Alli Webb, THE MESSY TRUTH: How I Sold My Business for Millions But Almost Lost Myself

Alli Webb, THE MESSY TRUTH: How I Sold My Business for Millions But Almost Lost Myself

Zibby interviews Alli Webb, founder of the world-famous blowout salon chain, Drybar, about her empowering and insightful memoir, THE MESSY TRUTH: HOW I SOLD MY BUSINESS FOR MILLIONS BUT ALMOST LOST MYSELF. Alli shares what it was like to start a business that took off seemingly overnight. She also discusses the struggles she faced in her marriage and with her teenage son, who had to enter rehab, and how she eventually spiraled into a deep depression. She emphasizes the importance of transparency and the impact of sharing her story with others, especially other women who might be going through similar experiences. Finally, she describes her current projects, which include a new massage concept (Squeeze) and a humidifier company (Canopy).


Zibby Owens: Welcome, Alli. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself. Congratulations.

Alli Webb: Thank you. You don’t have to read it. You can listen to it. There’s an audio version.

Zibby: It’s too late because I actually read it. Oh, well. Next time.

Alli: You did?

Zibby: I did, yeah.

Alli: It’s funny. I’ve been doing podcast interviews. People have read bits and pieces of it. It always makes me really happy when someone’s read it. What’d you think?

Zibby: I thought it was great. I think you curse a lot.

Alli: I do curse a lot. That’s who I am.

Zibby: I love it. I felt like I was just — I don’t know you. I’m about to know you. I imagine this is how you just talk. I felt like I was listening to someone talk. I was getting all this amazing advice. I loved how you showed us the pitfalls. I particularly loved the epilogue, that things don’t all end happily ever after. That’s okay too.

Alli: The afterword.

Zibby: The afterword, sorry. The afterword.

Alli: I was like, wait, is there an epilogue? The afterword, yeah. The afterword is super fun, huh? I feel like we probably shouldn’t talk about that so that people can have to read it to read that part of it.

Zibby: Don’t fast-forward to the afterword. Forget I said anything.

Alli: You can fast-forward once you buy the book. I’m saying don’t talk about it. Listen, we’ll be kind of cryptic here because you know what the epilogue — now I’m going to start calling it that. You know what the afterword is. I think there’s a lot of speculation of what that is. Not as a PR stint, but I just haven’t wanted to talk about it for a lot of reasons. Putting it in the book, my agent and people were like, “You got to put it in. This book’s going to hit, and then it’s going to be information that’s relevant and timely.” That was rough, but I’m doing much better now.

Zibby: I don’t like hearing any of those “You got to do this” when it comes to my own personal information. I get it. I see from the book’s perspective why they want that. I get it.

Alli: The whole book, as you, I’m sure, would agree, is a very transparent look into my life, my business, like you said, the pitfalls, the ups and downs of growing a business and all the things we go through as humans while we’re doing our lives and running our companies or our jobs and whatever. It would feel disingenuous to me and to my audience. We had a little pitfall there at the end that I didn’t see coming that I felt it was important to include because it’s part of the messy truth. It’s part of the realness of what we go through in life. Like I said, the advice I was given was to put something in, and I agreed with it. Also, I was not totally thinking straight at that time. My agent is one of my best friends. To get that insight of somebody who is looking from the outside in was really helpful.

Zibby: I totally get that.

Alli: People are saying, what are they talking about?

Zibby: I know, sorry.

Alli: No, it’s good.

Zibby: Hopefully, they’re completely intrigued and run out and buy this book right now. I was really interested in the rise of Drybar and how it came about. It’s one of those ideas where you’re like, of course, that’s such a good idea. Why does this not exist? Why didn’t it exist? I didn’t realize that you started it to help moms at home who didn’t have time to do this. Tell listeners more about this or the inspiration behind your starting Drybar. Then fast-forward to why you want to talk about it to everybody now.

