The Ledger

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Opinion
Lemkin: Strategic Arms Race M&A Waves Are Likely a VC Myth
“A couple of times I've said on the other side, I don't know that it creates such a strategic arm race that everyone just gets picked off instantly. That, that might be a VC partial myth.”
Jason Lemkin Aug 20, 2026 ▶ 15:48 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Opinion
Stebbings: AI developer tools like Cursor remain dramatically underpriced
“So no, I don't at all for Cursor or for any of the dev tools. I think it's still dramatically underpriced. When you look at Mark Benioff spending three hundred million on Anthropic, it's 3.7% of developer salaries. I think that's relatively small.”
Harry Stebbings Jul 11, 2026 ▶ 33:12 ⁠Why OpenAI and Anthropic Won't Win the App Layer | Glean Founder · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lauritsen: Claude and Cursor generate over 50% of Legora's code
“Actually, I took a look recently, and it's Claude and Cursor on the top, and there's like, I think it's like two percent between them. So they are really, really close. And then it's, you know, miles above the next engineer. So they're way above 50%.”
Jacob Lauritzen Jun 6, 2026 ▶ 10:29 Inside Legora's Tech Stack: Why Token Maxing is Failing Enterprise Startups | Legora CTO · 20VC with Harry Stebbings
Opinion
Lauritsen: Compute deficits force AI coding tools into harmful vertical integration
“Obviously they don't have enough compute. They can't train their own models. They probably have to train their own models. It's I just think it's a shame that the industry is, is vertically integrated in that way.”
Jacob Lauritzen Jun 6, 2026 ▶ 37:43 Inside Legora's Tech Stack: Why Token Maxing is Failing Enterprise Startups | Legora CTO · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Feldman says Jensen Huang overrode Nvidia lawyers to adopt AI tool Cursor
“I think what's happening is the leaders are tipping. I think even Jensen told a story that, that he was battling with his own internal lawyers around the use of, I think it was cursor, and finally he just decreed. We're gonna do it. And I think I got that righ…”
Andrew Feldman May 26, 2026 ▶ 41:08 Cerebras CEO on the Future of Data Centres, Token Costs & Memory | Should US Companies Sell to China · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Cursor deal would be the largest private venture acquisition ever
“If this deal closes in three months, This is the biggest ever privately held venture acquisition, period, full stop, end of story.”
Rory O'Driscoll Apr 23, 2026 ▶ 3:39 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Assertion Supported
Clements: Cursor cloud agent accounts for 35% of merged PRs
“You know, the cloud agent product, which was new as of like October 30th, so it's only been in market for three months, is now responsible for 35% of merged PRs in cursor.”
Miles Clements Mar 9, 2026 ▶ 5:10 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Assertion Supported
Clements: Cursor's AI agent product usage grew 15x last year
“The agent product grew 15 X last year.”
Miles Clements Mar 9, 2026 ▶ 5:07 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Assertion Contradicted
Clements: 90% of Cursor users are daily active agent users
“90% of cursor users are daily active users of the agent product.”
Miles Clements Mar 9, 2026 ▶ 5:02 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Calacanis: 60-70% of Cursor model calls use Anthropic's API
“Apparently, 60 to 70% of Cursor model calls are still using Anthropix API, okay?”
Jason Lemkin Mar 5, 2026 ▶ 1:12:29 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Calacanis: Barclays approved Cursor as its first agentic AI coding tool
“Barclays had just rolled them out. Okay. That was the first agentic coding product that was approved at Barclays.”
Jason Lemkin Mar 5, 2026 ▶ 1:08:33 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Anthropic generates roughly $1B annually from Cursor
“Right now, it's great for Anthropic to get an extra billion or so a year from Cursor.”
Jason Lemkin Jan 15, 2026 ▶ 11:16 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Prediction Not yet assessed · timeframe Nov 2030
Tunguz: Cursor will retain 75% of its users in five years
“And so as long as they're able to continue to grow, I bet they hold on, I don't know, five years from now, 75% of their audience.”
Tomasz Tunguz Nov 20, 2025 ▶ 12:36 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Disclosure
Casado: Every Single Company I Work With Uses The Cursor AI Assistant
“I would say every company I work with uses cursor, right?”
