The Ledger

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why aren't all 97 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 7 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

Prediction Held up
Lemkin: A $100 billion startup exit will happen within a year
“The big exits will solve it, right? The whizzes and the, I mean, we thought whizz was big. Now we have cursor. Now I'm going to win the bet of a hundred billion dollar exit in the next year.”
Jason Lemkin Apr 30, 2026 ▶ 1:05:12 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Assertion Not checkable as stated
Murdock: Baseten's Deal With Cursor Yielded Scale but Little Profit
“I think cursor was pretty smart in the base 10 contracts from last year with cursor. I don't think there was much profit in it for a base 10. They just got revenue and they got scale from it, but they didn't get a lot of earnings.”
Jerry Murdock Aug 22, 2026 ▶ 9:39 The AI Bubble WILL Burst | Should we be fearful of Chinese Open-Source | Jerry Murdock
Opinion
Stebbings: The $1 Billion Valuation Has Become the New Series A Standard
“I think a billion dollar valuation is the new series, eh? And you're like, whoa, Harry, whoa, whoa, kiddo, calm down, listen to the facts. We used to do a fifty million post and hope it would become a 1,000,000,020 x, without dilution, blunt. Now, you enter at…”
Harry Stebbings Aug 7, 2026 ▶ 33:58 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Opinion
O'Driscoll: SpaceX has far more differentiation than Cursor's IDE wrapper
“There is a lot more fucking differentiation in putting rockets in the sky than there is making forking an open source IDE and running it on top of Claude code.”
Rory O'Driscoll Apr 23, 2026 ▶ 20:05 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Cursor doubled revenue from $1B to $2B in three months
“Cursor announces their movement from a billion to two billion in revenue in, in three months. Rumors of secondary round being done at fifty billion.”
Harry Stebbings Mar 5, 2026 ▶ 1:03:10 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Opinion
Jerry Murdock: Most companies view AI coding assistant Cursor as obsolete
“Most of the companies, their view, as they've told me, is cursor is obsolete.”
Jerry Murdock Feb 28, 2026 ▶ 0:00 The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Cursor could lose half its revenue this year to Claude Code
“I think there's a chance that Cursor loses half of their revenue this year with the cannibalization of them by claw code.”
Harry Stebbings Feb 9, 2026 ▶ 11:26 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Assertion Not checkable as stated
Harry Stebbings says Claude Code cannibalized Cursor's business overnight
“Claude Code, Has cannibalized a lot of Cursor's business overnight and everyone's canceling Cursor.”
Harry Stebbings Jan 31, 2026 ▶ 17:41 20Growth: How Wix Built a $100M Marketing Machine | Why LTV is BS and Why Time Return On Investment is the Most Important Metric | How to 10x Your Growth: What is the Next Great Channel with Omer Shai, CMO @ Wix
Opinion
Lemkin: Anthropic Solved AI Coding; Cursor and Replit Just Grafted On
“Claude figured that out. Cursor didn't figure this out. Replit and Lovable and Bolt didn't figure it out. I can tell you the story. Claude figured it out. Anthropic, the guys, you know, once they quit OpenAI, they figured it out and everyone grafted on this, i…”
Jason Lemkin Dec 4, 2025 ▶ 1:02:50 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Opinion
Shlomo: AI software building is not a winner-take-all market
“Software building as a category is gonna grow insanely fast. I think our notion from the previous age of venture capital where a winner takes it all is wrong. And I think this category is going to be so big that everybody will take a niche at some point.”
Maor Shlomo Nov 24, 2025 ▶ 55:30 Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings
Assertion Partly supported
Mercor scaled from $1M to $500M run rate in 17 months
“We scaled the business from one to five hundred million in the last 17 months, which is the fastest revenue growth of all time. One month faster than Cursor's time.”
Brendan Foody Sep 15, 2025 ▶ 0:17 Mercor CEO & Co-Founder, Brendan Foody: How They Grew from $1M to $500M in 17 Months · 20VC with Harry Stebbings
Opinion
Lemkin: Vibe coding TAM is 50x to 100x bigger than developer tools
“The TAM really is much bigger than cursor. It's much bigger than cursor or windsurf. It could be like 50 or a hundred times bigger.”
