Drybar Founder Alli Webb on Starting a Business in 2010 Versus Now


One of the defining brands of the 2010s was Drybar. The popular chain of blow dry salons helped define the so-called experience economy, leading to numerous competitors and copycats. But of course, to go from a single location to a national chain is difficult in all kinds of ways, both personally and operationally. On this episode, we speak with Drybar founder Alli Webb on the experience, which she talks about in her new book titled
The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself.
We also discuss the truth about raising money, her new chain of massage studios, how to select the perfect retail location, and how operating a business is different in 2023 than it was 10 years ago. This transcript was lightly edited for clarity.

Key insights from the pod:
On losing herself in the business — 4:45
Why she founded Drybar — 7:09
Rapid growth in the 2010s — 10:55
How Drybar competed on costs — 13:29
Finding hair stylists — 17:22
Taking money off the table — 25:01
Fundraising from private equity — 28:57
Overlap between Drybar and Squeeze — 32:55
Choosing locations for shops — 36:10
The big differences in the market now — 40:23

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Joe Weisenthal (00:52):
Hello and welcome to another episode of the Odd Lots podcast. I'm Joe Weisenthal.

Tracy Alloway (00:58):
And I'm Tracy Alloway.

Joe (01:00):
Tracy, have you ever been to a Drybar? I just thought I'd start this conversation as simply as possible.

Tracy (01:06):
You don't mean a bar that isn't serving alcohol?

Joe (01:10):
No, but if there were I would like that, but no.

Tracy (01:13):
I think those are called coffee shops, Joe. No, I have in fact been to a Drybar. I remember when Drybars first became a thing and it was this sort of novel concept that you could go someplace and have your hair blow dried by a professional, sometimes while having a drink or like watching silly movies on TV. It was different to how it had worked historically because normally maybe you would go to your local hair salon to get a blow dry or often you would just have a blow dry after getting your haircut or something like that. But it became this really big thing.

Joe (01:47):
Absolutely and I will say I have never been to Drybar.

Tracy (01:51):
You have never been, I assume.

Joe (01:52):
I have never gotten, I think a proper blowout, but I've gotten my hair done for TV and so I guess that's the closest I've gotten. But also I just sort of remember when they started popping up and it felt like one of those businesses and business models that sort of defined the 2010s maybe, or defined a certain era, and this sort of idea of diffusion of brick and mortar with booking on an app and the proliferation of new kinds of stores. Like, that felt like a big part of the 2010s economy.

Tracy (02:26):
Stores which were providing a service and also an experience because I remember the experiential portion of it was a big part of the offering. So again, you could go get your hair blow dried for 40 or 60 minutes or however long it takes, and you could have a cocktail while you did it.

Joe (02:43):
They did? You could have a cocktail?

Tracy (02:45):
Oh my gosh, yes. That was a big part of it and a lot of the stores, well, I'm thinking of one in particular because it is going to be the topic of this podcast. The original Drybar offered, they would have movie screens, like TVs built in and you could watch like rom-coms from the early 2000s. It was great.

Joe (03:06):
The experience economy, you're right, that was like such a big part of the story or that was such a big part of what people talked about, people wanting to have high quality experiences, something above maybe some of the old dingy physical retail, physical service locations of the past. I do think that it really sort of redefined a category.

I'm interested [because] obviously that exploded during a specific year in time. The rise of smartphones, low interest rates, so VCs investing in fast -growing concepts of various sorts of digital and physical, loose labor markets and the ability to hire lots of people fast. And so, like, thinking about those business conditions, modern business conditions, how they've changed, lessons learned from that period, of course, sort of a go-go era for fundraising and so forth. I think there's still more to learn.

Tracy (03:55):
Absolutely. I mean, things have changed as you just mentioned, but I think the desire for services/experiences is something that we still hear about today.

Joe (04:04):
Well, I'm excited. We really do have literally the perfect guest to talk about all of these things. We are going to be speaking with Alli Webb, she was the founder of Drybar, also author of the The New York Times bestselling book, The Messy Truth: How I Sold My Business For Millions, but Almost Lost Myself, amazing title. And she's also gone on to found more businesses, including a franchise chain of massage therapy locations. So sort of sounds like Drybar for massages. So Alli, thank you so much for coming on Odd Lots, thrilled to have you here.

Alli Webb (04:36):
Well, thanks for having me and I love your conversation about Drybar. You guys really nailed it.

Joe (04:41):
The title of your book is so good. How did you almost lose yourself?

