May 05

Breakfast with Andy Weissman, Partner at Union Square Ventures

Last week, an eclectic group of InSITE Fellows — from aspiring venture capitalists to law students to genomics PhDs — gathered to have breakfast with Andy Weissman. And, as a former attorney, early veteran of AOL, co-founder of betaworks, and partner at Union Square Ventures, Andy delivered a little wisdom for everyone.

As he recounted the trajectory of his career, it was hard not to feel both comforted and terrified at the same time. After college, Andy decided to attend law school by process of elimination. Having hated the summer he spent on Wall Street and lacking interest in medical school, he chose the third standard professional career path available to college grads at the time. Shortly after graduating, he found himself hating the drudgery of the law firm life.

Unlike many InSITE fellows, who actively seek networking events and informational career chats, Andy was almost resistant to the chance encounter that would mark a significant turning point in his career. In order to stave off a job offer from a persistent rival law firm, he agreed to interview with a company in Virginia. It was called AOL. Andy described the unforgettable moment that he arrived for his interview, dripping with sweat in his customary suit, watching the throngs of young people clad in shorts and t-shirts literally running around the office, as if physically propelled by their excitement. Listening to his vivid recollection, it sounded like the same energy that attracts us all to the tech community and groups like InSITE. Needless to say, Andy took the job at AOL, setting up his subsequent transitions to betaworks and USV seamlessly. (In reality, as Andy told us, his career choices were more of the right-place-right-time variety).

On one hand, it was comforting to know that when Andy was sitting in our chairs, he had not plotted out any of these moves; he could only connect the dots in retrospect. He was quick to acknowledge how much timing and luck had to do with it, which was actually rather daunting. After all, we are so used to being methodical about our careers, how do we account for serendipity?

In a way, this maddening theme — our desire to forecast the future but only getting a clear picture in hindsight — is at the heart of being a venture capitalist. A cereal box from Airbnb’s pitch — an investment which USV passed on — still sits in their main conference room as a reminder of a missed connection. Etsy’s recent IPO was a solid victory, but in the nine years leading up to this point, it was anything but a sure thing.

Turning to future trends, we discussed the exciting possibilities technology creates in emerging and frontier markets. In East Asia, for example, mobile technology like WeChat and Instagram have allowed shoppers and merchants to bypass the more traditional websites to execute transactions. In Kenya, the birth of m-Pesa, a mobile phone-based money transfer system, similarly transcended the need for conventional banks. Was this an omen that websites and banks will someday be obsolete, or can they exist side-by-side with mobile movement led by millions of people abroad? We can fashion our best hypotheses, but only time will give us a definitive answer.

Our lasting impression was of USV’s strong sense of identity. As Andy expressed, USV is very upfront about what differentiates it from the other well-known VCs. With a vocal social media presence, the firm conveys and intimate boutique experience, significant personal investment by the partners, guaranteed board involvement, and commitment to the investment through every growth stage. Andy acknowledged that this might not appeal to every entrepreneur, but the approach yields a more efficient way to filter out the best fits for both sides of the investment. As he noted, “venture is about decision-making, and our constraints facilitate decision making.”

We left the breakfast thinking that having a strong sense of self, rather than a defined direction, was the way to satisfy our craving for clairvoyance. While we’re certainly beholden to the twists of fate, both good and bad, the best we can do is work hard to build a strong skillset and identity, and trust that this will attract the right opportunities, whether the next hot company or a fortuitous job interview.

USV and Andy are certainly proof that it works.

Dahni Ma is a JD Candidate at NYU School of Law and an InSITE Fellow. She interns at New York Angels and has prior experience at Lyft and Google.

Joy Chua is a JD/MBA Candidate at Columbia and an InSITE Fellow. She has been a legal intern at BlackRock and Skadden and an associate at Capital Group.

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