messy."
- The Vulnerability Hangover: Webb discusses the fear of letting the public see the cracks. She realized that by maintaining the "perfect" image, she was actually alienating the very women she wanted to serve.
- Delegation of Soul: One of the most interesting threads is how she learned that you can't delegate your mental health. You can hire a CEO (which she did), you can hire a PR team, but you can't outsource the emotional labor of your own life.
- The Pivot to Authenticity: Post-Drybar, Webb has moved into new ventures like Squeeze and Beckley. But she’s doing it differently now. The book marks the transition from "polished founder" to "human founder."
It’s Not a "How-To," It’s a "How-It-Felt"
Most business memoirs follow a predictable arc. Problem, solution, growth, victory.
Webb breaks that.
The arc here is more like: Success, hidden pain, public victory, private collapse, slow rebuilding.
She’s kinda over the idea that we need to be "slaying" all the time. It’s refreshing. It’s also a bit scary for people who still believe in the myth of the perfect balance. Webb basically looks at the camera and says, "Balance is a lie, and here are the receipts."
What We Get Wrong About Alli Webb
People think she just "got lucky" with a hair trend. They forget she was a professional stylist first. She spent years in the trenches. She knew the texture of hair. She knew why women felt intimidated by high-end salons.
The "messiness" she talks about in the book also applies to the early days of the business. It wasn't a sleek machine. It was a scrappy, desperate scramble. She recounts the early days of mobile blowouts—driving around L.A., dragging her kids along, trying to make it work. It was never clean. We just saw the yellow umbrellas and assumed it was.
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The Post-Book Evolution
Since the release of the book, Webb has become a bit of a champion for "radical honesty" in the entrepreneurial space. She’s active on social media, but the tone has shifted. It’s less about the perfect hair and more about the "honest" day.
She’s also been vocal about her relationship with Adrian Koehler and their podcast, "Raising the Bar." It’s a continuation of the themes in the book—discussing the friction between high performance and high-quality relationships.
Actionable Insights From the Mess
If you're reading this because you feel like your life is a disaster while your LinkedIn looks great, here is what you should actually take away from Webb’s journey:
- Audit Your Identity: If your business disappeared tomorrow, who are you? Webb struggled because she was "Alli from Drybar." Don't let your tax ID become your personality.
- The "One Thing" Fallacy: You can have the biggest business in the world, but if your internal world is vibrating with anxiety, you aren't winning. Webb’s book is a plea to prioritize the internal over the external.
- Stop Curating the Struggle: When Webb started being honest about her son and her divorce, she found a deeper connection with her audience than she ever did with a hair tutorial. Vulnerability is a better marketing tool than perfection.
- Define Your Own "Enough": The exit didn't make her happy. The growth didn't make her happy. Happiness came from the messy work of therapy, boundaries, and admitting she didn't have it all figured out.
Messy by Alli Webb is essentially a permission slip. It's a permission slip to be a high-achiever who is also a work in progress. It tells us that you can build something world-changing and still be a bit of a wreck sometimes. And honestly? That's a lot more inspiring than a "perfect" success story.
The next step isn't to go out and buy a franchise. It's to look at the parts of your life you're currently hiding—the parts that feel "messy"—and realize they might be the most important things you have. Start by being honest about one thing today that isn't "fine." That’s where the real growth starts.