Alli (04:45):
Well, I mean the book really goes into a lot of it, but it's a long story. More or less, building a business over the last 10 years, which was an incredible journey and we definitely captured lightning in a bottle and it was intoxicating and exhilarating and amazing.

But a lot of my personal life in the background kind of fell apart. There was divorce and rehab and depression, you name it. It was a lot of navigating real life stuff alongside growing this massive amazing business. It's kind of like if a business book met a memoir and had a baby, that's kind of what this book feels like to me anyways, because it's really the coming together of the stories of all the things that I learned and lessons and takeaways from building a business as someone who didn't go to college and doesn't have a fancy business degree.

But then also like the underpinnings of it all and how you lose yourself. If you ask any entrepreneur, they will tell you the same thing. You get so invested in this thing that's like a baby to you and you kind of easily lose sight of a lot of other things personally in your life and yourself.

The response to it has been overwhelmingly positive and just helped so many women and people are just relating to it and [are] like ‘Oh my God, that's me and I felt like I was reading about me and that's my story.’ It is fascinating to me to put out stuff that I don't think people talk about enough in such a public context and then for people to relate so heavily to it has been, I mean, such a joy and privilege for me.

Tracy (06:21):
I should say, first of all, thank you for coming up with this idea because it has been enormously helpful in my own life as someone who has like fairly untamable, very thick hair that gets super poofy in the summer especially. And nowadays we take the concept of Drybars, I mean, it's gone beyond the brand. You think about Drybar, you think about a hair salon that is exclusively operating drop-in blow dries, basically. So it really became a thing. But back when you founded the company, and this was obviously a new and novel concept, maybe just to begin with, could you talk about the business opportunity as you saw it back then? What was the gap in the market that you were able to identify?

Alli (07:09):
I mean, I should say that I wasn't a business person looking for a hole in the marketplace, although that's great if you are, I just wasn't. I just felt like there was not a place to go get a good blowout at an affordable price. And I think I had felt that my entire life just as somebody who also has hair that's curly and frizzy and hard to manage, I was always kind of frustrated. And as a kid, I would go to the hair salon and beg my mom to blow out my hair. I mean, I was always on the hunt and I was always into my hair as a kid. I think on some level, subconsciously I wanted something like a Drybar my whole life.

Fast forward to becoming a professional hairstylist in my early twenties and then spending so much of my life doing hair and working in salons. I think I intuitively, instinctively knew that there had to be a better way to get a blowout. And there was two pretty bad choices out in the market, which was like the discount chain, which I'm sure you've been to, or your fancy hair salon, where they're charging you so much money and upselling you on other things. There just wasn't anything like it.

But what ultimately led me to Drybar was that I started a mobile blowout business. I had been a stay-at-home mom for a couple years. My boys were two and four, and I started running around LA in my Nissan Xterra blow drying my mommy friends because that was the world I was very much in at the time.

I posted an ad that said I'll come over and blow out your hair while your baby's sleeping and I would charge 40 bucks. And again, for me, it was like, if I don't charge that much money, more people will call me. It wasn't a very sophisticated business plan, but that's what I hoped for and sure enough, they did.

And I realized during that, because I got so busy while I was operating my mobile business because I was pretty good at what I was doing and because I was only charging 40 bucks, I was so crazy busy. That’s when the kind of light bulb went off for me and was like, wow, at the right price point, women will do this a lot.

I got so busy and I came to a crossroads. Am I going to expand this thing mobile-y, or do I open a brick and mortar instead of me going to them, have them come to me? Which is obviously ultimately what I decided to do and I went to my brother and asked him to help me with all of this. It was such great learning, even though I didn't make any money at my mobile business, but who cares because it informed what would become Drybar.

I realized during that time, it all really crystallized for me that, at the right price point in a beautiful space, a great blowout can be something, an affordable luxury that women do once a week, twice a week, whatever it is. We have plenty of clients who don't even wash their own hair anymore because the price point was right, the experience was great, and I realized nobody else was doing anything like this. And so it was like a prime opportunity that I really felt like I kind of stumbled into.

Joe (10:02):
Can you talk about growth? And when I think about 2010s business culture, I think of magazine covers where like, this founder just raised X million dollars, this founder just had a huge exit, this 28-year-old is now a billionaire.

Alli (10:18):
Total addressable market, right?

Joe (10:19):
Total addressable market. This just sort of money growth culture and, you know, obviously as you talked about, there's a sort of, presumably you are not the only one that there was like a real dark side to this and a personal cost, etc. But can you talk a little bit more about the sort of decision to take your idea and make it, you know, you raised money and you expanded and became a national, maybe international brand. Can you talk about that sort of choice to like, okay, we have to go for this and we have to grow big and we have to deliver results?

