1/ Bill Gurley became a Benchmark partner in 1999. That same year Craig McCaw asked me to spend time in their Sand Hill Road office so we could more easily make early stage investments together. Having the opportunity observe Benchmark's DNA up close was a fantastic way to learn.
2/ Benchmark was founded in 1995 by Bob Kagle, Bruce Dunlevie, Andy Rachleff and Kevin Harvey. By maintaining my friendships with Benchmark partners since 1999 I've been able to observe the consistency of their investing style. For example, venturedesktop.substack.com/p/the-merits-o… 
3/ "This alignment shines through clearly across the partnership — whether it is Sarah Tavel talking about her investment in Chainalysis, Chetan Puttagunta explaining the logic behind his investment in Sketch, or Eric Vishria responding to a "request for startup" in Open Source:"
4/ There's more than one way to be a successful investor, even though some people believe their way is the only way. Benchmark's bottoms up "Our job is not to see the future, it’s to see the present very clearly" resonated with me. It is also the most enjoyable investing style.
5/ Someone challenged me to describe Benchmark's DNA in a dozen tweets. My attempt to do that follows. The key is that everything (e.g., culture, structure) follows from the passions of the partners. There are other ways to be successful, but this particular DNA makes them happy.
#1 “We love the day-to-day work with the entrepreneurs, which prevents us from scaling. We don’t have an ability to offload any part of our relationship in the way we practice it, to anyone other than ourselves. That’s a strategy." Peter Fenton
#2 "The Series A market is the most durable and consistent part of the post-angel fundraising cycle because it represents the point at which an idea or a product turns into a true company and starts to incur more costs." Matt Cohler
#3 "Series A financings are usually mostly about people costs, the costs of salary and benefits and office space required to build a small and growing team, and those sorts of costs per unit don't change by orders of magnitude over time in way other technology costs can." Cohler
#4 “My partner Bruce Dunlevie uses the phrase, ‘What could go right?’ If you have remarkably asymmetric returns, you have to ask yourself, “How high could up be?” This is the defining attitude needed in VC investing. When they work .... Wow.” Bill Gurley
#5 “The only way as an investor and entrepreneur to make outsized returns is by being right and non-consensus.” “You can only lose one times your money. You make bets and you have to be willing to be wrong a lot. You can be wrong 70% of the time and be brilliant.” Andy Rachleff
#6 “Good judgment comes from experience, which comes from bad judgment.” “When I first arrived at Benchmark, it was like, ‘Nothing can go wrong.’ There was an IPO every week. And then, wham! The door came down hard.” Bill Gurley
#7 “Ultimately when evaluating an early stage company, I say it’s a combination of art and science. The art is understanding how products work, the science is knowing how to measure it. The earlier the company, the more it is about art...." Sarah Tavel
#8 “Virtuous loops are the flywheels that covert your users’ engagement into fuel to power you forward. The strongest virtuous loop is a network effect. Virtuous loops are really hard to create. Most products don’t have them.” Sarah Tavel
#9 "Before an investment we focus on the quality of the person we’re going to work with. There are three attributes that define greatness in our world: (1) a profound, deep, innate motivation; (2) the ability to learn and (3) the ability to attract great people.” Peter Fenton
#10 "Benchmark, is a majority decision-making process, where the majority of partners need to approve a deal in order for the deal to get done. But it’s still very important for every one of the partners to meet and interact with the entrepreneur." Matt Cohler
#11 “When a great team meets a lousy market, market wins. When a lousy team meets a great market, market wins. When a great team meets a great market, something special happens.” Andy Rachleff
#12 “Be a learn-it-all, not a know-it-all.” ‘We get it wrong a lot, but what’s interesting is when you get it right.” Peter Fenton
A dozen tweets isn't enough to say everything. But this gives you a sense of what I have learned.
There are many other ways to be successful.
A dozen tweets isn't enough to say everything. But this gives you a sense of what I have learned.
There are many other ways to be successful.
