How to Make Flexibility Your Startup’s North Star by Jenna Abdou


When Alexis Maybank discusses how photographers utilize Project September - an app making the visual world instantaneously shoppable -  she describes it as a “living portfolio where they can unlock new relationships with viewers.” The demographic is different than the fashion bloggers and influencers the New York-based team expected. However, similar to the portfolio, the young startup is “living;” One of the most accurate and meaningful ways to represent a company’s evolution. 

In today’s featured interview, Alexis asserts why flexibility should be a founding value at your startup and provides three frameworks for entrepreneurs to lay a sustainable foundation to launch and scale their businesses.

If You Wait to Be Certain, You’ll Never Launch

Project September was inspired by a “collection of a-ha moments” that Alexis experienced while running Gilt Groupe, the flash sales site she founded in 2007. Throughout her tenure, she witnessed a drastic shift in the way customers were discovering, browsing, and purchasing merchandise. A telling example stems from her time as CMO when the number of shoppers visiting Gilt from Pinterest rose from zero to five percent in a single month. “It seemed like it happened overnight,” she reflects. “Millions of people were coming to the site after discovering products from individual tastemakers who had massive followings across the social web. It was a whole new way of discovering products and shopping.” Project September was born to provide a platform for fashion bloggers and influencers to utilize the imagery they are creating and immediately tag items to be purchased. Shoppable clothing, handbags, shoes, and accessories are represented on the app with green dots. Creators receive 8% to 15% of every transaction that occurs through their photos. 


Project September’s mission to “unlock the visual world” is vast and will undeniably evolve in unexpected ways. The photographers, as well as the make-up artists and stylists who are using the platform, are demonstrative examples of tapping into unique segments in the market.  “I’m a big believer in getting any business out into the public domain as quickly as possible,” Alexis says. “You never know what you’re going to discover, how people are going to use your product, and whether you’re building in the right direction.” The key is to closely observe user behavior, quickly adapt, and deliver features that enhance their experience. Alexis and her team are at the onset of these learnings and are eager to engage with creators and members. 

Ground Your Team in Flexibility and Diversity 

From the outside looking in, the iteration process at startups, which occasionally implies completely abandoning your plan, is intimidating and mysterious. With nearly two decades of operating experience, Alexis follows two founding values to streamline her team’s efforts: Flexibility and diversity. 

To start, it’s helpful to define the tenets in the way Alexis practices them as a founder. 

  • Flexibility is “the ability to adapt to changing environments and think about problems from new angles.” 
  • Diversity is reflected in a group of individuals who approach situations from unique perspectives, enabling your team to make the best, hardest, and smartest decisions.

The first piece of advice Alexis shares with early stage entrepreneurs is: Be flexible. 

“Flexibility is one of the most important core values you can establish as a part of the ethos at your company,” she says. “No matter what people say, your business will evolve from the get go. There will be highs, lows, left turns, and right turns. It will never be a straight line.” The only and wisest, way you can prepare is to assemble a team of individuals who are eager and capable of navigating the uncertainty. The goal is to cultivate four habits: 

  1. An innate sense to anticipate what is or may be coming
  2. The ability to quickly adjust how you run your business 
  3. Readiness to tackle new opportunities
  4. Grit to overcome unforeseen challenges 

To ensure she hires individuals who fit this criteria, Alexis ingrained flexibility into her recruiting process. “In every single interview I did at Gilt, I let people know up front that that they were signing up for a high growth environment where their role could change three times over the course of the year. I know it sounds scary, but it’s a sign of success,” she asserts. For example, a team member who is responsible for both women’s and children’s merchandising may only focus on a fraction of one department, such as accessories or handbags, in the future. “Although your role appears to be shrinking on paper because you are overseeing a single department versus a few, it’s likely getting much bigger,” she continues. “You’re managing a larger revenue stream for the business and significantly growing your team.” Alexis urged all prospective team members to anticipate and accept this possibility before joining the company.

People fight growth because they perceive their role is getting smaller.

It is important to recognize and vocalize that these conditions aren’t exclusive to a startup’s early days. In fact, they will accelerate as you scale. This is particularly true for fast growing companies to which Alexis remarks: “Cycles are so compressed in hyper-growth scenarios that what might happen for a startup over the course of a year can happen to you in a quarter.” She witnessed dramatic hyper-growth at both eBay and Gilt. From 1998 to 2002, eBay grew from a team of 40 to 4,000, with team members operating in 23 countries. Gilt similarly experienced massive increases in sales; Growing their team to over a thousand individuals in under five years.

The only way to successfully scale at this pace is to develop a team that thrives on the intensity of a fast-paced culture. This is where diversity of personalities is most important. Your business requires individuals who can uncover a wide range of new and hidden opportunities, while simultaneously executing to elevate your team’s competitive advantage. 

Diverse personalities enable you to view opportunities and challenges from all the right angles.

It’s human nature to be attracted to and seek out individuals who think and act the same way we do. In startups, this often entails irrationally optimistic individuals “who have never seen an idea they didn’t like.” While enthusiasm is important, founders solely hiring individuals who share their outlooks and strengths can be a debilitating crutch for companies. A big picture thinker herself, Alexis strongly advises entrepreneurs to partner with leaders who she describes as “caretakers” to achieve operational balance. 

