The Ledger

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Opinion
O'Driscoll: AI reverse acqui-hires are regulatory shams leaving dead target companies
“We actually, in both of those cases, that's a pure pretense to get the government off of us, right? Everyone knows both of these companies are toast because in the case of Scale AI, in theory, Meta owns 50% of it, and in theory, their business is selling to ev…”
Rory O'Driscoll Sep 11, 2025 ▶ 18:00 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Assertion Open · timeframe Aug 2028
Lemkin: Cognition mandated 80-hour weeks and laid off 30% of acquired startup
“Well, I guess today, Cognition laid off 30% of the folks they bought, and they offered to buy out all the other 200 employees. They gave them a nine-month package. They told them they either had to work 80 hours a week, six days a week in the office, or they s…”
Jason Lemkin Aug 7, 2025 ▶ 1:08:15 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Opinion
Lemkin: Windsurf was dead without access to Anthropic's Claude
“Windsurf without Claude was dead. That's why he had to find a deal that night, that weekend when OpenAI died.”
Jason Lemkin Jul 24, 2025 ▶ 8:27 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Assertion Supported
Cognition added roughly $80M in run-rate revenue in six to eight months
“Yeah, look, I don't want to get into exact numbers, but even with the windsurf deal aside, like not including that at all, we are basically, we've done roughly that as well in the last six to eight months.”
Scott Wu Jul 18, 2025 ▶ 27:28 Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 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
Opinion
Mohan: Big tech AI tools lag because employees lack existential threat
“If we had shipped the same quality product that some of these hyperscalers have shipped, we'd be out of the market a year ago, but they probably still have their jobs right now.”
Varun Mohan Jun 2, 2025 ▶ 25:04 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Opinion
O'Driscoll: Windsurf deal was amazing for Green Oaks, less so for others
“It was an amazing outcome for Green Oaks, and then increasingly less interesting thereafter.”
Rory O'Driscoll Jul 17, 2025 ▶ 13:45 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Cognition memo stated Windsurf had $82 million ARR
“The memo that Cognition sent to his employees was that they're buying an eighty-two million dollar AR business, ok?”
Jason Lemkin Jul 17, 2025 ▶ 1:26 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Opinion
Lemkin views Replit and Lovable as cheap at $2B valuations
“If I could invest in Replit or Lovable at two billion compared to Windsurf, it seems like a much better deal. Like, I think it's, I think it seems cheap.”
Jason Lemkin Jul 17, 2025 ▶ 37:37 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: Cognition could make Windsurf better in 90 days than pre-deal
“This could be better than it literally in 90 days windsurf could be better than it was before this deal. It is entirely possible. It could be a better company than it was before this deal.”
Jason Lemkin Jul 17, 2025 ▶ 22:35 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 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
Opinion
Mohan: VS Code's UI limitations held back Windsurf's product experience
“Part of the reason why we, the product experience wasn't as good actually was because we were stuck in VS code. And VS code didn't give us the UI capability to make the product much better.”
Varun Mohan Jun 2, 2025 ▶ 20:14 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 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
Prediction Not checkable as stated
Varun Mohan: Open-sourcing Windsurf front end would not harm adoption or success
“I don't think it would affect, affect much if we had to make it open source, because most of the work that it's kind of like the thing I said before, right? You know, Google is, yeah, they have a front end, but the front end is just a single box. And if they o…”
Varun Mohan Jun 2, 2025 ▶ 1:02:14 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lemkin: Virtually all growth-scale tech CEOs currently have hiring freezes
“Every CI CEO I know that's at growth scale has that isn't windsurf has some version of a hiring freeze going on, right? Even no matter unless the growth is insane and it's all you can hire, but you got to get rid of somebody, right? It's all AI first. And so i…”
Jason Lemkin May 8, 2025 ▶ 43:04 Benchmark vs a16z: Why Stage Specific Firms Win · 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 Held up
Lemkin: New thin-wrapper AI IDEs will continually emerge
“In, in six months, if these are rappers, more, a new windsurf is going to emerge. It's just an IDE on top of the same models, right?”