Alli (10:55):
Yeah, it's certainly a choice and not everybody wants to do that. I mean, you get a little taste of that and it's hard to walk away from it. I think we all knew that we were onto something really special and it was, we did have to make some hard decisions like, obviously this is going to change our lives significantly. Do we really want to go for this?

There was so much demand, there was so much request to open more stores and more markets and it was going to be a whole thing to really go for this and to really grow this thing. We had to really lock arms and decide that that's what we wanted to do, because it was going to really change our lives, which it did in every conceivable way. I think I see lots of businesses that decide not to do that, to grow at a more organic, slower pace.

I mean, obviously for us, maybe not obviously, but for us to grow, we were going to have to raise capital because even though Drybar was successful, our first few stores were successful, they didn't throw off enough money to grow the way we wanted to, or the pace in which not only, I shouldn't say wanted to, I should say like the pace that we needed to because we knew a lot of people were on our tail and there were so many copycats popping up left and right, who, humbly, were just not nearly as good as we were and didn't totally understand what we were doing, but saw an opportunity. It's like you open up a salon and throw some chairs in. It’s just so not that simple.

And so think we felt a little bit of pressure, like, if we're going to really go for this, we’ve got to move fast and in order to move fast, we need to raise money. And so then we raised like our first two or three million with friends and family, because they were, and this is also not super common, but friends and family were practically throwing money at us because they saw the writing on the wall that like, this was a great opportunity.

And so yeah, I mean we ultimately came together to make this decision that we're going to really go for this and grow this thing and that meant so many other things that I, at the time, I knew nothing about, like how you grow and scale and hiring and all the complexities that go into that. But there was a lot of pressure because if we were going to do it, we had to do it now and otherwise we were going to fall behind. My brother found an investment banker and we went out and did like a formal process in probably year, like two maybe? And decided to really like, no pun intended, blow this thing up.

Tracy (13:25):
Sorry, I'm a fan of puns.

Alli (13:28):
Oh, I have a lot of them.

Tracy (13:29):
Oh, good. Excellent. Can you talk a little bit more about the business model itself? Because I mentioned in the intro, going to a Drybar was a nice experience. It wasn't like you're going to a budget hair salon and just getting this thing done for the cheapest price. But at the same time, the price you were charging for blowouts was very reasonable, especially when compared to a more higher-end salon. So how did you actually contain those costs? Like, where did the savings actually come from?

Alli (14:00):
Well, I mean, it wasn't easy and our margins were razor thin, to your point, because the amount of money we spent on the build out to make it look the way it looked and to make it feel high-end, but just not have the high-end price tag. The name of the game for us was volume — see, there's another pun.

Tracy (14:22):
All of these are flying right over Joe's head I think.

Joe (14:25):
No, no, I got that one!

Alli (14:26):
Women like volume, big hair.

Joe (14:30):
Bigger hair, closer to God. Isn’t that what they say?

Alli (14:32):
That's right and it is a true statement, don't let anybody tell you differently. So we knew that we needed to do a ton of blowouts a day. Just to give you an example, what I mean by a ton, like we thought in our Brentwood location, which was our first location that had eight chairs, we thought if we do 30 to 40 blowouts a day, that's good business and whatever.

We completely underestimated the demand and we were doing more like 80-ish blowouts a day, which very quickly turned to a hundred blowouts a day once we were fully staffed. We were open from 7:00 AM to like 9:00 PM, you could theoretically do that. So once we realized that we could do so many blowouts, we were open seven days a week, 12 hours a day, we could theoretically do it.

It really was about volume. We had to get those numbers in order to make the business work, which by the way, didn't always work because as you might imagine, supply and demand was a real thing. For us, the supply was hair stylist and it was hard to get, extremely hard to get great hair stylists in and it's just an interesting market. I'm a hairstylist myself, it's like our strengths are our weaknesses. Like, I'm a little flaky, I'm usually late to most things and so are most hair stylists, not all. Just getting hair stylists who were okay just doing blowouts all day long, understandably, so many stylists wanted to grow their business and do cuts and color and Drybar was more like a stop for them, not like a destination.

That part of it was really hard getting and training stylists to the level of which we wanted them to be, all of that. So it was a tough business model in terms of getting that to all work. In some stores and sometimes we did it better than others, we had a gajillion different strategies on recruiting and staffing and all of that. But the business model only worked if we did X amount of blowouts per day, per store, which we were, for the most part, able to really pull off.

