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 151 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 8 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
Avoiding stock volatility is the primary advantage of staying private longer
“I think the biggest advantage is the avoidance of volatility in your stock price and sort of employee management. And so, you know, I think You know, if you can kind of steadily grow or control your stock price in the private markets, even if it's a slight dis…”
Rory O'Driscoll: Stripe will only IPO when private market capital dries up
“The only time Stripe will go public, we've said this on a call before, is when the capital available in private markets is towards ransom.”
Taneja: General Catalyst has invested $1B across funds into Stripe
“Stripe. You know, it's about a billion dollars.”
Taneja: General Catalyst will hold Stripe for 25 years
“You know, we'll, we'll have a 25 year kind of hold probably on, on Stripe in some form or the other.”
Taneja: Payments experts dismissed early Stripe as a niche business
“When I invested in Stripe, all the guys that I called the new payments were like, this is a niche thing, like why are you doing it? I kid you not.”
Taneja: General Catalyst's best returns come from seeding and creating companies
“I mean, look, our best returns have come from seeding companies like Stripe and Andurl or Creating companies like Kayak and Livongo and Camille and others, and so.”
Taneja: Stripe remains General Catalyst's best-performing investment of all time
“I think you would have to give that to Stripe still.”
O'Driscoll: The IPO window is always open for $50B companies
“Look, the window is, was, and always has been open for Databricks and Stripe. They just don't want to go through the window, right? There's no, like, The windows open and shut for the two billion dollar market cap IPO. The window is always open for the fifty b…”
O'Driscoll: Stripe will succeed in its IPO regardless of listing structure
“The very biggest, when Stripe finally goes public, they can do whatever they want. They can do a direct listing and not raise any primary capital. They could do the Google type option, and no matter what, it'll all be fine.”
Airwallex leadership voted 90% against Stripe acquisition offer
“It's surprisingly only one people wanted to sell. Like literally like, 90% of people said, you know, they think we can build a bigger business.”
Jack Zhang would have made $3B accepting Stripe's acquisition offer
“If I know Stripe gonna get to a hundred billion, I mean, I will probably make, like, at least three billion dollars.”
O'Driscoll: Klarna needs public capital access while Stripe commands infinite cheap private money
“If you're a Klarna, if you're a financial player where access to capital is really important, you know, you are fundamentally a lender. I think being public and having access to money in all its different ways makes sense. If you're a high growth AI company or…”
O'Driscoll: Capital flows to venture will fall if major IPOs stay delayed
“If on the other hand, if those keep pushing out, then at some point it becomes really hard to have all this money in private illiquid assets when you have pressures on your endowment and all that. And then at that point you would see the money go down.”
Hulme: Stripe is not listing publicly anytime soon
“But some of our best portfolio companies like Stripe aren't listing anytime soon, and they're finding ways to deliver liquidity.”
Singlehurst: Passing on Stripe's down round was a mistake
“I think that was a mistake. I think we should have put more in them.”
Singlehurst: Baillie Gifford passed on Stripe's $50B down round
“We first invested in Stripe at about a thirty billion dollar valuation but we didn't take part in the down round that they did whenever that was, 20, 22?”
Bookman: Databricks and Stripe raised massive rounds primarily for employee liquidity
“They're raising, Databricks is raising most of that to deliver secondary to employees, including to deal with some tax issues, and I know that's what Stripe did, and Josh, I think, is doing most of these.”
Entrée Capital and Designer Fund have sold nearly 50% of Stripe holdings
“I think we've both exited close to 50% or just on 50% of our holdings in Stripe to date.”
Aaron Levie: AI agents will lower startup barriers like AWS and Stripe
“If Shopify caused businesses to get started because it lowered the barrier to being able to sell online, if AWS caused applications to get started because I was like, oh, I could just build an app and run it in the cloud. I don't have to think about servers an…”
Stephens: Every Big Founders Fund Win Had a $100B Advocate
“If you look at any of the big outcomes across our portfolio, whether it's you know, Spotify, Stripe, Airbnb, Palantir, SpaceX, Andrel stem centric. So if you look at all of these big outcomes for us, every single one of them, there was someone on the team bang…”
Akkina: MIT Endowment Remains Liquidity-Constrained Until Major Unicorns Like Stripe Exit
“We're less liquidity constrained now than we were say at the beginning of last year, but the major issue still continues to be that there's all these big companies like Stripe, for instance from the last cycle that have not had liquidity events yet. And so unt…”
Empowered engineers are foundational to top tech companies like Tesla and Apple
“There is nothing more than, more important than empowered engineers. And if you look, you know, if you look at companies like Tesla, SpaceX, Google, Amazon, Stripe, Apple, that's the foundation of every one of those companies, empowered engineers.”
Big Tech success does not guarantee success at new startups
“They get somebody from Amazon, they get somebody from Stripe, somebody that's clearly experienced what good looks like. But then they assume that just because they were successful there, that they're going to be successful in our company. And that's not a true…”
Writing product narratives forces deep thinking and accelerates execution
“Like Stripe, Amazon, they believe think deeply to really. So for example, the written narrative is a way to force you to really think Think things through and then you're gonna move a lot faster.”