Jason Lemkin Jul 24, 2025 ▶ 11:25 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Assertion Supported
Cognition negotiated and signed the Windsurf acquisition over a single weekend
“Get, get to a verbal agreement on Saturday, hash out all the details and the terms and the legal on Sunday, get everything signed and done on Monday morning.”
Scott Wu Jul 18, 2025 ▶ 6:05 Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 20VC with Harry Stebbings
Assertion Supported
Cognition initiated cold outreach to acquire Windsurf on a Friday night
“We reached out cold Friday evening and our first conversation was Friday night.”
Scott Wu Jul 18, 2025 ▶ 2:04 Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 20VC with Harry Stebbings
Assertion Supported
Cognition learned of Windsurf's Google deal at the same time as the public
“We found out, honestly, on Friday, the same time everyone else did, that all of this was happening, and that this was the split, and that it was Google”
Scott Wu Jul 18, 2025 ▶ 1:20 Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Cognition acquired Windsurf with $82M revenue and $100M cash
“Stupendously good optics plus eighty two million of revenue plus a hundred million in cash plus great injury. They win.”
Rory O'Driscoll Jul 17, 2025 ▶ 23:51 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Not publicly verifiable
O'Driscoll: Kleiner Perkins made ~4x return on initial Windsurf round
“The round, the first round that Kleiner did was at four 50, probably 500 post, so four X plus or minus.”
Rory O'Driscoll Jul 17, 2025 ▶ 14:50 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Windsurf grew from $12M to $100M ARR in four months
“Their numbers, they published or the whisper numbers were roughly accurate by twelve million at the end of last year to a hundred million by April.”
Jason Lemkin Jul 17, 2025 ▶ 5:31 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Not checkable as stated
O'Driscoll: Google deal implicitly valued Windsurf's residual business at $400M
“If open AI was buying for three billion and Google buying everything for three billion and Google pleasingly is buying everything except the revenue on a hundred million bucks for 2.6 billion. Implicitly it's valuing the revenue and the hundred million and the…”
Rory O'Driscoll Jul 17, 2025 ▶ 4:49 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Opinion
Lemkin: Windsurf was hopeless before recent deal
“Windsurf was hopeless before this deal.”
Jason Lemkin Jul 17, 2025 ▶ 22:25 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Windsurf was set to raise capital at a $3B valuation
“It's worth remembering that they were about to raise money at three billion pre. Three months ago, which would have been a down outcome.”
Rory O'Driscoll Jul 17, 2025 ▶ 15:10 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Insight
Mohan: First-mover advantage stems from learning faster and discovering next ideas first
“And then two, I think it kind of boils down to what does it mean if you're first, that means you get to learn from the market faster. And that means you're first to the next idea too. Because you see where all the dead bodies are in your category.”
Varun Mohan Jun 2, 2025 ▶ 7:15 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Insight
Varun Mohan: A truly great product idea shines even in its crappiest version
“When you have a new great idea, even the crappy version of that idea is already amazing. Like, it already proved something amazing”
Varun Mohan Jun 2, 2025 ▶ 17:46 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2030
Mohan: No AI model provider will hold an untouchable monopoly
“I don't think we're anywhere near the point in which you're going to have someone who's the defining leader of having a great model and no one else can touch it for years, right?”
Varun Mohan Jun 2, 2025 ▶ 51:37 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Prediction Not checkable as stated
Mohan: Asynchronous AI agents will only handle simple coding tasks short term
“What are going to be done asynchronously remotely are things that where the task is so easy. That it can actually get it done properly. Like the complex tasks are still going to get done in windsurf in the short term, right?”
Varun Mohan Jun 2, 2025 ▶ 39:10 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Disclosure
Windsurf closed major enterprise contracts before hiring any salespeople
“Before we hired our VP of sales who was really awesome. We actually closed some very large enterprises inside the company without any salespeople, some very large enterprise.”
Varun Mohan Jun 2, 2025 ▶ 57:26 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Disclosure
Mohan: Windsurf abandoned millions in revenue to pivot to code AI
“Despite the fact that we had, we were making a couple million in revenue off the previous business.”
