What Comes After a $275 Million Brand? Drybar Founder Alli Webb on Messy

What do you do after building one of the most iconic beauty brands in the world?

If you're Alli Webb, you start over.

In this episode, Cris Gordon sits down with the founder of Drybar and Messy to unpack what really changed between building a $275 million business and launching a brand in today's creator-first world. They discuss why authenticity is becoming every brand's biggest advantage, what founders get wrong about building community, the lessons Alli carried from Drybar (and the ones she left behind), and why embracing the messy middle might be the smartest business move you can make.

Whether you're building a business, growing a personal brand, or looking for your next big chapter, this conversation is packed with honest insights, practical advice, and the behind-the-scenes stories you won't hear anywhere else.

New podcast episodes drop every other Wednesday, hosted by Cris Gordon, Head of Beauty at MMC.  

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Transcript

SPEAKER_02 0:00

I remember in those early days of dry bar people being like, you created a new category in a multi-billion dollar industry. I didn't really mean to do that. I just did it. I'm not the only woman out there who's like, I just don't want to be like such a slave to my hair. I just wanted there to be another option for women to feel really beautiful. Embrace the hair that you have. That's that's the tagline, right? I'm just doing what feels right to me in this like stage of my life and my career and my hair.

SPEAKER_00 0:29

Messy and all the things that you're building. What would you say is something that you really either hope happens or that you're really excited about looking forward to the future? Well, you know, I really think it's a brand new day, and you know what that means. It's time for another episode of Brandedly Speaking. I'm your host, Chris Gordon, and today we're sitting down with the legendary Allie Webb. Most of the world knows her as the visionary hairstylist and mom who built Drybar into a household name. But today, we're looking past the perfect blowouts. Allie's here to talk about the reality of life after selling an iconic business, the journey of finding her identity beyond her title, and her incredible new brand, Messi. And we get real about some plastic surgery updates. This conversation gets into chapters most people keep private, from navigating major life transitions to defying aging standards and choosing authenticity over an image of perfection. And what I love about this episode is that Allie and I have known each other for many, many years. She was the golden standard when it comes to PR branding and building something in beauty that had a lifetime of success. And so what I want you to learn from her isn't just a one-parter, it's a two-parter. And we had so many amazing conversations that need an extension. So here's a little tease, and we'll have a part two soon. All right, Allie. So I'm really excited because obviously you and I have known each other for a long time. I have watched your career as a beauty PR girl for the last two decades for literally my entire life. Like I and I loved it and I idolized you. And I was literally, it was actually like my dream to work with you. So I'm my dream is being realized, which is the most fun thing. Um, and the reason is because you built something so iconic, and now you're in the middle of building again. You built Dry Bar. I think there was all this like amazing news and this huge success around the brand. It is still a such an iconic brand. And now you're onto building messy. And that's really what I want to focus on because I think you're in your like next chapter in so many ways. I think like you're embracing this like new part of your life in a lot of different ways, like new home, new everything, new brand. My question for you though is is it feel like a lot of pressure after you built and exited for what 225, 250 million?

SPEAKER_02 2:39

Well, 275 million.

SPEAKER_00 2:40

Okay, 275 million exited for. And now you're building another brand. Does it ever feel like a lot of pressure to build again?

SPEAKER_02 2:47

Yes, it it definitely is. I mean, I think in the beginning when I decided to start Messi, which was quite quite a pivot from what I was doing with Dry Bar, you know, it was like I, you know, for 16 years I built a brand about, you know, the perfect blowout, and now I'm like, well, not so much anymore, you know. And so I, you know, I felt like it it was good because it was so different, and I and you know, my advice to other entrepreneurs is always like, you know, take something and make it better, you know, and for me it was like learning to embrace this hair instead of like the perfect blowout. Um but there is a lot of pressure because you know what I don't want it to feel like is like it has, you know, it's it's just dry bar is such a as you said, an iconic brand, everybody knows it, it's a household name. And so to build another brand that has that kind of cachet is is hard, you know. And I'm actually like, you know, Messi is about a year old and I'm and I'm learning that. I mean, I when we opened Drybar, it was like there was nothing of its kind. So you know, and we had to do it right, and it wasn't like we just got lucky, it was a lot of hard work and a lot of very intentional decisions, and and that is how I've approached Messi, which is like I'm look I looked around at all the other hair brands, and I'm like, nothing is really speaking to it like we are. You know, but that being said, it's still like we're entering into a market that is highly, highly saturated. I mean, you know, there's eight million hair brands, and there's you know, there's like just skin and fragrance and hair brands, there's just so many of them where you know, getting market share in dry bar was so much easier because there was nothing. Yeah, you know, and I was able to create this brand that didn't exist, you know. And I and I remember in those early days of dry bar people being like, You created, you know, a new category in a multi-billion dollar industry, which was pretty awesome. I didn't really mean to do that, I just did it, you know.

