Is there anything Alli Webb can’t do? From style to beauty and even public relations, the entrepreneur and businesswoman took time to find what truly resonated with her passions before ultimately launching Drybar in 2010, followed by massage boutique Squeeze and, most recently, Brightside, an infrared yoga and sauna studio on the West Side. With all the success her start-ups brought, Webb found herself facing major challenges.
With the newfound courage to take a step back and address that sometimes you really can’t do it all, Webb found a way to enjoy the wild journey life offers. In her new book, The Messy Truth, hitting the stands on Nov. 14, Webb recounts the ups and downs that led her to where she is today.
Alli Webb Photo by Taleah Meshae
Prior to founding Drybar, you were a hairstylist yourself. What initially got you interested in that world?
During that period, I was in the process of discovering what truly resonated with me and understanding my passions. Hair has always held a special place in my heart, and there’s this part of me that thinks I ventured into beauty school simply to master the art of the perfect blowout for my own locks. I received my training at Toni & Guy and subsequently gained valuable experience working under the guidance of John Sahag in NYC.
What made you want to expand into opening other businesses, like Squeeze and Brightside?
Deciding to venture into Squeeze was a no-brainer for us. We saw a gap in the market, much like the one Drybar filled. On one end, you had high-end salons where you’d shell out a fortune for a blowout, and on the other, discount chains that left a lot to be desired. Squeeze aimed to occupy that sweet spot in the middle that was missing. The idea was sparked by my brother, who, unlike me, couldn’t enjoy blowouts and was fed up with the limited massage options available.
What sets Squeeze apart is our app—it’s like the Uber or Postmates of massages. Everything is at your fingertips, from booking to tipping. We wanted to make the experience as customizable and convenient as possible. Just like Drybar, Squeeze is backed by the same fantastic founding team, and we’re excited to bring the same level of excellence to the world of massages.
What’s the connecting thread between your businesses? On the surface, these all seem to be self-care and wellness-related, but I’d love to hear from you what connects these.
What ties Drybar, Brightside, and Squeeze together is this common thread of creating spaces that make people feel good, inside and out. It’s this shared mission of making people feel pampered, confident and just downright good. Whether it’s your hair, your skin or a moment of zen, each brand is like a piece of that feel-good puzzle. They’re not just places; they’re experiences that leave you walking out with a little extra pep in your step.
Your book is hitting the stands 11/14—congrats! What inspired you to write The Messy Truth, and why now? I think the overarching reason for writing this book was to really share and illuminate that it’s not easy to be an entrepreneur. I wanted to kind of give a glimpse behind the scenes of what it was like to grow a business of the magnitude of Drybar and how it was to also kind of lose myself. So many things in my life fell apart during the course of that 10-year run— divorcing Cam, my son going through rehab, and then me going through depression. Those are pretty massive life events taking place in my 40s. The more I put out there about my personal experiences, both with learning how to run a business with trying to figure out how to stay afloat in my personal life, I found that it really resonated with people and women mostly, and I wanted to write this book to just highlight a lot of what I’ve been through, so it can help people on a personal and professional note for anyone on their entrepreneurial journey. I also wanted to destigmatize a little bit of the illusion that we might be in about what it’s like to run a business and raise a family. And I’ve gotten a lot of feedback already from the book about the “balance is bullshit” chapter because it is, and we’re trying to do the best we can, and most days, we don’t check all the boxes, but we check as many as we can.
Alli Webb Photo by Taleah Meshae
What are some unexpected things readers will learn about you from reading the book?
In the book, you’re gonna discover a lot about me that’s not the glossy surface stuff. During the Drybar days, it was this whirlwind of excitement and success, which, don’t get me wrong, I loved. But in the midst of it all, I kind of lost sight of what truly made me happy. I was living for everyone else, pleasing everyone around me, but not taking a second to look inside and figure out what was really filling my cup.
I had this wake-up call, realizing I wasn’t feeling great inside, and all those external validations from Drybar and relationships were like a quick fix that didn’t last. And guess what? I’m still working on it, still figuring out what really fills me up from the inside. It’s a journey that never really ends, you know?
I’ve come to terms with having a bit of an ego and maybe missing out on some humility. It’s tricky when people put you on this pedestal, showering you with attention and praise. It’s nice, but I’ve learned not to let it be my only source of feeling good about myself. After selling Drybar, I went all-in on this quest for love and let everything else slide. That’s a regret, for sure, but I’m learning not to let your own growth take a backseat to whatever else is happening.
So, buckle up because the book spills all the real stuff, the hard lessons and the ongoing journey of spending some quality time with myself.
What is your best piece of advice to give someone looking to join the entrepreneurial space?
Always keep a beginner mindset so that you’re always learning and growing.
Alternatively, what is a piece of advice someone told you that you’ll never forget?
My mantra is: Be kind and treat others the way you hope to be treated. One of my favorite quotes is from Gandhi, who said, “Be the change you want to see in the world.” And that’s kind of the philosophy I subscribe to.
Since you’re very involved in the beauty and wellness space, can you tell us a little bit about your self-care routine? I’m really cognizant of wellness in general. And I take really good care of my skin, I take really good care of my body, and I try to eat really well. I exfoliate my skin and use serums. I really don’t blow dry my hair as much as I used to. I go in my infrared sauna and cold plunge at least two to three times a week, I lift weights two to three times a week, I walk a ton daily, and I drink a ton of water. I do a lot of things to take really good care of myself. Also, one of the things I think that really impacts wellness is what things you’re doing for your brain. I got this thing about writing down seven things every morning that you’re grateful for, excited for, etc.
So, what’s next on the horizon, both personally and professionally?
I’m always brainstorming new business ideas, it’s kind of a curse at this point. I have a really strong calling to help and give back to other entrepreneurs, which is also why I wanted to write my book. If I can grow a business, so can you! I just wrapped our first Blueprint Mastermind series with Jaclyn Johnson and Marina Middleton, where we help entrepreneurs take their businesses to the next level, and we’re excited to expand this series so we can continue to support entrepreneurs.
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