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 41 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 2 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
Lemkin: Databricks and OpenAI IPOs will be nail in coffin for SaaS
“I think it will be the nail in the coffin for almost every public software company. And what I mean is when Stripe and data, like, okay, there's OpenAI, there's Anthropic, we can put them in a different category, right? They clearly are on many levels. When Op…”
Flanagan: ChatGPT scrapes 1,500 web pages for every single referral visit
“Six months ago, it was 250 pieces of content scraped, and they give you one visit back. Today, it's 1500 pieces of content scraped, and they give you one visit back.”
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…”
Bek: Cloudflare projects agent traffic will exceed human traffic 1,000x in 5 years
“I think it was Cloudflare this morning said that in five years from now, we'll have 1000 times the amount of agent traffic to human traffic.”
Lemkin: Only infrastructure SaaS companies are winning two-pronged AI customer growth
“To be a two-pronged AI beneficiary, you have to be able to monetize your AI, and you have to attract new customers. There's two prongs, and the ones that have done it so far are close to infra, right? Cloudflare, Twilio, Mongo, Datadog and even DigitalOcean”
O'Driscoll: Anthropic's revenue multiple is lower than Palantir's
“It's a much lower revenue multiple than Palantir. It's kind of comparable with Cloudflare for God's sake in the public markets.”
Lemkin: Three of today's top six B2B stocks will retain 2026 leadership
“My Pekumumusukus, Pekumumusukus, Palantir, Cloudflare, Mongo, Shopify, CrowdStrike, Snowflake, I'll bet you 10 grand, three of them are in the top six of this cohort at the end of next year.”
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…”
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…”
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.”
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…”
Randle: Top public SaaS platforms trade above 15x NTM revenue
“You have, I mean, Palo Alto, CrowdStrike, Cloudflare, Datadog, Palantir, all these companies trade above 15 times NTM revenue again.”
Lemkin: Growth momentum is software's only defense in the AI age
“I'm betting on momentum is the only thing that's going to save us. Save us in the age of AI. So I'm betting on overpriced Palantir, Cloudflare, which is re-accelerating and benefiting from AI, and Shopify which is gaining market share.”
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…”
Cloudflare will inevitably reach $5 billion in annual revenue
“We're on a path From a billion dollars of revenue to five billion dollars of revenue, that's inevitable that we'll get there. It's just a matter of how long.”
Prince: Startups are doomed if co-founders struggle to split responsibilities
“If it's not totally clear, Then it can become really, really bad.”
Prince: Baillie Gifford's average holding period is 16 years
“Like Bailey Gifford, who's, you know, one of Kleffler's, you know, top investors in a Scottish firm, their average holding period is 16 years.”
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, …”
O'Driscoll: High-multiple tech stocks remain vulnerable during paradigm shifts
“And I think what you saw in the case of AppLoving and Cloudflare is it turns out high-priced stocks At the start of a paradigm shift, no matter how amazing the quarter is, are just vulnerable to disruption.”
Lawson: Cloudflare's DNS position gives it an ideal product expansion surface area
“I always admired the product surface area that Cloudflare had. Because they sit at this super strategic intersection of the world and then your website. And then you can ask the, and it's a dashboard. So once you're inserted into the DNS, and you're proxying a…”
Cloudflare never raised angel or friends-and-family capital before its IPO
“So like at Cloudflow, we never raised like angel money. We never raised from friends and family literally until we were going public. And then we let, let folks like that invest in the IPO, but we didn't do it otherwise.”
Prince: Being Silicon Valley outsiders forced Cloudflare to focus on building
“I think part of Cloudflare's success was we were nobodies. Like we didn't know anyone and we didn't get invited to all the fun parties and we weren't part of the cool kids group. And I think as a result, there was, we just focused on How do we, you know, build…”
Prince: Cloudflare's first 1,000 customers shared no common ideal customer profile
“In our case, you know, it was the first thousand customers were all over the place, and they, I can't tell any, like, discernible pattern between them, except for that they were, you know, crazy enough to sign up for us.”