SPEAKER_00 4:48

Be you know, and so now everyone's trying to figure out how to do that, and it's like almost like more contracted.

SPEAKER_02 4:55

And that's the thing, I'm not I wasn't trying to figure out how to do it then, and and I'm not necessarily trying to figure out how to do it now. I'm just doing what feels right to me in this like stage of my life and my career and my hair, you know. So it but yeah, there's a lot of pressure. I really am trying to not like feed into that pressure of like and it's like it doesn't have to be as big as dry bar. I you know, I really do think there is like something very poignant and poetic about messy and this like messy revolution that we're trying to get women to embrace. And it happens to be well timed, you know. It's like I'm not the only woman out there who's like, oh, I just don't want to be like, you know, such a slave to my hair and like the blowout and this and that, and you know, and so I'm I'm trying to get women to embrace it more and more, and I think it's it's a challenge because they've known one thing for so long, which listen, I helped which you helped to create that narrative that that narrative, and and now I'm just saying, like, let's just try it another way. And and not to say I'm anti-blowout or anti-dry bar, I mean it's my legacy, but I just wanted there to be another option for women to feel really beautiful, kind of like in their own skin, in their own hair, you know, and and whatever that takes.

SPEAKER_00 6:08

Yeah. And do you feel like I mean you've helped so many women, you've been a mentor to so many, you've had your messy collective, you have your book, and you have so many of these amazing outlets to kind of teach people the lessons that you've learned. Is there an unexpected lesson that you've learned already in this next phase of your journey that kind of like took you by surprise?

SPEAKER_02 6:25

Yeah, I mean, there's lots of lessons, you know. It's like I said, like building messy in such a saturated space is is harder than like I said, it was building dry bar. So I'm you know, we've and we just I mean, we when we launched dry bar product lines, it was like in 2012. A very it was such a different world, and like you know, social media was was nowhere near nowhere near what it is now. So, you know, and and the whole influencer world didn't really exist back then. It was like we launched in Sephora, and Sephora was the one who was telling consumers what to buy, like they were informing all of that. Now it's largely influencers, and then you have to pay influencers and you have to like you know, and it's like how do you do it in a way that feels authentic and organic, not like this person's being paid to do this thing. So so yeah, and I feel a little like aged out a little because I'm not like 20. Well, gosh, I was 35 years old when I started dry bar, but it it's it's it's a different world, so it's a lot of learnings that that are different for me now of like getting, you know, making sure we're we're staying relevant, we're doing all the right things, you know, and and I have I have an amazing team who's a lot younger than me. Um, and you know, just trying to learn the ropes. I mean, you you see what I'm posting.

SPEAKER_00 7:43

I actually I love your content. I love it, and I what I love though about you is that you're willing to try it. And I was just having a conversation about how so many people are s get so stuck in their ways because either they were successful in one area and they're like, this is the way of and now the way of the world is so different, and they're not willing to change. And I think that that's exactly it.

