Building a Category Then Challenging It: Alli Webb’s New Vision for Hair

0:00Hey guys, welcome back to Skin Anarchy. This is a very special episode. We have such an iconic guest with us today. I am such a stan and have been for a long time. As many of you know her, she created one of the biggest brands in the hair care industry. And I think everybody has tried it at this point. Without further ado, I want to introduce you guys to Alli Webb, who is the founder of Drybar and now the founder of Messy by Alli Webb. Welcome Alli. I'm so, so honored to host you. Thanks so much for having me. No, it's truly a pleasure. And I can't wait to dive in to everything that you're doing now.

0:29But I would love to kind of have you walk us down memory lane if you could talk to us about Dry Bar, because Dry Bar was a phenomena, you know, it really took the industry by storm. And I just want to kind of dive into that. Like what got you into the hair care industry to begin with? And like, where did it all begin for you? Well, it really all began, you know, when I was a kid growing up in South Florida with like all the humidity and my naturally wavy hair, which I now really embrace and love, hence messy, was just really challenging for me. And, you know, I didn't go to college and just didn't feel called to that and went to beauty school when I was in my early 20s.

1:03And just I could make the argument to learn how to blow out my own hair. And I just always had this obsession with my hair and hair in general and blowouts. And fast forward to many, many years later, after trying many things and having many lives and careers, I had moved to L.A. when my kids were born. I thought I was going to be a stay-at-home mom and, you know, arguably the hardest job that there is, you know, being a mom. And as much as I loved being able to stay home with my kids and felt like that was so lucky to be able to do that, I really missed doing something for myself. And so I started this mobile blowout business in L.A., I guess in around 2008, 2009.

1:37and I was only charging 40 bucks to go to women's house to do blowouts, which is kind of unheard of then and now. And during that time, I realized that there was a really big hole in the marketplace for an affordable, great blowout. And my mobile business was really taking off, but I felt like I wanted to expand, but didn't want to do it mobily. So I went to my brother, Michael, who's my business partner forever and said, hey, I have this idea to turn basically my mobile business into a brick and mortar. And that's really how the idea for Drybar came about. You know, I felt like I knew there were enough women out there like me who were kind of seeking, you know, a great blowout and a great experience.

2:16And it just didn't exist, you know, which is, you know, the cornerstone for any great idea or business is like, you know, something we all want that doesn't exist. And so at the right price point and the right experience and customer service and ambiance and all of that, I thought maybe this would work. Having no idea at that time, it would turn into what it did. I mean, that was something I don't think any of us really anticipated. But, you know, we started at$35 and, you know, I have such a wealth of knowledge of hair and blowouts that I felt like I was, you know, uniquely qualified to do it.

2:48And it worked. Yeah, no, it definitely worked. I mean, it's so inspiring because I love when I talk to founders who have created like a category because that's like a totally different thing than just like creating a product within an existing space. You know, my questions are always like, well, where did you discover that like, wow, this is an entire category? You know, like this doesn't exist. Like I know what you just said, like if that makes sense, like you want to create something people need. But it's like, when does that happen when you're in your journey where it's like, oh, my God, like, you know, this is a whole different niche that I've kind of put together, you know, through this whole endeavor.

3:21Well, I think coming up with something that is a problem or something you're trying to solve. And usually that comes from personal necessity. Right. It's like, like, we obviously didn't invent blowouts. We just created a much better experience for them and a much better price point and, you know, and everything that came along with it. And that's, you know, always my advice to other, you know, women or founders or just people. I mean, I have two sons who are in the throes of trying to figure out what they're doing with their lives. It's like, you can take something that already exists and make it a hell of a lot better.

3:51It's really paying attention. And I think that like anybody can think of something that you really enjoy, but you wish it was better in some way, you know, and then there's an opportunity. And I see them around me all the time. It's like a blessing and a curse. You know, it's like I walk into a restaurant or my favorite coffee shop or whatever it is. And it's like, I love this. But if they did X, Y, and Z, it would be even better, you know. And I think that that's, you know, while I didn't set out to change an industry, it just was like, truly, it never even occurred to me. I was just like, I always wanted there to be a place where I could get an affordable, great blowout, you know, in a great setting.

