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 58 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 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: Building AI copilots is an incumbent strategy, not a startup opportunity
“I think Copilot 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 Copilot.”
Grimshaw: AI software will sell work and outcome SLAs rather than seats
“I think the way to encapsulate would be this idea of selling the work, not the software, and that we'll move from a paradigm where you might think of it as moving from what we see right now as a copilot and moving to what I think about as a control center, whe…”
Grimshaw: AI copilots are an incumbent strategy, not a startup opportunity
“I think Copilot 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 Copilot.”
Grimshaw: Tens of millions of software engineers will become AI engineers
“Tens of millions of engineers would become AI engineers versus like hundreds of thousands of ML scientists. That would beget the need for an application sort of framework for AI and tooling for that computing environment.”
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: Slower, high-quality growth beats rapid growth in the wrong ways
“And often cases, I'd rather take less growth in the right ways than more growth in the wrong ways.”
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: Applying Stripe's Playbook to Segment Was Detrimental
“At Segment, there was a lot of pressure, and we did also in a positive way, learn lots of lessons from Stripe, but we were very different to Stripe, even though we would develop a sole product. And too much of the Stripe lesson was Detrimental actually to bein…”
Grimshaw: AI will yield new software architectures and business models
“And I think if AI is to be the force that it can be, I think you will get a new architecture and new business model emerging from it versus what we only see right now, which is kind of a sustaining architecture, which is just that of a co-pilot.”
Grimshaw: AI software will sell finished work outcomes rather than seat licenses
“The way to encapsulate would be this idea of selling the work, not the software. And that we'll move from a paradigm where you might think of it as moving from what we see right now as a copilot and moving to what I think about as a control center, where we'll…”
Grimshaw: Unlike AI, mobile was merely a UX shift with identical architecture
“And in that way, I think it will be very different to mobile, which was mostly another UX but the same architecture, the same business models.”
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.”
Grimshaw: LLMs will centralize media trust in established subscription brands
“I think as a function of LLMs, trust centralizes, and there's huge economies of scale to subscription businesses and advantages, and so it's a silly, silly fun idea, but if we're in media.”
Grimshaw: AI applications will capture massive value and pull through infrastructure
“I think in the arc of time if it is a shift like the internet was in many ways the applications, Which might not look like an applications, right, in the way that we think of them, but might look more like, you know, this control center idea will have profound…”
Grimshaw: Early AI application sign-up spikes resemble 'high fructose corn syrup'
“Like, I think there can be a lot of high fructose corn syrup of adoption. Like, there's an amazing magical moment in a wow, right? When you go experience ChatGPT for the first time, or some of the imagery models for the first time. The rate of adoption of, lik…”
Grimshaw: VCs should prioritize founder respect over founder friendliness
“One is founder friendly. Like, I don't think you should be founder friendly. Not that you shouldn't be friendly, obviously. But I think that the higher purpose is like founder respect and friendly can imply like cheerleading, yes, person, et cetera. And I thin…”
Grimshaw: Venture investments are only complete upon LP distribution
“It's only a great investment in some sense when the, you know, shares are distributed to a broader shareholder base in terms of distribution or the like. I think people forget about, you know, in, in, in the push for forever funds and forever, you know, people…”
Grimshaw: A founder's rapid rate of learning beats knowing jargon
“The fact that they're willing to say, I don't know, and quickly learn, and grok it is really, I think, like the most important thing, that rate of learning, and in fact, I'd say most of us saw it as a strength.”
Grimshaw: The best entrepreneurs continuously make mistakes, but always new ones
“The very best entrepreneurs are always making mistakes. The really great ones are just making new mistakes each time, and I think there's a lot of truth to that, and so that slope and pace is is the most important.”
Grimshaw: VCs who enforce generic checklists distract and burden founders
“I've been in some board meetings where investors don't really get the product, don't really get the strategy that has to be pursued. They're trying to apply like procedures and checklists, you know, versus strategies specific to the instance. It becomes a repo…”
Grimshaw: Product and customer come before data, which should only validate
“We should always start from like product and customer, not data. And data should be in some sense validation, not learning.”
Grimshaw: Key VC gut check is whether you can recruit for startups
“And so the gut check, the real question I think about a lot which gets to that sort of holistic nature of it is how do I imagine recruiting for this?”
Grimshaw: Investing on normative worldviews without market dislocations is dangerous
“I think it's dangerous in many ways, and this is sort of To think, oh, the world should work this way. And now I'm looking for people who also think the world should work this way, but don't really have the strategy for cracking that open, or there's no disloc…”
Grimshaw: Benchmark is first institutional capital in 50-60% of deals
“I think it's something like 50 to 60% of all the investments we make, we're the first partner. I might want to use the word real, right? But like first sort of institutional investor, so to speak.”
Grimshaw: Roughly one-third of Benchmark investments occur at inception
“I think it's something like 30 odd percent. We're like literally the first investment. We don't use the term incubation. I'm sure there's a bunch of things we've done. People would call incubations. We don't use that term, but like, I think probably about a th…”
Grimshaw: Specialist VCs follow fixed playbooks while generalists seek new adaptations
“I think that the specialist can become a bit more physicist. Like here's the playbook, here's the rules. And I think of myself as a biologist in that you're constantly looking for like new adaptations, new variants”
Grimshaw: Rapid market shifts can be dangerous for early-stage startups
“First of all, you don't need, as a startup, too much market or too much market changing hands really fast can be dangerous. As a startup, you could only take on so much.”
Grimshaw: LangChain Currently Has More Capital Than It Needs
“At LangChain, obviously, like we have more capital than we need right now.”
Grimshaw: Made only one investment between late 2020 and late 2022
“Well, I think I made one investment between like end of summer 20 20 And end of twenty-twenty-two.”
Grimshaw: User Focus Matters More in VC Than Metrics Frameworks
“And the most important thing is always like, who's the user and why do they care? If you ground yourself in that always, instead of sometimes a sort of like whirlwind of other, you know, framings from investing, it'll probably serve you pretty well.”
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: VC diligence should feel like planning an adventure, not an examination
“In diligence, I think it should not feel like an examination. It should feel more like looking ahead at the future together and stepping into shoes together, which is the sort of work you'll be constantly doing with a founder. Sometimes I'd say it should feel …”
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”
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: Innate founder capability cannot be coached
“I don't think it was coaching, but per se, but you can't coach height. Gotta have it.”
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: 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…”
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: 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.”
Grimshaw regrets missing early investments in Figma, Plaid, and Scale AI
“Dylan at Figma, Zach at Plaid and Alex at Scale, and I have enormous respect for all three of them got to know all three of them really early, and I just, I struggled with it.”
Late-stage startups spend roughly 3x more per seat on Figma than Slack
“And so how that actually plays out is probably a third of the company from my surveying has paid seats inside of Figma, and they pay about three times as much as they would for something like Slack.”
Grimshaw: Banks lack incentive to offer open account authentication APIs
“Now they have no incentive to do that because if they let you do that, it's easier to move money out, and they don't want you to move money out because they make money on you storing money there. That's how a bank works. You get lock in to other products, but …”
Grimshaw: Missed investing in Plaid by over-intellectualizing bank incentives
“And I, you know, I probably got, I got too intellectual about it.”
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: Most software today is just a database with a form
“What's most software? It's a database with a form on top of it for users to manage information, put information, get information out.”
Grimshaw: AI Startups Win by Building Business Models Orthogonal to Incumbents
“There's so much wrapped up in, in, in the arc fundamental business As in company architectures and all the systems internally and all their operatings around that, that it's really hard to just change, right? That's why it ends up being asymmetric competition.…”