The Ledger, every show

“If we start, all we're doing, we're investing more money in late stages. We're lowering our returns. That's all we're doing because our commitment is fixed. It's not like we're going to be more committed. So we're, you could say we're getting more cash on cash…”

“I personally think that oversupply of capital is historically a good thing for innovation insofar as it creates higher degrees of entropy.”

“I've never seen ever seen a venture investment from the early stage standpoint become bad because of valuations in the flip side. I've never seen one become great because of valuations going in.”

“Product market fit. Which, I mean, if I hear that again, that's where, big data, whatever big data went to, or Synergy I mean, it's such a tautology, you know, it's like, yeah, ok, people want what you've built a product that people want to buy, it's so insigh…”

“Benchmark probably isn't going to be around in 30 years.”

“So last time I did an all hands meeting at Docker was three years ago, and there were 60 employees that, that we'd spun out of the prior company, and the valuation was zero. So we'd gone from over a 1,000,000,004, 1,000,005 to zero, and I was working with some…”

“Our customer isn't, it's not the founder. We say it is, but it's really the purpose of the founder, and it turns out that purpose, if that's the customer, One of us may be deviating from that, and we can keep each other accountable, and that happens internally…”

“We have faith that every year, some number above zero companies will be founded that are going to be worth more than ten billion dollars, and then about every two or three years, a company's going to be found out it's going to be worth more than a hundred bill…”

“As an LP. And that's, well, that's crazy. And this is-... But for this, for the super majority of my investment in benchmark, I'm paying limited partner rates and management fees.”

“One benchmark, no pun intended, I guess, one measure of quality for the firm will be how good our failures are. Webvan was a really good failure.”

“It turns out that a bad idea well executed is a problem because then you give it more money. Or a good idea, poorly executed, well, that hurts because you think, oh, I mean, we can think of companies like Friendster and think, oh, but the bad idea of poorly ex…”

“There have been examples and we're, we don't, there's some awkwardness to talking about it publicly. One of the ones is probably a good example is Tinder. And, you know, Barry Diller said, what do you want? And it's like, well, we want equity in Tinder.”

“I think that somewhere between AI, crypto, and Not AR VR, sorry for the future AR VR. But I think those areas don't have the incumbency of some of the traditional, you know, network effect giant trillion dollar market cap companies.”

“Now that doesn't mean we're going to have eight partners And a growth fund. And then there's some hard lines where you just say, but this is, you know, getting closer to people who are embody our values, but at a different stage in their career, that's okay wi…”

“The founding two or three employees set the culture. And it doesn't change unless there's some catastrophic event where it has to get reborn, but good luck with Elon at Twitter. You know, that culture was set in motion, and its root system goes so deep.”

“One of the bigger risks that's going on in 2021 is there's a lot of invested capital is going in to market preconditions that either don't exist or are still too early to support the economic development of the businesses.”

“If you zoom out, Harry, big picture, if the company works, if it really works, it doesn't matter.”

“If you think your role is to provide the answers, then I think you probably shouldn't be in the boardroom.”

“Benchmark won't be around in 50 to 75 years, nor will most of the companies we work with”

“One of the major oxygen supplies For consumers, especially, is free and open distribution, and I think we could say pretty emphatically that that has evaporated in the last five years”

“The other variable on, you know, this topic specifically that you'll hear people focused on is ownership stake, and I think ultimately that is a bigger determinant of returns than anything related to the valuation going in, and I say it specifically for early …”

“In many ways, by definition, the startup companies that do the best invest and get going in very narrow, almost ill-defined, if not completely invisible markets”

“The best founders make me feel like Number one, I can never control them, and I never want to control them. Number two, that given an opportunity to do the insane, reckless, non-conservative versus the rational, logical, they'll prefer the insane and the reckl…”

“Because if you're in that meeting, and the entrepreneur makes you feel safe and calm, and, ah, you know, kind of, ah, very much in the linear mindset, ah, they're not likely to, you know, profoundly change the world.”

“We had to actually follow, in many ways, follow the instincts of the best people of their generation, because they're chasing the things that have the highest rate of change, that are at the intersection of a collision of different sectors and segments”

“Doing open core on a developer tool is not going to get you very far.”

“If you try and monetize and constrain adoption, you're just gonna open the door for another company to come in and compete with you”

“The issue, the single biggest issue facing open source business models is not I don't think hosted versus packaged like Red Hat. It's how do you deal with Amazon?”

“And I think it's a near certainty Amazon's gonna do a hundred billion in revenue in AWS.”

“You have a company that's gonna, ah, it's on its path to be, and it is, about a 90% market share player.”

“And machine learning is the game of kings.”

“We have a burn rate bubble, meaning companies have lost, they've numbed themselves to the fact that you have to eventually replace the capital that you're burning with operating income”

“This is not like, 99 to 2001, where it went like that. I think it's much more of a long tail”

“The overwhelming positives of a few of the companies in this unicorn ecosystem will overwhelm the losses”

“Unless there's something proprietary in the open source, which by definition it's sort of already out there and open I think it's very difficult for a license to protect you from Amazon coming up with good enough in a competing service.”

“In the case of everyone who's left this firm, and I've never seen this in the history of investing, you study all these firms, every single partner fired themselves”

“They're like, 25, thirty million. I could get it wrong. I'd probably piss one of them off if listen to this.”

“And the last two or three investments I've made were an example of the following, which is that there's, there was an angel in the ecosystem who saw a deal going down and they said, you know, you probably should talk to benchmark. And when they did, we committ…”

“One of the things I found is when there's secondary selling, it does tend to clarify people's interest in price. It's one thing if you're just selling this, you know, equity on the cap table, but when you're selling your own shares, you start to get really foc…”

“And a board represents a governance structure. And so there are many people who, like myself, are highly anti-authoritarian. If we see authority, we immediately don't trust it. And so that's one of the challenges, that you create a structure that has the super…”

“I think so much of the art of early stage venture is to ask the question of, can you unlock consumption? Can you tap into a latent potential energy of demand that can be made kinetic through a product experience that's radically easier to engage with and more …”

“I think those are positive ways of pressing what are arguably are two very deficient traits for a operating CEO focus and, you know, collegiality can be very defining as a great CEO set of character traits.”

“There's no substitute for being great in the venture business than practicing it, and if I viewed this as a 20 to 30 year career, the sooner I got started, the better”

“In the case of Zenly, we had a point of view that, you know, we now have ubiquity of smartphones, and there's a set of enabling features inside of those phones that could really change how we interact with people in the world. And in the case of Zenly, it's th…”

“A bulk of what we try and do at the early or Stages of a company is to not give product strategy, because I think that's something that's really best done by the product authors, but to ensure that the questions are being asked”

“When we were in the business model of dot cloud, that wasn't happening. We were subscale. Amazon was competitive in a way that I think it was clear to some of us that the business was no longer viable.”

“We would have never imagined that in less than a year, you know, Docker would achieve ubiquity, and now it's a, you know, household name for developers”

“I think that the notion that you could buy 25% of a early stage company that has some demonstrable momentum is, is gone.”