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.

Website: itsmessy.com

Instagram: @alliwebb

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INTRO

Welcome to She Wears the Pants, the podcast that celebrates and empowers female founders at every stage of their journey — from launching groundbreaking startups to creating lasting legacies.

I’m Ashley Deland, a business advisor with over a decade of experience driving over 25 million in revenue for my clients and collaborating with top industry leaders. Together, we’re going to redefine what’s possible — because it’s not just about wearing the pants, it’s about rewriting the rules and becoming unstoppable.

Welcome back to She Wears the Pants, the place where high-growth women come to build companies that match their calling. I’m your host, Ashley Deland, and today’s guest is a rare leader whose work reshaped an entire industry and redefined what it meant to turn frustration into a category creation.

Alli doesn’t just build brands. She reimagines what’s possible and what ambitious women in business can look like. Alli, welcome to She Wears the Pants.

CONVERSATION

Thank you. Thanks so much for having me.

Do you ever get tired of hearing your own intro?

No.

(laughs) No?

No. You’re just trucking along, doing your thing, and it’s easy to forget all the stuff you’ve done. It’s nice to be reminded because I don’t think about that very often. When you hear it, it’s like, “Oh right, I did that stuff.” That’s pretty cool.

It’s funny because we’re in the day-to-day grind of being a founder and a mother. We don’t always look like this. Most days it’s a messy bun running after a three-year-old.

Yes. Life gets heavy.

Tell us a little bit about your background and how you got started in the entrepreneurial world.

I think it was kind of in my blood. My parents were entrepreneurs. My brother and I worked in their business when we were kids — a clothing business in South Florida. I grew up watching them run a business.

I didn’t think, “I want to grow up and start my own business.” My jobs were always working for other people, which really served me well and laid the groundwork for what I ended up doing.

When I decided to go to beauty school — I’m a longtime hairstylist, which is really how Drybar came to be — I worked for a salon owner named Sean Peters. I was watching him because I wanted to learn hair, mostly blowouts. What I didn’t realize until years later was that he was running the shop from the chair. Problems came to him constantly, and he handled them in real time.

I didn’t think I was paying attention to how you run a business, but I thought about it constantly while building Drybar — the way he did things and what I absorbed.

I didn’t go to college or get a business degree. I hated school. School is great if that’s your path — it just wasn’t mine. I moved to New York City and started working. All of those jobs prepared me for who I ultimately became, and the experiences helped fine-tune my approach to entrepreneurship.

It’s all those small things over time that you don’t notice in the moment, but they become fundamental.

Exactly. I tell my kids and anyone who will listen to pay attention to what you actually love doing.

When my kids were the age yours is now, that’s when I started Drybar. I thought I’d be a stay-at-home mom. I love my kids deeply, and I wanted to be a mom. I just also wanted something for myself.

That fulfillment matters. You know when you’re in the right spot. And that can happen at any age. Whatever fulfills you, the experiences along the way prepare you for what comes later.

Talk to me about the moment you had the kahunas to say, “I’m doing this and I’m giving it my all.” What was the turning point?

I don’t think I operate in fear. That’s probably the big difference between someone who wants to be an entrepreneur and someone who doesn’t. I always thought, what’s the worst that could happen? We could lose money. No one is going to die if the business doesn’t work.

I wasn’t scared of failing. I believed it could work, but I didn’t know. I felt like we get one go-round. Go do the thing you really want to do.

I’ve always had that compass — I’m going to do what I want to do, not what everyone thinks I should do.

That’s the kahunas — trusting yourself and taking the chance.

Exactly. Nobody really cares what anyone else is doing. Everyone is focused on their own life.

I’m building again now after selling Drybar. I want it to work, but fear won’t stop me. Nobody knows what’s going to land. You just keep going.

What has success or failure taught you about who you had to become?

Fearlessness and leadership. When we first started Drybar, I didn’t know how to lead. I was lost. Over time, with feedback from people I trusted, I learned the leader I wanted to be and the impact I wanted to have.

I used to walk into stores and get angry if things weren’t right. I learned how to channel that energy better.

Who did you have to stop being, and who did you have to become?

My brother once told me everyone was scared of me. It was hard to hear, but I understood it. My obsession with perfection came across as harsh.

That obsession was a superpower — founders care differently — but fear doesn’t build culture. I had to change my approach.

People always ask me about what’s been the greatest thing about this journey. To me, that’s one of the things that really resonates — I did make people feel really good. And that, I think, is the holy grail of all we do.

I agree with you. The legacy component is not always the product or service or what you’re delivering. It’s how people feel.

I love building. By the time we sold Drybar, we were ten years in. It wasn’t a small business anymore.

At the same time, my personal life unraveled. My mom passed away quickly from lung cancer. My son went into rehab. I got divorced.

The business didn’t need me to survive anymore, and that gave me space to deal with my personal life. I felt like I had done what I wanted to do and was ready for the next thing.

When you wrote The Messy Truth, did it ever feel unsafe sharing so much?

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. That’s why I shared it.

When you realize your story is in service to others, everything changes.

Exactly. Helping others feels the best.

From early entrepreneurship to building again now, what’s been the hardest part?

Learning who I am and what feels good to me. Over time, I’ve learned what I’ll tolerate and what I won’t.

I moved to Nashville recently. I didn’t need permission.

Where did the idea for Messy come from?

During COVID, I stopped blow-drying my hair and noticed how damaged it had been. I started experimenting with my natural texture.

I paired haircare with mantras like “I am enough.” Messy is about embracing what you already have.

What message do you want future generations of women in business to hear?

Don’t let anyone else control your destiny. Trust your instinct. Surround yourself with people who believe in you and tell you the truth.

Where can listeners find you?

You can find Messy at itsmessy.com and I’m @alliwebb on Instagram.

OUTRO

Thank you for tuning into another episode of She Wears the Pants. If this resonated, share it with a friend, rate and review the show, and subscribe so you never miss an episode.

Until next time — keep rising into the woman your calling requires.