Success is usually sold to us as a highlight reel of clean lines, crisp white marble, and exponential growth charts. We see the polished finish, not the sawdust on the floor. But when Alli Webb, the force behind the $100 million Drybar empire, released her memoir Messy by Alli Webb, she basically blew up that entire narrative. It’s not just a book about blowouts. Honestly, it’s a autopsy of what happens when your professional life skyrockets while your personal life feels like it’s stuck in a category five hurricane.
She built a brand that defined a decade of beauty culture. Then she walked away from her marriage. Then her kids struggled. Then the business she lived for started to look different from the inside out.
If you’re looking for a "10-step guide to scaling your startup," this isn't it. You've probably read plenty of those already. Instead, Webb gives us the grit. She talks about the guilt that eats you alive when you’re opening your 50th location while your home life is fracturing. It’s raw. It’s uncomfortable. It is, as the title suggests, incredibly messy.
The Illusion of Having It All
We’ve been fed this lie for years. The "Girlboss" era—which Webb was arguably a face of—suggested that if you just worked hard enough and had the right aesthetic, you could balance the scales perfectly. Messy by Alli Webb serves as the definitive end to that era.
Webb is surprisingly candid about the cost of Drybar. She started it with her husband, Cameron Webb, and her brother, Michael Landau. That’s a lot of family eggs in one very high-pressure basket. While the world saw a massive success story—over 150 locations and a product line in every Sephora—Alli was navigating a crumbling marriage and the intense pressure of being the "face" of a brand while feeling like a failure behind closed doors.
She doesn't sugarcoat the divorce. It wasn't a "conscious uncoupling" that was easy and breezy. It was painful. She writes about the reality of being a "non-custodial" parent for a period, a detail most public figures would hide out of fear of judgment. That's the thing about this book: it’s not trying to protect a reputation. It’s trying to tell the truth.
Why the "Overnight Success" Narrative is Trash
Drybar didn't just happen. It was a grind. Webb spent years as a professional stylist, driving from house to house with a trunk full of hair products. She noticed a gap: women wanted the salon experience without the $300 cut and color price tag.
- She saw a problem.
- She tested a small-scale solution (Straight-at-Home).
- She realized she couldn't scale herself, so she built a system.
But the "messy" part isn't the business logistics. It’s the emotional toll of the pivot. When you go from being a stylist to a CEO, your identity shifts. Webb discusses the friction of losing herself in the brand. When people see you as "the Drybar lady" instead of a human being, the isolation is real.
Messy by Alli Webb: The Business Lessons Nobody Teaches in B-School
Most business books focus on the "how-to." Webb focuses on the "at what cost." This is the nuance that makes the book a standout in the business category. She touches on the complexity of working with family, which is something many entrepreneurs face but few talk about with such honesty.
Managing the dynamics between a brother and a husband while trying to disrupt an entire industry? That’s a recipe for burnout. Webb reflects on the moments where the business became the only thing they talked about at the dinner table. There was no "off" switch.
The Identity Crisis of the Founder
One of the most profound parts of Messy by Alli Webb is the exploration of what happens after the "exit." When you sell a majority stake or step back from daily operations, who are you?
Webb found herself in a position many dream of: massive financial success and freedom. But that freedom brought a terrifying vacuum. She talks about her subsequent ventures—like Squeeze and Okay Humans—and the realization that you can't just "repeat" the magic of the first time without also repeating the work. And sometimes, you just don't have the same tank of gas left.
She also addresses the "Mom Guilt" factor without the usual platitudes. She’s honest about the fact that she wasn't always there. She missed things. She was distracted. And she has to live with that. It’s a refreshing departure from the "I just wake up at 4 AM and meditate so I can do everything" trope that dominates LinkedIn.
Depression, Rehab, and the Bottom
The book takes a sharp turn into territory most business memoirs avoid: clinical depression and the need for intensive help. Webb details her time in a treatment facility. This wasn't a "spa retreat" for the wealthy; it was a necessary intervention for a woman who had reached her breaking point.
- The Trigger: A combination of a second failed relationship and the realization that she couldn't "fix" her way out of her feelings.
- The Process: Stripping away the "Alli Webb" persona. No phones. No fans. Just the mess.
- The Takeaway: You cannot run a business effectively if your internal infrastructure is collapsed.
The vulnerability here is what makes the book rank so high in terms of emotional intelligence. She’s not asking for pity. She’s providing a roadmap for others who are currently "faking it" while they're breaking.
