Miles Grimshaw
Partner, Thrive Capital. On 2 shows, 2 appearances, plus 2 compilation re-airs not counted. The Shows tab opens the full record on each.
investor@milesgrimshaw ↗LinkedIn ↗thrivecap.com ↗
Miles Grimshaw is an early-stage tech investor known for backing software, developer infrastructure, and AI companies including Airtable, Benchling, Cursor, and GitHub. After starting his venture career at Thrive Capital, he served as a General Partner at Benchmark before rejoining Thrive Capital in 2024.
2shows
2appearances
60statements
7resolved
3supported
0contradicted
43%fully supported
37said about them ↓ Everything Miles Grimshaw said on any show that made the record, most notable first. Each card names its show and opens the statement there.
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: Avoiding growth funds prevents pricing conflicts with founders
“Our job, we're really focused on how do we scale the company, those companies, right? And how, as part of that, having a relationship that doesn't get sort of adulted by this question of the us making another commitment decision. It's like we're in and we're n…”
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.”
The other half of the tape: Miles Grimshaw's own voice is left out of every number here. Other people bring the name up 36 times in 14 episodes across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Harry Stebbings 18Miles Clements 8Jack Altman 4David Rosenthal 2Ben Gilbert 2Vince Hankes 1Everett Randle 1
Statements about Miles Grimshaw, by other people (1)
Top VCs on a Cap Table Primarily Serve as Hiring Signals
“So, to start, I will say that I think it is very true that one of the most important things that great investors do for you is Is that they make other people want to join your company. And so for better or for worse, if you have miles from thrive or say benchm…”
Every mention by year
tap a year for its mentions
20VC 32
Acquired 4
2026 8 mentions in 1 episode
2025 4 mentions in 3 episodes 1 per episode
- Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
- Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
- Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
- every mention in 2025, scene by scene →
2024 3 mentions in 2 episodes 2 per episode
2023 8 mentions in 5 episodes 2 per episode
- Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings
- Guillermo Rauch: Why Great Companies are Defined by How Many Things They Say No To | E1069 · 20VC with Harry Stebbings
- Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
- 20VC: The Biggest AI Leaders on What Matters More; Model Size or Data Size & Where Does The Value in AI Accrue; to Startups or to Incumbents
- Vince Hankes: Why We Put $300M into OpenAI; Sam Altman's Pitch; Lessons from Josh Kushner | E1009 · 20VC with Harry Stebbings
- every mention in 2023, scene by scene →
2022 4 mentions in 1 episode
2018 2 mentions in 1 episode
One line per show, most statements first. The link opens Miles's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| 20VCLEDGER | Partner, Thrive Capital | 1 +2 | 58 | 43% 3/7 | full record on 20VC → |
| ACQUIREDLEDGER | Partner, Thrive Capital | 1 | 2 | — | full record on Acquired → |