SPEAKER_02 8:01

It's like you have to be willing, no matter what you're doing, is like look around and be like, what do I need to do here? And and really frankly, like what you know, it's like we need to get what I'm trying to do is get women to embrace the hair that they have. That's that's the tagline, right? Embrace the hair that you have. And so how do I do that? And it's and it's not the same way I did it at dry bar. So it is a lot of learning and there is a lot of like trial and error. And and listen, that was true for dry bar too. You know, it's like I think I just posted something the other day, it was actually yesterday, I don't know if you've seen it yet, but I was like, you know, people don't remember or might not even know that when we we opened that first shop in Brentwood, it was like gangbusters and crazy, and then we opened the second and third location and it was crickets. It was like nobody was there, and we were like, are we really just a one-hit wonder? And is like that it? But it wasn't. It took a lot of marketing effort. It took, even though we had had a tremendous amount of PR, and you know, we're very quickly like the darling of the industry, but still nobody was coming to Studio City or West Hollywood, if you can believe that, because now they're our two busiest locations. But it took a lot, you know, we were doing groupons, I was going to like all these like schools and like setting up a table and selling discount blowouts. Like, we did a lot of marketing to get those, to get people in those women in those doors. And and it wasn't overnight, you know. And looking back, it seems like oh, dry bar was an overnight success. It really wasn't. So it's actually like a reminder for myself that like you have to pull a lot of levers, you have to try a lot of things to see what's gonna work and grab. And it's and yes, part of it is like getting something that goes viral and and that, but I but I in what I've learned so far, it's like it's not just one thing happening, it's like a multitude of things that have to happen. And and it there's like, I don't you probably know this better than me, but it's like you have to get your product like in front of somebody like eight times. Eight times before they'll actually consider buying it, you know, which is like I mean, even though And yet the funnel has also collapsed.

SPEAKER_00 9:57

So like people will buy faster if it's all down the right stream.

SPEAKER_02 10:00

I feel like I'm a little too old for all this, but you know, luckily I have a young team that's like, this is just how it is now, and I'm listening to them, which is also like definitely something I learned in the dry bar era, but it's like bringing on people who are good and better at things that you're not. And in in my case, like I really know hair and I really understand like product development, and I'm very proud. And if you read the reviews on on Sephora or our website of our product reviews, there are phenomenal.

SPEAKER_00 10:27

Messi is amazing. Thank you. Like it is amazing, and it takes a lot for me to embrace my natural hair. A lot.

SPEAKER_02 10:33

But even like your, you know, I know you blow out your hair because your hair is very, very curly, right?

SPEAKER_00 10:36

But it's like our rough dry cream, which is really like when I was in the South of France, it was like I was using, I was like, oh my God, it was like a lifesaver. And I and again, it takes a lot for meatables frizz. Yeah, but it takes a lot for me to embrace my natural hair. But I think that's probably why it's a little bit harder to educate the consumer and move the consumer over the same kind of challenge that you had with dry bar. You're having again kind of in the new age, but around a topic that is deeply personal. I mean, hair is I've been in beauty for a long time, and hair is super, super personal. It really is relationship to my own.

SPEAKER_02 11:09

And I think even for me, it took me a while. So I really understand that it takes, you know, the everyday consumer a while. Like when I I remember very vividly the first event I went to, you know, I do a lot of speaking, and I remember the first thing that I spoke at when I wore my hair like this. And I remember people being like, whoa, like she's a trainer, where's her blowout? Yeah, I mean, and they're like, Wow, your hair looks amazing. And I actually weirdly prefer my hair like this. And I say weirdly because I've literally spent my whole life in home. I love it.

SPEAKER_00 11:38

I think it's like sexy and cool and careful.

SPEAKER_02 11:40

You know what's funny is we keep seeing like videos, and I've got to find more of these, of like uh girls who are like when they meet a guy and their hair's blown out, and then they they start dating for a while, and then they all of a sudden like start letting their hair be natural, and he's like, I love it. And I've talked to so many men who are like, my wife or my girlfriend has naturally curly hair, but she never wears it that way, and I wish she would.

SPEAKER_00 11:59

Even when I was my husband says it all the time, right?

SPEAKER_02 12:02

Wear your hair natural. Yeah, it's funny, you know. And I mean, my boyfriend loves my hair like this too. He loves the variety, like he loves that sometimes it's straight and sometimes it's like this.

SPEAKER_00 12:10

But yeah, my husband's like, which Chris am I gonna get today?

