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
Randle: Tech offers far more $100B opportunities today than 15 years ago
“The outcomes are much, much, much larger in today's in today's technology landscape than they were 10 years ago, 15 years ago, there's more bites at, you know, potential hundred billion dollar, trillion dollar companies.”
O'Driscoll: Benchmark will hire replacement partners and remain successful
“Benchmark will be fine. So let's start with that. They'll find two other people to fill those slots and they'll be fine because they've been fine for 30 years.”
Lazarte: Sierra's Bret Taylor met Benchmark over dinner rather than pitching
“So I think on Brad's case is like, I think he had dinner with the partners. It was more like a conversation than a pitch.”
Lazarte: Most of my Benchmark deals are sourced via active outbound
“No, so the majority, like the majority of what I do is like outbound. Like the majority of what I do is outbound.”
Lazarte: Benchmark's lack of process and small team are key advantages
“And I actually think that this is a big advantage for benchmarks, like, because we don't have any process, and we have a small team, it's easier for us to, like, change things, right?”
Hommels Secured Early Facebook Shares via Benchmark Partner Matt Kohler
“And at that time I needed to figure out how I get into it, and then I, for two months, called everybody I knew in in In the valley, and I ended up with Matt Kohler, like a little coincidence, because I was at Benchmark as a VC, and he was with Benchmark, and s…”
Vishria: Only sponsoring Benchmark partners see deal vote tallies
“Nobody knows what the votes are except the sponsoring partner.”
Vishria: Benchmark is investing at its highest pace since 2011
“There's a lot of uncertainty, but we've been more active than we've been since 2010 and 2011.”
Vishria: Benchmark has no sector specialists and maintains four to six partners
“I am not a sector specialist and nobody at Benchmark is. And I think the fundamental idea with Benchmark is there's a small group of people, a small group of partners who are all equal. And right now it's five of us, but sometimes it's four, sometimes it's six…”
Vishria: Passes on viable startups if he cannot pitch recruits
“When you look at that, I ask myself that question. And if I answer is like, you know what, I think it's a cool business. It'll probably work, but I just don't understand how I can make that pitch. Then I don't do it. Like, that's my, like, I just, I don't do i…”
Sequoia and Accel are Index's primary consumer Series A competitors
“Clearly, clearly the folks at Sequoia are a big fierce competitor, and the folks at Acceler are fierce and, you know, I would say there are a number of different players, but those come to mind for consumer stuff. Certainly Sequoia comes to mind a lot. Benchma…”
Siroker: How he negotiated 8% Series A dilution with Benchmark in 2013
“My very first Series A, I got, you know, I got benchmarked to agree to, you know, I think it was maybe eight percent or something.”
Siroker: Optimizely tried to acquire Amplitude when it had four employees
“I tried to buy Amplitude when there are four people. In fact, they were about to raise their, I remember we're sitting at, I think at Chipotle and Soma with Spencer. And I, to this day, I'm so impressed with, I just, I was offering him insane amounts of money,…”
Tavel: Peter Fenton is the single best VC at developing founders
“I've learned from Peter because his, EQ around people, what motivates us, what drives us what the, what holds people back, and how important that is in the, you know, the arc of any company that we end up investing in, this watching, helping those founders bec…”
Tavel: Benchmark waived board seats only once in seven years
“There, in my seven years at Benchmark, I think I've seen one example where we broke the model on, on board, and it was for a small crypto related company.”
Tavel: Benchmark's model ensures 100% post-investment alignment with founders
“But more often than not, it creates conflict that's unnecessary, and it's just very different than our model, which is like, okay, now that we've invested, we are 100% on the side of your side of the table, and let's make every round as successful for you as p…”
Tavel: Benchmark partners make only 1-2 new investments annually
“Our way of thinking of things that benchmark is that each of us makes one or two new commitments a year.”
Lacaillade: SCS Financial Is Not Invested in Benchmark but Wants to Be
“Yeah, it's a good question. Probably, probably benchmark.”
Grimshaw: Operating without firm hierarchy makes being yourself the hardest challenge
“In many ways it was you be you, like you be, You totally kind of unfiltered and as authentic as you are, and the best version of you will be the best investor. And I think in many ways, when you get rid of structure in this, there's no like level to be had or,…”
Grimshaw: Benchmark's equal partnership aligns incentives across all portfolio companies
“We're an equal partnership, so it's a whole firm commitment. No person is incentivized to do more, help more one thing versus another. A founder really gets the whole partnership.”
Grimshaw: Waiting for a Perfect Pitch Before Pitching Benchmark Is Silly
“Like some, sometimes there's a, ah, I'll only pitch benchmark when I got the perfect pitch. Like that's silly. That doesn't need to be the case”
Grimshaw: Relying on vertical benchmarks can undermine startup innovation
“There's moments probably where those metrics are the wrong things, right? Like where benchmarking perfectly to the playbook of that vertical, like you're going to break it in some way. It's going to look different in some way.”
Grimshaw: Venture investing should be commitments, not bets
“If you think of investing as betting I think you spend a lot more, you know, a lot more energy on the funnel and winning the first, like you're placing chips on a roulette table. And I just don't, I don't think of it that way. I really think of the work we do …”
Grimshaw: Benchmark backs only about three inception-stage startups per year
“The N of that in a given year, even for that percentage is like three companies, right? And so it's not like we're doing 30, ah, that way and again, you know, so, so the N is small.”
Benchmark won't re-judge founders in future rounds based on early pitches
“We're only early. And so you get sort of a chance of it, but also we're not going to be able to, we're not going to re-judge you in the future based on what you told us now, because whereas other funds might.”
