📺 Stream EntrepreneurTV for Free 📺

The Co-Founder of Gilt on What Her First Job at Ebay Taught Her About Running a Company Now the founder of Project September, Alexis Maybank explains why fortune favors the bold.

By Nina Zipkin

entrepreneur daily
Project September

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

As the co-founder of Gilt.com, which brought the big city sample sale experience to a massive online audience, Alexis Maybank has a unique understanding of how to reach digitally savvy style mavens -- and disrupt an industry.

The Gilt Groupe pioneered the flash sale model, in which luxury items would be highly discounted for 24 to 48 hours. At its peak popularity, the site reached users in more than 90 countries and had relationships with more than 6,000 designer brands. At the point the company was sold to Hudson Bay in 2016, it had a base of 9 million users.

Recently, the fashion industry veteran returned to her startup roots to disrupt again. Her latest venture, launched last year, is Project September, which takes the classic fashion spread you would see in magazines like Vogue, and turns it into a streamlined shopping platform, with specialized green dots highlighting which of the items users can buy. If something catches your eye, you can shop for it right away.

Users can scroll through curated images from major industry influencers like Project Runway judge and Marie Claire editor Nina Garcia, model and activist Christy Turlington and Instagram star and entrepreneur Patrick Janelle. The platform has more than 20 million SKUs and has partnerships with more than 7,000 brands. Users who curate pages can earn 6.5 to 10 percent commission when people click through to buy the clothes or accessories in question. Since the company's launch this past fall, the users base has been growing 30 percent week over week.

We caught up with Maybank and asked her 20 questions to figure out what makes her tick.

Related: 10 Entrepreneurs Reveal What They Wanted to Be When They Grew Up

1. How do you start your day?
I have three small children and a startup. Both are 24/7 hour jobs. I look at my schedule for the day, get sufficiently caffeinated, make sure the kids are set for their day, and then I head into my first meeting. I have always identified personally as an athlete, and since my mornings tend to start with a bang at 6.00 am, I do my workouts in the evenings.

2. How do you end your day?
It's a little flipped with how people start their day. I put kids to bed, finish up work and then I go catch up on the morning news and work out. I was very influenced by the HBR Article, The Making of a Corporate Athlete, that studies how people in business have sustained high performance across long careers.

While the study focuses on many elements, and I definitely recommend this reading, one conclusion reached was that typically people push themselves too hard mentally and emotionally daily, but not hard enough physically. They found that this linearity erodes your effectiveness and resilience and this resonated with me. When I feel strong and fit, I feel focused and so much more prepared for anything that might come my way each day.

3. What's a book that changed your mind and why?
Machiavelli's The Prince . It's amazing how true it was in the 1500s in Italy as it is at times in the business world. It's a good reference how you keep your own counsel to a certain degree and remember where and how to elicit the best feedback. It's also that interesting mix between being loved and being respected, and how you think about that especially in a mission-driven startup environment.

4. What's a book you always recommend and why?
The Wind-Up Bird Chronicle by Haruki Murakami. It's important to intentionally jolt yourself out of your routine and comfort zone. I typically find myself reading articles and news, so I periodically force a work of fiction into my readings, particularly creative or surreal ones. I describe Murakami as akin to artist Salvador Dali if he had chosen to write literature instead of paint. I found myself thinking about other cultures, perspectives and perceptions in new ways in the time that followed reading his work.

5. What's a strategy to keep focused?
In an environment where I'm juggling so much, I always try to have the three things, that no matter what pops up in a given week, I absolutely must get done. It allows me to follow through on the things that I really need to accomplish.

Related: 10 Entrepreneurs Share the Best Advice They've Ever Received

6. When you were a kid what did you want to be when you grew up?
I always thought I would be the next Jacques Cousteau. For me it was the exploration, the excitement, going to new areas. I thought I never wanted to work in an office. All of those reasons combined led me to think that I wanted to be a world famous marine biologist.

I spent so much of my life exploring, typically in far-flung geographic corners of the globe, and I got this interest from my mother and grandmother. This turned out to be one of the best forms of training for entrepreneurship: how to navigate the unknown, learn in new settings, read people and make decisions with not enough information. What started as a desire to be the next Jacques Cousteau turned into a passion for exploration, a curiosity to learn new things, and a comfort in being out of my comfort zone.

7. What did you learn from the worst boss you ever had?
The importance of consistency. There is no worse feeling dealing with boss who constantly changes his or her mind, varying moods and reactions or changing strategic direction. A lack of consistency leads to so many losses, needless amounts of stress and just a negative political environments in that work context.

8. Who has influenced you most when it comes to how you approach your work?
I learned a lot working under Meg Whitman in her first four years as CEO at eBay. She was one of the first very senior women in Silicon Valley. Her ability and style as she worked across different teams made her a terrific leader, that allowed her to connect, motivate, challenge and really command the attention of so many groups and inspire them. Most importantly under her leadership of eBay the company went from 50, 60 people to tens of thousands. It was certainly a terrific experience that I was able to draw upon in my own context of rapid growth and managing everything from corporate strategy to business culture and do it well.

