Startup Success: A Look at the Making of

You’ve likely heard of by now. It has quickly become a guilty pleasure (no pun intended) of ours, along with fellow fashion-loving young professionals (YPs) across North America. Gilt Groupe has altered the landscape of e-commerce and revolutionized the way that we shop and attain luxury. With, the traditional rules of retail are drastically changed with a simple concept: the beloved sample sale is moved online. Enthusiasts of fashion and luxury can now attain brands like Christian Louboutin, Gucci, Louis Vuitton, Hermes and the likes at lower prices and with an accompanying adrenaline rush to match. No longer reserved for a leisurely Sunday afternoon, shopping has become what the founders call competitive, addictive, urgent and thrilling. affords its members special access to expertly curated and rousing merchandise, culinary offerings, and experiences on a daily basis, many at insider prices. Gilt’s tasteful buyers search the world for the most coveted brands and products, including fashion for women, men, and children; home decor; artisanal ingredients and hotels and travel experiences. Offering promises of accessible luxury, continues to draw a growing number of fans who have a love for high-end fashion and merchandise, many of whom religiously and shamelessly log in at noon and race to fill their shopping carts with the exceptionally discounted items before others can.

Two New York City-based YPs, Alexandra Wilkis Wilson and Alexis Maybank, along with Kevin RyanMike Bryzek and Phong Nguyen, launched in 2007. From a small startup in a tiny, dingy office on West 19th street to a game-changer in online retail in just years, Gilt is currently valued at more than $1 billion. No big deal, right?

The story behind is clearly an inspiring one for any YP with a great idea, good connections and a lot of drive. Gilt Groupe set out to do what had never been done before. In cities around the world, designers had long controlled sample sales by staging anonymous, makeshift locations and strictly limiting invitations to an extremely fashionable, connected and in-the-know set. Bringing the sample sale online meant a total change into unfamiliar territory. It meant convincing elite, global brands to support a new startup that was attempting to replicate the long established sample sale experience on an online platform. It also meant a full-time commitment to the risk and uncertainty that comes with leaving behind corporate jobs for a small startup.

Written by Alexis Maybank and Alexandra Wilkis Wilson, By Invitation Only: How We Built Gilt and Changed the Way Millions Shop provides is an in-depth portrayal of the building of In simple, digestible terms,By Invitation Only discusses the creation of the business from the ground up based on a good idea, solid working relationships, networking, building trust in the brand and both fostering and maintaining connections. Identifying the need for balance in both personal and professional life, the book also touches on things like dating and marriage (both Maybank and Wilkis Wilson live in Manhattan with their husbands and children), working with friends (Maybank and Wilkins Wilson were friends before they were business partners), seizing opportunity and incorporating passion into jobs and life in general. It also addresses the inevitable challenges faced, like balancing competing needs of all parties involved and overcoming growing pains. It is peppered with checklists for readers to help gain an understanding of their own business ventures in everything from if it is a good idea in the first place to whether or not you are taking good risks and if it has the potential to be viral.

Wilkis Wilson was recently in town at Miracle10 in Toronto’s Yorkville neighbourhood, an event hosted by FGI Toronto, where we sat down with her for a few minutes. Admittedly, it is difficult not to be intimidated by her when in her presence. Striking, fashionable, super successful and also a wife and mother, she seems to balance it all harmoniously. She gave us a few pointers on everything from challenges and fears when starting a business, to simultaneously managing her thriving career with family.

You and Alexis both left safe, corporate jobs in favour of following your passion and building a startup. What was most challenging part of a startup?
After business school, I made the shift to move from finance to more fashion and retail and luxury. I had been fortunate enough to work for some high-profile brands like Louis Vuitton and Bulgari then and a lot of that experience offered transferable skills when it came to the creation of My experience in working for luxury brands was helpful with what I did functionally with trying to convince best brands to go online. Any time you have a new idea, the challenge obviously comes in having someone consider it, but my background and passion for the fashion industry helped. It’s important to make the most out of transferable skills and your work experience. provides a way for young professionals to attain designer clothes and other luxury items at relatively affordable prices. How important is looking the part when it comes to your career and using clothing to “fake it until you make it?”
I think it is important to dress appropriately for whatever profession or environment you want to be a part of. I think there’s a saying that goes, “dress not for the job you have, but the one you want to have.” At the end of the day, though, you’re dressing for yourself. If you look good, you will probably feel good about what you are doing. Personally, when I dress up a little bit and wear heels, I do feel more confident and empowered. This is especially the case in situations when I need to project confidence in myself but also display an image of the brand itself. Of course, there were times in the early days when we are working a mile a minute, rolling up our sleeves in the warehouse, getting dirty and stuffing boxes – and there’s nothing glamorous about that. But when meeting with CEOs of the world’s biggest brands, it was important to look the part. In general, be aware of both your image and your environment when dressing for the day.

What was your most notable recent purchase?
Oh my gosh, I shop a lot. I don’t even know. When I shop, I shop for the entire family and am always buying things online for my kids and husband in addition to myself. I do the majority of my shopping on Everything we sell has been curated to reflect a specific taste and we harnessed ourselves as the typical customer. It’s honestly just easy and reliable. 

How do you balance work with family?
It isn’t a daily balance, but more of an average over periods of time. Some days I will be more dedicated to the jobs, and other days I have more flexibility and can get home and spend more time with the kids. I am lucky enough that both of my parents live in New York and are very involved with them and my husband has his own career but also has a great deal of control over his schedule. 

What did you learn from writing the book? Was the process everything you thought it would be?
I have so much respect for people who write for a living and who do this 24/7. It took Alexis and I a while to gather our thoughts and gather all the examples, lessons and stories we wanted to share. We are used to quicker execution and results. It was a much slower process than expected. It took about a year to write the proposal alone. The finished product has really been so worth it for us to speak to so many people, mainly women, across North America. We have hopefully inspired people to think about entrepreneurship in being honest about the real challenges and successes we faced.

Do you have any advice for young entrepreneurs?
We have a checklist in the book (pages 75-76) to help determine how your idea is a good idea and if the timing is right to pursue it. Timing is so important in personal and professional life. It has to do with so many factors. For me it was great timing, I had just gotten married and I thought it was a good time in my life to work really hard at something that I was passionate about. It is certainly scary; you could invest two years of your life in something that will blow up in your face and not go anywhere, but you have to be open to take that risk and with the possibility of failure. Deep down you need to believe it will be successful, need to have that inner confidence to propel you forward. You’d be really well suited if what you’re doing in your profession doesn’t seem like work and if you wake up happy to do it. Life is short, you should love what you do if you can and hopefully success will come.

By Invitation Only: How We Built Gilt and Changed the Way Millions Shop makes a great summer dockside read for the young aspiring female entrepreneur (or any entrepreneur, really).