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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.”
Vlad Tenev Jul 14, 2025 ▶ 0:19 Robinhood Founder & CEO, Vlad Tenev: Robinhood’s $85BN Resurgence & Tokenizing SpaceX & OpenAI · 20VC with Harry Stebbings
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.”
Dom Holland Apr 13, 2022 ▶ 15:35 20VC Exclusive: Fast's Domm Holland on What Really Happened at Fast? Were they really Burning $10M per Month? Where did Bolt Succeed Where Fast Did Not? What is It Really Like To Have Stripe Invest in your Company?
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…”
Jason Lemkin Aug 27, 2026 ▶ 1:10:21 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
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 …”
Hemant Taneja Sep 22, 2025 ▶ 1:32:52 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
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.”
Harry Stebbings Jul 17, 2024 ▶ 43:30 Pedro Franceschi: What Brex Needs to do to be a Public Company | E1178 · 20VC with Harry Stebbings
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.”
Dom Holland Apr 13, 2022 ▶ 15:24 20VC Exclusive: Fast's Domm Holland on What Really Happened at Fast? Were they really Burning $10M per Month? Where did Bolt Succeed Where Fast Did Not? What is It Really Like To Have Stripe Invest in your Company?
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…”
Jason Lemkin Aug 20, 2026 ▶ 26:03 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
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.”
Jason Lemkin Jul 23, 2026 ▶ 1:02:58 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
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.”
Jason Lemkin Jul 23, 2026 ▶ 58:36 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
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.”
Tobi Lütke May 4, 2026 ▶ 12:16 Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada · 20VC with Harry Stebbings
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…”
Sebastian Siemiatkowski Feb 16, 2026 ▶ 20:37 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
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,…”
Rory O'Driscoll Jan 8, 2026 ▶ 1:09:49 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
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.”
Rory O'Driscoll Dec 22, 2025 ▶ 1:02:17 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
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,…”
Hemant Taneja Sep 22, 2025 ▶ 1:08:15 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
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 …”
Hemant Taneja Sep 22, 2025 ▶ 1:19:59 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
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…”
Jeff Lawson Sep 11, 2025 ▶ 1:15:38 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
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…”
Jason Lemkin Aug 21, 2025 ▶ 6:53 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
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…”
Rory O'Driscoll May 22, 2025 ▶ 31:41 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
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…”
Rory O'Driscoll Apr 17, 2025 ▶ 1:05:31 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
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.”
Jason Lemkin Apr 3, 2025 ▶ 50:30 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
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.”
Peter Singlehurst Mar 19, 2025 ▶ 52:21 Peter Singlehurst: Lessons from Turning Down Stripe, Coinbase and Losing Money on Northvalt · 20VC with Harry Stebbings
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…”
Harry Stebbings Mar 14, 2025 ▶ 37:02 20Product: How to Design and Build Products in a World of Agents | Why AI Will Kill Many SaaS Products | What Products Will Thrive and Die in a World of 100M Developers with Matt Biilmann, Co-Founder and CEO @ Netlify
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.”
Laela Sturdy Aug 16, 2024 ▶ 36:29 Laela Sturdy: Life Inside Alphabet's $7BN Growth Fund | E1190 · 20VC with Harry Stebbings
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.”
Kaz Nejatian Aug 14, 2024 ▶ 43:45 Kaz Nejatian: How Shopify Built a $90BN Business to Last 100 Years | E1189 · 20VC with Harry Stebbings
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.”
Harry Stebbings Jun 3, 2024 ▶ 52:23 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
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.”
Harry Stebbings Apr 17, 2024 ▶ 43:40 Vickie Peng: Why the Best Product People Actually Build Less Product? | E1141 · 20VC with Harry Stebbings
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.”
Harry Stebbings Feb 19, 2024 ▶ 26:26 Roger Ehrenberg: Why VC Returns Will Get Worse & Why LP Incentive Structures are so Broken | E1117 · 20VC with Harry Stebbings
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.”
Jason Lemkin Jan 4, 2024 ▶ 53:55 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
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.”
Geoff Charles Dec 6, 2023 ▶ 40:25 Geoff Charles: How To Hire Product Teams & Increase Product Velocity | E1091 · 20VC with Harry Stebbings
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.”
Harry Stebbings Oct 27, 2023 ▶ 2:54 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
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.”
Harry Stebbings Oct 20, 2023 ▶ 20:33 20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open
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…”
Harry Stebbings Oct 18, 2023 ▶ 11:25 Beezer Clarkson: Are LPs Open for Business & Why Do LP Incentive Mechanisms Need to Change? | E1073 · 20VC with Harry Stebbings
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…”
Miles Grimshaw Sep 18, 2023 ▶ 56:41 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
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.”
Henri Pierre-Jacques Jun 24, 2022 ▶ 7:38 Henri Pierre-Jacques: How I Founded Harlem Capital; Our $134M Fund | 20VC #901 · 20VC with Harry Stebbings
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…”
Jeanne DeWitt Grosser Mar 9, 2022 ▶ 25:05 20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St
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,…”
Reid Hoffman Dec 7, 2020 ▶ 33:43 20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset
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.”
Jean-Denis Greze Sep 7, 2026 ▶ 33:32 Town vs Instinct vs GrokBot | Why the AI Assistant Market Is Not a Bubble
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…”
Eno Reyes Aug 29, 2026 ▶ 58:53 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
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…”
Jason Lemkin Aug 20, 2026 ▶ 22:39 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
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…”
Rory O'Driscoll Jul 29, 2026 ▶ 1:12:27 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
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.”
Rory O'Driscoll Jul 29, 2026 ▶ 1:18:59 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
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?”
Jason Lemkin Jul 29, 2026 ▶ 1:14:28 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
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.”
Rory O'Driscoll Jul 23, 2026 ▶ 55:50 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
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.”
Miles Clements Mar 9, 2026 ▶ 45:30 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
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.”
Harry Stebbings Mar 2, 2026 ▶ 48:06 Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman · 20VC with Harry Stebbings
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…”
Oren Zeev Feb 2, 2026 ▶ 39:30 Oren Zeev: Why AI Growth Expectations Are BS & Won't Last? Why GPs Shouldn't Tell LPs Their Strategy
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.”
Harry Stebbings Dec 22, 2025 ▶ 17:13 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
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