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Miles Grimshaw

Partner, Thrive Capital · 1 appearance on the record, plus 2 compilation re-airs.

computed by AI from the episodes · how this works → · full disclaimer →

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.

58statements → 20claims → 7claims resolved → 43%fully supported → 3.64/5average certainty → 2.22/5average debate potential → 3.9/5argument clarity · the sources → 33said about them ↓

3 supported 4 partly supported 0 contradicted 13 not checkable as stated how the 20 claims stand · each chip opens the sources

10 predictions · 10 assertions · 4 opinions · 26 insights · 8 disclosures · every statement was checked. The predictions and assertions are the 20 claims: statements the public record can support or contradict. 7 are resolved, and 13 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Miles argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
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.”
Miles Grimshaw Sep 18, 2023 ▶ 42:24 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
67% certainty 3
75% certainty 4
none yet certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

Argument clarity: do they answer the question? how? →

3.9 / 5 directness 4.1 · coherence 3.9 · precision 3.7 · compression 3.2

redirected or did not address 9 of 49 assessed questions (18%). Watch them ▸

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

256 words/min while actually speaking · 33.7 um and uh per 1k words · 23.4 false starts per 1k · 30.2% of pauses land inside a clause

Measured by listening to the audio itself: 16,315 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

How the interview went all their pushback → series average →

Across 3 rated episodes:

host pushback ▾ 3.3/10
pushed back at the host ▾ 3.7/10
setup questions received 57%

Everything Miles Grimshaw said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight
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.”
Miles Grimshaw May 24, 2024 ▶ 15:58 Sam Altman, Arthur Mensch and more discuss:Which Startups Are Threatened vs Enabled by OpenAI?|E1156 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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…”
Miles Grimshaw Nov 24, 2023 ▶ 13:55 The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085 · 20VC with Harry Stebbings
Opinion
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.”
Miles Grimshaw Nov 24, 2023 ▶ 19:05 The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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.”
Miles Grimshaw Sep 18, 2023 ▶ 0:00 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Assertion Not checkable as stated
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.”
Miles Grimshaw Sep 18, 2023 ▶ 15:49 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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.”
Miles Grimshaw Sep 18, 2023 ▶ 32:36 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Disclosure
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.”
Miles Grimshaw Sep 18, 2023 ▶ 39:41 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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…”
Miles Grimshaw Sep 18, 2023 ▶ 56:41 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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.”
Miles Grimshaw Sep 18, 2023 ▶ 1:05:22 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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…”
Miles Grimshaw Sep 18, 2023 ▶ 1:05:42 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Opinion
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.”
Miles Grimshaw Sep 18, 2023 ▶ 1:08:06 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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.”
Miles Grimshaw Sep 18, 2023 ▶ 1:08:35 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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.”
Miles Grimshaw Sep 18, 2023 ▶ 1:09:58 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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.”
Miles Grimshaw Sep 18, 2023 ▶ 1:18:15 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Prediction Not checkable as stated
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…”
Miles Grimshaw Sep 18, 2023 ▶ 1:23:54 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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…”
Miles Grimshaw Sep 18, 2023 ▶ 1:24:42 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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…”
Miles Grimshaw Sep 18, 2023 ▶ 1:38:48 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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…”
Miles Grimshaw Sep 18, 2023 ▶ 17:41 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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.”
Miles Grimshaw Sep 18, 2023 ▶ 22:25 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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.”
Miles Grimshaw Sep 18, 2023 ▶ 23:13 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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…”
Miles Grimshaw Sep 18, 2023 ▶ 27:02 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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.”
Miles Grimshaw Sep 18, 2023 ▶ 31:58 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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?”
Miles Grimshaw Sep 18, 2023 ▶ 33:19 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Insight
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…”
Miles Grimshaw Sep 18, 2023 ▶ 36:28 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings

Show 24statements(34 left)

The other half of the tape: Miles Grimshaw's own voice is left out of every number here. Other people bring the name up 32 times in 13 episodes on 20VC. 1 statement on the record names them. every mention, with the transcript →

Who brings them up most Harry Stebbings 18Miles Clements 8Jack Altman 4Vince Hankes 1Everett Randle 1

Statements about Miles Grimshaw, by other people (1)

Insight
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…”
Jack Altman Nov 3, 2017 ▶ 8:42 20VC: What Is Core To The Best Investor - Founder Relationships, The Biggest Risk For Founders In The Early Days & Why EQ Is The Most Important Trait For Managers with Jack Altman, Founder & CEO @ Lattice

Every mention by year

tap a year for its mentions
0043852017201820192020202120222023202420252026episodesmentions
0352017201820192020202120222023202420252026episodes it came up in
0042.5852017201820192020202120222023202420252026episodesmentions per episode
2026 8 mentions in 1 episode
2025 4 mentions in 3 episodes 1 per episode
2024 3 mentions in 2 episodes 2 per episode
2023 8 mentions in 5 episodes 2 per episode
2018 2 mentions in 1 episode
2017 7 mentions in 1 episode

Appearances (3)

EpisodeDateSpeaking time
Sam Altman, Arthur Mensch and more discuss:Which Startups Are Threatened vs Enabled by Ope compilation May 24, 2024 1m
The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085 · 20 compilation Nov 24, 2023 3m
Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | Sep 18, 2023 1h 18m
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