Tracy (16:50):
I am glad you mentioned recruitment and training, because I get the sense that this was kind of important for the business model as well. So talk to us a little bit more about how you identified the right hairstylists for the business. As you mentioned, it might not be that every stylist wants to spend their entire day just blow drying hair. And then secondly, how much of the labor force was flexible? Was everyone working full-time or were people coming in and doing it for like three or four hours to sort of add on to their main job?

Alli (17:22):
Exactly, we tried to be as nimble and flexible as possible with stylists because of that reason. It is very labor intensive and I really always understood that some stylists really loved it and could do like a six, seven, eight hour shift. Other stylists were like ‘I can't do this for more than a few hours.’ Like, I get it, no problem.

Especially in the early days, I was like, ‘I will take whatever you can get if you can only come in and do four blowouts, fine.’ It was that dire — dire is not the right word, but it was that crazy and busy and of course I was doing tons of blowouts in those early days to accommodate people. I would sit or stand at the first chair and blow out hair and be able to like, manage the front desk.

I mean, those were crazy times. We were really flexible in terms of what stylists wanted to do, and how many days a week they wanted to work because we knew we had to be in order to get people to like, it was like a hodgepodge of stylists getting them in. Then the other big challenge, as you might imagine, is making sure that those stylists are really great. And that was the other thing, it was like there was a subset of stylists who'd been doing this for a long time and, and they were great and we didn't need to do a lot of training. And then there were stylists who were newer, out of beauty school and they didn't have a lot of training.

And so we needed to spend a lot of time with them, but we didn't have that time. We weren't doing much training, which was getting us in trouble because for me it was obviously really important that the blowouts were top-notch. We do one thing and we better do it really well. So it was really stressful to get a stylist in there who wasn't at the top of their game.

So that piece of it was challenging and I would eventually build out a very robust training program, but that wouldn't be for years or would take years. We were always tweaking that, but I felt really strongly about the certain culture that I wanted to have in the shops. And so it was like, there were stylists that were just not the right fit for Drybar. They didn't want to just do blowouts. They didn't want to be washing their client's hair. They wanted to take a break in between every client and for better or worse, it was like you would do a handful of blowouts and then take a break or take your lunch or whatever, but you were working the whole time and you were in Drybar.

That wasn't something that every stylist wanted and not the typical culture of hair salons. Even as I grew up in hair salons, it was like people would take smoke breaks all the time and there was like a more casual nature about it. Not always, the really busy salons weren't like that. But we were a really, really busy shop so we needed that kind of work ethic and that just wasn't for everybody, which was totally fine.

That was something that I always would preface with stylists when we were opening a new store because we have 150 locations. I would say the first like 50 or so I went to every single opening until I just physically couldn't anymore. But I used to say to the stylist, I would do this kind of rah rah, like what we call the new hire orientation where I would sit basically in a group setting and talk to the stylist about who I was, why this idea came to be, what our core values were and all of that. I would also say, ‘Every one of you sitting here may not end up staying here because this may not be the job for you. You may not like this.’

This is a very fast paced hustle bustle. You've got to thrive in chaos, enjoy this, that part of it, or it might not be the best job for you. You know it doesn't have to be for everybody and so that was the mentality of the shop. And we didn't have access to every single hairstylist that there was out there. We were pretty picky from both a technical styling point and like, we want you to be a really nice person who has over the top customer service because that's a huge part of the business model, and it was the most challenging part of the whole thing.

Joe (21:11):
So, I mean, what I imagine the challenges that you faced early on with hiring and recruiting and retaining talent were like this precursor to probably what hundreds of thousands of entrepreneurs across the country these days, particularly in the Covid era of higher labor turnover, like tearing their hairs out.

And I have to imagine, as you said, you eventually couldn't go to every opening, not every new stylist got to hear a pep talk from Alli Webb. What are the broader lessons that you imparted to hiring managers at locations, at Drybars or some of your newer ventures, including Squeeze, I know you're not the CEO, but the co-founder of the massage [chain]. Like, what do people need to know about identifying talent who will be committed to the operation? Like what did you learn about how to scale that sort of identification?

Alli (22:03):
I mean, we always did these, like pre-hires before anybody even walked in the door. We had a team of people who would talk to potential employees just to get what we would call the cultural interview piece of it, which was like a pretty candid conversation, just trying to get to know somebody.

