The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 230 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 5 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Grimshaw: Almost all Benchmark capital goes into initial investment checks
“If you would hit the spreadsheet of our investments almost all the capital we invest is the very first very first time we partner.”
Grimshaw: Benchmark uses no deal sheets, memos, or data room presentations
“We have no deal flow list, no sheet, there's no memos there's no data room presentations.”
Grimshaw: Building AI co-pilots is an incumbent strategy
“Most of what we've seen has been co-pilot stuff, and I think co-pilot is an incumbent's strategy. Incumbents own distribution, they own data, they own the UX, and they own a business model that all aligns to a co-pilot.”
Grimshaw: AI startups building co-pilots won't create massive value
“And so I think the opportunity offered up to a startup being a co-pilot for something else, like probably won't be that amazing. And there might be pockets of it where it can really work, but the opportunity to disrupt is to be orthogonal to the incumbents.”
Emil Michael would have told Travis Kalanick to reject Benchmark's coercion
“Had I talked to him that day, I would have said, Travis, walk out of the room. If you want to rip up the papers in front of them and we'll get, you know, get a lawyer and whatever. This is ridiculous. You know, there's, this is unfair. This is coercive. And we…”
Gurley: Trying to call the market top is a VC's biggest mistake
“I think you have to invest as a venture capitalist over the cycle, like over a 20 or thirty-year period, and the biggest mistake you could possibly make is trying to call the top.”
Eisenberg: Equal partnership structures foster safer, more collaborative VC firms
“One of these about the equal partnership is you're not worried about your economics or even negotiating them subconsciously. And that makes the partnership more of a safe space and more of a collaborative space. And I think it's one of the really powerful thin…”
Gurley: Benchmark passed on Jack Dorsey's Series A pitch for Square
“Another one that's very similar, and it wasn't me, it was a different partner, but I don't think I was helpful, was Jack That brought Square to us on the A.”
Eisenberg: More startups die of indigestion than starvation
“You know, when I was at Benchmark, they used to say that more companies die of indigestion than die of starvation. I actually think that's still true.”
Gurley: Failing to pursue Google at 25 employees was my biggest mistake
“My biggest mistake was clear because I brought Larry and Sergey in to present when there were 25 employees, and we didn't lay chase.”
Fenton: Benchmark Won't Exist in 50 to 75 Years
“Benchmark won't be around in 50 to 75 years, nor will most of the companies we work with”
Tavel: Benchmark does not delegate operational work to platform teams
“At Benchmark, our model is that we don't delegate any part of our job. We've tried not to scale our business and just be focused on scaling the founders with whom we work. And so that means that there isn't a talent partner that is doing recruiting calls for m…”
Gurley: Benchmark will not invest in a startup without a board seat
“We won't invest without a board seat. It's a tenant that we have that a lot of other firms don't.”
Gurley: Entry price is irrelevant for startups with 100x return potential
“I think the real caveat to it is if this company we're talking about has optionality to be a hundred X or be a fund maker kind of company, then certainly entry price does not matter.”
Gurley: Benchmark should have accepted Google's $100M valuation offer
“So I had a meeting or my firm benchmark had a meeting with Larry and Sergey where they said, will you invest at a hundred pre? And we should have said, yes, I would tell myself that.”
Gurley: Venture capital inherently favors younger investors
“I think venture capital bends towards youth. There's a hustle element. There's a curiosity element. There's a lot of these really big outcomes are started by people that are 19 to 21.”
Gurley: Capture late-cycle market upside rather than playing defensive
“The best way to protect against the downside is to enjoy every last bit of the upside. I've got no incentive to change my operating principles or the way I go about doing the job just because I think one day the cycle might end. And so I'm going to be operatin…”
Gurley: Venture firms must dwell on missed winners, not bad investments
“Because of the asymmetry situation that I talked about, we do dwell on the decision errors that led us to miss big winners. We don't dwell on the decision errors that led us to make a bad investment.”
Gurley: A VC's long-term reputation dictates their future deal flow
“You know, if you're going to be a successful venture capitalist, For two or three decades, you're going to have a reputation, and your reputation is going to be a part of what allows you to win or not win investment opportunities in the future, and so you'd be…”
Belsky: Venture capital is inherently a non-scalable business
“I think one thing I also learned from the team is that it's not a scalable business. I've always admired how the team over the years has defied many of the spotlights of seduction, whether it is building an online database or a website for a Entrepreneurs to u…”
2018 crypto startups secured nine-figure valuations based solely on white papers
“And then what's different though, from ad tech is that, and it makes it even harder is that you're often investing in a white paper or a deck. There's no code or traction that you get to invest behind. The company often has, you know, over a hundred million do…”
Easy venture capital diffuses focus and makes pivoting to profitability dangerous
“When companies are able to raise a lot of capital easily, they naturally take on more of a growth orientation. Yeah, I kind of think of it as you can turn the wheel towards growth, and you, or you can turn the wheel towards profitability, and all these compani…”
Lasky avoids VR application startups due to long market trough
“So I've stayed away from investing in, in the application space, primarily because the development teams are really expensive and you'd have to kind of keep them funded through what could be a fairly long trough, maybe three, you know, three to five years.”
