Alexandra Wilkis Wilson, CEO of the addictive beauty app GlamSquad, tells Glamour’s Cindi Leive the secrets of her multiple-start-up success.


Bright Lights, Big Job Wilkis Wilson in her New York City office

In the business world, everyone talks about being a “disrupter.” (As I type this, odds are good there are at least seven panels being held in your town on how to disrupt your career, industry, or life.) But Alexandra Wilkis Wilson, 39, is the real disruptive deal: She quit her finance job to shake up the fairly traditional luxury-fashion world with her flash-sale site, Gilt, in 2007. (Perhaps you’d like to thank her for your discounted Louboutins?) Now she’s rattling the salon business with the successful beauty app GlamSquad, which lets you order up at-home hair, makeup, and nail services in New York City, Miami, and Los Angeles, with more cities on the way. (“Start-ups are addictive!” says this mother of two.) In other words? She’s comfortable challenging the status quo and thinks all women should be too. I sat down with her by the makeup mirrors at GlamSquad’s New York City headquarters to hear more.

Cindi Leive: You’ve said that as a child you were always the girl with the lemonade stand. Did you know back then you’d want to start things for a living?

Alexandra Wilkis Wilson: I don’t think I did. I was very caught up in my résumé as opposed to following my heart. But I was entrepreneurial by nature. I always want to improve things, but my suggestions got overlooked in big corporate environments. In retrospect, it’s obvious that I should have been at a start-up.

CL: Did you learn anything in finance that you still apply to your life today?
AWW: Banking teaches you to have an eye for detail. You really need to double-check, triple-check your work. And you have very little control over your schedule, so that was valuable later, because start-ups have so much unpredictability. But I’m not personally motivated by cultures of fear. They turn me off.

CL: And you saw that in finance?
AWW: A lot. I remember getting many of my [assignments] through voice mail. So I would see the little light pop up on my phone and my heart would skip a few beats in panic. Finance was a culture of “speak when spoken to,” and they didn’t welcome ideas from junior people. It used to frustrate me—just because I’m young and junior doesn’t mean I can’t have value. At both Gilt and GlamSquad I love hearing from people at all levels of our organization.

CL: So you had these secret signs you wanted to be an entrepreneur—what gave you the courage to actually do it, with Gilt?
AWW: I was working at Bulgari [in 2007]. And I could sense a slowdown was coming. Not because I’m a macroeconomic genius—

CL: You smelled the recession?
AWW: I could see clients were curbing their spending. And my mother had taught me to shop for [luxury brands]—she’s from Cuba originally, where they’re sort of a treasure hunt to find. I remember finding a Prada skirt for $50 at the original Boston Filene’s Basement when I was young and getting so excited. I thought if we—one of my best friends, Alexis Maybank, and our other Gilt cofounders, Kevin Ryan, Mike Bryzek, Phong Nguyen— could sell [luxury fashion] at a discount, that to me was success.

CL: And you once sold 40,000 Louboutins on the site in a couple of hours. What were some of your other milestones?
AWW: What’s so funny is that sometimes the biggest wins are the most challenging. That sale was something that should have been so exciting, but we ended up with so many women on the wait list. I’m sure we caused a lot of angst!

CL: And how did you come to GlamSquad?
AWW: I had been at Gilt seven years, and I ran into two guys that I went to Harvard with, Jason Perri and David Goldweitz. They showed me the app they launched, a beauty services start-up called GlamSquad, and I thought, This is amazing. I am totally going to use this. I’d be falling asleep at night thinking about ideas for GlamSquad. A few months later—it was my husband’s birthday; I was embarrassed that I was carrying cupcakes!—I met them at a nice hotel bar, and they said, “Let’s cut to the chase. We want you to be our CEO.”

CL: So you effectively interviewed for CEO without realizing it.
AWW: They saw my passion for what they were building. I think being able to recognize what you love doing and figuring out if you could actually turn that into a profession—that’s what keeps you engaged.

CL: Do you think of yourself as a tech person or a beauty executive?
AWW: I don’t even know what I think of myself as. I’m not able to code, but I have so much respect for anyone who can—it’s a valuable skill. Alexa Hirschfeld from Paperless Post taught herself basic code, which I think is inspiring. You can be a better manager of others when you really understand what they do.

CL: Every great businessman or -woman says, “You have to be willing to fail,” but it’s so much harder in practice. How do you establish the kind of culture where it’s OK and even encouraged?
AWW: Address in advance that something is a test: “We’re going to learn if this is going to be successful or not.” And if it isn’t, that’s OK. Move on. You can’t predict the wins. I always say, it’s OK to make mistakes. Just let’s not make the same mistake twice.

CL: And what’s the best advice you ever got about work?
AWW: Be your own best advocate—you have to fight for what you want.

CL: That sounds like a salary-negotiating tip too.
AWW: If you ask respectfully, I think others will respect you. And there’s nothing wrong with asking people for help, throwing out that crazy idea. But I’m a rare breed in that I enjoy cold-calling. I enjoy meeting people I’ve never met before. Many of the brands that we sold at Gilt came through my relationships, but so many of them came from my walking up to strangers at trade shows literally all around the world and introducing myself: “Hi, I’m Alexandra from Gilt. Do you know what Gilt is?”

CL: So it wasn’t that you were hyperconnected—you were just ballsy.
AWW: Yeah. I’m not afraid of rejection. I’ve never been afraid of rejection.