4:26And I really tried to make it something that I wanted to do, like something that I, you know, as a busy mom woman, and you know, it's why we put the chick flicks on the TV and had Wi-Fi and the little cookies, which surprisingly were always such a big fan favorite. It was just like all those little touches made it really special, not to mention the customer service and how you retreated and it looked high end, but didn't have the high end price tag. I mean, it was just, you know, I can go on and on with all the little things. And that's really, I think how you make anything successful is like paying attention to all those small details.

4:57And unfortunately, that's missed a lot in business, you know, and people kind of skim on that stuff or don't think about it. And, you know, for me, it's like that intensity around detail, I think, is what makes you stand out. Absolutely. No. And I, you know what I really love about, and this, I've noticed this with a lot of the brands that were kind of in that era of when Drybar was starting off, was that there was so much like uniqueness back then in the beauty industry. Because like when I discovered Drybar, for me, it was a very unique as a consumer, very unique experience. I was like, I love packaging.

5:27I love the branding. I love the feel of the products. And that was amazing as a consumer. But like nowadays, I feel like people are just gravitating towards a recipe, you know, of what that kind of brand looks like at the end, you know. And so I would love for you to speak on this about, I mean, you started with a very unique idea, but you scaled it to a 200 million plus acquisition brand. You know, that's huge. But I feel like nowadays people are starting at that end goal. you know what I mean? And kind of working backwards. And it's like, I'd love for you to kind of speak on this. What is that starting place and that mindset of like, when you want to create a brand on that scale?

6:01Well, it is interesting. And while I think it's great that like a lot of colleges and stuff are now, you know, having entrepreneurial programs for students, which is great. But I do think understanding your business kind of, I still believe in like, you know, the crawl, walk, run kind of philosophy of like, you know, starting small, figure out what you're doing, be open to pivoting, being nimble and seeing what works and what doesn't. I mean, we changed lots of things as we went, as we were growing, you know, and learning and not putting the cart before the horse. You know, it's like I see also a lot of businesses who are like, oh, I have this brand and I want to or some sort of retail concept and I want to franchise it.

6:38And it's like, well, is it actually franchisable yet? Is the demand out the door? And so I think it's like really like honing in on what you're doing and making it the best it can be before you start thinking bigger. And not to say that you don't want to think big, but, you know, I think there's kind of a natural cadence. And that's kind of how I approached what we were doing. You know, it was like, we had no idea if it was even going to work, you know, and then once it did work, it was like, okay, we need to keep growing and scaling. And then there's just so much to that. You know, having the right people in place, having, you know, systems and all that, which was completely out of my wheelhouse at the time, which I had to kind of learn as we went.

7:16My approach is like starting small and building something very intentionally and paying attention to what's working and what's not working and where you need to like shift and change to get to that end goal. I think it's very hard to work backwards. And I think that that is something that we see a lot because everybody wants to be an entrepreneur. And it's like, I want to make a bunch of money and start this thing. And of course, we've all heard it a million times. It's like, if you're not doing something that you're really passionate about, it's really hard to work hard at it, you know, because it's like you have to really love it.

7:44And for me, it was never about the money or growing it big. It was just about doing something that I truly enjoy doing every day. You know, so you kind of have to come from that starting point, too. So it's, you know, it's a lot of things and they all have to work together. And, you know, not every idea is a good idea. And I talk to a lot of, you know, budding entrepreneurs. And sometimes I'm like, huh, I don't know how that's going to work. And then, you know, and then even a great idea is a dime a dozen. It's like, you have a great idea, but where's the execution? Who's going to run it? How are you going to run it?

8:13It's like, there's just so many factors into being successful. Absolutely. No, and you know, that kind of makes me wonder also, because we hear so many success stories. I feel like nowadays in social media is so good about the highlight reels of everyone's life, you know, and that's great. I mean, I love celebrating everybody, but I think there's not enough about like what it really takes, right? Like behind the scenes, you brought up like being a busy mom and there's so many things in the entrepreneurial journey that I wonder, you know, like where is that content? Where's that information? So I'd love for you to kind of share some with us, like some war stories maybe of like when you felt like, what am I doing?

