The Gilted Age

Photography by Christopher Logan; Styling by beckiemartina, re-stylists 

In just four months, NYC moms Alexandra Wilkis Wilson and Alexis Maybank grew their passion for sample sale shopping
into a members-only “flash sale” e-commerce site alluringly coined Gilt Groupe, a lunchtime guilty pleasure at first only whispered on the lips of in-the-know fashionistas. Aimed at motivated customers with some disposable income and limited time, Gilt reaches a sophisticated and dynamic clientele—much like its founders. In just over four years, the pair of Harvard Business School grads, who met as undergraduates at Harvard in a Portuguese language class, have grown their “shop by appointment” model into the web’s ultimate source for deals and steals on high heels and high-end handbags.

Now, with over five million members and a bevy of incarnations within their brand ranging from Gilt Baby & Kids to Gilt Taste’s gourmet foods, from Park & Bond’s menswear offerings to Jetsetter’s luxury travel packages, the duo share more than a penchant for bargain shopping and business strategies as both are working wives and mothers to children under the age of two.

And while they’re often mistaken for one another—using that to their advantage during hectic times when they need to stand in for each other at the office—Alexis and Alexandra are two moms with similar hopes for their children, but each with a parenting style all her own.

We sat down with the sample-sale savvy pair to talk motherhood and Mr. Valentino, and the world they’ve created in which the two actually can co-exist.

Alexis, you’re currently due with your second child, a boy, in two and a half weeks. Rumor has it that you were wearing uber-high heels very far into your pregnancy. Has your daughter Thomasina followed in the footsteps of Mom and caught the fashion bug yet?

Alexis: She’s 16-months-old now and obsessed with anything that can be a necklace, but that’s all in terms of fashion. I think she’d prefer to run around in a bathing suit as opposed to dresses.

How would you describe your children’s personalities?

Alexis: Thomasina is very active. She loves to throw balls, go climbing, and when she sees a rock she goes scrambling up it.

Alexandra: My son, Conrad, is 22 months. As you can see today, at a photo shoot with 15 unfamiliar faces in the apartment, he’s not fazed. He’s very enthusiastic, very friendly. He’s like that on the plane; when we fly somewhere he literally wants to say “hi” to every passenger that walks by and he’s surprised when people don’t say “hi” back.

You’re raising Conrad bilingual. Why was that meaningful for you?

Alexandra: My mother is actually from Cuba so it’s important to me that he be comfortable in both English and Spanish. I actually speak five languages and my husband went to high school in Switzerland so his French is really good, but we thought: let’s start with two languages and then we’ll introduce more when the time is right.

You both live in New York City. How do you spend a typical weekend with your families?

Alexis: We’re always out playing in Central Park. In the snow, rain, any time, any weather. We bundle [Thomasina] up and we go out. We also do the museum thing quite a bit. The craziest one we went to was the Children’s Museum of Manhattan. Oh my, I felt like afterwards I needed a cocktail it was so crazy. But [she] loved it.

Alexandra: We live really close to The Metropolitan Museum of Art and one Saturday afternoon Conrad was running around the Temple of Dendur and saying “hi” to all the Roman and Greek statues and looking at the Egyptian mummies. I look at my husband and, even though I grew up here, I’m still amazed at how lucky we are.

What excites you most about parenting right now?

Alexis: My favorite thing is watching Thomasina grow, develop and become her own little person. Watching her discover a new word or learn how to scale her high chair in ten seconds.

Alexandra: Two weeks ago, Conrad said “I love you” for the first time and that was a really special moment that I’ll remember

Tell us about some of the challenges of having children fast approaching the Terrible Twos.

Alexandra: I expect that there are going to be challenges in parenting at all ages. At this stage, Conrad is opinionated but he can’t always communicate it. That must be frustrating for a child.

Alexis: The most challenging thing is obviously balancing work and family. Each day you either feel like you’re a better professional woman, other days you feel like you’re a better parent. You never feel great at both.

So, how did becoming a parent change your approach to work?

Alexandra: The first two years of building Gilt Groupe were so physically and emotionally demanding I think it would have
become very tough to enter motherhood at that stage. For those who know me both professionally and personally, they know it was hard for me not to be multitasking, so I was on email pretty quickly after becoming a mother, but I did actually take 12 weeks physically out of the office.

Take us about the behind the scenes of being a working mom. How do you both do it?

Alexis: We have a wonderful woman who helps us during the week and then my mother helps quite a bit, too. My mother is also a very accomplished chef so I know [Thomasina is] eating well. There’s nothing Thomasina doesn’t eat at this point which is all a credit to my mother.