Jason Lemkin Jul 17, 2025 ▶ 39:13 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Insight
Greze: AI wrappers face broken economics paying suppliers 70% margins to compete
“And the problem with the frontier is, I have zero pricing power at the frontier. And I mean, I think this is what happened to Cursor, right, at the end. It's like, you can have huge market share and customers love you and everything, but if you're paying your …”
Jean-Denis Greze Sep 7, 2026 ▶ 52:14 Town vs Instinct vs GrokBot | Why the AI Assistant Market Is Not a Bubble
Assertion Supported
Stebbings: Cursor just sold for $60 billion after only four years
“Cursor just sold for sixty billion dollars after four years.”
Harry Stebbings Aug 29, 2026 ▶ 54:39 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Prediction Not checkable as stated
Reyes: Enterprises will hesitate to adopt Cursor due to model lock-in
“However, I do think for that, most of the enterprises are going to have a second look at the idea of sort of seeding their software development lifecycle to a provider who is one, likely to be model locked, and two has an existing sort of history or pattern of…”
Eno Reyes Aug 29, 2026 ▶ 37:43 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Prediction Not checkable as stated
Reyes: Cursor will struggle to stay model-independent and orient around Grok
“It's going to be a very hard story to become Model independent, or rather stay model independent when you're attached to a model lab. So they're going to want to push Grok, the models, the products are going to become increasingly oriented around Grok, and tha…”
Eno Reyes Aug 29, 2026 ▶ 36:58 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Opinion
Cursor Is the Best AI Agent Startup Outside Sequoia's Portfolio
“It's probably cursor. One, they're in one of the most important markets. But second, where there was a lot of chatter around AI wrappers, they were the first company to really understand that you could post train models and actually be, go deeper into the stac…”
Julien Bek Aug 24, 2026 ▶ 1:18:55 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Insight
O'Driscoll: Price hardly matters in winning VC deals unlike PE buyouts
“In venture deals, if you're in the right thing, it almost doesn't matter what you paid. You see cursor for details, see open router for details, right? This is the exact opposite. This is fine, precise financial engineering. If you're wrong by 20%, 30% on pric…”
Rory O'Driscoll Aug 20, 2026 ▶ 50:40 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Prediction Not checkable as stated
Lemkin: Cursor's Origin Will Replace GitHub's Workflow Within Months
“I mean, cursor launched origin, right? Which would bought graphite or whatever. It's going to become a GitHub entire workflow replacement in a couple months, right?”
Jason Lemkin Aug 20, 2026 ▶ 1:04:07 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Assertion Partly supported
Stebbings: SpaceX closes $60B takeover of Cursor
“SpaceX closes the sixty billion dollar all stock takeover of cursor, minting thousand X returns for the likes of Alipartovia Neo. Open AI startup fund is a mega winner who invested six to eight million dollars very early, which Rory, I thought of you when you …”
Harry Stebbings Aug 20, 2026 ▶ 1:12 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Assertion Not checkable as stated
O'Driscoll: OpenAI and Anthropic training data spend exceeds non-Cursor AI app revenues
“There's probably more money being spent on training data for the foundation models, you know, the Mercosurge and that, than pretty much any app company outside of Cursor. In fact, probably the sum of all the apps companies outside of Cursor, right, you know, a…”
Rory O'Driscoll Jul 23, 2026 ▶ 38:16 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Prediction Open · timeframe Jun 2029
Stebbings: Cognition and Factory will thrive due to model independence
“I respectfully disagree, and that's why I actually think both Cognition and Factory will do very well, because they're model independent”
Harry Stebbings Jun 6, 2026 ▶ 37:17 Inside Legora's Tech Stack: Why Token Maxing is Failing Enterprise Startups | Legora CTO · 20VC with Harry Stebbings
Opinion
O'Driscoll: Anthropic is a better standalone AI bet than xAI
“Would I prefer, on a standalone foundation model, lab bet, would you prefer to own Entropic than X.AI plus Cursor plus the Frankenstein of Twitter? Yeah, you would, but at least it's a full-stack story now.”
Rory O'Driscoll Apr 23, 2026 ▶ 19:16 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2036
O'Driscoll: Cursor Deal Will Be Private M&A Peak for Next Decade
“I think this will stand as the high watermark of private M&A for a decade.”
Rory O'Driscoll Apr 23, 2026 ▶ 24:00 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: xAI's $60B Cursor deal may not close due to unmet milestones
“I wouldn't be surprised if it doesn't close, because I think there are a big milestone that needs to be hit. The Cursor needs to make progress, and maybe I'm wrong.”