That was even like in the early days before we opened the first location, I used to have a hairstylist come over to my house to blow out my hair. That was like the job interview, which was awesome and not always awesome. But anyways, and part of that process just for me in that very small scale was getting to know their personality, and it kind of goes back to what I was talking about, that this job isn't for everybody.

So as we scaled and grew, those culture interviews became essential because you could tell very quickly the conversation was like, why do you want to do this? And like, what do you love about this? And for me and for our team, what we always like to listen for is somebody who really enjoys being in the service industry. They enjoy making people feel good and giving and sharing this amazing talent they have as a hairstylist with others, just like the way people would show up on calls, like prepared and ready and answering questions with a lot of excitement and enthusiasm about the brand. On the contrary, as you would imagine, the stylists who were really quiet, really soft spoken, didn't get the sense that this was like something they were really excited about or loved.

It feels like it sounds simple coming out of my mouth, but it is that basic. Like, I really want to do this and be a part of this brand, and I love this company and I love hair and I love styling and making women feel great. That's the first barrier to entry for us is like making sure that at least that piece is there and you're going to show up and be kind and nice. That is an intangible thing that you must simply have in order to be successful. So if you don't even have that, there's no point in going any further and like I said, as we grew, there was a team that was instructed to really listen for this kind of stuff and make sure that we were bringing in the right personalities as well as great hair stylists.

Tracy (24:20):
So you talked a little bit about the grind and how intensive this whole process of building a business actually was. And of course, that's a big portion of what your book is actually about, this idea of losing yourself in your business, your baby. I'm curious though, it sounds tough and you're sort of like working and working until you get presumably to like the big payoff of some sort. And I always wonder with new startups, how much money are you able to take off the table in the beginning? Like, how do you balance building the business and investing in it versus rewarding yourself for the hard work that you're actually doing?

Alli (25:01):
Well, I love this question because I think it's such an important thing to point out. It's a tricky one because I know that people want to ultimately make money and they want to be successful, and that largely looks like making money. I get that and I feel that too. I mean, just like anybody else, I really like making money and I like money and nice things, but money wasn't the big driver for me in this business.

And I feel like it feels to me like a mistake that a lot of entrepreneurs make. They're only looking at the money and the opportunity to make money, sell a company, whatever, versus doing something that they just really love. I feel so strongly about this, and if you look at like, some of the most successful companies in the last couple decades, and you hear the founder's story, it has always started from some sort of personal necessity, something that they felt like in their heart of hearts that they could make better and do better.

The reward is, is it working and the success of the company being felt and growing this thing and the excitement and the adrenaline that you get from building something that people love and providing all these jobs and all this opportunity and all of that. I mean, for me, that was really what I loved a lot more than like ‘Oh, we're going to build this thing to sell it.’

It was never ever that conversation for us. I think I started to realize after a couple years in this thing, like having never had any experience in M&A and going public and all of that stuff that I didn't even know that happened in the world. Like I was so naive back then, and as I started to like pay more attention to that, and I was starting to become friends with more founders, and I was starting to be in these rooms where people were talking about buying and selling companies, I was like ‘Oh my God, that might be us one day,’ and that was an exciting part of it.

I mean, obviously we sold it 10 years after we built it, and I would say in a year, like after we had raised a bunch of money, obviously everything changed and ultimately we raised $75 million and now you have investors and that is what they're thinking about. That is good for them to be thinking about and moving the business in the right direction but all of that was so new to me when I started. I mean, this whole thing really just started out of a passion to find my purpose in my life and to do something that I really loved to do and I loved it. I mean, I loved building that business and I loved every second of it.

I was in that shop seven days a week. I mean, I couldn't get enough of it and that is so much more valuable than any dollar amount to have that. Like, I love what I'm doing and what I get to do every day, so again, once I realized like, oh, we might actually be able to sell this thing, like, oh, we're going to actually be able to make a lot of money. That was really awesome but just not what I went into this thing thinking.

Joe (28:05):
I want to ask you a question about fundraising. I have heard that VCs or investors don't still necessarily have a great grasp of the business model of rapid growth physical locations. And so there's sort of like investors who sort of understand physical operation. And then there's VCs who probably often think in the idiom of software and five people in a room growing to something that a billion people can use.

And that a lot of these sort of like modern concepts of physical growth locations, whether it's like a Drybar or a Cava or something like that, sort of exist in this middle space and investors don't have a great understanding of it. Was that the case for you when you first went out trying to explain to them your vision? And do you think investors these days feel like they have a better handle on these types of startups?