SPEAKER_02 12:12

And it's fun, you know, it's like you have like a different, it's like a the spice of life. And and even with like when I was in Necker Island, and not to be like bougie and name-droppy, but you know, I I I actually was having a conversation with Richard Branson, who like his late wife who recently passed away, he was like mad at me. He's like, You ruined my, you know, and I was like, What? And he's like, Well, my when I met my wife, she always wore her hair curly and I loved it curly. He's like, and then, you know, years later, all she always had it blown out, and I much preferred it curly. And I was like, You gotta be kidding me. And I was just launching Messi, you know, and so there is that undertone, and and and for me, it's always been like Mary Kate and Ashley Olson, you know, who was like, I feel like I don't even know if everybody, if like the younger generation even knows who they are.

SPEAKER_00 12:55

Oh my god, I can't even, don't even say that out.

SPEAKER_02 12:57

I know, but it's like their hair, you know, and that just and you see it more in ads, like it's definitely a thing now. And I think it's also we're in the generation of, you know, women who are like air drying, you know, which for me, air drying is tough because, and I'm sure for you too, it's like if your hair is really curly and frizzy and you just let it dry and like leave it up to the hair gods, it's it's it's kind of a crapsheet we're doing. That is act is exactly why, you know, I made this product that will help you like tame the frizz and like the twisting method or braiding it or just doing something to like help calm down that frizz. And and that, you know, and so listen, it's like I think there's there's room for all of it, but it's it's definitely an interesting but amazing challenge. Like I'm so proud of it and I'm proud of what we're doing, what we stand for.

SPEAKER_00 13:43

I love the packaging and I I I like love the logo and I love the sayings, and I I think that it really speaks to this evolution that you've had as a woman. And I think that you've been showing the world about embracing every part of who you are and be transparent. You're so transparent. I actually love it. You're like so no BS. I'm like, no, and I love I think that's I think that's like one of your best qualities, actually, because I think that so many women are are able to look up to you, are able to see that like some of their maybe like things that they consider an insecurity can be something that they embrace and that can ultimately turn into a smashing success because they get to see it in you.

SPEAKER_02 14:19

Well, I think that we we've lived in the highlight reel for far too long.

SPEAKER_00 14:23

Yeah. Yeah. And you always just like cut through the noise and you say and you say the thing. You always say the thing. I always say the thing. I well, I I think it's I think that that is unfortunately that it has to be brave, but I think in today's world, like it is brave to say the thing because everyone's like very polished or too media trained or way too like Instagram friendly. Yeah. And you've just been able to kind of like pull back the curtain of your life and and talk, whether it's on stage or on podcasts, about all the different areas of what you've learned, where you've grown, where you've had setbacks. And I think that in your embracing this next evolution of yourself, of your hair, of teaching other women that they can embrace this, you've also embraced a a very open conversation around the work that you've chosen to get done, how you've chosen to embrace entering your 50s and being in that next phase of you. And the news just came out about your facelift and you were very open about it. And I love that. But I want to talk a little bit about that and what it felt like to kind of go through the process and also then to be open about the process.

SPEAKER_02 15:19

Yeah. Well, you know, I'd been thinking about it for a long time. And, you know, and I think this the I mean, I think like a lot of women, it's like, you know, aging is hard. And and I don't, and listen, I don't, I'm like to each their own. I'm not saying go out and get a facelift. Like it's, you know, it's like whatever feels right to you. For me, it was just something that I had been like thinking about for a long time and had done a lot of research and was looking at a lot of other women who had done it. And, you know, when I did, we did put it out in People magazine. Thank you very much. Um, you know, I I did tag in my post like Kat Sattler, who who is another woman I know I, you know, we're kind of friends, and she had a facelift on, and I and I remember I I really watched her stuff and I was really interested, and and it was it was quite a dramatic before and after. And and she didn't look bad before. She just and and when you see her before and after, it's like she didn't look like she became a different person. She just looked like a better version of herself, you know, and I think that's really what I was going for. And and it was for women like her who went before me who were like gave me the confidence to go and do it because I was like, oh, okay. Because I think what I had historically thought about Facebooks is like, you look crazy, you don't look like yourself, you look like this weird version of you. And I was like, I don't want that, you know. So it was like about finding the doctor, but most importantly, I think to my point about other people doing it, it's like I just didn't want to be a gatekeeper. And I, you know, we all know that there's tons of like very famous people out there, I'm not mentioning any names, who have done a lot of stuff to their face, which is like cool. Yeah, that's great. But like, don't make it seem like you have it, and like the skincare you're using has changed your face. It's just that drives me nuts. You know, it's like I I do think, and again, I'm like, I'm not as as nearly as well known as a lot of those women who are, but they are to me, and it's funny because we were just talking about, you know, like the the the response was overwhelmingly positive. And then there's, you know, there's a few of those people who are like, you know, it why what is this that we're saying to women that women this is the new standard of beauty? I'm like, it's it's not. It this was just right for me. Yeah, and you you are potentially looking at other women who are telling you, oh, if you do this and that, your face will look like this. When it's not true, they've done work. And it's like, it's cool, just admit it, you know. And that's that's really been important to me, which is why I've been public about it, because it's which I think has been my whole kind of MO my whole life, is like if I did it, like if she did it, I can do it, which you know obviously was in the dry bar era, but like now it's like, yeah, like I did this and I feel really good about it, and I don't I didn't change my face, like I just enhanced it, you know, is how I kind of see it. I love it.