Jason Lemkin Apr 23, 2026 ▶ 3:03 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Assertion Partly supported
O'Driscoll: Cursor loses money despite generating $4M per employee
“Cursor does four million per employee. Salesforce does 700 per 700,000 per employee. Oh, Cursor must be more efficient. Well, it turns out Salesforce has 30% operating margins and Cursor's losing a lot of money. Why? Because they spend a whole ton on tokens, r…”
Rory O'Driscoll Apr 16, 2026 ▶ 1:11:26 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Opinion
Reyna: OpenAI, Anthropic, and Cursor are enterprise AI's only blue-chip brands
“I think, like, the two companies that today have been able to make it is, or three companies, if you want, OpenAI, Anthropic, full respect for them, Cursor. The three of them, I think, for me, are, like, Cursor has killed enterprise unbelievably well. Yeah, th…”
Carles Reina Apr 11, 2026 ▶ 38:46 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
Prediction Held up
Clements: Cursor will build specialized coding models for enterprise users
“Cursor is going to build specialized coding models that are going to serve specialized coding tasks, especially for a lot of enterprise users.”
Miles Clements Mar 9, 2026 ▶ 7:23 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Disclosure
Clements: Accel's initial Cursor investment was priced at 4-5x year-end ARR
“Actually, this company is growing so quickly that on a multiples basis, you know, our first investment was at like four times, five times year-end ARR.”
Miles Clements Mar 9, 2026 ▶ 9:13 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Prediction Not checkable as stated
Acharya: AI dev tools Cursor, Codex, and Claude Code will all grow
“The desire and demand for software, both to make it and to consume it, is dramatically more than the supply that we have today, and I think there is a developer and developer adjacent archetype for whom Cursor is going to be perfect, Codex as an app, Codex as …”
Anish Acharya Feb 9, 2026 ▶ 12:04 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Assertion Supported
Anish Acharya: Early AI market leaders from 2023-2024 have maintained their dominance
“In this product cycle, what's actually interesting is a bunch of the early leaders from 23 and 24 have maintained their lead. You know, we talked about Harvey. That's a really impressive company. You know, Gamma is a really impressive company. You know, Cursor…”
Anish Acharya Feb 9, 2026 ▶ 1:15:26 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Prediction Not checkable as stated
Harries: AI will push product managers into growth or product engineering
“Yeah, I think PMs move to either growth, so you combine the PM role with marketing, and depending on your size and how strong your engineers are, you do more or less of the PM, or many PMs will actually move towards product engineering, which is they're somewh…”
Luke Harries Jan 11, 2026 ▶ 51:54 20Growth: The $6.6B Growth Engine Behind ElevenLabs | Why ElevenLabs Do Not Have PMs | The 7 Part Launch Playbook to Crush All Launches with Luke Harries, Head of Growth @ ElevenLabs
Prediction Open · timeframe Dec 2028
Jason Calacanis: Cursor will maim Figma and SaaS incumbents by lowering NRR
“I think the bigger risk for so many vendors is that it maims Figma... HubSpot and box and even anthropic using it, they don't leave, they renew, they don't buy as many seats, right? Because the team is also using cursor, but of course they don't churn. The log…”
Jason Lemkin Dec 18, 2025 ▶ 47:15 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
Insight
Shlomo: AI apps can fix low margins by training proprietary models post-distribution
“Kerser came out, I think it was two weeks ago, or maybe a few weeks ago with their own model, right? Composer. And this is like an, a nice way to like think about strategy of those types of businesses. So think about Kelsa, right? I don't know how the margins …”
Maor Shlomo Nov 24, 2025 ▶ 43:29 Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings
Opinion
Lloyd: Autocomplete has stronger enterprise PMF than agentic AI
“In the enterprise market, I actually think the thing that has most product market fit is like autocomplete. Which is not the sexiest type of AI. So it's not agentic AI. It's like cursor's original product or even co-pilot.”
Zach Lloyd Oct 17, 2025 ▶ 17:37 20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp
Prediction Not checkable as stated
Lloyd: Prompt-driven development, not autocomplete, is the future of software
“I don't think autocomplete is the future. So I don't feel like I'm like seeding competitive ground here to Cursor. The future is more like developed by prompt.”
Zach Lloyd Oct 17, 2025 ▶ 30:19 20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp
Prediction Open · timeframe Jul 2030
O'Driscoll: Anthropic will not cut off Cursor from model access
“I think it'd be very stupid of Entropic to just cut off a, probably the largest customer at the knees. And I, and the one thing, they're not stupid. So I don't think they will.”
