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
Disclosure
Stripe founders asked Robinhood not to tokenize their shares, says Tenev
“I've shared this viewpoint with Patrick and John, and they give me some variant of, oh, well, we're just a small Irish family company. Please don't tokenize my shares.”
Assertion Supported
Holland: Excessive burn rate killed Fast, not investor Stripe
“Having Stripe as an investor isn't what killed our company. Having too high a burn is what killed our company. There's just no other way to put it.”
Prediction Not checkable as stated
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…”
Prediction Open · timeframe Sep 2035
Taneja: Stripe will become a $1 trillion company in 10 years
“I think Stripe's gonna be a trillion dollar company. He's gotta give it 10 years, you know, so I'm, we're, it's a compounding business that, you know, Patrick and John always say infrastructure is hard, but it also compounds, and they're sort of steadily just …”
Opinion
Harry Stebbings Argues Stripe Is Not a Good Business Due to Competition
“I don't think Stripe is a good business because you compete against ad yen and checkout and your biggest customers will compete.”
Assertion Not checkable as stated
Holland: Stripe never engaged in mob attacks or criminality against Fast
“I have never once witnessed a mob attack by Stripe or any sort of organized criminality of any type, I'll tell you.”
Prediction Open · timeframe Aug 2031
Lemkin: >51% chance OpenRouter drives 20-30% of Stripe's revenue in 5 years
“I think it'll be like the scale acquisition. It will be the start of something that gets bigger, whether this brand exists or whether even this product exists five years. I don't even think this product will exist in five years, but I think it will be, I think…”
Prediction Open · timeframe Jul 2029
Lemkin: Stripe-PayPal Acquisition Premium Will Land at Around 35%
“So it's probably just a dance from 28 to 35. And then it gets parked with advent to while they figure out antitrust and capital issues.”
Prediction Open · timeframe Jul 2029
Lemkin: PayPal's Board Will Ultimately Accept Stripe's Acquisition Offer
“The board rejected it, right? And the fact that the board rejected it means to me that they're going to accept it.”
Opinion
Tobi Lütke: Stripe is a bad proxy for IPO timing strategy
“I think they are really bad proxy for what you should be doing. Because most people aren't. So I think it's a much saner strategy to, like, do the flip to public as a minor financing.”
Disclosure
Siemiatkowski: Adyen winning Spotify forced Klarna to pivot from checkout wars
“We have been trying to compete with Stripe and Adyen for five years, and we were like losing it. Like they were just, you know, crushing us. And we were like, this is it. And Adyen had just signed with Daniel X, Spotify, my neighbor. And I was like, this is ov…”
Insight
O'Driscoll: Late-stage VC has bifurcated into sub-$400M and mega-private tiers
“There really are two different late stage businesses now. It used to be late stage was, I remember Meritech would say, beyond 10 Million is late stage, and you'd think 10 to a hundred million was quote late stage. Now, late stage is 10 to four hundred million,…”
Prediction Open · timeframe Dec 2026
O'Driscoll: Anthropic will likely IPO in 2026, but Stripe will not
“I think Stripe, least likely, take it off the table. My gut would be Antropic gets it done.”
