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 66 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 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
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.”
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.”
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…”
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 …”
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…”
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.”
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: 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…”
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.”
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 …”
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…”
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.”
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…”
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…”
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: 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.”
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…”
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.”
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…”
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”
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…”
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.”
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…”
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…”
Prince: B2C consumer software markets are far more random than B2B
“So the B to C stuff, that just feels, that's, that seems far, far more random.”
Matthew Prince: Founders who stay too long harm their companies
“There is a right time to step away from the company that you founded. And I think there are people who have held on to it too long and sometimes, you know, at the detriment of their company and some of the really smart people that could take the company over.”
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: Being married to your co-founder is the worst dynamic
“I mean, the worst, and people make this work, so there's an exception to every rule, but the worst is being married to your co-founder.”
Prince: Almost all startup founders begin with wild, massive 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 …”
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.”
Prince: 'Strong opinions weakly held' fails when employees blindly follow CEOs
“What I've found is hard about that is that as, you know, a successful CEO, you will say something and everyone thinks, well, that, that must be right.”
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.”
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: 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: Founders must project a grand vision for fundraising and recruiting
“When you're fundraising, you have to present a big picture. When you're recruiting, you have to present a big picture. When, even, even when you're just trying to keep your mental health of why is this so hard? You have to believe in that big vision.”
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…”
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: AI is fundamentally just statistics under the hood
“Today we'd call it AI, but it's all just statistics under, under the hood.”
Matthew Prince: Throwing noise at data streams preserves user online privacy
“You can't eliminate signal, but if you can throw enough noise at it, that's another way to prevent tracking and preserve privacy.”
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…”
Prince: Choosing co-founders is a founder's second most important life decision
“And, you know, the probably most important thing that you do in your life is pick who your partner is in, in, in, in, you know, whether it's marriage or whatever, whatever you believe in. And I think then the private second most important thing, if you're a fo…”
Russia sanctioned three tech CEOs together: Benioff, Prince, and Zuckerberg
“There's, there are three tech executives that that got sanctioned at the same time. Yeah, you already interviewed Benioff, who was one of them, it was me, And then, ah, and then Zuckerberg.”
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.”
Co-founders should minimize skill overlap to maximize total problem coverage
“So it's like a Venn diagram where you want circles that have a tiny bit of overlap so that there's some ability for the people involved to relate to one another. But ideally each of those circles has a ton of space covering the problem area to do that.”
Prince: Co-founders should start as colleagues, not friends
“So I think you inevitably, if you do it right, become friends. But I think what you want to start out as is colleagues.”
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.”
Prince: Cyber threat levels correlate with budget size, except for human rights groups
“There's almost a perfect line that is, the smaller your budget is, the less cyber threats you face, the bigger your budget, the bigger the cyber threats you face, with one notable exception, which is civil society and human rights organizations.”
Matthew Prince: Founders need a big vision for fundraising, recruiting, and resilience
“When you're fundraising, you have to present a big picture. When you're recruiting, you have to present a big picture. When, even, even when you're just trying to keep your mental health of why is this so hard? You have to believe in that big vision.”