8:48Or like, you know, where is this going? It's like every day. I mean, we used to joke that it was like running businesses like playing whack-a-mole, you know, that carnival game. And someone actually bought us that in one of our offices because it's truly like, you know, you just don't know what's coming every day. And every day is usually full of a bunch of problems that you didn't plan for and some that you did. And I think in order to be a successful entrepreneur, you have to like enjoy that chaos and the craziness that's surely coming every day, especially when you're running a company. And, you know, in my case that had like 10 ,000 employees open seven days a week, there was really no break from it.

9:24You know, so it was just a constant stream of issues and problems and things that you kind of always have to be okay with solving. And I'm such a natural problem solver, like give me a problem and I'll, you know, try to figure out a solution. So I think that's probably the hardest part is that you have to have very thick skin for that. And I think that I developed that, you know, as we went. I mean, there's so many more stories. I mean, even from like, you know, as a consumer of driver, you know that like our, maybe you know this, our phones, when you call to make an appointment, aren't in the shops.

9:54You know, we had to have a call center, which was also like, I was like, I don't want to be in the call center business. I don't know anything about that. But we found that it was incredibly hard to answer the phones while you're in the shop. So we had to have someone off-site answering the phones, which was a problem in many ways in and of itself. For me, my priority was the customer standing in front of me in the shop and making sure that experience was really great. And then, you know, I mean, gosh, the first week we opened Drybar, I had, I told everybody, let the phones go to voicemail. We'll call people back, which is not great, but it was a better alternative, you know?

10:24So it was just like thing after thing after thing like that. And just, they just kept coming up all the time. And, you know, not to mention like hiring stylists and training them. And like, you know, you could find a great stylist who was an amazing hairstylist, but kind of didn't blend in with like over the top customer service that I really wanted. And like the barrier to entry was like, you have to be a really nice person and you have to be really like kind of drink the Kool-Aid with customer service and being like over the top kind. And I felt like while we were, you know, delivering great hair, it was the entire experience that I believe made Drabar so special.

10:57It was like the way you were treated, the way you felt when you walked in. And that took a lot of like curating, choreographing to get that right. None of it's easy. You know, it was all very intentional, very challenging, but very worth it. You know, and it just it was like, I mean, gosh, every day was something. And, you know, in the early days to the first couple of years, like I was basically, you know, manager, district manager. So I was fielding all of that in the beginning, which was fun. But it was, I mean, fun, like I say that loosely. But I'm also a big believer in like you kind of have to do every job as the owner so that you can, you know, inform on that and you really understand it.

11:35So it was just wild, you know, in those early days. And we were totally always understaffed. We never had enough stylists. And there's a good problem to have. We had so much demand and much less supply. So that was, I mean, it was just problem after problem. But you have to love it, you know, and I did. No, that's, I love what you said about you have to kind of know, like you wanted to know how to do everything because this is something that's, I think, very, very unique in the entrepreneurial world where it's like, you do have to know your business from the inside out. I've heard that many times from a lot of founders when I'd love for you to expand on that a little bit, right?

12:08Because I think we're living in such a fast culture right now where everything is like, give it to somebody else, give it to AI, give it to, you know what I mean? Like allocate, allocate, allocate. And it's like, where do you find that balance as a founder where you're like, okay, I have 24 hours in a day and I have to get everything done, but then still knowing your business down to the DNA, down to every single job and role. I mean, where do you think all of that really is anchored in, you know, especially when you're starting out? Well, I mean, I think that I'm going to talk out of both sides of my mouth because I do think that you do need to have a great team and you do need to be able to delegate, you know, especially as a founder.