SPEAKER_00 18:02

And I think that it was I mean, it's inspiring for me too. I mean, I just I had a mommy makeover like right after you look incredible. Thank you. And it was really hard because I'm like, I'm gonna be really open about it. But it's like people come for you. I mean, people come for you, and it's like, and you have to be ready for the fact that people are gonna have opinions on a lot of different things, and then what's right for you is not gonna be right for somebody else. But if you can help just one person, then it's it's a great thing. So I love that you've been able to be open about it.

SPEAKER_02 18:24

Yeah, and I think that, you know, like with what you did, it's like you know, talking about it and being open about it, it's like our bodies as women go through a lot. When you've had like 17 kids, so it's like it, you know, it's I had my boobs done years ago too, because it was like I breastfed for five years, and it was like uh, you know, my body changed. And and I know that some women feel really strongly like you should just let it be what it is and change. And I'm like, yeah, but I don't I don't want to do that. You know, I want I want to do what I want to do, and I think it's it's such a personal decision, and whatever feels right for you, I you know, wholeheartedly go embrace it.

SPEAKER_00 18:57

Yeah. I love it. Well, what would you say if you were looking at the next 10 years of your life and Messi and all the things that you're building is something that you really either hope happens or that you're really excited about looking forward to the future?

SPEAKER_02 19:12

Well, you know, I really think that Messi has a lot of potential for longevity and be to become even more of a lifestyle brand because it is such a like lifestyle embrace, you know, and you know, I'm exploring a lot of different things, you know. I mean, mentoring has always been really important to me. And so I have a couple of projects brewing that feel really like good to me to give to give back to other women, to teach other women. It's part of why I wrote my book, The Messy Truth, was like because I want to, you know, share all that I've learned, you know. And so I think I will continue on this path of like mentorship and and growing, but it's hard to say where I'm gonna go. You know, I could I would never have been able to predict that that I would have gone in this direction with hair, but I love it, you know. So I'm I'm more I mean, you know this about me, I'm kind of like fly by the seat of my pants, like what feels right. And I'm very decisive as a human. So I'm like, I know what I want. And and you've got strong intuition. I do have strong intuition. And and I've been really lucky that a lot of interesting opportunities have come my way and a lot of things, you know, I that I thought I wanted to happen didn't, you know.

SPEAKER_00 20:17

All right, Ali, where can we find you and follow along?

SPEAKER_02 20:20

Um, you can find find me on my Instagram at Ali Webb. Um, you can find us at it's messy.com, or now I'm trying to embrace TikTok and I'm the Ali Webb on TikTok. So yeah.

SPEAKER_00 20:30

Amazing. All right, and thank you so much.

SPEAKER_02 20:32

Uh Messi It's fora. Yes, and it's the best favorite product. What's your favorite product out of all of them? Oh god, that's a great question. Well, we did just launch a new dry shampoo that's a silky dry shampoo vegan soak, so it doesn't dry your scalp out, which so I love it so much. I love it.

SPEAKER_00 20:45

All right, awesome. Thank you. This podcast is for informational purposes only. The views and opinions expressed by guests are solely their own and do not necessarily reflect the views, policies, or positions of MMC or any of its affiliates. Guest appearances do not constitute an endorsement.