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Why the early-stage focus?
The depth of the relationship that forms between a founder and lead investor when a company is in its formative stages is extremely unique and fulfilling to me. Partnering at the earliest stages grants me the opportunity to develop this bond with each founding team I work with. As it compounds with time, a high degree of trust and intellectual honesty develops. I believe this explains why the longest-tenured board member is often a founder’s first call during hard times. Being in this position absolutely increases the meaning of the work for me. It’s also the case that many tough questions a company faces must be answered well before product-market fit. What would be the fun in missing out on this leg of the journey?
You’ve zeroed in on enterprise cloud companies. Why?
While most of my peers were fixated on the meteoric rise of platforms like Facebook and Twitter, I developed a fascination with enterprise technology while working at Cisco. At the time, it’s impact on society felt underappreciated, and I wanted to better understand why. So much of our daily lives revolve around products and services delivered by businesses. Connecting the dots, the ability to build products that create leverage for these businesses is a profound opportunity to impact the way we live and work, which I am drawn to as both an investor and person. As software continues to devour the world, I am particularly excited by products that enable the engineers, data scientists, designers and product managers who build and scale these products and services.
Is there an emerging technology that most excites you?
Without question, deep learning and its limitless applications within large industries such as logistics, finance, healthcare and agriculture. I believe we are just scratching the surface of its ability to drive meaningful business impact, even as the field begins to question whether we are near the edge of its performance. There is something energizing about helping technology find its way outside of Silicon Valley to help fuel broad economic growth, and I think deep learning is the most promising technology in this regard that I have encountered in my career.
In school, you studied business, not engineering. How has this affected you as an investor?
While I initially felt a little insecure as an early-stage investor without an engineering background, I have come to believe it is more an asset than a liability. Having to grasp new technical concepts for the first time forces me to think from first principles and construct my own mental models. I have found this often forces me to think practically at the right times. The elegance of a new product is a beautiful thing, but it can mask a founder’s failure to answer existential questions: What problem does it really solve? Is it the best solution? Can it be easily copied? Answering those questions early on is key to the success of any startup, and I believe starting from first principles is the right way to go about this.
What do you look for in founders?
A handful of words come to mind: raw intellect, competitive spirit, rationality, curiosity, empathy and charisma. I believe these are some of the key attributes that dictate a founder’s ability to exercise sound judgement, persevere through difficult times, and perhaps most important, command access to talent and resources they don’t deserve at the time.
If you weren’t a venture investor, what would you be doing?
Definitely something in the music industry. For a brief period, I seriously considered playing guitar full-time with a band I was a part of. While I have few regrets about the career choices I’ve made, I really miss it as a creative outlet. During my undergraduate studies, I combined my interests in music and business and worked for a talent management agency. With hindsight, trying to spot promising artists at the right time was great training for venture capital!