12:42I think a mistake that I certainly made and something I see people make is like you being as the founder or CEO or whatever, being kind of the bottleneck for everything. You can run into a lot of trouble that way because it slows things down. So, you know, the willingness to offload certain things I actually do think is incredibly important. But that being said, you know, I think for me, I felt I would, you know, clean the shop and clean the bathrooms, like wash hair. You know, I wanted to not only know how to do everything really well, but also be a role model for the kind of environment I wanted to create, which was like, we're all in this together and we all work together as a team, you know?

13:18So I had to, you know, kind of walk the walk as well as I always felt like that was important for my team to see that like, I'm not, I'm not above doing anything. And I have a unique perspective and understand everything that you're asking, that I'm asking you to do, I've done, you know? So I think that's important as an owner so that you really have an understanding of all the things that are happening, you know, within your company. But yeah, there's a real need also to, you know, make sure that you're, you know, again, I hear it all the time with founders who are just so overwhelmed with so much because we hold our company and everything so precious and we don't want anyone else, you know, to potentially mess something up or do it differently than we would.

13:58And I felt like that for years, you know, and eventually like had some coaching and realized that like I've got to let other people make mistakes and that's the way that they learn and that's the way we grow and that's the way that they feel really empowered and feel like, you know, they have some real skin in the game. So, you know, it's such a both and of like, you got to be okay with some people making mistakes and maybe not doing it the way you would. And, and even as like, you know, a CEO, especially the second time around for me is like, you know, I really think of everything as like, I'm here to serve my team, not vice versa.

14:31You know, it's like, I give my team a lot of autonomy and, you know, a lot of like room to do what they need to do and try to be more of, you know, additive and serving them instead of them serving me, which I think is a shift, you know, from like, you know, 10, 20 years ago, how CEOs were. And also trying to be really mindful of hierarchy. You know, I always want people on my team who, you know, are kind of down to do whatever needs to be done. And that just happens in an organization, you know, from people being understaffed or not having enough people or not having the right people. So it's such a mixed bag.

15:03I'm sorry, that was such a long answer. No, it's a wonderful answer. And I thank you for going into it because it is something like, you know, because I just wonder because there's these brands that I, I mean, Drybar became such a phenomena, right? And you never get to look behind the scenes. You never get to understand like, what is it that happens inside such a large company and such a large brand where things are moving so cohesively because that's what it looks like to consumers on the surface. Everything's so well put together. But like you said, you know, there's a lot going on in the background.

15:31One of my biggest questions for you, honestly, is just this idea that now we're going into this cancel culture, right, as a society with beauty brands. I've seen this a lot. And I don't know what your thoughts are on cancel culture, but I worry a lot, you know, for new founders and new entrepreneurs, because I feel like people have great, you know, like they come into beauty with this like really enthusiastic mindset and they want the best. They want to create the best. But then all of a sudden you do one thing and the internet is just going to turn on you, you know, and they're going to be like, I can't with this brand.

16:01How do you feel about that? I mean, do you think it's a lot different than it was when you were starting out? I mean, what are your general views on that? Yeah, I do think it's different because when Drybar started in 2010, and that's when Instagram started. So we came into the world when it wasn't quite as socially driven as it is now. And I've had things happen over the years, but yeah, I'm not a fan of cancel culture. Or, you know, it's like when I think about founders and people who are trying to, you know, start a business and presumably to make something better, to put something out there, that's really hard and vulnerable.

16:36And then, you know, to be canceled, why? Maybe I'm just too old, you know, that I'm like, it's just so negative and toxic, you know, to be like, I'm going to cancel a person like, you know, and listen, like, I probably am much more guarded than I would be. even though I talk about a lot and I can be very vulnerable. And, you know, my book, The Messy Truth is a very vulnerable depiction of my time growing dry bar and then all this shit that happened in my personal life. And I'm very open about that stuff. But I'm very closed mouth when it comes to like politics, religion, anything like that, because that to me is like when people get very upset.

17:13Of course, like I wish the world would be a better place if everybody could have their opinion and not have to go to like such a crazy height where people are really take it so personally and get so mad. And it's like, so for me, I just kind of stay away from it because it's just so personal and so tender to people. But I wish it didn't have to be that way. You know, I think that I really have a lot of respect and give a lot of, you know, kudos to people who are putting themselves out there, putting their brand out there and really giving it a shot. It's very hard, you know, to put yourself out there.

