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TBPN Disclosure
Prince: Cloudflare seeded internal AI OS with secret human operators
“So we built something called Cloudflare OS. Which allows, you know, anyone on our finance team, legal team, you know, accounting team, finance anyone that's out there at the company to be able to have access to tools and really figure out how, how their job ge…”
Matthew Prince Jun 10, 2026 ▶ 30:15 Cloudflare CEO Predicts AI Agents Will Outnumber Humans 1,000-to-1
TBPN Opinion
Prince: Companies Cutting Junior Hiring Due to AI Are Making a Mistake
“I think a lot of companies are doing this wrong, where they're saying, like, we're not gonna bet on, on, on the new people coming out of school, because, you know, AI is gonna replace them. I mean, these kids know how to use AI better than anyone else, so we'r…”
Matthew Prince Jun 10, 2026 ▶ 32:10 Cloudflare CEO Predicts AI Agents Will Outnumber Humans 1,000-to-1
BIG TECHNOLOGY Assertion Contradicted
Prince: Google search query volumes are declining for the first time
“What we're seeing though, is that for the first time in history, searches across the major search engines, Google in particular, are actually on the decline.”
Matthew Prince Aug 13, 2025 ▶ 1:10 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Assertion Not checkable as stated
Prince: Getting a referral click from Google is 10x harder today
“Today, it's almost 10 times as hard to get a click, to get a visitor from Google to your site.”
Matthew Prince Aug 13, 2025 ▶ 3:01 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Assertion Partly supported
Prince: 75% of Google search queries are answered without a click
“In fact, about 75% of queries to Google now get answered on Google itself.”
Matthew Prince Aug 13, 2025 ▶ 3:28 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Prediction Not checkable as stated
Prince: AI-driven web will cause media consolidation and reduced content
“Again, I think that that's just going to mean that over time we'll have more consolidation in the media industry. We'll have less and less content. We'll have actually more salacious headlines as people are chasing The content that is, is left that's out there…”
Matthew Prince Aug 13, 2025 ▶ 6:29 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Assertion Supported
Prince: Google's AI Overviews pushed its crawl-to-click ratio to 18:1
“The ratio 10 years ago of crawls from Google to clicks was two crawls, one click. Six months ago, it was up to six crawls one click, and that's all because of the answer box. What the AI overviews, which they've rolled out over that time, have done is they've …”
Matthew Prince Aug 13, 2025 ▶ 7:41 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Prediction Not checkable as stated
Prince: Strangling publisher incentives will eventually degrade AI systems
“If we strangle off the business model of those places, if we strangle off the incentives for content to create for content creators to create content, then we're actually going to end up strangling the AI systems as well, because there's, if there's no content…”
Matthew Prince Aug 13, 2025 ▶ 9:28 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Prediction Not checkable as stated
Prince: Strangling creator incentives will ultimately hurt AI companies
“In order for AI to get better, you have to have original content. People have to be going out and creating that. And right now we're strangling off all of the incentives for that content creation, which not only hurts content creators, it will ultimately hurt …”
Matthew Prince Aug 13, 2025 ▶ 15:41 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
Prince: AI bots should pay heavily for content so humans read free
“Humans should get content for free again, because we've kind of paywalled way too much, frankly. And robots should pay a ton for it. Because again, every time a robot ingests something, it's in service of, Hundreds of thousands, if not millions of different hu…”
Matthew Prince Aug 13, 2025 ▶ 18:41 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Prediction Not checkable as stated
Prince: AI will eliminate creator subscription revenue by summarizing podcasts
“That will go away as well, because what will happen is the AI company will ingest the podcast and then summarize it on, on their page.”
Matthew Prince Aug 13, 2025 ▶ 20:02 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Assertion Supported
Prince: AI web scrapers brought down entire publisher websites with traffic
“Starting really 18 months ago is that those companies said, hey, I know we hired you in order to stop the Chinese hackers, but we have this new threat that's there... And it was only when we actually saw the data and we saw how AI companies were taking content…”
Matthew Prince Aug 13, 2025 ▶ 30:34 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Disclosure
Cloudflare blocks AI bots by default on monetized or paywalled web pages
“What we've done is we've actually tried to identify with real narrow precision. What are those pages that are on the web that have some indication that they are going to be monetized. And generally that is look at, is it behind a paywall or is it, does it have…”
Matthew Prince Aug 13, 2025 ▶ 33:31 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Assertion Supported
Prince: Major legitimate companies completely ignore robots.txt
“And there's some just, there's some, even some big legitimate companies that completely ignore robots.txt.”