Alli (28:57):
Well, I mean, it feels like the Wild West right now. I think retail is so tough right now that I don't blame VCs and all these guys, I mean, it's like you just don't know. It's so hard to predict what's going to happen right now, so it's such a funky time.

I actually had this thought not long ago, like, I wonder, I mean, part of the success of Drybar I think was when we started it, we only wanted to raise like $10 or $15 million that first round. We ended up raising $25 million because we went with private equity, we never went down the venture capital [route], and they wanted to put in more, as they do. And I think it was, again, a very different time.

Retail was very sleepy at that time in 2009 when we first started Drybar, and then Drybar resonated and took off and we raised the first like three million with friends and family, which got us like to a couple of stores, but the buzz was there and the PR was there and women were like telling other friends.

So we had that in our corner and by the time we were in these rooms with these private equity guys, granted, you can picture the scene, it's like me and my big personality, and then these guys in suits, and they're like ‘What are you doing? You're blowing women's hair and talking about puns and ridiculous jokes. It's so annoying.’ But they didn't quite get it yet, but they're like ‘My wife's been talking about this thing, or my daughter's been there,’ [it] was that kind of general, like in the air, ‘we've heard about this. It seems to be getting a lot of attention.’

And of course there were the conversations of like, ‘Are you going to do nails and makeup too, because you can, and you're doing a hundred women a day, why don't you do this?’ Of course, I had to say, no, we do one thing, we do it really well. That turned off a lot of investors who didn't want to get involved in Drybar, which was like, no problem, but not the right fit.

So there was a lot of trepidation of how do you scale this thing when they didn't really understand it to begin with and again, back to our initial projections of doing like 30 to 40 blowouts a day when obviously we far outseeded that. We were in LA and our second location, which is a franchise, was in Dallas, which obviously makes a lot of sense, but there was still a lot of, have we proved the concept, is this something that really works far and wide across the country?

And then there was still kind of a question mark from a lot of people, my brother included, who was always like, we got to prove the concept, we got to prove the concept. And I was like, I just think it works where women have hair. And that was my very bullish and maybe naive idea, but we kept going and we knew we had something really special and magical. And so we kept going until we found the right partner and they really understood our vision and didn't want to change it and wanted to really lock arms with us and partner with us, which was Castanea, which is now known as Stride and so that's how it all went down.

Tracy (32:17):
So I want to move on and talk about your new business Squeeze, which I've seen described as sort of the Drybar for massages. And so I guess my first question is listening to you describe, again, like the grind of starting another business, why are you putting yourself through all of this again? And then secondly, how much overlap is there in terms of the business model between Squeeze offering massages and the Drybar offering blowouts?

Alli (32:48):
Well, first of all, I am not in the grind. Thank you very much. I'm very happy to not be in the grind

Tracy (32:53):
Smart, fair enough!

Alli (32:55):
It's a great question. Like, no thanks and it's funny when my brother, this is really my brother's idea, and when he, as a bald dude who never got blowouts, his frustration in the marketplace was around massage because as someone who went to the local chain, which you know who I'm talking about and had a pretty bad experience from having to call every location to book, the decor was like, eh, and the massage is very hit or miss.

The whole process was just so clunky that he was so frustrated that there wasn't a great place for him to go for a massage as someone who liked to get a weekly massage, even though the price point was, was good at the local chain. And then of course if you went to a spa, it was the same conundrum that you had at Drybar, the spa would be really expensive, just like a high-end hair salon was really expensive for a blowout.

So the similarities in the problem were pretty much the same. And so when we were like in the last couple years of Drybar, Michael really wanted to start this. Obviously we didn't have the bandwidth for it, and I, to your question, did not want to go back into the early stages of building a business. So I was like, nope, not doing that . But then we went to Brittany Driscoll, who's the CEO and our co-founder and who ran marketing at Drybar for several years and she was on her way out of Drybar, was like going to explore new opportunities and we said, hey, we have this idea for a massage concept because for the reasons I just mentioned, we wanted something different and better that didn't exist, which is always my advice to entrepreneurs is like, you do not have to reinvent the wheel.

Like obviously we did not invent blowouts or massages. We've just created a much better experience and price point and a million other details around them that nobody's paying close attention to. And the big differentiator of Squeeze though is that there's an app that you, even though it's a brick and mortar and you go in for a physical massage, there's an app that you book all your preferences on from like, if you like oil lotion and the type of music you like. There's a very intuitive body that you press on like, I like a lot of pressure here but not here.