Insight
Taneja: Private markets function like public markets for elite startups
“I think for the very best companies, private markets behave like public markets. There's a secondary market, you can liquidate, so your shareholders can take liquidity, employees can take liquidity, you have access to credit, you can do M&A, your stocks value,…”
Opinion
Taneja: Retail should get top private tech access, not bottom VC funds
“Giving people access to SpaceX and Stripe, you're not gonna regret it. It'll, it'll do right by them. You'll feel proud of it. What you don't want to do is, Take retail and put it into you know, the bottom quartile of the venture capital funds that lose money …”
Assertion Not checkable as stated
Lawson: Most of Stripe's non-core product portfolio does not drive meaningful revenue
“I have heard whispers that a lot of their product portfolio is not really contributing to the business. It really is the core business, which is, you know, pretty common. I'd say probably the same of, you know, largely the same of Twilio too, right? It's a, it…”
Prediction Not checkable as stated
Lemkin: Upcoming tech IPOs could trigger a double bubble
“We might get the next wave of IPOs that are even better very quickly, and the amount of froth that that could create in the ecosystem, the amount of just returns to LPs could create a bubble on top of a bubble, because times might just get much better in the n…”
Assertion Supported
Stripe offered nearly $1.2B to acquire Airwallex in 2018
“Essentially it's a complicated deal construct. Essentially it's eight hundred million on the cap table, and three hundred fifty million to me and my co-founders, and I think it's a fifty million dollar I think twenty-five million dollar to the employees, of th…”
Jack Zhang May 26, 2025 ▶ 1:00:51 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Prediction Open · timeframe May 2032
O'Driscoll: Four or more venture exits will top $65B in 5-7 years
“If there's not four exits, Above sixty five billion in the next five or seven years, then the people who bought Stripe, SpaceX, Databricks, OpenAI and Antropic are screwed. So I don't think they're screwed. So I think there's going to be, this trend is going t…”
Opinion
O'Driscoll: Late-stage startups staying private is a massive public policy failure
“And it's a massive public policy failure because what's happened here is this. It is more attractive for companies to stay private and access capital from GPs who are paid two and 20 plus to make those investments than it is for those same companies to go publ…”
Prediction Partly held up
Lemkin: Stripe, Figma, Chime, and Canva will IPO within 18 months
“Stripe, Figma Chime, the list of folks north of five hundred million, ok, Canva, three billion, that are gonna IPO in the next 18 months.”
Assertion Supported
Singlehurst: Stripe trades at a lower multiple than Adyen while growing faster
“Stripe is priced even, even less than Adyen. If you just look at it on a multiples basis, and it's growing quicker.”
Prediction Not checkable as stated
Stebbings: Stripe's value and internet GDP will soar via AI entrepreneurs
“I think Stripe will be massively more valuable. In a world that we now enter, because I think there will be so many people who are enabled to create stores, entrepreneurial endeavors, and will inevitably use the default of Stripe as their payments mechanism th…”
Disclosure
Sturdy: VCs passed on Stripe citing high valuation and commodity market
“When I did that deal, I remember talking to lots of other investors and the pushback would be it's in a commodity market. It's valued too high. There's not real differentiation.”
Opinion
Nejatian: Stripe-Shopify relationship is the most value-creating in software history
“And this Stripe-Shopify relationship Is likely the most value creating relationship in the history of software. It would have been Intel, Microsoft before Intel and Microsoft had had divorce is too hard a word, but had like the thing they did.”
Prediction Open · timeframe Jun 2028
Stebbings predicts Stripe will remain private for another four years
“I think Stripe will still be private in four years time.”
Opinion
Stebbings: Unbundling Stripe and competing with the Collisons is stupid
“Unbundling Stripe and going up against the Collison's Seems like a really stupid idea.”
Prediction Held up
Stebbings: Stripe and Databricks Will Not Go Public in 2024
“I don't think Stripe or Databricks will go out in 24.”
Prediction Didn’t hold up
Lemkin: Stripe will go public in 2024
“I think so. I think 2024 is the year of you might as well go public.”
Opinion
Facebook and Stripe Have Struggled to Expand Beyond Core Markets
“Whether it's like Facebook trying to enter the B to B space, whether it's Stripe trying to actually go from like developers and SME to finance teams in, in, in the enterprise. It's hard. And we actually haven't seen that much success.”
Assertion Supported
Stebbings: Ex-OpenAI and Stripe staff raise $20M on $100M valuations
“You have person leave stripe or leave open AI or hugging face, and they raise 20 on a hundred. And that's happening more and more.”
Prediction Held up
Stripe and SpaceX Will Not Go Public in 2024
“I don't expect Stripe or SpaceX to go out next year, and Databricks alone won't be enough to crack open the IPO windows.”