Matthew Prince Aug 13, 2025 ▶ 34:59 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Assertion Partly supported
Prince: Google uses a single crawler for search, ads, and Gemini
“Google's crawler does five different things, at least. One is it checks if you have an ad on a page. It makes sure that if you're putting an ad for Procter & Gamble, Procter & Gamble product up, it's not against a pornographic site or something like that. So i…”
Matthew Prince Aug 13, 2025 ▶ 35:35 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Disclosure
Prince: Cloudflare is adopting the HTTP 402 code to charge AI bots
“There's actually an original one of the protocols set out a four or two response and that response says payment required. And so we're actually tapping into that exact original specification to say when a robot tries to access, access a page, Where there's an …”
Matthew Prince Aug 13, 2025 ▶ 37:47 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Prediction Not checkable as stated
Prince: Crawler paywalls will create a dynamic marketplace for content
“And so that's the sort of thing where I think a marketplace over time can develop where original valuable content will get compensated and there will be a clearing price in the market once we have that scarcity that's created by that wall.”
Matthew Prince Aug 13, 2025 ▶ 39:14 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Prediction Open · timeframe Aug 2030
Prince: Global regulators will force Google to split its web crawler
“I am also a hundred percent certain that regulators are paying a ton of attention to this. And that around the world, you will see them force Google to split their crawler out into announcing exactly what it is doing.”
Matthew Prince Aug 13, 2025 ▶ 45:14 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
BIG TECHNOLOGY Assertion Not checkable as stated
Prince: Open web content growth has plateaued amid fewer domain registrations
“By all the measures that we can see, it's actually kind of plateaued and is actually flattened out in terms of in terms of content. You see fewer domains getting registered. You see fewer new websites going online.”
Matthew Prince Aug 13, 2025 ▶ 45:58 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
Prince: 99 percent of AI spending is currently being lit on fire
“I believe today that 99 out of, cents out of every dollar spent on AI is just being lit on fire. But that one cent that's out there Is gonna generate real returns.”
Matthew Prince Aug 13, 2025 ▶ 49:38 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
Prince: AI support agents and lawyers lag coding due to lack of debuggers
“On the other hand, you know, I am, I, I'm still quite skeptical that the AI customer support agent that, that is a much harder problem or the AI lawyer that is a much harder problem because it's just harder to tell whether something actually worked or didn't. …”
Matthew Prince Aug 13, 2025 ▶ 50:44 Can We Save The Web From AI? — With Cloudflare CEO Matthew Prince
NO PRIORS Assertion Supported
Prince: Google Clicks Are 10x Harder to Get Than 10 Years Ago
“The data that we have also substantiates that and shows that compared with 10 years ago, it's become 10 times harder for the same piece of content to get a click from Google than it was before.”
Matthew Prince Aug 7, 2025 ▶ 5:24 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
NO PRIORS Prediction Not checkable as stated
Prince: AI Traffic Drop Could Starve Web Content and AI Training
“What I worry about is that if the value creation model of the web has been all about how do I get traffic The new interface of the web isn't going to send you traffic, and if that's the case, if content creators can't get value from selling a thing or a subscr…”
Matthew Prince Aug 7, 2025 ▶ 5:57 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
NO PRIORS Insight
Prince: AI Markets Should Reward Creators for Filling Knowledge Gaps Over Traffic
“Their very algorithms, as they come across a piece of content, they prune off that content Which is already kind of part of the meaty part of the cheese, whereas the parts that are in holes are actually super valuable to them, and so I actually think that if w…”
Matthew Prince Aug 7, 2025 ▶ 14:59 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
NO PRIORS Opinion
Prince: Fixed-Sum AI Licensing Deals Are a Mistake for Content Creators
“I think the mistake that a lot of content creators did was they actually did deals that don't scale as the business models of the AI companies scale with them. So if you do a deal that's like, twenty million dollars and you get all my content, I mean, that's a…”
Matthew Prince Aug 7, 2025 ▶ 21:13 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
NO PRIORS Assertion Not checkable as stated
Prince: AI companies fear Google most due to its privileged content access
“Why Google is so important is when you talk to all of the other AI companies, Google is the one company that they're the most afraid of. And that the reason that they're most afraid of them is because they think that they have privileged access to content in a…”
Matthew Prince Aug 7, 2025 ▶ 28:32 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
NO PRIORS Prediction Open · timeframe Aug 2030
Prince: Smartphones will soon run local models matching current ChatGPT
“It is not particularly long before you're running something which is the equivalent of kind of the current generation of ChatGPT on your iPhone or your, or at your Android device.”