Varun Mohan Jun 2, 2025 ▶ 10:58 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Disclosure
Varun Mohan: Windsurf is a 100% in-person company
“We're an in-person company actually right now. Yeah, we're like a hundred percent in-person company.”
Varun Mohan Jun 2, 2025 ▶ 25:16 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Assertion Not checkable as stated
Mohan: Non-developer built apps replacing $500K in sales tools using Windsurf
“Internally at our company, we have someone who's a non-developer who leads partnerships that has used our product and built apps to replace a lot of sales tool spend, like over 500,000 dollars of sales tool spend internally.”
Varun Mohan Jun 2, 2025 ▶ 13:03 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
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
Opinion
O'Driscoll: OpenAI's $3B Windsurf acquisition makes strategic sense at 1% of valuation
“It's one percent of the market cap to play In one of the largest use cases for AI and one that, you know, the core constituency of developers loves. It just makes total sense for open AI.”
Rory O'Driscoll May 8, 2025 ▶ 2:44 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
Assertion Partly supported
Lemkin: Greenoaks backed Codium before the team pivoted entirely to Windsurf
“When green Oaks doubled down on windsurf, it was codium, which essentially the company abandoned three months ago. Every, every engineer was repurposed to build a better version of cursor called windsurf.”
Jason Lemkin May 1, 2025 ▶ 1:02:20 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: Major AI labs will inevitably acquire an AI coding app
“If they don't do if they don't do Winsurf now, the line of other coding apps outside the OpenAI office is going to go around the frickin' block. And at some point, someone's gonna buy something.”
Rory O'Driscoll Apr 24, 2025 ▶ 7:50 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Prediction Not checkable as stated
Mohan: Technical-adjacent non-engineers will use Windsurf to build software
“As the technology gets better and better, people that are technical adjacent are going to be using Windsurf as well. And we're already seeing this, by the way, at some of the companies.”
Varun Mohan Jun 2, 2025 ▶ 32:10 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Insight
Mohan: Startups win no awards for doing the wrong thing longer
“One of the weird things about startups is that you don't win an award for doing the same wrong thing for longer.”
Varun Mohan Jun 2, 2025 ▶ 4:26 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
What-if
Varun Mohan: Windsurf should have pivoted to code AI three months earlier
“I still beat myself over the head on why did we not pivot from the GPU virtualization to the code AI company three months earlier? I think we had the signals, but we waited until the companies we were working with were starting to go belly up before we actuall…”
Varun Mohan Jun 2, 2025 ▶ 5:22 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Prediction Not checkable as stated
Mohan: Windsurf prioritizes 10x-ing developers over serving non-engineers
“So I think we're focused on the former. We're focused on the former and a consequence of that is the latter, right? Because the technology underneath is capable of doing that, but the focus is definitely the former.”
Varun Mohan Jun 2, 2025 ▶ 14:29 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Disclosure
Mohan: Windsurf skips early Figma design stages when building apps
“Internally right now, when we build apps, we're not very, very quickly going to Figma at the very beginning if the app can be built Very fast inside.”
Varun Mohan Jun 2, 2025 ▶ 35:14 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Assertion Not checkable as stated
Windsurf's custom AI model processes hundreds of billions of tokens daily
“And now it processes hundreds of billions of tokens of code a day, that single model. And it's running on our own GPUs.”
Varun Mohan Jun 2, 2025 ▶ 29:50 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Assertion Not checkable as stated
Varun Mohan: Over 50% of internal R&D projects at Windsurf fail
“Probably 50% of the things that we try inside the company or more actually fail.”
Varun Mohan Jun 2, 2025 ▶ 16:02 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 20VC with Harry Stebbings
Disclosure
Over 50% of Windsurf's revenue comes from enterprise customers
“Probably of our total amount, it's like over 50% is, is, is actually enterprise.”
Varun Mohan Jun 2, 2025 ▶ 30:37 Windsurf CEO & Co-Founder, Varun Mohan: AI's Biggest Acquisition to Date! · 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: AI coding startup Windsurf operates 100% in-office
“I know windsurf's a hundred percent in the office.”
Jason Lemkin May 1, 2025 ▶ 1:27:12 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
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