Webb, the 48-year-old founding father of blowout empire Drybar and writer of The Messy Reality, went straight from highschool to New York, the place she jumped from job to job till she landed on styling hair, a profession she by no means left.
After getting married, shifting to Los Angeles, and having two children, Webb started touring to shoppers’ houses and styling hair on demand—a service that rapidly blew up amongst busy girls within the Brentwood space. Alongside her brother and then-husband, Webb spun the idea into Drybar, which has since grow to be a family title and vacation spot for on-the-go dependable hairstyles throughout the U.S.—and a enterprise capital darling.
It wasn’t at all times straightforward, and in her new e book, Webb is open about her errors and regrets. Particularly, she struggled with extreme burnout, particularly balancing tough household points, together with the loss of life of her mom and her older son’s time in rehab.
In an interview with Fortune, Webb—a self-made multimillionaire—walks by constructing her model from scratch, establishing herself in a crowded area, trusting her instincts, and taking cash off the desk with every VC spherical—regardless of what common knowledge may suggest. The next has been frivolously edited for readability.
Are you able to inform us a bit of bit about the place you grew up and what your childhood was like?
I used to be born on Lengthy Island, New York, and I grew up in South Florida. My mother and father had been entrepreneurs, not an enormous shock there. That’s actually the place I acquired my entrepreneurial spirit. I grew up watching my mother and father function a enterprise and discovered firsthand how you can do it, and how you can bend over backwards for purchasers. It was an upbringing that might prove to essentially serve me as I acquired older and began Drybar, however one which I didn’t even actually take note of as a child.
What was life like rising up financially for you? Did your mother and father educate you about cash administration?
They didn’t. I’ve by no means managed cash nicely. I watched my mother and father run their enterprise and undergo the ups and downs due to the seasonality of their enterprise. I don’t suppose I had a very sturdy sense of how you can handle cash rising up. Although we had cash at occasions, it was up and down.
My mother and I used to buy groceries each Saturday—it was like a ritual of ours. And he or she at all times, at all times made me store from the sale racks. She cherished a superb deal, so I grew up with that mentality of discovering a superb deal, however I didn’t stick with that. However now I like to purchase what I like to purchase, and I don’t like essentially searching for a sale. However possibly that’s simply due to my mother.
I don’t suppose I grew up with a powerful sense of how you can handle cash. That may come later in life, after I was married for the primary time, and we had been actually watching cash.
What was your very first job? Did it educate you something about cash or dealing with funds?
My very first job actually was working at my mother and father’ retailer. I think about they paid me, however I don’t completely even bear in mind. My very first job outdoors of my household enterprise was working at Specific, in the event you can imagine that. I feel Specific remains to be round. I favored the concept of getting my very own cash, as a result of I used to be at all times asking my mother and father for cash for no matter I needed. And naturally, that got here with strings, and ‘what are you utilizing it for?’ I bear in mind feeling an actual sense of freedom as soon as I used to be making my very own cash and had a bit of bit extra autonomy over how I spent it.
While you enrolled into faculty, did you have got a stable concept of what path you needed to absorb your life?
I didn’t go to school. School wasn’t for me out of highschool. I used to be fairly confused about what I needed to do with my life. And I used to be actually perplexed by how all of my associates knew what they needed to do and other people had been going to school have a fairly sturdy concept of what they had been going to do with their life, which was like, loopy to me—to have an concept of what you wish to do at 18 or 19 years outdated.
So I moved to New York Metropolis, the place I lived for mainly all of my 20s, and labored plenty of totally different jobs. That felt like my faculty expertise. I used to be determining how you can maintain myself and how you can pay my lease, and I actually cherished it. I jumped from style to PR to hair, and discovered how you can sort of maintain myself, which I suppose is an identical expertise as faculty.
Stroll us by founding Drybar.
I’m a longtime hair stylist. I’ve been doing hair for, gosh, one million years now. I began after I was 20 and I went to magnificence college in Boca Raton, Florida, the place I grew up. After which I moved to New York and did hair there, after which I moved to L.A., the place I had my boys.
I used to be a stay-at-home mother for about 5 years, after which I began a cell blowout enterprise referred to as Straight At House. I used to be solely charging 40 bucks to go to a lady’s home and blow dry their hair, which is fairly cheap for any metropolis, particularly L.A. It was throughout that point that I spotted there was this beautiful huge gap within the market. There was nowhere for girls to go for an inexpensive blowout in a very nice place, and have an ideal expertise.
There have been the low cost chains the place you didn’t actually know what you’re getting, or there have been the high-end salons which had been very costly, and the stylist needed to make use of that point to do reduce and shade. I noticed this small alternative, and that very a lot got here from my cell blowout enterprise. The worth level appeared proper. I assumed if we might cost little sufficient, girls would do that usually. That was sort of the entire concept for the enterprise mannequin.
It was positively a threat as a result of nothing like this had ever been finished. To do blowouts at $35, you would need to do plenty of blowouts in a day. There was an enormous query mark if this enterprise would work, and in the end, girls went actually bonkers for this concept.
Actually what we found was the magic of Drybar: Having anyone else do your hair and feeling actually nice, and having that confidence. We opened the primary one in Brentwood, Los Angeles. Out of the gate, we had been so busy and it was so loopy. We didn’t see it coming, and we knew in a short time we had been going to must hold increasing, as a result of there was a lot demand.
How was it working along with your brother?
