Alexandra Wilkis Wilson, co-founder of Gilt and now GlamSquad, spoke with us about the triumphs and challenges involved with launching not one, but two, successful startups. She encourages young entrepreneurs to find their mentors and figure out what they’re good at, while also being careful not to overextend themselves and burn out. As a company expands, she advises new organizations to hire carefully, selecting for cultural fit and passion for the brand. Wilson doesn’t believe in failure — she believes in tests. She thinks each opportunity is a moment to overcome a personal and professional hurdle. And finally, she advises entrepreneurs to remember the power of kindness. “Genuinely build your personal networks. … Be a good person,” she said. Wilson’s success has garnered her the honor of being the first ever recipient of Endeavor Miami’s IMPACT Award. She will be honored alongside Jim McKelvey, co-founder of LaunchCode and Square, at a gala held on Nov. 18.
How did you get your start?
Prior to Gilt, I had a more corporate path and career. I went to into banking, and I went to business school. I worked for Louis Vuitton and Bulgari. During school, I always I knew I wanted to get into the fashion industry. Then, in the summer of 2007, I got together with the Gilt co-founders. The idea was to bring the concept of NYC sample sales to the internet. I loved shopping in a sample sale format, enjoyed it for years, and thought it was exciting to take high brands, but have them at more affordable prices. But a lot of designer brands didn’t sell online in 2007, so it was kind of radical both on the supply side and also from the consumer behavior end. Women, who were our target consumer, weren’t used to buying high-end fashion online. It was usually more of a brick-and-mortar experience. We changed the way a lot of people shop. It was exciting and definitely not easy. All startups are challenging, raising money, scaling, keeping up the pace of growth, hiring, firing, all of those things are important.
How did GlamSquad come about?
Well, I ran into two guys I went to college with — David Goldweitz and Jason Perri — who told me that they launched a beauty services business. I was already an advisor for Gilt and for Birchbox and Rent the Runway. I got excited about GlamSquad and became an advisor to the company. I started using it and found myself filled with ideas. I was passionate about what the company stood for — making women’s lives easier at an affordable price. We charge $50 for blowouts in the comfort of your own home every day. A few months later, the team approached me asking about what I was going to do next. I thought I was going to go into venture capital, but then they asked me to be the CEO. I told them that I wanted to be a co-founder, to which they said, “Absolutely.” Here we are, over a year and a half later. Today, GlamSquad is a mobile services company. You can download the app and visit our website. In Miami, we offer two beauty services for hair and makeup.
What were some of your startup challenges?
One of the challenges for creative people and teams is that there’s never a lack of ideas. There’s always so many ideas it’s hard to execute on all of them. Sometimes you have to stop and prioritize what you want to focus on. For me, it’s especially hard to say “no” to ideas … whether it’s new services or expanding to new cities. But I’ve gotten very disciplined recently to say, “No.” I think that’s the hardest thing because the entrepreneurial nature is to get excited by newness, but we need to continue to grow and focus on the existing business first.
How did you choose your team?
Hiring is so important. Getting it right when you’re growing quickly is tough, and you can sometimes misjudge. In many startups, the pace of growth can become overwhelming, but what we have found is that any new hire needs to be a good cultural fit with relevant experience. A lot of what a new hire can contribute is the ability to learn as you grow. In the case of Gilt and GlamSquad, there wasn’t a blueprint of, “This is exactly how we do things.” Not every idea is a success, but the key is not to make the same mistake twice. You need to find people who are passionate about what you’re building, who believe in the future potential. You need someone who has a can-do attitude, who doesn’t need to be micromanaged, because it’s hard to devote a ton of time to really micromanaging people. Everyone is going a million miles an hour. Startups aren’t for everyone, and some people like predictability and structure and in a startup you have to function with a flexible, adaptable perspective.
I’m tremendously honored to receive this award. It’s the first time they are doing this, because Endeavor Miami is only 2 years old, so I feel humbled and inspired. I care a lot about Miami and do want to live here one day. I’ve been close to Endeavor for many years; I went to graduate school with one of the founders. I think Endeavor is creating an incredible ecosystem for current entrepreneurs and inspiring future entrepreneurs.
What is Endeavor Miami doing for the city?
I think Endeavor is valuable for local South Floridian entrepreneurs because it provides an incredible network of mentors who are going through some of the same challenges, so marrying experience with newness and creativity is powerful. I don’t know too many successful big organizations that have had years of traffic and experience doing that. Endeavor Miami is a startup itself, it’s only 2 years old, but it has so much experience behind it. That’s incredibly helpful and powerful to entrepreneurs. If I was a Miami-based entrepreneur earlier in my career, I would have been thrilled to be part of this network.
Why did you pick Miami as the third launch city for GlamSquad?
I have many ties to Miami. My mother is Cuban and I grew up in New York City, but I would come to Key Biscayne during the summers for my whole life, because my mother is a teacher, so she had the summers off. I got engaged in Miami, and I got married here. My kids love it as well. We have many many friends here. I’m also on the board of Perry Ellis, which is headquartered here. It was very strategic that we picked Miami as the third launch city — there wasn’t really even a debate about which city to expand to. We knew the market pretty well, and we view Miami as a melting pot of diverse cultures. Also, the humidity doesn’t help most people’s hair, and many women in Miami tend to be beauty conscious. Women here like to look good, they are social, and like to be seen in public. We think they would appreciate the conveniences of not having to drive to the salon. We also think this service can help tourists coming to town, who might not have a rental car but need to get to a salon.
How do you tailor a look to a specific city?
Glamsquad has standardized looks across all markets, both on the hair and makeup side of things, but can tailor a look based on the client. Because of the intense humidity in Miami, our team uses more styling products to help combat that.
What’s the most popular look in Miami?
The Weekender here because of its beachy waves, and as far as make-up, the Bronzed Beauty is pretty popular here.
What inspires you?
I love trying different types of apps and companies and I get inspiration from them. Like this past weekend, I booked a Pager, which is like on-demand health service, to get a flu shot. Within 10 minutes, a nurse came into my home and gave me a shot. It was great. I also like Kitchensurfing, which brings chefs into your home to cook for you. … I also read a lot of tech magazines like CrunchBase, Mashable, TechCrunch, AlleyWatch, Dan Premack’s Fortune newsletter called Term Sheet, Women’s Wear Daily, and the New York Post for a little gossip.
Did you ever feel like you were going to fail?
I don’t like the word fail. I like the word test. You should always create an environment where you’re testing mistakes and learning from those mistakes. Not every idea that you have is successful and if you learn from those ideas and analyze them, that’s the key to success, growth, and innovation. A lot of entrepreneurs will burn out. After Gilt, I was physically worn out. A lot of people go through that and don’t really talk about it that much. You have to do things to stay sane, healthy, and motivated. Arianna Huffington often speaks very publicly about the importance of sleep. At the Huffington Post, they have have sleep rooms, and encourage workers to go take a nap. I think that’s so great.
What parting advice do you have for female entrepreneurs?
All entrepreneurs face similar struggles. In the case of female entrepreneurs, we’ve made a lot of progress. There’re so many great examples of big, disruptive companies founded by women, which is helpful and inspiring for the future generation. One thing I learned along the way was that my mentors didn’t have to be women. I benefitted from great mentors who were both men and women. In general, three things I say to anyone is to figure out what you’re good at, figure out what you’re passionate about, and work on genuinely building your network and relationships. What goes around comes around and if you do kind things for people, when you need help, it will happen. Be a good person.
Readers of The New Tropic can receive $25 off of their first GlamSquad appointment by using the code TNTGLAM at checkout.