17:44And, you know, and I think we should be praising that, not, you know, not the other direction. Yeah, no, I couldn't agree more. And thank you for answering that because I think it's important to hear, you know, from people who've done what you've done to hear that. Because I think I've seen this a lot and I'm not in it and I've not gone through it, but I know I've watched people go through this whole cancel phase of their brand and it always breaks my heart because you pour so much of yourself into this, you know, and it's not just a project for people. It's their life. It's their savings. It's their, you know, everything.

18:18And then for the internet to just then turn on, I mean, it's just so disheartening. You know, and I think we just live in a day and age where you just also, you have to be very aware of what you're doing. And, you know, and I mean, listen, I think self-awareness just as a practice, as a human is really important. And, you know, and I am aware of the things that I say and I do and same for my brand and my company and And really do try to make sure that I'm not offending anybody. I personally just don't love conflict and don't want, you know, and every now and again, if I get something, you know, some comment online or something negative, I just, I don't engage in it because I'm like, I'm not going to have a fight with the person I don't even know, you know, and you keep people around you that, you know, keep you honest and things that are important to people.

19:03It's like, you know, I try not to be completely dictated by it, but I also don't bury my head in the sand over it too. So it's an interesting kind of delicate balance of kind of walking that line, I guess. Yeah, no, that's a really good point. And I was going to actually ask you this about like the advisors that you bring on at a certain point in the growth of a business. Like what is that vetting process really like where you're like, I need to be able to trust this person as like my right hand. What was that like for you? I mean, when you were at that stage where you're like, I need to bring in more people.

19:33But having that trust that you built in these people to guide you when you needed that guidance, you know? Well, I mean, it takes time and we've certainly hired people, you know, early on in Drybar that weren't the right fit. And you kind of, you know, sometimes, unfortunately, you have to go and not even unfortunately, it's like it's such a learning, you know, to bring on people who you think are going to be right and then they ultimately aren't. And for me, I really rely on my gut and the way I feel about somebody. And I mean, you can call it a little woo-woo, but it's like somebody's energy is very important to me.

20:01And I feel like I can usually tell within minutes of meeting somebody if it's going to work or not based on how they show up, how they talk. And it's like an intangible thing that I couldn't even explain to you how or why that works, you know. And I've gotten it wrong, you know. I mean, there's been people that we brought on that were like, I thought this was going to work, but this isn't going to work, you know. And so I think it's, first of all, being very discerning and really trusting your gut. Like I've never been a big resume person. Like, of course, I want to know someone's experience and what they've done.

20:29But it's more about like the in-person conversation, you know, really understanding where they're coming from, how passionate they are about what we're doing. And not everybody's like that. And sometimes it's just a chemistry thing and it doesn't fit and that's okay. And you have to kind of learn. And I think, again, it's really trusting your gut about people and putting your ego aside, you know, especially as a founder. It's like, and that's a tough one for me. You know, it's like, you know, my name's on my brand. And so it's important for me to like, you know, it's a personal thing, too. So I want to make sure anybody who's advising me or on my team believes in my vision.

21:06And then, you know, and then I can let them run with it, you know. But it's like, it's not always easy and things change. And, you know, a lot of the people that have worked for me over the years, you know, they were ready to try something different. And I always had my blessing. And even in like, you know, like I mentioned, we had up to 10 ,000 employees at one point at Drybar. And, you know, most of those were stylists. And my team used to be like, you know, we're training an industry here, which we were. And a lot of times we would train somebody they'd work for us for less than a year and then they'd move on to something else.

21:33And my team would be so frustrated because it's like we spent so much time on this person training them. And I never felt that way. I was like, I feel like it's karmically very good. You know, they've worked for us. They've given a lot of like time and energy to us. And now they're going and taking the skill that we gave to them and bringing it out into the world. And I felt like it was all great, you know. And I think that that's part of like not holding anything too precious and like letting people like continue to evolve and being a small part of their journey always felt really good to me.