Alli: I was a stay-at-home mom, a longtime hairstylist when I was in my early twenties. I went to beauty school and really fell in love with it and spent the next ten years or so doing hair off and on. Then I moved to LA from New York City with my then husband, Cameron. We had our boys. I also, by the way, thought I hit the jackpot in just that. I was like, I don’t have to work anymore. I can just stay home and take care of my kids. Didn’t realize what a big job that was. I really loved being home with my boys. I felt really lucky that I was able to be a stay-at-home mom. I loved every second of it. It was five years of that, which is a good chunk of time to be a stay-at-home mom, for me anyway. Then I just started to get the itch to do something for myself. Because I’d had all this time and experience in doing hair, it seemed like a logical step to start a mobile blowout business where I was doing — my whole idea for this was that because I was so enmeshed in the mommy community and culture in LA — when I first moved to LA, I had just had my first son, so I was in all the mommy groups. I was in total mommy world. That’s all I knew in LA. That was my resource of women.

After five years and feeling frustrated that I wanted to do something for myself, I was like, well, I can do blowouts in my sleep. I had girlfriends and whatever who had curly hair and always wanted me to blow out their hair. I was like, I think there’s a little bitty business here. That’s truly all it was at the time. I was like, let me go get out of the house for a couple hours, blow out my mommy friends’ hair. That’s what I marketed to. Again, this was fourteen years ago. There’s was a Yahoo! group called Peachheads. It was five thousand moms in LA. That was the thing that I posted and said, “Hey, I’m a stay-at-home mom. I’m a longtime hair stylist. I’m thinking of starting a mobile blowout business where I’ll come to your house and blow out your hair while your baby is sleeping,” because I’m talking to moms. I really thought about was genius because I knew my only me time was when my kids were napping, which was the holy grail of time, as you know. I was like, let me come over and do something that women would really like and appreciate. I also realized people wouldn’t do it if it was $150. If it was forty bucks, which was — my big business plan was two twenties. Women would do that all day long. Easy peasy. Therein lies how the mobile business got started, which is called Straight-at-Home. What I didn’t see coming was that I was stumbling, inadvertently, upon something that was going to, obviously, become massive. I just didn’t realize. I started this business. I was so happy. I was getting out of the house for a few hours, making a little extra cash. I’m sure I didn’t actually make any money between gas and driving around LA, but I didn’t even care about — I’ve never cared about the money. We can get to that later. Even in building Drybar, it was always about the purpose and happiness that I was looking for.

I was really excited. This business was booming. I was so busy all the time, which is really the crossroads that I came to that would eventually lead to Drybar because I couldn’t handle all the demand, and at forty bucks a pop. I was pretty good at the blowouts. They were telling all their friends. I got so busy so fast. I was like, what now? Realized I had to either keep operating at this pace, which was going to be pretty small, or build an actual brick-and-mortar, which is when I went to my brother Michael and said, “Hey, I think I should turn my mobile business into an actual shop. Instead of me going to them, they come to me.” He’s bald. He’s like, “What? Why can’t they blow out their own hair?” I was like, “First of all, you grew up with me and this frizzy mop that I — but okay.” His wife at the time had naturally straight hair. He was like, “I just don’t know that I totally get this.” Also, really thought it was going to be event driven. If you’re going to a bat mitzvah or a birthday party or a wedding or whatever, then you come in for a blowout. What I didn’t know was that it was going to be for women who had straight hair who wanted waves and volume and curl. I just thought it was going to be for women who had hair like me that was unruly, and they wanted it done. Turns out most women want what they don’t have, and so we had a massive audience of women who were going to come in. We have all different age ranges. That’s really how the whole thing came to be.

Zibby: As it was growing and your life was getting out of control, when was the turning point where you’re like, something has to change here?

Alli: You mean while the business was thriving? It’s like anything. When you’re operating at a breakneck speed — the best way to describe it was, we were on a rocket ship. We were moving so fast. My kids were so young when I started the business. My boys were three and five. My mom has since passed away, but we moved my mom wherever we went. She was with the kids. It was total chaos in the best way. My life changed. It was a 180-degree change. Drybar became like a third child for me and Cam. We were married sixteen years in total. The year after we got married, we had Grant. Then we had Kit. Then we had Drybar. It truly happened that quickly within the first five years. I now realize, looking back, I knew subconsciously that the love between us wasn’t totally right. We were best friends, which I now also know was totally modeling my parents’ marriage, which is another fucking book. I realized that. As Drybar is growing and we were a year in — obviously, there’s just so much in between, which of course, I talk a lot about in the book, the growing and everything. I would say at year seven, the writing was starting to be on the wall that we’re probably going to sell this thing at some point or go public or whatever. We had also gotten the business to the place where, which I talk a lot about in the book, where we had brought on a professional CEO. We had started to bring on more people who were kind of doing, essentially, what I was doing, but it had to get on a bigger scale. That wasn’t my thing. I was the visionary of the company. I didn’t want to be a CEO. I didn’t want to be the head of operations. For a long time, I still was doing frontward-facing stuff, like press and product development and making sure the experience of the shop was right. Really, ultimately, everybody else was starting to do a lot of what I had done.