Prince: Cloudflare Succeeded Because Its Founders Were Silicon Valley Outsiders
“I think part of Cloudflare's success was we were nobodies. Like we didn't know anyone and we didn't get invited to all the fun parties and we weren't part of the cool kids group. And I think as a result, there was, we just focused on, How do we, you know, buil…”
Matthew Prince: Low-drama co-founder dynamics set an organization's overall culture
“And I think a lot of times the fact that, you know, she and I have been doing this now for, you know, over 14 years and We have hard conversations, but we get along. We don't have fights. We're really, we're low drama. I think that that echoes down through the…”
Cloudflare co-founder Lee Fahlberg was diagnosed with frontotemporal dementia in his 30s
“Instead, it turned out he had a pretty rare neurological condition called frontotemporal dementia. It's the same thing that Bruce Willis has, but, you know, Lee was in his thirties, which is extremely rare for something like this.”
Prince: Founders should pick complementary opposites rather than friends as co-founders
“Instead of picking someone who I'm friends with, let me pick somebody who is actually kind of the opposite to me.”
Matthew Prince: Cloudflare's founding vision was to run the internet
“If you go and you watch the TechCrunch pitch, there's a judge at the end of it, and he asked, what's your vision? And I was like, our vision is to run the internet.”
Prince: Every pre-IPO Cloudflare investor generated at least 10x returns
“Everyone who bet on us pre IPO made at least 10 times the money that they invested with us.”
Prince: Cloudflare never raised angel or friends and family money pre-IPO
“So like at Cloudflow, we never raised like angel money. We never raised from friends and family literally until we were going public.”
Henry Schuck: ZoomInfo was third highest-valued software company on relative basis
“Going into that earnings report on a relative basis, we were the third most valuable software company in the world. From evaluation purposes, snowflake, cloud flare, us”
Cloudflare designated Michelle Zatlyn as temporary CEO in public succession plan
“When we went public we had to go through, like, a succession planning exercise, you know, if Matthew gets hit by a bus who steps in as a CEO and the board decided, and I think this is publicly filed that, you know, Michelle would step in on a temporary basis a…”
Cloudflare splits decisions: Prince controls product, Zatlyn controls go-to-market and HR
“Today at Cloudflare, as we think about things, when we have a question of what product to build, ultimately, I'm the one who makes the decision on, on that. But Michelle has a ton of input and is, is helpful. But at the end of the day, it's my decision. On the…”
Prince: Cloudflare's first 1,000 customers shared no discernible pattern
“In our case, you know, it was the first thousand customers were all over the place, and they, I can't tell any, like, discernible pattern between them, except for that they were, you know, crazy enough to sign up for us.”
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.”
Prince: Michelle Zatlyn originated the idea for Cloudflare
“And it was actually Michelle who was like, that's the idea. We're building that. And so it wasn't really even my aha moment. It was actually Michelle's.”
Matthew Prince Was Debt Broke When Starting Cloudflare in 2009
“When we started Cloudflare, I was debt broke. Like I, if we hadn't raised money in November of 2009, like I wasn't sure how I was going to pay my rent. I'd already borrowed a bunch of money from my mom”
Prince's management rule: Check personal health issues when employee behavior abruptly changes
“And I try now when people you know, their behavior changes dramatically. To ask, you know, is there something going on in their personal life? Is there something going on with their health? Is there something else that's out there?”
Prince: Cloudflare required multi-million dollar enterprise contracts to achieve scale
“We knew in order for this to be a big business, we needed to sell to really big banks and governments and financials, hospitals, and we needed to sell like multi-million dollar contracts on a regular basis.”
Matthew Prince: Prioritizing Cloudflare ruined personal relationships during early startup years
“I feel very fortunate to have dated some just incredible people over, over the years, and especially during the time of starting, starting Cloudflare, and it could have worked out with almost any of them but I think what happened was, you know, your company ca…”
Matthew Prince made his first money selling illegal fireworks in fourth grade
“In about fourth grade or so I had access to a bunch of illegal fireworks. And I would sell them at school, which was, made me really popular with the other kids, but not so popular with their parents. And so I think that that, that probably something around th…”