Martin Casado Jul 28, 2025 ▶ 40:53 a16z GP, Martin Casado: Anthropic vs OpenAI & Why Open Source is a National Security Risk with China · 20VC with Harry Stebbings
Prediction Open · timeframe Jul 2028
O'Driscoll: 100% of developers will buy AI coding assistants
“A hundred percent of developers are going to buy a tool like Cursor, like Winsor, because that's how development is done now, like GitHub.”
Rory O'Driscoll Jul 17, 2025 ▶ 39:51 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Cursor Is Raising Funding at Reported $28B Valuation
“I mean, Cursor are raising more money now, and I think it's a reported twenty eight billion dollars. Just going to your point on like the escape velocity that this 0.00001% have being so much more than ever before.”
Harry Stebbings Jul 3, 2025 ▶ 1:09:35 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Prediction Not checkable as stated
Harries: Traditional PMs Will Shift 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 May 23, 2025 ▶ 52:56 20VC: ElevenLabs Head of Growth on Why You Do Not Need PMs | The 7-Part Launch Playbook That Gets 700K+ Views Per Product | The Truth About CAC, Payback & Performance Marketing in AI with Luke Harries
Opinion
O'Driscoll: Microsoft Open-Sourcing VS Code Signals Relative Weakness
“If you were the developer behemoth, which was Microsoft, the fact that you have to do this now to remain relevant at a zoom out level, This is a sign of relative weakness, not absolute weakness.”
Rory O'Driscoll May 22, 2025 ▶ 1:05:22 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
Assertion Supported
Hacker: Duolingo PM built initial chess course prototype using Cursor
“He was able to build this first version just using cursor and a bunch of AI tools. And the prototype is what convinced us that we should do this.”
Severin Hacker May 19, 2025 ▶ 41:16 Duolingo Co-Founder, Severin Hacker: How AI Impacts the Future of Work and Education · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: VCs in Cursor's $10B round would sell for $30B
“I guarantee you the VCs at the ten billion dollar round will take a quick three X.”
Jason Lemkin Apr 24, 2025 ▶ 4:46 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Disclosure
Lazarte: Benchmark participated in a funding round for Cursor
“So we made, like we participated in one round of cursor.”
Victor Lazarte Apr 14, 2025 ▶ 51:57 Benchmark GP, Victor Lazarte: The 3 Traits All the Best Founders Have · 20VC with Harry Stebbings
Insight
Podjarny: Easiest AI tools fit workflows without needing complete user trust
“When you think about AI solutions as a whole, if I think kind of broader mental framework, the solutions that are easiest to adopt right now are the ones that really don't require any change in how you work today, and they just provide you with some magic, and…”
Guy Podjarny Nov 29, 2024 ▶ 10:44 Guy Podjarny: The Future of AI Software Development - What is Real & What is BS | E1232 · 20VC with Harry Stebbings
Insight
Lemkin: Runner-Up Startups Get Acquired When Number One Is Taken
“That's how number two and number three get bought. Not because there's a panic for land grab, but because I didn't get what I wanted, right? That, that, that's when you got to be really thoughtful as number two because that that's when you get bought as number…”
Jason Lemkin Aug 20, 2026 ▶ 15:13 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Assertion Supported
Lin Qiao: Almost all AI coding startups now fine-tune custom models
“In coding space, Cursor probably is one of the pioneers starting to tune their model, and now almost all coding companies tune their own models.”
Lin Qiao Jul 20, 2026 ▶ 26:38 The Open-Source AI Reality | How Token Costs Will Fall 10X & Usage Will Explode 100X | Lin Qiao
Assertion Contradicted
Stebbings: Cursor Hit $4B Valuation, Targets $6B By Year-End
“Cursor has hit four billion, and it's targeting six billion at the end of the year.”
Harry Stebbings Jun 11, 2026 ▶ 40:04 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Disclosure
Legora's engineering team uses both Cloud Code and Cursor
“It's Cloud Code, it's Cursor.”
