AS A CHILD, Jess Lee dreamed of becoming a manga comic artist. She’s now the CEO of Polyvore, one of the most innovative and influential shopping platforms for fashion, style, and interior design.  How does one go from child artist to a high-powered successful female executive in the hyper-competitive world of Silicon Valley and fashion?  The answer: don’t be afraid to challenge yourself or others, fake it until you make it, and oh yes… keep it weird.

“I had a lot of culture shock,” says Lee recounting the beginning of her time at Stanford in 2000. She grew up in Hong Kong. Week one, Freshman year, the infamous Band Run arrived at Larkin; the Tree pranced around so passionately (or perhaps drunkenly) that he ended up smashing a window. Shortly after that first revelatory Stanford experience she was mind-blown by the bizarre debauchery of social norms we all know of and love to recount at Full Moon on The Quad. Lee quickly learned “Stanford kind of celebrates the weird.” And as happens with most of us, she fell in love with the communal sense of unbridled self-expression found on The Farm.

Speaking of bridles, becoming a comic artist was not a parent-approved career according to Lee. Fortunately, at Stanford she found another form of art that spoke to her, perhaps an even (proudly) geekier one.  Of all the places to find a new creative outlet Lee unashamedly admits it happened in 106A. “The rush you get from solving one of the little puzzles.  Each function is a little puzzle and then you compose it into a larger program, its just fun!” Spoken like a true CS nerd.

Lee standing by some love letters their users send in

As graduation drew near, Lee received some advice in a Google interview with Marissa Mayer (now CEO of Yahoo!) that has been instrumental in her career. She was struggling between taking a new position at Google, as opposed to the one she had already accepted at Intuit. Mayer encouraged her to take the most challenging path, where she would learn the most. She knew Google would be a much bigger challenge, and so as a newly minted CS grad she was given an incredible opportunity fresh out of college to run a whole product (Google Maps).

Intriguingly enough, Mayer’s advice that led Lee to join Google also led her to leave the company. Lee joined Polyvore in March 2008. First, just an avid user of the site, she emailed the founders, challenging them to make the site even better.  Surprisingly, they invited her to take on the challenge herself and work for them.  At the time Lee was happy to be working at Google, but she knew Polyvore was the bigger challenge. That leap of faith led to recognition as an honorary cofounder, and the position of CEO followed not too long after. Lee emphasizes that it all came about because she chose to continuously embody the idea of meeting challenges head on, in whatever form or direction they appeared.

Despite her rapid ascent to the top of the company Lee explains that she made a lot of mistakes and to this day is plagued by that constant what-am-I-doing feeling.  Lee admits that she often abides by the fake-it-until-you-make-it-rule.  She concedes that it is actually quite prevalent in the startup world — “There are no rules.  There are no clear bibles on exactly what to do at every stage of your company.  You just try to figure it out as you go along.” Keeping up with Silicon Valley start-up social norms, the first sale for the company (made by Lee) was done completely on the fly.  During a customer call-in, she came up with an ad product to sell before it even existed.

Lee’s boldness paid off and Polyvore has since become a monumental sales generator, out striding Instagram, Twitter, and Pinterest.  Revenue and profits aside, the company is blazing trails online in an even more important way. According to Lee, technology is democratizing fashion, just as Stanford has a community that encourages self-expression, technology platforms like Polyvore are empowering the individual to genuinely and unabashedly be themselves.

In the case of the Polyvore users are given the tools to create “sets” or collages of their self-inspired outfit or home design concept with self-sourced items and mood related pictures. The liberty to be brave, weird, and utterly genuine to oneself can be clipped from any source and incorporated into one’s own creation. With over 20 million unique visitors per month, there’s alot of personal style and expression being shared. Similar to other online social platforms Polyvore users can follow one another. As individuals from all over the world define their own sense of style and share it on the Internet, the fashion hierarchy is flipped on its head.  Potential trendsetting power is being given to everyone and Polyvore is playing a big hand in the revolution of the power politics of style.

Though Lee has long since graduated Stanford, the spirit of her Alma Mater (and the Tree) still lives within. She attends Comic Con every year while fully suited up in the wardrobe of one her favorite comic characters. Reflecting back she proudly states, “We’re weird and we revel in it.  That’s what I love about Stanford.  You can be yourself and be true to whoever you are.”