Fenton: The most successful startups launch in narrow or invisible markets
“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”
Fenton: Ownership stake drives early-stage VC returns more than valuation
“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 …”
Rachleff: Equal VC partners must step down if not giving 110%
“The only way to manage an always equal partnership is if you're not willing to go a 110%, you have to opt out.”
Lynn: Optimal venture capital fund size is $300M to $400M
“No, I think it's a 300 to four hundred million dollar fund, and the reason is, A, you know, when I look at the people I really respect and admire, the Sequoias and the Benchmarks, I mean, that's what they've proven out, and I've added emergence to that mix in …”
Benchmark is the best venture firm at managing generational transitions
“And so what it means is, and I think that, you know, right now there's probably, you know, no one that does this better than benchmark in this space where they're continually bringing in young people and growing them from, you know, from, you know, relatively …”
Top VC firms will be forced to adapt to new funding models
“Sequoia, Benchmark, Andreessen Horowitz, they're not going away anytime soon. This isn't like, we're out to beat them and kill them. Not in the same way Airbnb is not going to delete hotels overnight. It's going to change how hotels work. I think that's a bett…”
O'Driscoll: Benchmark, Foundation, and Eclipse each hold 8–9% of Cerebras
“Ah, you just, because you see, Harry, you just listen to Twitter, but if you go and you actually look up the S-one, they have eight or nine percent ownership, right? Because I do these things, because every VC reads an S-one the same way, you read the front pa…”
Green: Sequoia, Benchmark, and Index succeed because they excel at recruiting
“I truly think that's why Sequoia and Benchmark are great and Index are great because they help founders and entrepreneurs recruit amazing talent and people want to work for those funds portfolio companies.”
Junestrand: Benchmark offered Legora the lowest seed round valuation
“The round, there was another firm that wanted to preempt us for the A round, and they gave a very competitive term sheet for this series, for the series seed. Much higher price than Benchmark. Benchmark was, I think, the lowest price out of any seed fund.”
Randle: Benchmark targets over 5x net returns for LPs
“This is one of the reasons why I'm extremely excited about benchmarks, competitive position in today's market, because we can go to LPs. We can say, Hey, we're shooting for higher than five X net. We have the historical track record to back it up. And we have …”
Randle: Benchmark constrains fund sizes to survive downturns and retain LPs
“We're like, let's constrain our fund sizes. Let's be careful about what we do. So we don't get too over our skis, where we can easily weather a crash, and LPs aren't going to go fleeing once there's a crash, because we've been very careful with our capital, an…”
Randle: Initial investment failure relieves pressure for new VC partners
“There's going to be nothing better for you than if your first investment sucks. Because once you do one and it fails and you realize it's not the end of the world and like life goes on and like LP still love us and like you're not fired, then you feel really c…”
Randle: VC needs a new taxonomy for evaluating AI companies
“AI app companies are meaningfully different than SAS companies in like a dozen different ways. Yet we keep trying to shove all the metrics From these AI app companies into the frameworks that we created for SAS.”
Benchmark offers backdated carry pools to newly joined General Partners
“I also know Benchmark are extremely generous in terms of like backdated carry and being brought into this carry pool for this fund with fireworks and with McCore and with Legora and with Manus and with many others.”
Junestrand: Legora would not have connected with Benchmark without YC
“And so by being in YC, we raised money from Benchmark, who we would have not been introduced to if we weren't in YC.”
Junestrand: 99% of Benchmark portfolio companies reach Series B
“I think there's some stats that, like, 99% of benchmark companies end up raising a Series B. That's the only stat you need to hear.”
Stebbings: Benchmark has executed the best AI strategy of any VC firm
“I don't think any firm has played AI in the last 18 months as well as Benchmark have done, despite the team churn that they've had.”
O'Driscoll: Historically, a16z captured 10% of top VC outcomes, Benchmark 6%
“In a less competitive time, the best firm in terms of percentage of total outcomes was Andreessen. They got 10% of the good outcomes. Benchmark got six, and everyone else bunches in the two, three, four, five percent rate, right? In other words, when there was…”
O'Driscoll: Portfolio construction matters because consecutive bad funds hurt brand-name VCs
“I think it always matters. You know, your people actually lose money as distinct from thinking about losing money, and particularly when they lose money, two funds in a row, even a brand name firm can hit a bump, right?”
Lazarte: Benchmark rounds are defined by founder quality, not check size
“And a benchmark round is when there's a founder that is very capable going after a very big market, and as long as you have that, like, that's a benchmark founder, it doesn't matter if you're raising, like, five million or if you're raising, like, two hundred …”
Lazarte: My first check at Benchmark was $55M into HeyGen
“My first check at benchmark was a fifty-five million dollar check into HeyGen.”
Lazarte: Benchmark bans partners from voting 5 on investment opportunities
“So like, we vote from one to 10, and like, you can't vote five.”
Lazarte: I have done four Benchmark deals, co-founding one of them
“Yeah, so I've done, so I mean, I've done four companies since I started at Benchmark. Three have been this way. And then the fourth one, I actually, I'm a co-founder. So I started the company with someone that, that I knew for a long time.”