Nov 13

Leadership Breakfast with Andy Weissman

When is the best time to email a Venture Capitalist to get their attention? How does one recruit great talent for a startup? How is the startup landscape in NYC expected to change in the next few years? These were some of the questions five lucky InSITE fellows, including myself, got to ask Andy Weissman (@aweissman; at a recent leadership breakfast.

In case you’re wondering, the answer to the first question is 5 am! I’ll leave it as an intellectual exercise for the reader to guess why.

The InSITE Leadership Breakfast series is a biweekly event designed to give InSITE fellows the chance to interact with and learn from a leader of the NYC Startup Community. Past leaders have included Steve Martocci, Chris Dixon and David Tisch.

At the most recent Leadership Breakfast with Andy, he talked about his new job as a partner at USV, the firm’s highly successful investment thesis (and the importance of a VC firm to stick to their first principles), and some of USV’s recent investments, including DuckDuckGo ( and Codecademy (

One of the things that really appealed to me was Andy’s philosophy on what he calls “Disruptive Innovation” as a first principle for entrepreneurship. The traditional approach has been to take an old world (offline) phenomenon, copy it and bring it online. However, this does not always cause “disruption” and lead to success. Rather a disruptive idea is one that is radical enough to change the way business is done and redefine an entire industry. For example: Until recently, online advertising had been about replacing, what we have in the offline world (magazines/newspapers) and getting it online in the form of display advertising (think DoubleClick or popup banners). However, what truly disrupted this approach was Google Ads, which took the content displayed on the page and presented relevant text-ads. Not only did this enhance the user experience, but also transformed the traditional model of advertising. Andy hinted that there was a high possibility of such disruptions coming from products being built on top of existing major platforms (such as Tumblr, Facebook or Twitter).

Abe, Joe, Brian, Austin and Amrish would like to thank Andy for taking the time to meet with them and wish him good luck on his new role at USV. Thanks Andy!

Amrish Singh (@amrish), InSITE Fellow and NYU Stern MBA 2013

Andy Weissman is a partner at Union Square Ventures. Andy began his career in the Internet at AOL in the mid-90s, then managed a series of venture funds with Dawntreader Ventures. In 2007 he co-founded betaworks, which both created and invested in social, real-time applications and services. Andy was born in New York City and has a BA from Wesleyan University and a JD from Georgetown.

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