Real-World Takeaways from the Mess
If you’re reading this and feeling like your own life or business is a bit of a disaster, Webb’s story offers a few tactical insights that aren't your standard corporate fluff:
Boundaries aren't just for employees. Founders need them more. If your business is your only personality trait, you are in a dangerous position. Webb’s journey shows that the "hustle at all costs" mentality eventually sends a bill that you might not be able to pay.
The "Face" of the brand is a cage. If you are building a personal brand, you have to find a way to separate your worth from the company's valuation. When Drybar faced criticism or challenges, Alli took it personally. That’s not sustainable for a thirty-year career.
Family and Business require a contract. Not just a legal one, but an emotional one. If you work with family, you have to have "no-fly zones" where the business isn't allowed to enter. Webb’s experience suggests that without these, the business will eventually consume the relationship.
The Cultural Impact of Drybar vs. The Personal Toll
It’s hard to overstate how much Alli Webb changed the beauty industry. Before Drybar, you either went to a high-end salon for a full service or you did your hair at home. She created a "third space" for women. It was affordable luxury.
But Messy by Alli Webb forces us to look at the shadow side of that innovation. To create that "perfect" 45-minute experience for millions of women, the person at the top had to be perfect, too. Or at least appear to be.
She writes about the pressure of the "yellow" branding—the sunshine, the happiness, the "peace, love, and blowouts" motto. Living up to your own marketing is an exhausting way to exist when you're actually going through a divorce or dealing with a child in crisis.
What Most People Get Wrong About Success
We tend to think of success as a destination. We think, "Once I hit $10 million," or "Once I sell the company," I’ll be happy. Webb’s narrative proves that the "destination" often comes with its own set of problems.
She’s very open about the fact that money didn't fix her internal struggles. In fact, in some ways, it amplified them. It gave her the resources to seek help, yes, but it also created a high-stakes environment where she felt she couldn't afford to be human.
Actionable Insights: How to Navigate Your Own "Mess"
After reading Webb's account, it’s clear that the goal shouldn't be to avoid the mess, but to learn how to walk through it without losing your soul. If you are currently building a business or managing a high-pressure career, here is what you should actually do based on the hard-won lessons in this book:
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- Audit your "Why": Are you building a business because you love the work, or because you’re running away from something in your personal life? Webb admits that work was often an escape. Escapes eventually run out of road.
- Identify your "Board of Directors" for your life: Not for your company. Who are the 3 people who will tell you that you're spiraling before you hit the bottom? For Alli, it took hitting the bottom to realize she hadn't been listening to the warning signs.
- Practice "Selective Neglect": You cannot give 100% to your kids, your spouse, your business, and your health at the same time. Something will always be neglected. The key is to be intentional about what you are neglecting today, so it doesn't become a permanent casualty.
- Invest in "Internal Infrastructure": Therapy, coaching, and mental health days aren't "treats." They are maintenance. If you wouldn't let your equipment go 5 years without a service, don't do it to your brain.
- Own the Narrative: If things are going sideways, don't spend all your energy hiding it. Webb’s liberation came from finally saying, "This is messy." Once you name it, it loses its power over you.
Looking Ahead
Alli Webb is still an entrepreneur. She’s still a mother. She’s still a public figure. But she’s doing it differently now. The book ends not with a "happily ever after," but with a "happily ever after the work." She is proof that you can blow it all up, or have it all blow up around you, and still find a way to piece together something that feels authentic.
The legacy of Drybar is secure. But the legacy of Alli Webb, the person, is now tied to this radical honesty. In a world of filtered Instagram feeds and curated LinkedIn "wins," we need more mess. We need more people willing to admit that they have no idea what they're doing half the time, even when they're winning.
Stop waiting for the "clean" version of your life to start. It doesn't exist. Embrace the mess, handle the business, and for heaven's sake, take care of your head while you're doing it.
Next Steps for Your Career and Wellbeing
- Read the book: Don't just take the summary; feel the weight of the stories. It’s a fast read but a heavy one.
- Conduct a "Life Audit": Sit down and list the three areas of your life that feel the most chaotic. Pick one to address with a professional this week.
- Redefine your metrics: Instead of just tracking revenue or followers, start tracking your "peace of mind" score. If the revenue is up but the peace is at zero, you are technically in the red.
- Disconnect the Ego: Spend one hour a day doing something where you aren't "the boss" or "the expert." Be a student, be a hobbyist, or just be a person in the park.
Success is great. But sanity is better. Alli Webb had to learn that the hard way so we don't necessarily have to.