I started feeling the desire to step away a little bit. I was starting to pursue my own things. I was like, what’s going to happen when we sell Drybar? What happens to me personally? That’s right around the time I hired personal PR because I was like, I want to continue to build my own personal career and use this, parlay the success of Drybar into my own thing. What that looked like, I didn’t know. I just had the foresight to know. Then it was around that time that Cam and I decided to separate. Then it was also around that time that my older son Grant, who’s now eighteen, kind of went off the rails. As you know, there’s a whole chapter devoted to this. Everything unraveled at once. I had slowly started to step away from the business. Now the office that I shared with Cam, couldn’t go there anymore. Now my son — it will be interesting to see how I talk about this as I do press for this book because it’s so emotional to me, what my son went through. We were fighting for his life. It was bad. It felt like — maybe this is just how it happens a lot. When your life starts to unravel, it all unravels. I had lost my footing in the company. I wasn’t going to an office anymore. This was pre-COVID before people were not going to offices. Now I’m fighting for my kid’s life. I was like, you got to be kidding me. What happened here? The business is still off thriving. Other people were running it. Thank god for that because you would’ve never known from the outside looking in. It was really rough. It was a rough couple of years.

As a result of all those things, I fell into a pretty deep depression of trying to get this all figured out. It was so fascinating, what people think. I was actually just listening to — this is so random. I was listening to Jay Shetty’s podcast. Jada Pinkett was on it talking about her life. She was talking about a time in her life. She was saying there’s these days where you’re like, if I can just get out of bed and if I can just make it, she says, until four o’clock. I was like, man, do I relate to that. There’s those days where you’re like, I just don’t know how to get through the day without it all feeling like it’s all falling apart. From the outside, I had this great life. I built this great business. I had these adorable kids and this great marriage and all these things. It was all imploding. To answer your question of why talking about it now — we did put out a statement, which felt weird to me in and of itself. I’m not like Kim Kardashian and anybody really cares what’s going on in my personal life. It was more for the respect of the people involved in Drybar, which was five thousand employees. It was a substantial amount of people. Cam and I put out a statement about just the fact that we were separating and whatever. I opened up a little bit about that.

We talk a lot about this now more, but this was also five, six years ago. Our Instagrams and our social stuff is very much a highlight reel. We’re all guilty of that. We all want to look good and show good and whatever. I felt this, I don’t want to be disingenuous even if it’s just to five people. The fact that my marriage was falling apart, my life was falling apart, I was like, I’m not going to then go on Instagram and be like, hey guys. I was transparent about it. The response to that was so many people reaching out to me. I’m going through this too. Then a lot of, I’m not happy in my marriage either. Should I leave my husband? Then I was like, I don’t know. That’s out of my — no, you do what you need to do, but maybe it’s time to really look inwards, which is what I was doing. It was really interesting to me and quite fascinating and illuminating how many people were grateful, I think is the best word, for my transparency. Then it felt like, oh, I think I’m, maybe, helping people. Then I was like, if I can serve other people based on talking about my story and the fact that — I remember when we started Drybar and feeling this, almost, sense of pride because our stylists — I was just a hairstylist. I didn’t know the right people, and that’s why Drybar became successful. I didn’t have money, and that’s why it — I was just this regular girl who’s a hairstylist. I always felt this sense of, if I could do it, you could do it. That was the feeling amongst stylists at Drybar. If she did this, then I can probably do it.

It was the same kind of feeling I was getting in response and reaction to what I was going through, these other women who were like, oh, wow, you’re going through that. So I am. We all know this. When you know somebody else is going through something that you’re going through, it’s really comforting. The more I put out about that, the more it just helped. I know it helps because in the same way, if I read about somebody, especially somebody who I might admire or is doing something that I think is great, and their life is also falling apart, you’re like, oh, good, it’s not just me. To answer your question, I think that’s why I felt and have continued to feel this calling, more than anything, to be really transparent with what I’m going through. I think also, once you’ve been through, as I call it, the dark night of the soul, you feel, at least me, compelled to talk about that versus bullshit conversations. It’s just almost impossible to go back. Even right now, we just dived right in because it’s more interesting to me than talking about something superficial or surface or canned and whatever. That’s my very long-winded answer to your question.

