The Winner of the Dave McClure Shadow Contest!

The Swashbuckling Adventure Begins TODAY!

A few weeks ago, we ran an opportunity for someone to shadow one of Silicon Valley’s most influential figures for 2 weeks. After hundreds of applications and some incredible resumes “kill the cover letter” candidates, a winner was finally chosen: Stefano Bernardi.

Today, the adventure begins and Stefano will be broadcasting the experience through the @daveshadow twitter account. The final candidates were all incredible, but Stefano stood out for his dedication to startups and techy background.

(Summer interns, feel free to ask Stefano questions about the experience, or fish for secrets! i.e. Does Dave actually work for 16 hours every day?!)

Leaving Rome for Startup Paradise:

Stefano is a 24 year old aspiring entrepreneur from Rome, and has already done some pretty big things. In order to galvanize the Italian startup scene, he blogs about startups, is a champion social media user, organizes hackathons, worked as an associate at an Italian VC, and wrote for TechCrunch Europe.  His post on Quora to apply to be Dave’s shadow got over 150 up votes and his application included a showcase of development, design, and other startup skills.

Despite all this success, Stefano still felt constrained in Rome. Access to mentors, funding, and all the other important fuel that helps startups take off is still scarce in Italy, especially while compared to the Bay Area.   For Stefano, the opportunity to shadow Dave meant a truly life changing experience to get insights from one of the most well connected and successful investors in the world and the opportunity to break into the US startup ecosystem that offers opportunities unlike anywhere else in the world.

Ultimately, after getting the shadow position, Stefano quit his VC job in Italy, moved to the states, and now plans to launch a company at the end of his shadow opportunity.

What will it be like to be Dave’s Shadow?

Dave’s schedule is so packed (in fact he uses over 8 different calendars to manage his day to day), so it’s hard to know exactly what kind of experiences to expect during the 2 week stint.  However, a big part of Dave’s philosophy is that transparency is a good thing, so Stefano will be allowed a deeper understanding of how the accelerator team operates.  This means Stefano is going to be sitting in on accelerator meetings, listening to company pitches, meeting with mentors, attending big events (including the “Investing in Food Event” hosted at 500 Startups) and last but not least helping out and attending 500 Startups Demo Days.

For those not in the know, Demo Days is the time in which the entire class of startups coming out of 500 presents their business to a room full of investors and press looking to land checks and extra press buzz to carry them to the next level.

Stefano announced his goals earlier in his application and they ran the gamut from mastering internet marketing to learning how Dave makes his investment decisions — all opportunities that will be available during the shadow time period.

Join in on the Fun!

This is a ridiculously cool opportunity for Stefano, but he wants to make it a ridiculous opportunity for anyone who has an interest in entrepreneurship, investing, or what it is like be the world’s most well known pirate/investor. We got things started by creating a “piratelist” of challenges for Stefano to tackle and tweet about while he completes his shadow. This includes activities ranging from interviewing mentors to dressing up like a pirate one day — you can view the list as it gets added to and as activites are completed here. But this is a group effort:

Whether you want to add new tasks for Stefano to complete while he eats, breathes and tweets as Dave’s shadow, or if you have any questions about what it is like to be an entrepreneur in the 500 incubator you can get involved. Leave your recommendations and questions on the InternMatch blog or tweet @daveshadow with #piratelist and we will get back to you asap.

Stay tuned for updates on the entire swashbuckling shadow adventure at @daveshadow, @InternMatch, and with the hashtags #piratelist and #swashbuckling!