So by the time you walk in to Squeeze, the therapist already knows all of the stuff because you've had to have gone through the app and really filled out all your information and, and that that was a big undertaking. It took us over a year to build out this app that had all these bells and whistles that was super intuitive and nobody else has this. And it is the biggest differentiator of Squeeze, not to mention it's the same founding team as Drybar. My ex-husband Cam did all the creative, the same architect who built Drybars, everything is the same team and it is the Drybar of massage because it's exactly the same thinking as Drybar.

It's like, this is not being done well, we're going to go do it much better and if you read the reviews on Squeeze, they're literally all five stars. I mean, we've had such great experiences and so much of that comes from the learning from Drybar, especially Brittany having lived this world with us for many years and we knew what was working, what wasn't working and to date, I think we're doing a completely franchise model where Drybar was a little of both, but we've sold over 80 locations across the country. So you'll start seeing them popping up all over the place in the next year or so.

Joe (36:10):
Speaking of those locations, that actually fits right into what I was going to ask next. You mentioned that sort of generally Drybar you saw as being successful anywhere that women have hair, which is everywhere, but you must have thought specifically about the types of locations, whether they're in high-end malls or busy areas that are really optimal for opening a location these days.

Obviously there's all kinds of questions about what is even the future of offices and where and how people are going to work. What have you seen in terms of, or where is your thinking in terms of selecting locations in the year 2023 where you feel confident that it'll work at a time in which I think it's still very up in the air even where people are going to be working?

Alli (36:54):
It's such a good question and I think we're trying to figure that out right now too. I mean to go back in time a little bit, with Drybar, which I still kind of feel, and I do, just for the record, far be it for me to predict the future, but I really believe the pendulum is going to swing back to experiences. I think people are desperately hungry for being out in the world with other people again and having experiences. I think it's just taking a minute to get back to it.

That said, with Drybar we realized very quickly that being in a woman's daily routine, like being near a grocery store, being near her workout or where she liked to shop and where she liked to have lunch. We knew the importance of being in that mix of your daily use and that was always the guiding light of where we put a Drybar, like near and in the right area, which by the way can be really tricky.

I mean, we certainly experienced this the hard way that you could move, you could open a store in the right, like, mile radius, but if you were in the wrong shopping center on the wrong side of the street, you would never know unless you tapped local knowledge to know that it's really hard to park there and nobody likes to go there because of the way the shopping center is.

When an outside big corporate company comes in and it looks really pretty and the other stores are good, you're like, this looks great. Unless you get that local knowledge, which again, we have been burned on before, you don't really understand the neighborhood and how it functions and how women really use it. So it's an important but small and often overlooked nuance when you're, when you're looking at real estate to make sure that you really understand like, where do people park? Is parking a total pain? Is it easy to park? Is the location easy to access if you're in a mall? Which malls are such a dying dinosaur anyways as well but all those factors. We opened in Fashion Island Mall in Orange County.

Tracy (38:58):
Oh, I know that one!

Alli (38:59):
Well then you know we are strategically placed near the parking lot. It would not make sense for us to be like deep in the mall if you're like ‘Oh, I'm popping in. I have to go over to Fashion Island,’ which already could be a pain. How busy is that place? But like, at least we're at the very tip, we're near the Barnes and Noble, I don't know if that's still there, where you're like ‘Oh, I can just park and run into Drybar,’ and ‘Oh, there's an Ulta [Beauty] right there and there's a Whole Foods.’ So all of that was very strategic and how we always thought about our locations, making it as easy as possible for a woman to access us.

And then for her to be able to do two or three other things, so Drybar seamlessly fits into her day, which is similar thinking for Squeeze and in any location, in any kind of business that we open. And it's tricky like when you're going into New York City, because it's obviously a different animal than like the suburbs, but even still, are we near a subway? Can like a bunch of women walk to us? Are we near where they're going for other stuff? And sometimes it's like we always said, we couldn't afford to be on Main and Main, but we could be on the little side street off Main Street so we could afford the rent, but still be close enough where she can easily pop over.

Tracy (40:08):
What's been the biggest, I guess, noticeable difference between doing Squeeze in the current environment versus Drybar 10 or 20 years ago? Like what has most markedly changed for you?

Alli (40:23):
I think the biggest thing is costs and like getting stuff, for lack of a better word to our stores. Real estate deals seem harder. The construction prices are so much higher than they were when we started Drybar. Not always, but we could often go into a shopping center that had a full service hair salon because we would explain to them, ‘Listen, we're coming in and we're not going to take your lunch. We're not doing cut and color, we're just doing blowouts. And if you're really smart, you'll leverage us and we'll send you clients and they'll send us clients and a lot did and really got it.’

