Webb, the 48-year-old founder of blowout empire Drybar and author of The Messy Truth, went straight from high school to New York, where she jumped from job to job until she landed on styling hair, a career she never left.
After getting married, moving to Los Angeles, and having two kids, Webb began traveling to clients’ homes and styling hair on demand—a service that quickly blew up among busy women in the Brentwood area. Alongside her brother and then-husband, Webb spun the concept into Drybar, which has since become a household name and destination for on-the-go reliable hairstyles across the U.S.—and a venture capital darling.
It wasn’t always easy, and in her new book, Webb is open about her mistakes and regrets. Namely, she struggled with severe burnout, especially balancing difficult family issues, including the death of her mother and her older son’s time in rehab.
In an interview with Fortune, Webb—a self-made multimillionaire—walks through building her brand from scratch, establishing herself in a crowded field, trusting her instincts, and taking money off the table with each VC round—despite what popular wisdom might recommend. The following has been lightly edited for clarity.
Can you tell us a little bit about where you grew up and what your childhood was like?
I was born on Long Island, New York, and I grew up in South Florida. My parents were entrepreneurs, not a big surprise there. That’s really where I got my entrepreneurial spirit. I grew up watching my parents operate a business and learned firsthand how to do it, and how to bend over backwards for customers. It was an upbringing that would turn out to really serve me as I got older and started Drybar, but one that I didn’t even really pay attention to as a kid.
What was life like growing up financially for you? Did your parents teach you about money management?
They did not. I’ve never managed money well. I watched my parents run their business and go through the ups and downs because of the seasonality of their business. I don’t think I had a really strong sense of how to manage money growing up. Even though we had money at times, it was up and down.
My mom and I used to go shopping every Saturday—it was like a ritual of ours. And she always, always made me shop from the sale racks. She loved a good deal, so I grew up with that mentality of finding a good deal, but I didn’t stick to that. But now I like to buy what I like to buy, and I don’t like necessarily shopping for a sale. But maybe that’s just because of my mom.
I don’t think I grew up with a strong sense of how to manage money. That would come later in life, when I was married for the first time, and we were really watching money.
What was your very first job? Did it teach you anything about money or handling finances?
My very first job really was working at my parents’ store. I imagine they paid me, but I don’t totally even remember. My very first job outside of my family business was working at Express, if you can believe that. I think Express is still around. I liked the idea of having my own money, because I was always asking my parents for money for whatever I wanted. And of course, that came with strings, and ‘what are you using it for?’ I remember feeling a real sense of freedom once I was making my own money and had a little bit more autonomy over how I spent it.
When you enrolled into college, did you have a solid idea of what path you wanted to take in your life?
I did not go to college. College wasn’t for me out of high school. I was pretty confused about what I wanted to do with my life. And I was really perplexed by how all of my friends knew what they wanted to do and people were going to college have a pretty strong idea of what they were going to do with their life, which was like, crazy to me—to have an idea of what you want to do at 18 or 19 years old.
So I moved to New York City, where I lived for basically all of my 20s, and worked a lot of different jobs. That felt like my college experience. I was figuring out how to take care of myself and how to pay my rent, and I really loved it. I jumped from fashion to PR to hair, and learned how to kind of take care of myself, which I guess is a similar experience as college.
Walk us through founding Drybar.
I’m a longtime hair stylist. I’ve been doing hair for, gosh, a million years now. I started when I was 20 and I went to beauty school in Boca Raton, Florida, where I grew up. And then I moved to New York and did hair there, and then I moved to L.A., where I had my boys.
I was a stay-at-home mom for about five years, and then I started a mobile blowout business called Straight At Home. I was only charging 40 bucks to go to a woman’s house and blow dry their hair, which is pretty inexpensive for any city, especially L.A. It was during that time that I realized there was this pretty big hole in the marketplace. There was nowhere for women to go for an affordable blowout in a really nice place, and have a great experience.
There were the discount chains where you didn’t really know what you’re getting, or there were the high-end salons which were very expensive, and the stylist wanted to use that time to do cut and color. I saw this small opportunity, and that very much came from my mobile blowout business. The price point seemed right. I thought if we could charge little enough, women would do this often. That was kind of the whole idea for the business model.
It was definitely a risk because nothing like this had ever been done. To do blowouts at $35, you would have to do a lot of blowouts in a day. There was a big question mark if this business would work, and ultimately, women went really bonkers for this idea.
Really what we discovered was the magic of Drybar: Having somebody else do your hair and feeling really great, and having that confidence. We opened the first one in Brentwood, Los Angeles. Out of the gate, we were so busy and it was so crazy. We didn’t see it coming, and we knew very quickly we were going to have to keep expanding, because there was so much demand.
How was it working with your brother?