Alexandra, you often travel on behalf of the company. How do you get your Conrad fix when you’re overseas?

Alexandra: We Skype, we video chat and now he can talk on the phone to me. Even though there’s no replacement for putting a baby to bed and reading a bedtime story.

So let’s talk chronology, when did you have the idea for Gilt Groupe?

Alexis: Summer 2007.

And when did it launch?

Alexis: November 13, 2007.

Alexandra: We move really fast.

Alexis: But that’s part of the beauty of the Internet; you can have an idea and launch it in months, not years.

What about the idea of an online sample sale attracted you both as businesswomen?

Alexis: We felt if we’d drop anything, if we’d shape our own workdays around popping in line for ten minutes to check out what was at the Valentino sample sale, then it was something that might have legs.

You’ve sold everything on Gilt from the opportunity to ski with the US Ski Team to tickets for Fashion Week shows. Which sales have amazed or excited you most?

Alexis: We had Alexander McQueen’s last collection on the site. On a happier note, we had Mr. Valentino’s last runway collection; it was his very last show before he retired. We also sold men’s skirts from Thom Browne which surprised me at how quickly they flew off the shelf!

Alexandra: The first time we did Christian Louboutin was pretty crazy, too. We warned our engineers that it was going to be big and even with all the warnings they didn’t anticipate the online frenzy that the brand created.

How do you continue to grow Gilt Groupe when it was originally built around exclusivity?

Alexis: When we launched the business as members-only, it was the antithesis of e-commerce. You’re not supposed to draw
up a wall and not let people pass, but we did it and it’s allowed us to do some really unique things. Every time someone comes to visit the site we know exactly who she or he is, what they tried to buy, what they like to buy, the colors, the sizes, what they look at, every stroke of the mouse, if you will. So when an email goes out to millions of people, there’s over 3,000 versions of that one email reflective of what a person is interested in shopping for.

When a shopper loses out on a sale, how do you get them to come back again?

Alexis: We thought it would actually be hard to teach that.

Alexandra: I think they realized that it’s appointment shopping. If you really are interested in a particular brand and miss out once or twice, you learn.

Alexis: It’s usually just once! The very next time they get there at 12:01 PM Eastern Time.

Your book By Invitation Only (Penguin) shares the story behind Gilt Groupe’s meteoric rise. Was writing the book similar to running a business?

Alexandra: It’s a slow process. It’s a lot slower than how quickly we moved with Gilt.

Alexis: When [the publisher] told us it would be a year and a half to get the book out the door, we were like, “Really? It only took four months to get the business out the door!”

What do you hope readers take away from the book?

Alexandra: Hopefully, there’s a message in there for anyone whether it’s entrepreneurs looking to start a business or people who
can adapt entrepreneurial lessons to their day-to-day jobs or lives.

Speaking of sharing advice, have you received any parenting tips from one another that have been helpful as working mothers?

Alexis: Alexandra is so organized. I basically replicate every decision she makes because I assume she has invested tons of time researching every decision. I trust her instinct.

Alexandra: Alexis has a real adventurous side to her, a riding-horses-bareback type of thing. I think that sense of adventure is
really important especially with a boy. When we spend time together, I’m usually the one watching out to make sure the kids don’t fall and hurt themselves. She’s much more “let kids be kids, they’re going to learn for themselves.” I think she’s taught me a little bit of that.

So, what’s penciled into your calendars this year either personally or professionally?

Alexandra: We’re doing a lot more thematic sales that we didn’t do as much in the early days of Gilt. Sometimes women are just looking for the perfect trench coat or the little black dress, so now we mix the brands.

Alexis: I’ll have two kids under two this year, and I’m not sure I’m going to remember any of 2012!

By Invitation Only Tips For Modern BusinesswomenBy_Invitation_Only.JPG

Some key pieces of advice from Alexis and Alexandra’s new book which releases this

Hire to your shortcomings. When building any team, whether it’s part of a big company
or starting a family concept, you have to look at how similar or dissimilar you
are and hire to your shortcomings. If everyone is equally good at seeing the
big picture but not as good as looking at the details you could all very easily
be running down the same path in the wrong direction.

Get a sounding board. Always form your own informal board of directors that you
can turn to and ask questions so you have that unbiased source of feedback.

Network, network, network. It’s really true that you often do as well as those around you want you to do. Look at who’s in your life and who might be helpful for advice or business relationships; it’s a great place to start when you have no business track record whatsoever.

Seek out online resources. Harvard Business Review is a fun and easy business resource. You can download things for just a dollar or two, like how to put together an effective presentation to venture capitalists or investors.

Erika Thormahlen