Zibby: I’m glad you dove right in because this is what makes conversation and connection so interesting. Who has time, right? I don’t know.

Alli: Get to the good stuff.

Zibby: Exactly. I have gone through a divorce myself. I have four kids. I was a stay-at-home mom. I almost pulled my hair out. I stayed home for eleven years because I had twins and then six years later, had two more kids. I relate to a lot of things and was kind of hoping for — I also believe strongly in transparency. I think it’s the only way. I’m so glad it’s on trend because I’ve been doing this forever.

Alli: It is like, what is the point? To get into a deep connection with somebody and to be able to go more soul to soul and human to human, why would we do it any other way?

Zibby: I totally agree. I love that this whole instinct for the business and the sharing and the book and all of it is coming from your place of wanting to help others in whatever way and make people happier, whether it’s feeling good about themselves because their hair is behaving to not feeling like their own relationship is the only one that’s imploding. It’s amazing.

Alli: What I wanted to do, whether it’s been done or not before — I think it was Jay who said to me — the intersection of this book was interesting to him because it’s like — which is really what I was hoping for. There are a lot of business takeaways in this book. It is a lot, and to the point where we even went back several times and edited and reedited to bring in more of the business stories than we did in the beginning. It was a little too personal heavy in the beginning. To me, that was really the goal of the book. I want this book to be like, this is a kickass entrepreneurial journey, exploration where you’re going to learn a lot about the ups and downs of running a business and what worked and what didn’t work and use the fact of what I went through and what I learned along the way, because it really was like getting a master’s in business running this business having never run a business before, and then the flip side of what the personal side is. What I used to say in the early days when I used to do interviews was, business is business, and personal is personal. I think we all used to say that at some point.

Then I was like, no, I resend that. We are who we are. We take our shit wherever we go. To your point about transparency, of course, if we’re going through a divorce or fighting with our kids or whatever we’re doing, we’re going to show up energetically so different. To be trying to hide that versus leaning to it — I’m very transparent, obviously. When I’m going through something, I tell all the people around me, whether it’s my friends and family, people who I work with. Listen guys, this is what I’m going through. I’m going to be a little slow to respond. I may not be able to do that. I might have to cancel some things because I’m having a hard day. I might just do it an hour before because I just can’t muster up the energy to do that. If the people who are with you and love you and work with you are on the same page as you, it just makes everybody’s life easier and more understanding. People are so understanding of that stuff as long as you’re willing to be open about it. I think it’s an important human step that is so .

Zibby: I think it’s also good that you have the right people around you. Not everybody has that luxury. They could feel alone and not have the right people pulling for them, or they’re in environments where it’s not okay to share, which is much harder.

Alli: It’s unfortunate. I think that, go somewhere else, then. It’s so true. I just had a flash of, if you’re working in this really corporate environment and there’s no way you could share with your boss what you’re going through, let’s eradicate those places where you’re not allowed. Listen, I think the pendulum swings a lot in our world. You got to pull your shit together too. At some point, you have to go back to your job and whatever. A lot of the books that I’ve read in the last couple of years about going through heartbreak and divorce and all the things that I was going through — you know what it’s like when you’re going through that and you’re like, give me something to read that’s going to make me feel better. I have found a lot. I feel like I’m a real resource for that now. So many things I read were like, our society doesn’t allow time for grieving a heartbreak. It does for a death. Of course, I’m happy about that. You probably know this. I obviously don’t know the extent of your divorce, but I have been through some real, real hard heartbreak where I couldn’t get off the floor. The fact that our society doesn’t allow us some real time — even some of our friends. Everyone’s like, oh, yeah, you take a couple days, and then you get back out. Nobody died. It’s like, well, I don’t know if that’s really accurate. Building compassion and empathy for people and people rallying around you is really the medicine, which is why I think we should all live in community and communes.

Zibby: I would argue that there’s not enough time for grieving either. A week or whatever you could take off, that’s just to get through the paperwork. The work of grief takes forever and is unpredictable. There’s no perfect solution. I agree. I think professionalism is sort of an overrated, outdated thing. I’m constantly telling my team, I’m like, “Okay, it’s totally unprofessional again, but here’s how I feel.”

