Our Story: From Reformed NY Investment Bankers to Silicon Valley Edu-Tech Entrepreneurs

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By Emily Chiu & Chiara Piccinotti (Co-Founders, Apply in the Sky) Winning the award for “best web start-up” at Women 2.0’s PITCH Competition last November was a surreal moment for us. Here’s a visual for you: picture two first-time entrepreneurs, trying (successfully, we hope?) to hide our nerves, as we stood before a live audience of over 300 in San Francisco, preparing to pitch our company, Apply in the Sky, for the first time.

By way of background, at that precise moment it had been:

  • 458 days since we had gathered up the courage to ditch our cubicle jobs;
  • Less than a year since we had finally gotten comfortable with the panic of giving up our regular finance paychecks to bootstrap our way towards visions of self-actualization;
  • 63 days since we had launched our beta for Apply in the Sky (after slaving through 300+ bug fixes);
  • 2 weeks since our first big partnership conversation;
  • And less than 3 hours since we had each pulled all-nighters to put together our Women 2.0 slides and video demo… to present Apply in the Sky to the public for the first time.

For both of us, it had been a long journey from Wall Street to Silicon Valley. And, in many ways, we are atypical tech entrepreneurs: we are both women – women without technical backgrounds, one might add; neither of our parents are entrepreneurs (in fact, they’re quite conservative); armed with finance degrees from Wharton, we both started our careers in investment banking – a move that isn’t typically the first step towards founding a start-up; and we were surrounded by few examples of peers that would dream of throwing away competitive jobs and stable salaries to work out of a garage on something that no one had ever heard of.

And yet, here we found ourselves: two reformed investment bankers, over 2,500 miles away from New York City, smitten by the entrepreneurship bug, and absolutely beaming from the encouragement we were receiving from the fantastic team of Women 2.0 supporters. We think it’s really important what Women 2.0 is promoting: a strong support network to bolster (relatively atypical and unconnected) first-time entrepreneurs, like ourselves – not to mention, providing us with an incredible platform to promote our achievements and the encouragement to keep persisting through the ups and downs of entrepreneurship.

It’s hard to talk about women in entrepreneurship without stumbling upon the usual clichés, but seeing so many individuals (men and women) come together as a community to celebrate women in entrepreneurship was truly inspiring. Our original motivation to start Apply in the Sky was borne out of our very personal experiences (read: suffering) applying to business school – we could not understand why, in a process as important as applying to school, nobody was using technology to help applicants streamline a disjointed process and better navigate a stressful and remarkably time-consuming experience. So we took it upon ourselves to create a better alternative.

But our idea is much bigger than business school. As individuals who have navigated major professional transitions in our own careers with few benchmarks and peer compasses to guide our journey, our vision is to build Apply in the Sky into a platform to help others navigate and master major next steps in education and career. It may start with tools to alleviate key pain points in the admissions experience for higher education, but the broader goal is inspired by our own ongoing journey and desire to provide a framework through which people can more effectively navigate similar transitions.

To aspiring entrepreneurs, the advice we give most often is to pick a project you’re passionate about… and to surround yourself with mentors and resources that will challenge you and support you through this crazy process. We really believe that our passion – and the amazing people we have had the opportunity to call our mentors – is what ultimately brought Apply in the Sky to life, and propelled it from an idea to a real company. Or, at least, it’s what propelled two first-time tech entrepreneurs to the stage at the Women 2.0 PITCH Competition.