Jacob Lauritzen Jun 6, 2026 ▶ 2:44 Inside Legora's Tech Stack: Why Token Maxing is Failing Enterprise Startups | Legora CTO · 20VC with Harry Stebbings
Disclosure
Adam Foroughi: AppLovin Engineers Mainly Use Cloud Code, With Declining Cursor Usage
“Most people are on Cloud Code. Codex is utilized as well, and Cursor less of these days.”
Adam Foroughi Apr 27, 2026 ▶ 34:06 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
Insight
Masad: Enterprise customers rarely replace AI coding tools unless they fall behind
“Cursor has done well at enterprise sales. And enterprise is a very sticky customer and once they adopt something, it has to really fall tremendously behind, perhaps like GitHub Copilot, in order for people to replace it.”
Amjad Masad Apr 25, 2026 ▶ 29:32 Replit CEO: Why the SaaS Apocalypse is Justified & Why Coding Models are Plateauing | Amjad Masad · 20VC with Harry Stebbings
Insight
Clements: AI coding leads other verticals due to quick and durable value
“The reason that I think coding has become like the vertical in AI is because it shines on both dimensions. Like you can start using cursor in an afternoon and by that evening, like you're 10 times more productive. The time to value is very short. And then the …”
Miles Clements Mar 9, 2026 ▶ 2:12 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Assertion Supported
Clements: Cursor has 2x more agent users than tab autocomplete users
“There are two times more people using agents in cursor than using the tab feature.”
Miles Clements Mar 9, 2026 ▶ 4:57 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Prediction Held up
Jerry Murdock: Cursor will pivot strategy toward autonomous AI agents
“Now, my view is, yeah, well, but that team is really smart. They've got a lot of money and a lot of customers. They've got time to embrace autonomous agents, which is what I think they'll do. And they've got shots to pivot and figure out what the next directio…”
Jerry Murdock Feb 28, 2026 ▶ 4:35 The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings
Assertion Contradicted
Tunguz: AI coding assistant Cursor operates with just 30 total employees
“You don't have a lot of ESOP dilution because total employee count is 30.”
Tomasz Tunguz Nov 20, 2025 ▶ 2:47 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Opinion
Frosst: Cursor outperforms internal Cohere coding setup right now
“Right now? No, no, no, no. Cursors built a good product. Like, they built, you know, they've done really good UX stuff, and it's cool.”
Nick Frosst Sep 1, 2025 ▶ 1:12:13 Cohere Founder, Nick Frosst: How To Compete with OpenAI & Anthropic, and Sam Altman’s AI Disservice · 20VC with Harry Stebbings
Insight
Mignot: Workflow-integrated AI tools achieve significantly higher user retention
“Especially if it's inserted inside their workflow, you know, Cursor is a good example, you know, we've made a bunch of those type of investments, then in all likelihood, even if the numbers didn't show it yet, in all likelihood, the stickiness of that product …”
Martin Mignot Aug 11, 2025 ▶ 21:40 Index Ventures Partner, Martin Mignot: Figma, Scale, Wiz: Inside Index’s Decacorn Factory · 20VC with Harry Stebbings
Disclosure
Kansu: Cursor sees higher internal adoption and output than Windsurf at Duolingo
“Because internally at Duolingo, I'm seeing way more usage and way more creation come out of Cursor.”
Cem Kansu Jun 20, 2025 ▶ 26:18 20Product: How Duolingo Build Product 10x Faster with AI | Duolingo's Biggest Lessons on Paywalls, Push Notifications and In-App Purchases | Why Small Teams are the Future of Product | Why PMs Will Become Extinct with Cem Kansu, CPO @ Duolingo
Opinion
Mohan: Cursor succeeded early by prioritizing high-quality UI/UX
“I think for them just actually, I think they took a really good approach on building high quality UI UX. And that actually proved to be what people really loved. And I think that's like very impressive that they were able to do this right off the bat.”
Varun Mohan Jun 2, 2025 ▶ 46:07 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Disclosure
Duolingo pays for any employee AI productivity tool without mandates
“We don't mandate. Duolingo is surprisingly egalitarian and bottom up, and we just say, use AI tool or use whatever makes you more productive, and we pay for it.”