Alli: Wouldn’t it be beautiful to be able to figure out a way to be able to meld those together? Again, not to the point where everyone’s airing their dirty laundry constantly, but finding that middle ground of, here’s what I’m going through. I’m showing up, but here’s what I’m going through. Then there’s just a little extra compassion. That’s the world I want to live in, anyway.

Zibby: Yes, totally. On the other side of this business, do you find yourself coming up with millions of — are you an ideas person all the time? You have tons and tons of ideas?

Alli: Yeah, it’s like a curse. They don’t stop. I’m totally an idea person. We have Squeeze, which is this new massage concept that I’m so proud of. It’s totally taking off. We have eighty units in development right now. Brittany Driscoll, our former head of marketing at Drybar, is running that and just doing a beautiful job. I’d love to take credit for that, but it really is my brother’s idea. Obviously, he’s not partaking in blowouts. It was the same problem. Why is there not a great place for massage? There’s Squeeze. There’s Brightside, which is our infrared yoga concept. I joined with another mom who had a jewelry company in helping her get that into the next realm. Then I just started this Mastermind that I’m doing that’s really fun and is, again, helping other entrepreneurs. I speak at a lot of events. I’m sure I’m forgetting something else I have going on. Truly, I am always like, oh, shit, I didn’t talk about that because I forgot. I thrive in the busyness and the chaos of it. I’m also a work hard/play hard. I’m one of those people — I know this is controversial, a little. I’d rather be on a vacation and take calls and work a little bit and be on vacation. I’m like, you can work wherever. Yeah, Canopy president. See, I knew I’d forget something. Yes. I love Canopy. I’m so excited for that.

I get myself involved in a lot of projects. I like being busy. I like being fulfilled. I like trying different things to see where I land. I enjoy working. It’s that cliché. I don’t think of it as work. Therein lies the key and success of life. If you can find some balance in — which is funny because I have a chapter called Balance is Bullshit. I do believe that too. If you can find some daily — for example, I have a crazy couple weeks coming up, but I’m going away to Palm Spring for just a few days. I’ll probably do some work from there, but I’ll be in Palm Springs at this beautiful place. I love the balance of that. Sometimes I’ll work until eleven o’clock at night. Sometimes I’ll be done at four o’clock. Being an entrepreneur, you have that kind of luxury, which I think is what I love about who I am and what I get to do in my life. The ideas come fast and furious. It is always my advice to other entrepreneurs all the time. There are so many opportunities out there to improve things that already exist. Blowouts existed. Massages existed. Humidifiers existed. Jewelry. It all has existed. Just kind of fell into this. It can all be better. Why don’t we try to make what exists better? That’s always really been part of my mission. That’s always my advice. If you love this place that you go but they’re not doing a great job on whatever reason, which is, sadly, a lot of the cases for a lot of businesses, go do it better. You don’t have to invent the iPhone to be successful.

Zibby: Although, did you see that BlackBerry movie?

Alli: No, but I want to. I saw the preview for it.

Zibby: It’s really good.

Alli: I want to see it so bad. It’s so funny. My brother had a BlackBerry for so long. Even once BlackBerry was really dead, he would not get an iPhone. It was just this big joke with us. He liked that he could type without looking at the phone because of the raised buttons. I saw the preview for that months ago. I was like, oh, I can’t wait to see that. What an extraordinary case of not being willing to grow. I haven’t even seen the movie, but I’m excited. It was good?

Zibby: It’s a cautionary tale, but it’s also, sometimes things come you could never have predicted. I’m kind of dying to talk about this movie to somebody, but it’s okay. After you watch it, DM me or something. We can talk about it.

Alli: Okay. Oh, my god.

Zibby: Alli, thank you so much. I feel like we could’ve gone on forever. Thank you for The Messy Truth. Thank you for all the other stories that are in here and the lessons and the worksheets and all the other stuff and just for being willing to go there and make this time worthwhile.

Alli: Thank you so much. It was a very enjoyable chat.

Zibby: Me too.

Alli: Thank you for reading the book. Thanks for promoting it and all that stuff. I appreciate it.

Zibby: My pleasure. Bye.

Alli: Bye.

THE MESSY TRUTH: How I Sold My Business for Millions But Almost Lost Myself by Alli Webb

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