My brother and my ex-husband were my business partners at Drybar, and my brother and I have always been really close. When I was operating my mobile business, Straight At Home, he was seeing the success I was having from that. I went to him and said, I think I need to turn this into a brick-and-mortar, but I need help to do it financially. And even from a business standpoint. I knew I couldn’t do it by myself—I needed some help.
And then Cameron, my ex-husband, worked in advertising as a creative director, and is just brilliant when it comes to branding. So the three of us teamed up to start this thing. The beauty of that relationship, and the reason I think that partnership between the three of us worked so well, was because we all had such different skill sets and such different strengths and weaknesses. My brother was the guy doing all the spreadsheets and the stuff I don’t like doing and Cam was really brand. And so the three of us coming together just really worked.
What was the moment you realized the business had the capability to continue to thrive, and you were able to cross over into becoming a millionaire?
We definitely realized very early on. Within, I’m not joking, the first day. It was so busy, and we had seen what the rest of the week looked like in terms of appointments. We were like, we’re definitely onto something here. It was a very emotional day, because we realized that this thing could be really huge and there was a really big opportunity here to grow this thing into a big business.
I don’t know that I ever would have predicted on that first day, certainly, or even the first couple of months that it would turn into what it did. But we knew the writing was on the wall as soon as we opened and the demand and the excitement over this new concept was pretty amazing.
Can you talk about making your first million dollars, and your thought process when you finally realized that you hit that threshold?
We didn’t really make any money in the beginning. I was taking such a small salary. I’ll never forget, once we made one of our biggest hires—a president of retail—her salary requirement was so bananas to me, especially because I wasn’t making any money. But that would lead to us raising our first big tranche of money, which was about $26 million from private equity. When we did that, my brother and I both took money off the table. And that was when we made our first millions: when we took a sliver of that $26 million towards the company for ourselves.
Castanea Partners, which is now Stride Consumer Partners—it was really something they wanted us to do. They wanted us to have some of the fruits of our labor. At that point, we had 10 or 11 stores, I think. We were on this rocketship to success. My brother had also worked for Yahoo in the early early days, and he had made a lot of money on paper, but didn’t actually see any of that money, so he was anxious to take some money off the table once there was that opportunity, which I think is an important thing to talk about.
I do point this out in the book, The Messy Truth, because I don’t know if founders know that that’s an option. You build a business, and hopefully you sell it, and that’s where you make money. And there’s an opportunity to make money before you sell it, which is really my experience. Both times we raised money, the first time with Castanea, which was about $26 million, and then with another private equity firm called Roark, who put in $40 million, something like that. It got us to $75 million in total. And we took money off the table again at that round, and that was a really smart way for us to make money, especially in lieu of what happened to the world in 2020.
When you personally received your first big paycheck, what were your first thoughts?
When that money hit the bank, I wanted to hold onto it for as long as possible. But we bought our first house with that money and that was really where the majority of it went. With subsequent money, I would invest and I’ve never had any really crazy splurges. I did buy an infrared sauna for my house, which I thought was a really big splurge, and some bags and shoes, but nothing crazy. I really have invested all of it. I have a financial advisor and I’m pretty careful with my money. And I’m very, I wouldn’t say frugal, but I’m really responsible when it comes to managing my money now.
Do you have any advice for other entrepreneurs or business owners when it comes to money management or finances?
The expression ‘more money, more problems’ comes to mind because I think it’s so intoxicating when you make real money. How you deal with it is really important. I have a great team around me, and I’m constantly kind of making sure I’m living within my means. And I think there’s a propensity, when you have a lot of zeros next to your name, to live this really extravagant life.
I’m really cognizant of what I spend and don’t want to live outside my means because my means are very different now than they were 10 years ago, but I’m still aware of them. I’m not buying a private plane. Not yet, anyway.
What’s the most expensive thing you’ve ever purchased for yourself?
I went through this vintage car phase recently, where I bought a couple of Range Rovers. And then I was like, wait, I don’t need these cars, what am I doing? I’ve had a couple of moments like that, where I kind of splurge and, you know, for me, it’s a lot about experiences. I like to travel really well. And when I go places like hotels—this is probably not hard to believe, based on my business and what I’ve done—but I really love a nice hotel and amazing customer service and that sort of extravagance.
For me, it’s more about experiences than things. I have a nice modest house and a nice car and whatever, but nothing crazy or over the top, at least in my eyes. I like to spend more on experiences with people I love.
What was the biggest lesson that you learned from founding your own business? If there were something you could have told your younger self about running a business, what would that be?
On the other side of everything that I’ve been through in my life, and especially in the last few years, I’d say the biggest lesson is: I wish I had done more work on myself sooner and paid closer attention to what was happening for me. Being more present and developing more habits and tools to support the crazy pace that I was living my life at all for all those years.
