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I have been fortunate to grow up in an entrepreneurial family as both of my parents run their own small businesses. Whether we were at Disneyland or a baseball game, my father would always ask me the question, what is the business model? Through the exchanges, he would always come up with an angle that I had not considered. These challenges served me well when I went to New York City for Startup Weekend. For those not familiar with Startup Weekend, they are 54-hour business incubation marathons, where you compete against other teams to develop the best business ideas. You can learn more about Startup Weekend by visiting www.startupweekend.org.

Prior to coming to Startup Weekend, you need to come up with an idea for a business that has some type of technology component. You are given one minute to pitch your business idea to the crowd at the event. Afterward, everyone votes for their favorite ideas and teams are formed around top entries.

My idea was a mentorship app using geo-location. The idea centered on the concept that there are a few people in your life that you would like to pass on bits of wisdom. The bits of wisdom typically occur in the context of doing something. The idea was an app that allowed users to date and place a location stamp on certain ideas. These ideas would be stored and could later be retrieved by the person the user wished to mentor. While I always enjoy public speaking, I made the mistake of holding the microphone too far from my mouth and was told later that people in the back could not hear my pitch. Whether they could not hear my pitch or whether my idea did not resonate with the crowd, it was not selected and I had to quickly jockey to be part of a team.

I landed on a team with eight others, led by a lawyer that completed his undergrad at Harvard before going on to obtain his law degree from NYU.  His idea was a question-and-answer content site for individuals to easily interact with lawyers around the world.  With the help of other specialists supplied by the event organizers, we struggled with the business model throughout the day and the evening prior to the final presentations on Sunday night. As we approached midnight and took a break, our team leader sent a text to the team that he was dropping out of the event and would not attend the following day. Throughout the difficult task of business model validation, our team had shrunk to four members. We retreated to a local restaurant for a late-night dinner where we started the process of pivoting our business idea.

Without our lead subject matter expert, we started thinking of problems we might encounter and need the use of a lawyer. After refining our ideas we came up with a business model for an online service to help entrepreneurs navigate the legal complexities of starting their own business. We called our online service LegalSailing. The system combined a cloud-based, video e-learning app and an innovative navigation tree that offered video-based advice to legal questions based on the decision tree model. We worked throughout the night building a prototype interface with Ruby on Rails. We presented our business idea to a panel consisting of investment bankers, entrepreneurs, and technologists. We came in fourth place out of twenty teams grabbing, an honorable mention award.

The experience taught me that there are always opportunities for a team to excel when everyone maximizes the talent they are given. Even without our subject matter expert, we were able to think, pivot, and refine ideas relying on a lean business methodology. The experience in New York gave me new friends and a greater thirst for entrepreneurism and innovation.  The experience and post-event interaction with other lawyers to validate the idea has led to new opportunities and business ventures. I hope to launch a small online service with another lawyer in 2013.



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    Hello, my name is Matt Robertson. I love developing new skills, helping others and traveling around the world. I’m a very self-driven, competitive and tenacious individual. I graduated from the University of Virginia in 2014 with a Bachelor of Arts degree, majoring in Economics. I now work as an Analyst within Morgan Stanley’s Institutional Equity Sales & Trading Division in New York City.

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Video Interview

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    I desired a summer internship in 2013. Read about my accolades and attributes, and check out a video I made to help prospective employers get to know me better.

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