9. What's a trip that changed you?
When I was 17, in high school, I went away for a month and lived on a glacier in Alaska. It was an unbelievable experience. The independence at an early age, taking care of everything that you might need -- from figuring out where you are going to eat to how you are going to get it. You need to be ready for just about anything. It gave me the confidence to believe that no matter what, I'm going to get to the other side.

10. What inspires you?
I have a line of very strong and inspirational women that came before me in my family. A succession of self starters, who were strong and carved their own path. They were innately entrepreneurial, and a huge source of inspiration for me at every turn.

Related: 10 Successful Entrepreneurs Share What Inspires Them to Keep Going

11. What was your first business idea and what did you do with it?
I think the first big business idea was in 2007 was when I co-founded Gilt Groupe. The idea was simple; it wasn't big at the beginning. It was to bring the New York City sample sale to an online audience for the first time. We built something we loved for our friends, watched that catapult, grow and spread very quickly to so many people around the country and after that, around the world. All of this transpired in two to three years, reaching millions of people globally.

12. What was an early job that taught you something important or useful?
I joined eBay a year after I graduated from college. I learned something that I still tell young people today, which is to go to where the growth is. At 24, working at eBay as it scaled through one of the fastest cycles of hyper growth, I worked for the co-founder. As they needed capable people who were willing to raise their hands, I was able to start two businesses for eBay. The first was eBay Canada, one of the first international businesses and eBay motors. If you're flexible, it's amazing how much you can take on early in your career -- if you are at a place that is moving really quickly.

13. What's the best advice you ever took?
Susan Lyne, who oversees BBG Ventures, told me something that really stuck with me. Remember that a career is measured over many years. It's not one moment when you're feeling the highest sense of elation or your lowest sense of defeat. So stay focused on that and take solace in that. You're going to be measured by what you do in totality, not in that one moment.

14. What's the worst piece of advice you ever got?
Right as I was coming out of college, and I was going to work in a predominantly male environment as the only female. People would try to be kind, but would tell me that I must dress and act a certain way in order to fit in.I felt so uncomfortable and so not like me. A few years later I broke away from that and realized you are your own brand. And the more comfortable you are, the more confident and memorable you'll be. You'll be the most effective if you achieve your own personal style.

15. What's a productivity tip you swear by?
Organization is not my specialty. Navigating through chaos, I'm better at. But I have two. I really love Instacart and my notes app and check list on my phone. They save me so much time.

Related: 10 Founders Share What Their Worst Boss Taught Them

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
Project September, clearly. I use it to track everything that's trending for events like fashion week and in street style.

17. What does work-life balance mean to you?
To me, it is a myth, it is a unicorn. Having two full-time jobs -- my startup and my kids -- it's all about trade offs. Sometimes I'm a terrific professional or a terrific parent, but I'm almost never both at at the same moment. In any given day, decide which of the two are you prioritizing for that given period? You have to be willing to drop some balls along the way.

18. How do you prevent burnout?
For me, I have to force myself out of a routine. That's usually done by getting outside, unplugging for a day or a weekend. You need those uninterrupted blocks of time to think through solutions or figure out how you're going to tackle a problem. You just can't do that in the four walls of an office space.

19. When you're faced with a creativity block, what's your strategy to get innovating?
Get out of your routine with some regularity to keep from getting creatively blocked.

20. What are you learning now?
On the work front, it is video, and how we can make that instantaneously shoppable and thinking of technologies that we haven't seen yet. On the fun side, it's how to do a kick serve in tennis.

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at Entrepreneur.com. She frequently covers leadership, media, tech, startups, culture and workplace trends.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Side Hustle

These Coworkers-Turned-Friends Started a Side Hustle on Amazon — Now It's a 'Full Hustle' Earning Over $20 Million a Year: 'Jump in With Both Feet'

Achal Patel and Russell Gong met at a large consulting firm and "bonded over a shared vision to create a mission-led company."

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Side Hustle

How to Turn Your Hobby Into a Successful Business

A hobby, interest or charity project can turn into a money-making business if you know the right steps to take.

Business News

These Are the 10 Most Profitable Cities for Airbnb Hosts, According to a New Report

Here's where Airbnb property owners and hosts are making the most money.

Starting a Business

This Couple Turned Their Startup Into a $150 Million Food Delivery Company. Here's What They Did Early On to Make It Happen.

Selling only online to your customers has many perks. But the founders of Little Spoon want you to know four things if you want to see accelerated growth.


All Startups Need a Well-Defined Brand Positioning Statement. Here's a 3-Step Framework to Help You Craft One.

Startup founders often lack time but they should invest resources in identifying a winning brand position that will then drive all their strategic decisions.