Doshi: Stripe co-founder John Collison excels at all three product leadership archetypes
“John is interesting in that, like you know, he is He's one of the rare people who can do, I think, who kind of can do, and I've seen him do all three really well. In fact, there were many times when like John was managing certain teams on an interim basis at S…”
Doshi: Stripe co-founder Patrick Collison fits the visionary craftsperson product archetype
“My assessment would be that Patrick is very much a visionary craftsperson type person, so, you know, every time I've interacted with him, and I learned a lot from, you know, about product from interacting with him. That's been the conversation is, is the visio…”
Samani: Stripe was overhyped for merely processing credit card payments
“I had played around with Stripes APIs maybe a week or two prior. And I was quite frankly, not terribly impressed. I was like, you can take a credit card payment. Like, why is this the most hyped up company in the world?”
Grosser: Stripe's internal tooling and systems haven't scaled with sales headcount
“Honestly, like, we're hyper growth, and I think our, the underlying tool systems operations haven't scaled as quickly as we've Scaled salespeople. Data, rigor, velocity, those all hold us back.”
Grosser: Great sales reps can run effective calls without deep product knowledge
“A savvy salesperson can talk to somebody actually knowing very little about the product they're selling because what great salespeople do is ask good questions. And so if you can teach folks what questions to ask out of the gates, they actually can run calls p…”
Casalena: Squarespace monetizes GMV via a revenue-share partnership with Stripe
“We do monetize all of the payments flowing through the e-commerce platform. Long ago, we made a, we were one of the, I think, first large companies to do it. We partnered with Stripe to enable the, our merchants to get online and to accept payments. And as par…”
Ribbit Capital passed on early investments in Stripe, Adyen, and Stone
“Early on at Ribbit, we had the opportunity to invest in, in Stone, in Adyen, in Stripe, you know, in a number of companies that are relatively early stage. And we said, we're not doing payments right now.”
Shopify Remains One of Stripe's Largest Customers Instead of Building In-House
“They're certainly one of Stripe's largest customers, if not the largest, and yet it's a great relationship. And at any point, of course, Shopify could have brought that in house.”
Hsu claims DoorDash is the only major startup built from landing-page testing
“The only case where I know this might potentially have worked was I think it was paloaltodelivery.com or something, which then became DoorDash. I think it's the only sort of recorded case of this ever actually working, but if you look at all the other sort of …”
Young tech workers should join mid-stage growth startups like Stripe or Slack
“I think there's merits to all of them, but I would now lean more toward go to that medium-sized growth company. You know, if you can get in today at a company like Stripe or Slack, for example, I think you get incredible growth opportunities, and if you know, …”
Frantz: Stripe is a revolutionary payments company with extraordinary traction
“I think our most recent public investment, most recent investment in a private company that, that, that's been publicly disclosed is Stripe, which is a revolutionary company in the payment space with an extraordinary team and traction that's quite unlike what …”
Stripe Was Smart to Pursue PayPal but Refused to Overpay
“Smart deal to try and do, but they're clearly not willing to overpay as they see it.”
O'Driscoll: Stripe Reduced Its Share Count Over Past Four Years
“Their share count is down on three years ago, four years ago, which means they've been buying back stock.”
O'Driscoll: Stripe will monetize OpenRouter faster than standalone OpenRouter could
“I'm willing to bet Stripe will turn OpenRouter into money probably quicker than OpenRouter could do on a standalone basis.”
O'Driscoll: Stripe Generates Around $6 Billion in Net Revenue
“Stripe supports revenue net, which is around six billion plus or minus.”
Grinberg: AI documentation equalizes software docs and reduces Stripe's documentation edge
“Yes. But I think Stripe has plenty of places that they can differentiate. And I think it's a better world where everyone has documentation as good as Stripe's.”
Lemkin: Stripe received sole A+ grade in agentic API benchmark
“Over, over the weekend my nine nine six project was I built an agentic API grader where we went, I just had Claude, OpenAI, and Gemini together take the top 120 APIs and grade which ones they thought were the best, which tools I thought, 11 Labs everything on …”
Stebbings: Founders Fund closing $6B in new capital after deploying $3.3B in 11 months
“Founders Fund are closing in on six billion dollars of new funds. They invested the last 3.3 in 11 months in amazing businesses like SpaceX and Stripe and Anduril.”
O'Driscoll: Thrive executed exceptional stock-picking with Stripe, Databricks, OpenAI
“I mean, I think, we said it in one of the shows earlier on, Thrive has done an amazing stock picking job of backing Stripe, of backing Databricks, of backing OpenAI, and of backing them at scale.”
Lemkin: Stripe is a better bet than Adyen due to private flexibility
“So I'm going to bet on Stripe on this one, just because I think you have more flexibility today to respond to change.”
Rampell: Passed on Stripe's seed round when it was called Dev Payments
“Obviously I passed on doing the seed round of Stripe, because I'm a genius. It was called Dev Payments at the time.”
Rivera: Founder-led incumbents like Shopify and Stripe are not sleeping
“I think we've like for years have been trained to know an incumbent as a shit company that's large. That's basically like the definition. And I just don't know that that's the case right now because you have a bunch of companies that came up in an era of moder…”