Doing this job for almost 20 years now has taught me far more about people than about business. So let me first answer what I've learned about business, and in this case I mean the business of investing in startups. I started out as someone who had all the conceptual overhead needed to sound intelligent in our world, Porter's 5 Forces, the Innovators Dilemma, and Crossing the Chasm. I would, in my former firm's parlance, develop a "prepared mind" in a sector so I could see where the logical opportunities should exist. I became an expert on Storage, on Application Software, on SupplyChain. All of that, I came to realize, was useless without the alchemy of an entrepreneur who was playing around with explosive market forces. Yes we can look, and it helps to look with a lens, but the best ideas and companies aren't filling logical white spaces. They are touching nuclear reactor of some force that will yield, and yield quickly, to an entrepreneurial leader.
I also came to realize that at the beginning, no analysis can capture "what can go right" without sounding like you are clinically insane. Having seen the Series A pitch for Facebook, Uber, Snap, Twitter, VMware...$1B in revenue for any of those companies would have been nearly impossible to imagine. Yet in each of those cases, I vividly remember the meetings, the day, the settings...and this feeling that an exceptional entrepreneur had touched on something nobody else had understood at their level of depth and insight. Each in its own way felt limitless. I'll never forget meeting Evan Spiegel in 2012 at Sightglass in SF and leaving thinking, I know with all of my being that this person, this product, will give humanity back the playful joy of self-expression, which had been stolen away by then current social networks. Sometimes it's obvious.
Some other off the top of my head business lessons.
I'd be a fraction of myself without my partners.
Venture is a shoe-leather business, and you can only be great if you are out looking engaging and hustling.
Never turn down a company on valuation. It's a mental trap and allows for weak thinking.
Board's are responsible for ensuring the integrity of the Strategy, Structure, and Staff. If the strategy is clear, the structure of the org should be aligned to that strategy, and the staff should be aligned to that org model.
Entrepreneurial culture and professional culture will be in constant tension and conflict, and the art of the CEO is to balance both, and most CEOs don't.
Always, always pull the future forward on the organization you want.
The only time to lose fierce optimism is when you're out of money, in all other scenarios greatness is on the horizon.
What I've learned about people...the biggest lesson is that, simply put, the magic of human connection is the reason to do this job forever. The joy of being a partner, in the fullest sense, to a leader on the heroic journey of a startup inspires everything I want to contribute to this world. Regarding specifics, I've learned that the one variable that defines a great relationship above all else is trust. I believe that comes from clarity of purpose, and shared-purpose. If there's a "hidden agenda" it's immediately obvious to the subconscious mind, and it destroys trust. In a high-trust relationship, I've found CEOs adapt and evolve at a higher positive rate. If there is one distinguishing trait in the best people I work with, they are learn-it-alls, not know-it-alls. Another specific, I've also learned, as Peter Drucker said, where there are great peaks there are great valleys, and our job as a partner is to amplify the strengths and to recruit complements for the valleys. A final big lesson for me has been that motivation isn't a fixed constant. Everyone will go though periods, which can last for months at a time when they have lost faith or confidence in the potential of the business, and in those situations it's essential as a partner to be a foundation of support and belief. It never ceases to amaze me how motivation can and almost always does return in full.