By Invitation Only: A Story of Entrepreneur Passion and Leadership

4/17/12Follow @xconomy

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Gilt “was ultimately shaped by a series of good ideas that we enhanced, tweaked, and rejiggered along the way.” But one of the key inspirations for the business was their own experience hunting down bargains in New York designer sample sales together. They were convinced that other women shared the same passion, and that Gilt would give these shoppers an unprecedented opportunity to get the thrill of a luxury bargain online.

So Maybank had to figure out how to convey her startup’s potential by positioning herself as the target customer—willing to drop everything for a designer deal—without undermining her abilities as a shrewd, capable CEO. “She decided not to hold back; her passion and enthusiasm for the Gilt business could only help her pitch, she figured,” the book reads.

The risk paid off. That meeting was on a Monday, the term sheet came from Matrix on Tuesday and was finalized on Thursday. Three weeks later, after due diligence and legal work, the deal was closed.

Matrix’s Nick Beim (also an Xconomist) cited his decision to invest as one inspired by the impressive, top-performing Gilt founding team, a business model that could acquire customers and scale quickly at a relatively low expense, and potential for solving a big problem for brands. But arguably, most of that would not have been communicated as well at the pitch meeting by a toned-down Maybank looking to fit in with a room full of male VCs. This same passion and authenticity fueled both Alexis and Maybank as they wooed customers via e-mail, toured the country to build up Gilt’s cache in target cities, and deepened relationships with Gilt’s most loyal customers.

I asked Maybank if this pressure to look serious in order to score funding still exists today. “Young professionals and young entrepreneurs still struggle with the dichotomy of coming off as very passionate and uniquely qualified to do something, and garnering that respect that they feel like they deserve,” she said. “There’s always going to be that twinge that young entrepreneurs face.”

“Our bit of advice is to identify what makes you unique—stick with that,” she added. “You don’t have to reshape how you look, how you speak, or how you project yourself forward. If you do, you really undermine your own confidence.”

By Invitation Only is dripping in this same tried-and true-advice from the pair. Maybank and Wilson are unapologetically advocates for their own distinctive personalities and qualities as leaders, and don’t subscribe to the idea that a good executive needs to embody the perfect balance. “It’s OK to be lopsided—instead of well rounded—when highlighting the elements of your personality, appearance, or convictions that truly make you one of a kind. Neither of us is good at everything, but we’re both very good at some things,” they write.

Wilson is painted as … Next Page »

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