“You always need big idea individuals who think about the possibilities. At the same time, you need team members who are thinking about the potholes you can encounter on the road and are focusing on whether or not you are putting the right infrastructure in place,” she says. “I am a relentless, stubborn entrepreneur. I believe everything is possible and that we will find a way no matter what. I have to balance myself with someone who is very detailed oriented and factual in terms of what is being accomplished on a daily basis.” 

The mentality similarly extends to your advisors and mentors. Nina Garcia and Nicole Richie are a few of the thought leaders Alexis has assembled at Project September to help the team achieve its goals. 

Overall, Alexis approaches diversity as a balance and relies on regularly answering these four questions to ensure that she is building a well-rounded team. 

  • Who do we need on our team now? 
  • Who do we need in the future? 
  • Who do we need as advisors? 
  • Who do we need as a contractor or partner who serves a very specific purpose but is not required full-time? 

Take Control of How You Exist in the World 

Self-awareness is among the most telling habits you must cultivate to run a successful company. While startups are initially inspired by a founder’s vision, the future is largely predicated by the evolution of the entrepreneur themselves. This is reflected in your ability to build a diverse team. As a leader, you should constantly be asking: “How do I need to compliment myself?” In addition to surrounding herself with a “caretaker,” it’s critical for Alexis to bring on the right tech talent to build Project September. Co-founder Dustin Whitney currently leads the team as CTO.

Always balance yourself with people who look at the world differently.

Whether you're a first-time founder or a serial entrepreneur, it’s wise to recognize and fill in your blind spots as soon as possible. While you can hire designers and engineers to supplement tactical expertise, Alexis recommends founders are confident in these key business areas. 

  • As a founder, you must have a very clear understanding of your user’s pain point and how adequately your solution addresses their needs. Being your own target consumer enables you to grasp the challenges facing your audience, making it simpler to identify and tackle new opportunities. 
  • In the digital ecosystem, it’s critical that you have a thorough understanding of the back-end technology powering your product or service. It’s not vital that you know how to code or can build fancy features. You should, however, possess the knowledge to identify and hire experts to champion those efforts. Alexis refers to this as being a lopsided leader: “An individual who has deep expertise in one, maybe two areas, and a general understanding of the rest of the business.” 
  • Financial literacy and a clear understanding of how to manage your business from a profit and loss standpoint are non-negotiable. 

Daina Trout, the Founder of Health-Ade, describes running a business “as falling off a horse 1,000 times a day and getting back up every single time.” To reset her perspective and navigate the numerous challenges she faces as an early stage founder, Alexis relies on her favorite feedback she’s received as an entrepreneur: “You are never as good as you think you are nor as bad in any given moment.” 

“Working at a startup is like being in the trenches. You are literally in the trenches with your team; Thinking day by day. Every day is exuberating, exhilarating, painful, and painstaking in its highs and lows,” she says. “You can really beat yourself up sometimes. You experience the highs too high and lows too low but you have to regain perspective and say ‘Wow, that was a great day. Let’s celebrate and move on.’ Or, ‘Wow, that was painful. We learned. Let’s keep moving.’” 

Your career is built over the course of years. It never comes down to a single day or moment.

Now working on her fourth startup, Alexis remains enamored by the chaos and uncertainty of bringing new ideas to life which intensifies these feelings. “I love diving into the deep end of the pool and feeling the water levels a little above my head; Where I don’t know what’s going to happen or what our business is going to look like. It excites me, pushes me, challenges me, and keeps me on the edge of my seat,” she says. “A heavy dose of the unknown brings out my best thinking.”

Equally important, Alexis acknowledges that your journey as an entrepreneur will and should be different than your peers and competitors. “Don’t get caught up in what you think you should be doing or things you think should appeal to you, like teams or working environments. There are usually a few things, maybe even just two, that define whether you’re going to have a good experience. There’s no right answer.”

“Give yourself the ability to live your life in a way that you’ll look back and be really happy and content that you did. Don’t live with what-ifs. Playing small doesn’t serve the world,” she concludes, quoting Marianne Williamson. “Instead of shrinking our sphere of influence, especially as women, we should expand it.”

If you’d like to learn more about Alexis’ journey and Project September, tune into her Beyond the Headline interview and follow her on Twitter (@GiltFounder) and Instagram (@AMaybank).

You can also download Project September here. The team welcomes your thoughts and feedback at info@projectseptember.com. 


Images retrieved from Project September. 



Further Reading
  • How MeUndies Made Merchandising Their Competitive Advantage — When MeUndies thinks about their underwear subscription service they compare themselves to Netflix. What the streaming pioneer did for TV, the Los Angeles startup wants to do to your underwear drawer. The goal is to provide monthly subscribers with the staples they love while delivering elements of surprise - Think briefs with donuts and dinosaurs - right to your doorstep.
  • Seedling Relies on Childhood Curiosity to Inspire a Creative Team — On a recent flight home, I spent over an hour browsing a children’s play website, completely enamored by sets like Design Your Own Superhero Cape and Invent Your Own Insects. After sharing Seedling with everyone I know, despite few of my friends having children, I wondered why the brand struck a such a meaningful chord with me.
  • eero Designs Wi-Fi for the Smart Home Era — Nikhil Basu Trivedi, Principal at Shasta Ventures, recently distinguished exceptional founders by their ability to prioritize. “It all comes back to prioritization, speed, paranoia, and knowing that if you don’t iterate, even after finding product market fit, you can be disrupted by the next product,” he says.


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