Severin Hacker May 19, 2025 ▶ 11:05 Duolingo Co-Founder, Severin Hacker: How AI Impacts the Future of Work and Education · 20VC with Harry Stebbings
Insight
O'Driscoll: Lowering entry pricing for AI tools is shrewd upsell strategy
“Having tiers of pricing where you get lots of people using the base product and then escalating steps of value as you deliver more value probably is the simplified version of quote unquote value pricing in much the same way as open AI has 2202 thousand. Right.…”
Rory O'Driscoll May 1, 2025 ▶ 53:25 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Cursor, Bolt, and Windsurf struggled for years before exploding
“I mean, I know Cursor almost died, right? Bolt almost died, right? And then finally it hit for Cursor. I don't know the whole story of Windsurf. Even Windsurf was Codium before it, right? It wasn't even the same, like everyone talks about Windsurf. 90 days ago…”
Jason Lemkin Apr 24, 2025 ▶ 18:53 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Disclosure
Nayak: Harvey PMs Build Product Prototypes Using Cursor and Claude
“PMs on my team create prototypes all the time using cursor or using a Claude to show, you know, show their ideas.”
Aatish Nayak Apr 11, 2025 ▶ 26:41 20Product: How Scale AI and Harvey Build Product | Why PMs Are Wrong: They are not the CEOs of the Product | How to do Pre and Post Mortems Effectively and How to Nail PRDs | The Future of Product Management in a World of AI with Aatish Nayak
Assertion Contradicted
Stebbings: Cursor recently raised funding at a $9.6 billion valuation
“Cursor obviously just raised, I think it was a 9.6 billion dollar valuation.”
Harry Stebbings Apr 3, 2025 ▶ 8:53 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 Not publicly verifiable
Lemkin: RevenueCat doubled internal productivity using Cursor AI tools
“I, there's no question that I mean, RevenueCat, we're both an investor, did an analysis recently, and they got about 50%, two extra productivity using AI tools, about two extra productivity using Cursor and Codip.”
Jason Lemkin Apr 3, 2025 ▶ 25:13 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
Opinion
UiPath CEO Daniel Dines praises Cursor AI as a beautiful product
“But I've got really inspired by stories like Cursor AI. And my development team loves that product. It's a beautiful product built on the top of multiple LLMs, but just, it just works.”
Daniel Dines Dec 18, 2024 ▶ 1:41 Daniel Dines, UiPath CEO & Founder: Why Agents Do Not Mean RPA is F*** | E1240 · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Anthropic reaffirmed continued model supply to Cursor
“I also think Anthropic reaffirmed that they're happily continuing to supply”
Rory O'Driscoll Sep 3, 2026 ▶ 12:01 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Disclosure
Cursor is the most widely used AI tool among Shopify designers
“Inside of Shopify, the cursor is by far the most used tool in the design group.”
Carl Rivera Nov 14, 2025 ▶ 37:12 20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify
Disclosure
Mercor engineers rely heavily on Cursor, Claude Code, and Cognition
“Like, the amount of utility that our engineers get from Cursor and Cloud Code and Cognition is incredible, and same thing for-”
Brendan Foody Sep 15, 2025 ▶ 39:19 Mercor CEO & Co-Founder, Brendan Foody: How They Grew from $1M to $500M in 17 Months · 20VC with Harry Stebbings
Disclosure
Cliff Obrecht: Canva Uses Four Coding AI Tools, Led by Cursor
“We're running four coding tools at once, right? Cursor seems to be the one that's kind of leading the pack.”
Cliff Obrecht Sep 4, 2025 ▶ 13:27 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Disclosure
Harries: 20% of work is coding, written exclusively via Cursor
“So I still write code probably 20% of the time. The only code I write is through cursor, where I'm describing in the chat what I want done, and then it executes on my behalf.”
Luke Harries May 23, 2025 ▶ 53:24 20VC: ElevenLabs Head of Growth on Why You Do Not Need PMs | The 7-Part Launch Playbook That Gets 700K+ Views Per Product | The Truth About CAC, Payback & Performance Marketing in AI with Luke Harries
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