Grimshaw: Venture investing requires finding market dislocations over market timing
“I don't personally think about it as much from sort of a timing lens, so much as the investigation and the thinking of like, what's different, what's new, what's a dislocation, what's emergent.”
Grimshaw: Benchmark will accept adoption risk if market behavioral dominoes are falling
“Force of will can do a lot, but you know, it's got to feel like the, you know, you've got to feel like the dominoes got tilted over, you know, you're looking here, But the domino chain is, is sort of happening conceptually in the market or for behavior, whatev…”
Besvinick: Benchmark remains the standard among Series A venture firms
“Benchmark. They're still the standard in my opinion. As someone who knows what they're good at, doesn't deviate from it, I have a ton of respect for the people that I know personally over there, and I just think they're outstanding investors.”
eBay's original business plan and Benchmark investment focused solely on collectibles
“Jeff Skoll wrote the business plan for eBay with Pierre. And I got a copy of it when I joined the business and they were focused entirely on the collectibles market. Now their argument was collectibles market in in the U S I think was a hundred, you know, it w…”
Weil: Ron Conway and Benchmark succeeded with opposite investing philosophies
“In the same way you can look at like what Ron Conway has done and what Benchmark has done. They've both been massively successful and their investing philosophies could not be more different.”
Eisenberg: Aleph intentionally operates strictly as a single-stage fund
“It informs our investment strategy in general at Olive, which is a lot along the lines of benchmark, which is we like to work with partners. And that means we are a single stage, basically seed and a fund. We're not doing the big, big fund with the multi-stage…”
Gurley: Benchmark Maintained Early-Stage Focus as Peers Expanded to Multi-Stage
“So we have notably stayed focused on early stage investing, whereas most people have moved to multi-stage.”
Fenton: Benchmark Invested $3.25M for 27% of New Relic's Series A
“We put 3.25 million in to buy 27% of the company with a 20% management pool. That's a series of investment. There was no seed. There was no precede.”
Benchmark partners all invested in Michael Eisenberg's Aleph at launch
“My agreement when Benchmark, as Peter Fenton has so famously said, decided to get out of the imperial era of venture capital and focus locally, the partners at Benchmark were super supportive and went out on my own, so to speak, found a partner, Eden Shohat, a…”
Tavel: A great board member functions like a supportive, truth-seeking spouse
“What a great board member is, is similar to when you find the person that you're supposed to marry. If you're always just dating, and then you go on a speed date, and you meet with five people, and then you just decide to get married to one of those people, yo…”
Sarah Tavel: Benchmark has announced funding for only two of her six boards
“I'm on six boards, and I've announced two of them.”
Peter Fenton gave Ben Rubin a Benchmark credit card to explore ideas
“Basically, Peter Fenton was, hire who you need to hire, start hacking around, there is Benchmark credit card, and I trust you, and like, obviously, this sounds a little bit unfair, because it sounds super casual, but we had a plan of This is the space we're go…”
Wilkinson: Tiny would raise VC if a portfolio company needed $100M burn
“So I would say that if we had a business that was obviously in need of a large amount of capital, And we needed somebody at the table who was willing to take a big risk where we knew that in order to grow it into a billion dollar business, we'd need to burn a …”
Puttagunta: Software end-users must become product champions to avoid buyer friction
“Oftentimes if you don't understand that relationship and the user has not become a champion of the product, the buyer then has an enormous decision-making power, whether it's like a procurement process in large enterprises or whether it's a decision-making pro…”
Puttagunta: Assume competitors are smart and have uncovered unique market insights
“And I think the optimal strategy is to assume that everybody that is competing with you has actually had or has found some unique insight as to why the market is addressable in their unique approach. And so to assume that your competitors are all really smart,…”
Gurley: Benchmark Approves New Investments by Majority Partner Vote
“In that way, I thought that was interesting way she had phrased that, and so we simply have a discussion, and if a majority of the partnership wants to move forward, we move forward.”
Gurley: Price insensitivity in late-stage venture investing is not smart
“So this isn't, I don't think price insensitivity and high late stage investing is a smart idea, for example.”
Belsky: Assess hires and founders by exponential progression in successive conversations
“How do you hire people, and how do you find which teams to invest in, and one of the things I always apply is, is this someone whom every conversation is more interesting than the one before it, or is it a replay? You know, most people we actually meet, I don'…”
USV and Benchmark are rare exceptions to VC fund bloat
“Union Square Ventures, Benchmark, or some other exceptions to what I said.”
Reaching profitability requires daily discipline and tight prioritization of key tasks
“And getting to profitability takes an incredible amount of discipline. My partner, Mitch Lasky, he describes it as his daily act of will, where, you know, every day it's making the decision to do three things instead of the 10, and that is a muscle that you ha…”
Benchmark targets startups in small initial markets adjacent to massive ones
“When you are going after a small market that is adjacent to a big market that could eventually eat into a bigger market, that is the scene that I think we look for.”
Winning investments combine great founders with dynamically evolving market opportunities
“The nuance that I'll add, though, is that, you know, markets aren't these static things. They're dynamic. They're constantly evolving. They're being transformed by outside influences like technology disruptions or even secular trends, and so I really end up Fi…”
Crypto investing requires deep specialization and is unsuitable for non-specialized dabblers
“We're still so early in the game in crypto that we don't even know what the ad unit will be, where you will make money in the stack, and so it's a very tricky place to play, and it's definitely not a space for dabblers.”