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Matthew Prince

Co-Founder & CEO, Cloudflare · 2 appearances on the record.

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

founderexecutiveacademic@eastdakota ↗LinkedIn ↗cloudflare.com ↗Wikipedia ↗Instagram ↗

He co-founded Cloudflare in 2009, leading the company through its 2019 IPO and serving as its CEO. Prior to Cloudflare, he co-created Project Honey Pot and taught law at the University of Illinois Chicago School of Law.

66statements → 21claims → 12claims resolved → 50%fully supported → 4.09/5average certainty → 2.3/5average debate potential → 3.9/5argument clarity · the sources → 18said about them ↓

6 supported 4 partly supported 2 contradicted 2 not yet assessed 7 not checkable as stated how the 21 claims stand · each chip opens the sources

1 prediction · 20 assertions · 8 opinions · 27 insights · 8 disclosures · 2 what ifs · every statement was checked. The prediction and assertions are the 21 claims: statements the public record can support or contradict. 12 are resolved, 2 are not yet assessed, and 7 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 Matthew 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
Prince: The story of eBay starting with Beanie Babies is PR BS
“So, so the eBay example, you're like eBay started with Beanie Babies. So I've talked to the founders of eBay about that. That's complete and utter PR retrospective BS.”
Matthew Prince Oct 24, 2023 ▶ 11:59 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings

Their most notable contradicted claim

Assertion Contradicted
Cloudflare generated $7M daily shareholder value in its first decade
“At that particular time, we had generated something like seven million dollars in shareholder value every day since, since we had launched, including, again, weekends and holidays.”
Matthew Prince Oct 16, 2023 ▶ 1:04:49 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
none yet certainty 3
42% certainty 4
92% 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 3.8 · coherence 4.2 · precision 3.9 · compression 3.1

redirected or did not address 2 of 26 assessed questions (8%). 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? →

242 words/min while actually speaking · 22.4 um and uh per 1k words · 53.6 false starts per 1k · 32.9% of pauses land inside a clause

Measured by listening to the audio itself: 15,782 words across 2 episodes 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 2 rated episodes:

host pushback ▾ 5/10
pushed back at the host ▾ 5/10
setup questions received 25%

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

Opinion
Prince: The Bay Area is terrible for scaling companies
“It's, it is, I mean, when we were starting, and by the way, it's why it's the best place to start companies, but it's a terrible place to scale companies.”
Matthew Prince Oct 24, 2023 ▶ 7:35 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Assertion Supported
Prince: The story of eBay starting with Beanie Babies is PR BS
“So, so the eBay example, you're like eBay started with Beanie Babies. So I've talked to the founders of eBay about that. That's complete and utter PR retrospective BS.”
Matthew Prince Oct 24, 2023 ▶ 11:59 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Insight
Prince: Starting in a narrow niche creates local minimums that hinder growth
“Where it runs a risk is if you start, start to say, you know, we've got to do X. First of all, you'll attract people that think X is, even though you say the journey is much longer that they'll think that that's the end state. And then secondly, it might be th…”
Matthew Prince Oct 24, 2023 ▶ 14:24 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Assertion Not checkable as stated
Prince: Almost all successful startup founders begin with broad, ambitious visions
“It is very hard to find an actual startup founder that, that started out saying, we're going to do this small niche thing, and then it grew into this, is this big task. Almost everyone early on, you know, it's why founders, you know, can come across as so, so …”
Matthew Prince Oct 24, 2023 ▶ 15:10 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Opinion
Prince: Bootstrapped Tough Mudder might be more successful than Cloudflare
“I think it's an open question whether, you know, they've been more successful or we've been more successful. Like, they have no costs. They've got this thing that's just a machine that just kicks off a ton of cash, and he can go and focus on, you know, other t…”
Matthew Prince Oct 24, 2023 ▶ 25:55 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Opinion
Prince: Jeff Bezos is optimizing his life for Instagram
“And for a long time, I looked at like, you know, Jeff Bezos. I was like, wow, he seems like he has a pretty good life. He's not a pretty happy person. And out today, it seems like he's optimizing his life for Instagram, which is weird.”
Matthew Prince Oct 16, 2023 ▶ 9:19 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Insight
Prince: Most founders end up miserable or dead after leaving
“So I think that they, I think that there's, unfortunately, there's a lot of founders who, after they leave their companies end up either miserable or dead.”
Matthew Prince Oct 16, 2023 ▶ 9:49 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Insight
Matthew Prince: Broad platforms rarely originate from narrow product niches
“I think it's very rare to find someone who said, I started out just trying to build, you know, the platform for, you know, People to sell snowboards, and I, and, you know, and I ended up building, building Shopify, or I started out, you know, building that sma…”
Matthew Prince Oct 16, 2023 ▶ 46:42 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Opinion
Prince: Public market investors are better partners than VCs
“Public market investors are great because if they'll tell you the truth, because, you know, if they don't like what you're doing, they sell your stock.”
Matthew Prince Oct 16, 2023 ▶ 57:55 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Insight
Prince: Modest growth without scale is the worst outcome for startups
“The worst outcome by far Is the slog. Where you have these companies that are growing just enough that it feels like success is just over the next hill. And they, and so they can't stop But there, nobody cares about them anymore, and their investors are tuned …”
Matthew Prince Oct 24, 2023 ▶ 3:58 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Insight
Prince: Expanding a tiny niche product into Shopify is extremely rare
“I think it's very rare to find someone who said, I started out just trying to build, you know, the platform for, you know, People to sell snowboards, and I, and, you know, and I ended up building, building Shopify, or I started out, you know, building that sma…”
Matthew Prince Oct 24, 2023 ▶ 17:29 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Insight
Prince: Elite founder success requires identity to become the company
“To be as successful as Gates, to be as successful as Bezos, to be as successful as Benioff, not only do you have to love it, but it becomes you.”
Matthew Prince Oct 16, 2023 ▶ 10:32 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Disclosure
Cloudflare detected Russian cyber probing in Dec 2021 and warned governments
“We detected in December of 2021 the early indicia of Russia probing in a way that was similar to how they probed before they went into Georgia, before they went into Crimea, when they got more involved in Syria, and, you know, briefed government officials in b…”
Matthew Prince Oct 16, 2023 ▶ 13:33 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
What-if
Prince: Without Cloudflare, Ukrainian Defense and Global Communications Would Have Struggled
“Had we not done that, it would have been much harder for President Zelenskyy to get, get the message out on what was happening. It would be much harder to see what was happening on the front. It would be much harder to see the atrocities that the Russians Cont…”
Matthew Prince Oct 16, 2023 ▶ 14:29 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Assertion Not checkable as stated
China employs more people to hack Cloudflare than Cloudflare has employees
“There are more people employed by the Chinese government to hack Cloudflare than there are employees at Cloudflare.”
Matthew Prince Oct 16, 2023 ▶ 16:49 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Insight
Prince: Quick failure is the second-best outcome for venture startups
“If the wild success is the best outcome, the second best outcome. I would argue is quick failure.”
Matthew Prince Oct 16, 2023 ▶ 31:49 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Insight
Prince: 'The slog' is the worst outcome for venture startups
“The worst outcome by far Is the slog. Where you have these companies that are growing just enough that it feels like success is just over the next hill. And they, and so they can't stop. But there, nobody cares about them anymore, and their investors are tuned…”
Matthew Prince Oct 16, 2023 ▶ 33:12 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Opinion
Prince: The Bay Area is best for starting companies, terrible for scaling
“It's why it's the best place to start companies, but it's a terrible place to scale companies.”
Matthew Prince Oct 16, 2023 ▶ 36:49 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Assertion Supported
Prince: The eBay Beanie Babies origin story is a PR myth
“So I've talked to the founders of eBay about that. That's complete and utter PR retrospective BS. And the reason that a lot of stories look like that is because almost nobody Once, if you're in the, you're the journalist that, that, that you said before we sta…”
Matthew Prince Oct 16, 2023 ▶ 41:17 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Insight
Prince: Picking bad co-founders is the biggest mistake entrepreneurs make
“The biggest mistake that no, the biggest mistake that entrepreneurs make is picking bad co-founders. The second biggest mistake that they make is not setting their sights on an ambitious enough target”
Matthew Prince Oct 16, 2023 ▶ 50:06 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Opinion
Prince: Tough Mudder May Be More Successful Than Cloudflare
“I think it's an open question whether, you know, they've been more successful or we've been more successful. Like, they have no costs. They've got this thing that's just a machine that just kicks off a ton of cash, and he can go and focus on, you know, other t…”
Matthew Prince Oct 16, 2023 ▶ 54:04 Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings
Insight
Prince: Quick failure is the second-best outcome for VC-backed startups
“If the wild success is the best outcome, the second best outcome I would argue is quick failure. It just doesn't work. Right. And it falls on its face and dies. That's actually a really great outcome.”
Matthew Prince Oct 24, 2023 ▶ 2:35 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
What-if
Prince: Cloudflare would have failed by targeting a narrow startup niche
“If we had really said, we're going to focus on this and start there and, you know, constrain, like, and our marketing copy said, you know, Cloudflare is a service for startups and small businesses and did all those things. You know, if we'd started with the na…”
Matthew Prince Oct 24, 2023 ▶ 10:19 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings
Insight
Prince: Civil society organizations face disproportionate cyber threats relative to budget
“If you imagine an X, Y axis, and the X axis is sort of budget, right? And the Y axis is, you know, how many cyber threats you face. There's almost a perfect line that is the smaller your budget is, the less cyber threats you face, the bigger your budget, the b…”
Matthew Prince Oct 24, 2023 ▶ 10:36 Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings

Show 24statements(42 left)

The other half of the tape: Matthew Prince's own voice is left out of every number here. Other people bring the name up 17 times in 7 episodes on 20VC. 1 statement on the record names them. every mention, with the transcript →

Who brings them up most Harry Stebbings 5Santi Subotovsky 1

Statements about Matthew Prince, by other people (1)

Disclosure
Subotovsky: Emergence Capital missed out on investing early in Cloudflare
“So the biggest miss that I've had is when I first joined Emergence one of my good friends and classmates, Matthew Prince and Michelle, were getting started with Cloudflare, and I invited them to present here at Emergence, and I didn't know how venture worked, …”
Santi Subotovsky Jul 15, 2019 ▶ 35:15 20VC: Zoom From Series A to IPO, How VCs Can Provide CEOs with Additional Leverage and Why The Negative Effects of Signalling Are Very Real with Santi Subotovsky, General Partner @ Emergence Capital

Every mention by year

tap a year for its mentions
005210320192020202120222023202420252026episodesmentions
02320192020202120222023202420252026episodes it came up in
0021.54320192020202120222023202420252026episodesmentions per episode
2026 10 mentions in 3 episodes 3 per episode
2025 6 mentions in 3 episodes 2 per episode
2019 1 mention in 1 episode

Appearances (2)

EpisodeDateSpeaking time
Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20V Oct 24, 2023 21m
Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Ste Oct 16, 2023 54m
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