Who You Have to Become to Build What You’re Here to Build with Alli Webb
On This Episode
You don’t need permission to build what you’re here to build…
You need the courage to trust yourself.
In this episode of She Wears the Pants, Ashley Deland is joined by Alli Webb, New York Times bestselling author, beauty industry pioneer, Shark Tank guest and the founder who turned one simple idea, blowouts only, into Drybar, a category-defining brand. Together, they unpack what it really takes for a high-growth woman to build something iconic, lead at scale, and evolve without losing herself in the process.
This conversation goes beyond the highlights. Alli shares why she doesn’t operate from fear, what she had to change about her leadership as the company grew, and what it looks like to release a business when the startup season ends, especially as life gets heavy behind the scenes.
If you’re a woman building in real time, balancing ambition, identity, leadership, and the emotional cost of growth, this episode will help you refine your inner compass, strengthen your standards, and lead with more self-trust than noise.
In this episode, you’ll learn how to:
- Trust your instinct as your most reliable leadership tool, and move without needing permission
- Lead people with clarity and steadiness as your company scales
- Recognize when a season has ended, and exit with integrity rather than guilt
- Separate your identity from outcomes so success never becomes your only source of safety
- Build what’s next from self-knowledge, not external expectation
By the end, you’ll walk away with a clearer understanding of the woman you’re becoming, and the internal leadership required to build what lasts.
Meet Alli
Alli Webb is a serial entrepreneur, New York Times bestselling author, Shark Tank guest judge, and beauty industry pioneer. She is the founder of Drybar and the creator of Messy, a haircare line designed to support healthy, lived-in texture and a more freeing relationship with beauty.
What Alli Webb Taught Me About Building a Business Without Fear
She Wears the Pants | Ashley Deland interviews Drybar founder Alli Webb
Most founders talk about courage in hindsight. Alli Webb lived it in real time. In this episode of She Wears the Pants, Alli joins host Ashley Deland for an honest conversation about building Drybar from a simple idea into a national salon empire, the very personal unraveling that coincided with its peak, and what it actually takes to build again after you’ve already won.
If you’re a woman building a service business and wondering whether the sacrifice is worth it, or whether the next chapter is even possible, this one is for you.
She Didn’t Plan to Be an Entrepreneur. She Just Paid Attention.
Alli grew up watching her parents run a clothing business in South Florida. She didn’t study business. She didn’t have a five-year plan. What she had was a front-row seat to how a business actually operates, and a habit of absorbing everything around her.
“I didn’t think I was paying attention to how you run a business,” she told Ashley. But years later, building Drybar, she kept returning to what she’d watched her first salon employer do. He ran the shop from the chair. He handled problems in real time. He didn’t outsource his presence.
This is one of the most underrated business lessons for women entrepreneurs: the experiences you dismiss as “just jobs” are often the most formative education you’ll get.
Fear Isn’t What Holds Most Founders Back
When Ashley asked about the moment Alli committed fully to Drybar, her answer cut through the usual narrative about courage and risk. “I don’t think I operate in fear,” she said. “What’s the worst that could happen? We could lose money. No one is going to die if the business doesn’t work.”
That reframe, loss as recoverable rather than catastrophic, is something a lot of ambitious women have never given themselves permission to hold. The stakes feel enormous because we’ve made them enormous. Alli’s lens is simpler: you get one go-round. Go do the thing.
She’s applying that same lens now, building again after Drybar’s sale. “I want it to work, but fear won’t stop me. Nobody knows what’s going to land. You just keep going.”
The Leadership Gap Nobody Warns You About
One of the most honest moments in this conversation came when Alli talked about learning to lead. Early on, her perfectionism read as intimidation. Her brother told her everyone was scared of her. It was hard to hear. It was also exactly what she needed.
“My obsession with perfection came across as harsh,” she said. “That obsession was a superpower, but fear doesn’t build culture.”
Founders care differently than employees. That gap in caring is often mistaken for severity. The work isn’t eliminating the standard. It’s learning how to communicate it in a way that builds people up instead of shutting them down.
When the Business Succeeds and Everything Else Falls Apart
Alli didn’t gloss over what was happening in her personal life during Drybar’s peak. Her mother died quickly from lung cancer. Her son went into rehab. Her marriage ended. The business didn’t need her the way it once had, and in some ways, that created the space to face everything else.
“I felt like I had done what I wanted to do and was ready for the next thing.” Not defeat. Completion.
This is something Ashley named clearly in their exchange: the legacy of what you build isn’t always the product or the revenue. It’s how people feel when they walk away from an interaction with your brand, your business, your leadership.
Telling the Real Story
When Alli wrote The Messy Truth, she made a deliberate choice to be honest about the hard parts. When Ashley asked if that ever felt unsafe, Alli’s answer was clear: “I felt an obligation to tell the real story. When I started Drybar, there weren’t many visible female founder role models. The more honest I became, the more women told me it helped them feel less alone.”
This is the value of stories told without the filter. Polished success narratives are everywhere. Women building businesses in real time need something more grounded.
What She’d Tell the Next Generation
“Don’t let anyone else control your destiny. Trust your instinct. Surround yourself with people who believe in you and tell you the truth.”
Those two things, belief and honesty, aren’t opposites. The people who will actually support your growth are the ones who do both at the same time.
Listen to the Full Episode
This conversation between Ashley Deland and Alli Webb is the kind that stays with you. Catch the full episode of She Wears the Pants wherever you listen to podcasts. If it resonates, share it with a founder who needs to hear it.
Find Alli’s brand Messy at itsmessy.com and follow her at @alliwebb on Instagram.
