I can still remember my very first day at Goldman Sachs in mid ’91. An eager 22 year-old fresh out of Stanford, I had spent far more time patrolling the baseline of the Stanford tennis courts than I had in a suit and tie. I thought competing in college and low level pro tennis had prepared me for just about anything, but I was sadly mistaken. My two year stint at Goldman was brutal – lots of all-nighters, endless spreadsheets and pitch books. But, it was a seminal experience – I was introduced to Wall Street, and it was love at first sight. I started managing my own money (I had none – my first stock purchase was a 10 share odd lot), making mistakes and learning.
Fast forward to today. For the past 15 years I’ve had the good fortune of pursuing another passion – technology – while also getting to continue to invest, combining these two loves as a venture capitalist.
There are so many peculiarities about Wall Street (who knows what short interest is, why stocks often trade down on Mondays or why small cap stocks tend to stay small cap forever?). I don’t pretend to be an expert, but in addition to my time at Goldman Sachs, I’ve worked for a public money management firm and also invested in more than a handful of companies who’ve gone public. So, I’ve seen a fair bit.
Similarly, technology venture capital in the Silicon Valley is highly quirky. Technology areas get hot and then sometimes go cold (who remembers nanotech?), financing trends, like clothing, go in and out of style (who remembers Octane Capital? Hot late stage money went out of style but now new players have emerged. Is DST the new Octane?)
When you combine Silicon Valley’s quirks with Wall Street’s idiosyncrasies, surprises ensue, conventional wisdom breaks down and opportunities abound. Welcome to Where Sand Hill Road Meets Wall Street!