Matthew Prince Aug 7, 2025 ▶ 38:17 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
NO PRIORS Prediction Not checkable as stated
Prince: GPUs will speed-run 30 years of CPU efficiency in ten years
“We're going to speed run the last 30 years of CPU efficiency gains. In, in the next, you know, five to 10 in, in GPUs.”
Matthew Prince Aug 7, 2025 ▶ 40:00 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
NO PRIORS Prediction Not checkable as stated
Prince: Infrastructure regulating web bots will also regulate AI-connected browsers
“I think that that's, it, it'll probably be the same fundamental infrastructure that regulates how bots access the web, that ends up regulating how browsers access the web, and a browser that Takes data and then immediately feeds it back to an LLM might have mo…”
Matthew Prince Aug 7, 2025 ▶ 43:33 No Priors Ep. 126 | With Cloudfare CEO Matthew Prince
TBPN Assertion Supported
Prince: Anthropic is 30,000x and OpenAI 750x harder than Google for traffic
“As you looked at open AI, it was about 750 times harder than with the kind of Google of old to get traffic with something like anthropic is 30,000 times harder.”
Matthew Prince Jul 5, 2025 ▶ 1:29:59 Weekly Recap: The Soham Parekh Drama, Meta Attacks OpenAI, Trump's Mega Bill
TBPN Disclosure
Cloudflare enables free default blocking of uncompensated AI web crawlers
“Starting on July first we flipped the script. We made it as a default that if you're using Cloudflare that you can by default for free block any crawlers from taking your content without compensating you.”
Matthew Prince Jul 5, 2025 ▶ 1:31:05 Weekly Recap: The Soham Parekh Drama, Meta Attacks OpenAI, Trump's Mega Bill
TBPN Disclosure
Prince: Cloudflare is exploring creating its own stablecoin for micropayments
“We're looking at all of the different providers that are in this space, including potentially creating our own stablecoin that would be part of how these transactions you know, take place.”
Matthew Prince Jul 5, 2025 ▶ 1:40:07 Weekly Recap: The Soham Parekh Drama, Meta Attacks OpenAI, Trump's Mega Bill
TBPN Assertion Supported
Prince: Iran is targeting US financial and infrastructure firms with cyber attacks
“We're starting to see that Iran is targeting other other largely U.S. Financial services firms critical infrastructure firms to try and see, to sort of try and strike back from what is you know, how, how do they strike back against the US in a way that that, t…”
Matthew Prince Jul 5, 2025 ▶ 1:56:02 Weekly Recap: The Soham Parekh Drama, Meta Attacks OpenAI, Trump's Mega Bill
TBPN Insight
Prince: Prioritizing raw performance over power efficiency is a losing chip strategy
“We've seen this game before with Intel saying, oh, that doesn't matter. Like just get the most performance possible. You can water cool things, all kinds of things. That, that tends to not be the winning strategy over the long term, and so we do think that the…”
Matthew Prince Jul 5, 2025 ▶ 1:58:54 Weekly Recap: The Soham Parekh Drama, Meta Attacks OpenAI, Trump's Mega Bill
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
20VC 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
Bragging about company valuation is like bragging about mortgage size
“I've always thought that, that entrepreneurs who brag about how much they raised or what their valuation are, it's sort of like if you brag about how big your mortgage is it's, it feels sort of distasteful”
Matthew Prince Mar 17, 2019 ▶ 7:04 1331 How CloudFlare Broke $100m in ARR Securing The Internet, No $2.5B Amazon Acquisition
Prince: Raising capital just means you failed to generate enough revenue
“It's not necessarily something to be proud of. It just means that you didn't actually generate enough revenue yourself to cover the costs that you had.”
Matthew Prince Mar 17, 2019 ▶ 7:54 1331 How CloudFlare Broke $100m in ARR Securing The Internet, No $2.5B Amazon Acquisition
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