My brother and my ex-husband had been my enterprise companions at Drybar, and my brother and I’ve at all times been actually shut. Once I was working my cell enterprise, Straight At House, he was seeing the success I used to be having from that. I went to him and stated, I feel I want to show this right into a brick-and-mortar, however I need assistance to do it financially. And even from a enterprise standpoint. I knew I couldn’t do it on my own—I wanted some assist.
After which Cameron, my ex-husband, labored in promoting as a inventive director, and is simply sensible in the case of branding. So the three of us teamed as much as begin this factor. The great thing about that relationship, and the explanation I feel that partnership between the three of us labored so nicely, was as a result of all of us had such totally different talent units and such totally different strengths and weaknesses. My brother was the man doing all of the spreadsheets and the stuff I don’t like doing and Cam was actually model. And so the three of us coming collectively simply actually labored.
What was the second you realized the enterprise had the aptitude to proceed to thrive, and also you had been capable of cross over into changing into a millionaire?
We positively realized very early on. Inside, I’m not joking, the primary day. It was so busy, and we had seen what the remainder of the week appeared like when it comes to appointments. We had been like, we’re positively onto one thing right here. It was a really emotional day, as a result of we realized that this factor might be actually large and there was a very huge alternative right here to develop this factor into an enormous enterprise.
I don’t know that I ever would have predicted on that first day, definitely, and even the primary couple of months that it could flip into what it did. However we knew the writing was on the wall as quickly as we opened and the demand and the joy over this new idea was fairly wonderful.
Are you able to speak about making your first million {dollars}, and your thought course of once you lastly realized that you just hit that threshold?
We didn’t actually make any cash to start with. I used to be taking such a small wage. I’ll always remember, as soon as we made one in every of our greatest hires—a president of retail—her wage requirement was so bananas to me, particularly as a result of I wasn’t making any cash. However that might result in us elevating our first huge tranche of cash, which was about $26 million from non-public fairness. Once we did that, my brother and I each took cash off the desk. And that was after we made our first thousands and thousands: after we took a sliver of that $26 million in the direction of the corporate for ourselves.
Castanea Companions, which is now Stride Shopper Companions—it was actually one thing they needed us to do. They needed us to have a number of the fruits of our labor. At that time, we had 10 or 11 shops, I feel. We had been on this rocketship to success. My brother had additionally labored for Yahoo within the early early days, and he had made some huge cash on paper, however didn’t truly see any of that cash, so he was anxious to take some cash off the desk as soon as there was that chance, which I feel is a vital factor to speak about.
I do level this out within the e book, The Messy Reality, as a result of I don’t know if founders know that that’s an choice. You construct a enterprise, and hopefully you promote it, and that’s the place you earn money. And there’s a chance to earn money earlier than you promote it, which is de facto my expertise. Each occasions we raised cash, the primary time with Castanea, which was about $26 million, after which with one other non-public fairness agency referred to as Roark, who put in $40 million, one thing like that. It acquired us to $75 million in whole. And we took cash off the desk once more at that spherical, and that was a very good manner for us to earn money, particularly in lieu of what occurred to the world in 2020.
While you personally obtained your first huge paycheck, what had been your first ideas?
When that cash hit the financial institution, I needed to carry onto it for so long as potential. However we purchased our first home with that cash and that was actually the place the vast majority of it went. With subsequent cash, I might make investments and I’ve by no means had any actually loopy splurges. I did purchase an infrared sauna for my home, which I assumed was a very huge splurge, and a few baggage and sneakers, however nothing loopy. I actually have invested all of it. I’ve a monetary advisor and I’m fairly cautious with my cash. And I’m very, I wouldn’t say frugal, however I’m actually accountable in the case of managing my cash now.
Do you have got any recommendation for different entrepreneurs or enterprise homeowners in the case of cash administration or funds?
The expression ‘extra money, extra issues’ involves thoughts as a result of I feel it’s so intoxicating once you make actual cash. The way you cope with it’s actually vital. I’ve an ideal staff round me, and I’m always sort of ensuring I’m residing inside my means. And I feel there’s a propensity, when you have got plenty of zeros subsequent to your title, to dwell this actually extravagant life.
I’m actually cognizant of what I spend and don’t wish to dwell outdoors my means as a result of my means are very totally different now than they had been 10 years in the past, however I’m nonetheless conscious of them. I’m not shopping for a personal airplane. Not but, anyway.
What’s the most costly factor you’ve ever bought for your self?
I went by this classic automobile section just lately, the place I purchased a few Vary Rovers. After which I used to be like, wait, I don’t want these automobiles, what am I doing? I’ve had a few moments like that, the place I sort of splurge and, , for me, it’s quite a bit about experiences. I prefer to journey very well. And after I go locations like resorts—that is in all probability not exhausting to imagine, based mostly on my enterprise and what I’ve finished—however I actually love a pleasant lodge and wonderful customer support and that type of extravagance.
For me, it’s extra about experiences than issues. I’ve a pleasant modest home and a pleasant automobile and no matter, however nothing loopy or excessive, at the least in my eyes. I prefer to spend extra on experiences with individuals I like.
What was the largest lesson that you just discovered from founding your individual enterprise? If there have been one thing you can have informed your youthful self about operating a enterprise, what would that be?
On the opposite facet of the whole lot that I’ve been by in my life, and particularly in the previous few years, I’d say the largest lesson is: I want I had finished extra work on myself sooner and paid nearer consideration to what was occurring for me. Being extra current and growing extra habits and instruments to help the loopy tempo that I used to be residing my life in any respect for all these years.