But some landlords and some tenants, if there was already a hair salon, which there usually was in most shopping centers, could easily block us from coming. The same is true of Squeeze. There's a lot of massage concepts in a lot of places, albeit some of them aren't great, but they're there so that impedes us from coming there as well. So that is just a challenge that anybody deals with if you're going into any kind of business that already exists, which it did for Drybar as well as Squeeze, so you just have to get a little more creative with where you're going.

Joe (41:33):
I was going to wrap it right there, but just real quickly, so do tenants of shopping centers and malls, do they have stipulations frequently about the types of competitors or adjacent companies that can move in? I'd never thought about that before.

Alli (41:47):
They totally do. It definitely is not like one rule, it changes in my experience, it changes from center to center, but especially when you think of like, less probably in a mall, and I don't have a ton of experience with malls, but in like a strip center shopping mall, a lot of those tenants in their leases will have something that says another hair salon cannot open in here.

Joe (42:14):
Makes a lot of sense. Alli Webb, the author of the new book, The Messy Truth: How I Sold My Business For Millions, but Almost Lost Myself. Thank you so much for coming on Odd Lots. That was great.

Alli (42:24):
Thanks for having me. It was a fun conversation. I haven't talked about this stuff in a long time, so awesome.

Joe (42:28):
Thank you. That was really fun. Thank you.

Tracy (42:29):
Thanks so much Alli, that was great.

Joe (42:43):
That was really fun, Tracy. First of all, I mean it's obvious when she says it, but for example, at the end it hadn't occurred to me that such things would be in leases if you're going to open up a nail salon or a sneaker snore, a sneaker store.

Tracy (42:59):
Did you say a sneaker snore?

Joe (43:01):
Sneaker snore.

Tracy (43:01):
Sneaker snores!

Joe (43:03):
Or a karate studio or whatever you see in strip malls that you have some stipulation. Like, you can't just open another one next door, but it makes a ton of sense.

Tracy (43:10):
It does. I think also for shopping malls, I think the owner of the shopping mall wants differentiation and likes variety so they try to build that into a lot of their leases. No, that was really interesting. So it seems like Alli really kind of hit a sweet spot at that time period where she was offering a service rather than a good at a time when brick and mortar retail was experiencing a downturn.

We had that episode recently on dead malls and commercial real estate and in 2009, that was really the era of the dead mall and competition from online shopping and things like that. So she was able to identify something that people would still pay for and have to go to to receive in person.

And then secondly, I think one of the things that I found really interesting was the idea of having that flexible workforce and offering stylists the chance to come in for two or four hours versus a full-time position. So it feels like she also tapped into that sort of upswell of, I guess, gig work, which was also just beginning at that time.

Joe (44:21):
Yeah, no, like I said, it really felt like they sort of nailed a huge aspect of what I think of as, even though I have never been in a Drybar, my intuition sense of it, I guess, is strong enough that I associate it as one of those like defining brands of the 2010s economy. So many interesting details.

I mean, you mentioned that aspect of the labor force and I feel like what Alli was dealing with early on, it's probably [what] so many people are dealing with in the last few years of like, how do you hire people that are going to maintain the quality that you expect for you, your outward facing quality, that are going to stick around, that are going to maintain the brand? It felt like she had to deal with a lot of those things like from the beginning in a way in which many business operators probably never really struggled with that up until maybe the year 2020 or 2021.

Tracy (45:13):
Absolutely, and it'll be interesting to see her sort of replicate it in the massage market as well. Like where do you get all the masseuses from?

Joe (45:20):
I also really liked that point, and maybe we should do an episode on this at some point, like the art of location selection for a brand. You know, and the idea of like, when she said it, it makes a ton of sense, if the idea is you're going to be a convenient stop for women to get a blowout, then you want to be on the perimeter of the mall, not the inside of the mall. If you're at the inside of the mall, it obviates the whole thing.

The idea of proximity to parking. I think our friend who we've had on, Patrick McKenzie, has talked about this a couple of times with banks . That is a big thing in terms of you can have two locations that look very similar, but if one is not on the right corner in the right way, it's going to fail. And so maybe we should do an episode and we would talk to a commercial real estate broker about finding good locations for things.

Tracy (46:06):
Oh, that would be so interesting, let's do that and then we should go to strip malls and observe in real life. I would do that. Shall we leave it there?

Joe (46:13):
Let's leave it there.