A Conversation with Entrepreneur, Alexis Maybank

Alexis Maybank is the Founder of Project September, the first CEO of Gilt Groupe, and co-author of the New York Times bestseller, By Invitation Only: How We Built Gilt and Changed the Way Millions Shop.

Alexis is frequently invited to speak to audiences about her experiences as an entrepreneur and a woman in the start-up space.  She recently spoke with Elle.com about what it takes to become a successful entrepreneur…

For those who don’t know your career path, tell us about life before Project September.

Coming out of college [Harvard University], I chose to go out to Silicon Valley. Being from the East Coast, I thought so much was happening out there. New industries were emerging [and] there were so many places I could think to go in the continental U.S., so I graduated and ended up working for the co-founders of eBay. That was really right when it started; it was just a corner office suite and it had one founder, a cubicle away, and then a CEO two cubicles away. I really had no idea what Silicon Valley, the internet, or software was all about, but to me it was a place where there was a tremendous amount of growth, a tremendous amount of change, and possibility for me as an individual to take on new responsibilities. It was my first foray into consumer tech and finding ways that allowed the internet to connect people with those of similar passions—be that eBay or the fashion devotees I was later to connect better through Gilt, and then again now at Project September.

As someone who has been part of a few start-ups now, what sort of advice do you have for someone who wants to start their own business?

A lot of people want to be an entrepreneur, so it’s important to know that there’s a lot of ways to be an entrepreneur. One of the ways is to go about and start your own business. There are also ways that you can gain experience in the context of a larger business, like raising your hand to helm a new office. As you are gaining your skills to run your own business successfully, the first way is to think about how you can do so based on where you already are. Are there valuable earnings you can have because you are raising your hand to work on a new project or business unit, or a new context within your current workplace? Don’t turn a blind eye to this!
One of the most important things you can do is build an ecosystem of people around you who want to see you do well. That might be making appropriate introductions or providing mentorship or introducing others to key hires over time. It’s not just what you can learn at your job before you set out on your own, but also thinking about how you’re cultivating that ecosystem and keeping in touch with that group around you. Eventually that’s where you want to be really scrappy as an entrepreneur when you’re first getting your business up and running: hiring the right people, partnering the right way, getting feedback on what you’re doing.

What characteristics do you think somebody has to have if they want to start their own business?

First and foremost, without a doubt, is resilience. As an entrepreneur you are often failing as much as you are succeeding. You are falling on your face as much as you are stepping up and moving forward. You need that ability to get up, re-gather, think of what you are going to do next, not letting that misstep pull you down. Next, you cannot be afraid of looking stupid or not being perfect. You have to be okay with sticking your neck out, being willing to fall down, and knowing that you are more measured over time about how you are getting back up.
With resilience you are learning to be flexible and take feedback on how people are experiencing what you are building, you’re listening to what your customers are saying, you’re building these relationships, and making better decisions over time. That all really starts with that resilience and that willingness not to be perfect.

Do you have any tips to ask for a raise or to negotiate for a raise?

Well, I have had lots of men on my team and I have had lots of women on my team, and men are asking constantly. That’s one thing to just know as woman: by general rule, men are more generally asking than women.

How often would find that men were asking?

I don’t know, but they’ve got the squeaky wheel thing down! A couple things for women, though, is know our market rate! Ask others, “What are you earning? When people are approaching you for jobs, what is being offered?” That way you are kind of keeping your finger on the market. To do that research and not being complacent with that is definitely one [tip].
When it comes to asking for raise, you just have to do it in the right way. You may get a no, and that’s fine, but ask and make sure you know when you can come back and ask again. Exactly what you need to do in order to get to the next. If you are having that conversation to begin with, say, “Here is what I love about what I am doing, here is what I want to contribute, but I feel like it’s time for me to be reconsidered for this level and for this pay increase.” Make sure you are asking, “What do I need to do to get to that next level?” That way it becomes more quantifiable. It’s not just asking and getting a yes or no. If you are getting a no, understand what it takes to get to yes. Is it a certain quality of work output, is it accomplishments that need to be undertaken? Is it time or experience level? Don’t ask the question and then not understand what measurement will be put in place to get to that next level.

What is the best piece of career advice that you ever received?

That a career is measured over the course of the years, not moments. Over good decisions, over successes, not moments, failures, missteps, or bad comments. I learned that I needed to take a step back and look at my career not in that one moment that made me feel really bad, but what I had done not even in the past one or two years or last one or two hires, but that that career is built over many, many, many, many successive quarters and years and good decisions—never, ever made in that one moment where you felt really bad.

Read the full interview here