Prediction Partly held up
Stebbings: Tech IPO market will not re-open until H2 2025
“But I think it's going to be longer. Like, you know, it, you'll see it in the update coming out this weekend, but it's like, you know, data breaks, stripe, it's not going to be enough to actually crack open the IPO markets like we think it will be, I don't thi…”
Insight
Grimshaw: Applying Stripe's Playbook to Segment Was Detrimental
“At Segment, there was a lot of pressure, and we did also in a positive way, learn lots of lessons from Stripe, but we were very different to Stripe, even though we would develop a sole product. And too much of the Stripe lesson was Detrimental actually to bein…”
Prediction Not checkable as stated
Harlem Capital aims for consistent 3x-5x net returns over single outlier wins
“And so for us, like we're not targeting to be that one coin based outcome, that one stripe outcome, like we're saying over time, how do we get LPs to know that we can consistently generate three to five X net returns.”
Insight
Grosser: Pure product-led growth stops working beyond Series B
“So at Stripe, as an example, product-led growth, sort of like the online self-search channel was awesome for, let's call it a series A, series B company. The minute you get past that, it doesn't work anymore. You're not like, if you build it, they will come. P…”
Disclosure
Reid Hoffman passed on Stripe over valuation and regulatory payments risk
“Having been, you know, part of the five-person executive team at PayPal through its, you know, dogfight Existence of survival or death. I knew all the landmines in the payment industry. So they came to me and said, hey, we've got this deal, which is, you know,…”
Opinion
Greze: Silicon Valley hiring is no harder now than competing with Stripe at Plaid
“I don't find it crazy, honestly. Like I think when I was at Plaid and we were competing with talent for like Stripe, that felt like no harder than what I'm doing now.”
Prediction Not checkable as stated
Reyes: A massive M&A wave is coming for single-hit SaaS companies
“I won't be surprised to see a huge wave of M&A of these businesses, because they're still good businesses fundamentally, or you can make them good businesses, And they just aren't going to be, like, Stripe, or these massive things that capture fundamental piec…”
Opinion
Lemkin: OpenRouter is a niche product that conflicts with Stripe's DNA
“It's a niche, it's a wonderful niche product, but in the world of routing, Which everybody does. Databricks does. Replit does it. Lovable does it. Vercel does it. It's a niche product with two really good niches, but this is the risk to Stripe, is that they en…”
Assertion Not checkable as stated
O'Driscoll: Stripe Captures Standard 2.75% Fees Across Leading AI Companies
“They basically signed up all the AI companies that are selling shit online, right? And they shouldn't be getting anything like the money they're probably getting from the open AI and entropics in terms of interchange fees. But who's got time to optimize that s…”
Opinion
O'Driscoll: Revolut has more compounding upside than Stripe due to European TAM
“On a TAM basis, a plus or minus a hundred bill, there's just more compounding in those five hundred million exploited Europeans.”
Opinion
Lemkin: Stripe offers acceptable but mediocre acquisition prices to VC startups
“I've been on the other side of Stripe deals. They do what you would expect. They offer an acceptable but mediocre price from a venture perspective, right?”
Assertion Partly supported
O'Driscoll: Stripe's Annual Growth Rate Is Between 20% and 30%
“It's between 20 and 30, so it's not that much bigger, Jason.”
Insight
Clements: Only top 10 private tech companies can avoid IPOs
“With that said, I think that applies to like the 10 best private companies in the world. Like Databricks can do those things. Stripe can do those things. There's a lot of companies that just do need to get public.”
Opinion
Stebbings: Stripe's private status gives it an advantage over public rival Adyen
“If you look at Stripe and Adyen, I think Stripe have an inherent advantage in being private that Adyen don't have because they're public in what they can do, how aggressive they can be, how they approach product, you name it.”
Prediction Not checkable as stated
Zeev: Venture liquidity could surge in 2026-2027 driven by mega-IPOs
“By the way, that might change in twenty-twenty-six, in big way, in a big way, because there are a host of a host of huge, unprecedented size IPOs in the works now. You know, companies like SpaceX, and Stripe, and Databricks, and, you know, and others. So there…”
Assertion Supported
Stebbings: Founders Fund deployed $3B in under 12 months into mega-rounds
“Founders Fund, deploying three billion in under 12 months, but deploying it into Stripe, SpaceX, and Anduril.”