Rory O'Driscoll Jul 24, 2025 ▶ 18:00 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Assertion Not checkable as stated
Tenev: AI generates the majority of new code at Robinhood
“We've moved from, you know, GitHub Copilot, which is an auto-complete system, to Cursor, and now things like Windsurf, where, I mean, nearly all of the code is, is written by AI, and the adoption rate within engineering for us is, You know, close to a hundred …”
Vlad Tenev Jul 14, 2025 ▶ 3:20 Robinhood Founder & CEO, Vlad Tenev: Robinhood’s $85BN Resurgence & Tokenizing SpaceX & OpenAI · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lemkin: AI spending is actively cannibalizing legacy SaaS budgets
“If cursor did almost half a million, half a billion dollars in revenue in the same time, It sucked up an enormous amount of that dollar that would have gone to Okta and Salesforce, right? Five hundred million. That's a lot in that period of time, right? So AI …”
Jason Lemkin Jun 12, 2025 ▶ 49:50 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2030
Mohan: Non-developer AI coding tools and developer AI IDEs will converge
“I think with time, they're going to need to build out more and more tunables, more and more ways to configure the product with time. But I think for us, if we can deeply understand code, like large code bases, it'll naturally follow that with very little effor…”
Varun Mohan Jun 2, 2025 ▶ 14:52 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
What-if
Stebbings: Anthropic and Cursor Venture Investments Would Have Saved FTX
“When you look at FTX, their positions in Anthropic and Cursor actually would have saved them if they had the time to prove that out and they hadn't done the commingling. That would have saved their financial performance with those two investments alone.”
Harry Stebbings May 15, 2025 ▶ 18:23 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Assertion Partly supported
Lemkin: HubSpot engineers using Cursor are pushing out too many features
“Literally I talked with Yamini wrong on from HubSpot last week. Okay. This is HubSpot. She said now at HubSpot there with cursor, they are pushing out so many features. They can't put them into production anymore. She wasn't kidding. They're there. It said the…”
Jason Lemkin May 8, 2025 ▶ 1:09:51 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
Opinion
Lemkin: Destroying Cursor and Windsurf is existential for Microsoft's GitHub
“Co-pilot versus Cursor and WinServe is number friggin' one on their gotta kill list for Microsoft, number one. It's all over. It is existential for that, for GitHub to destroy them.”
Jason Lemkin May 1, 2025 ▶ 55:09 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
Opinion
Torres: Cursor's Fast Revenue Growth Is Fragile Due to Low Switching Costs
“The cursors and all that stuff, like you can easily switch to like windsurf and you can switch to this and you can go back to copilot and like, so that revenue could disappear. This is a brand new phenomenon and we do not know how it plays out.”
Elias Torres Mar 21, 2025 ▶ 49:08 Elias Torres, Co-Founder and CEO @ Agency: What No One Tells You About Selling Your Company · 20VC with Harry Stebbings
Prediction Not checkable as stated
Saper: B2B software vendors will survive AI-enabled internal code generation
“I believe that B to B software, I believe software vendors have an important role in the future, even if the bolts of the world, the curses of the world make coding cheap, easy, in some cases free.”
Jake Saper Mar 10, 2025 ▶ 50:26 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
Cursor and OpenAI Were Doomed to Clash Over AI Coding Economics
“Cursor and OpenAI were on a collision course already competitively because As we've discussed over and over again, and as I repeat every Monday in my partner meeting, coding was the model load, right, for LLMs, and Cursor is the dominant coding app, and OpenAI…”
Rory O'Driscoll Sep 3, 2026 ▶ 12:21 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Opinion
OpenAI Made the Right Strategic Decision in Cutting Off Cursor
“My guess is this was the right move for open AI. Like you go from someone that was both a partner and a competitor, right. And keeping them honest to someone that's now a direct competitor. And if it's only five percent anyway, Sam's losing no money. There's n…”
Jason Lemkin Sep 3, 2026 ▶ 13:55 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Opinion
Reyes: Enterprises View Cursor as an IDE, Not a Development Strategy
“I don't think that anyone really perceives cursor to be their primary enterprise software development strategy as much as an IDE, which is I think still a great business because they're still going to get a lot of usage, but that sort of is how I see them.”
Eno Reyes Aug 29, 2026 ▶ 1:23:46 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
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