The Ledger

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Insight
Lemkin: Autonomous AI agents could reduce Salesforce and HubSpot to dumb databases
“If the agent can run 24 seven autonomously, take all your data and build all the analytics, build all the dashboards, run autonomously out of it then your data can flow between apps and you won't even care where it lives and all the fears about headless become…”
Jason Lemkin Jul 2, 2026 ▶ 1:12:27 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Opinion
Lemkin: Anthropic's Claude holds no competitive advantage for most workflows
“As workflows expand to do everything, as agents do more, they will pick the LLM, and I see no competitive advantage to Claude for most workflows.”
Jason Lemkin Apr 30, 2026 ▶ 4:21 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Disclosure
Lemkin: Two of my portfolio investments from last year are now obsolete
“I have two investments I made last year. I love them. Those products no longer have a reason to exist today because of Claude.”
Jason Lemkin Feb 26, 2026 ▶ 20:13 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
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
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
Opinion
Sivulka: Salesforce will survive AI disruption due to human switching costs
“I think that ultimately I don't think they are. I think that I think that Salesforce Like, has built, again, like, a very, very, very sticky network effect with people, and people are the shifting function at the end of the day. It's not a technology problem. …”
George Sivulka Jan 22, 2025 ▶ 1:04:10 George Sivulka, Co-Founder & CEO @Hebbia: The Future of Foundation Models | E1250 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Franceschetti: AI spending as share of engineering budgets will fall net-net
“I think there will be two vectors in the opposite direction. The usage will increase. And so the five percent will become 50%, but the cost will go down. And so net net, I think it will go down.”
Matteo Franceschetti Sep 12, 2026 ▶ 20:01 Labour, Engineering, Social Media, GrokBots, Cybercabs: 7 Predictions for How AI Changes the World
Insight
Frankel: Embedded, Mission-Critical SaaS Workflows Will Survive AI Disruption
“The more embedded you are, like the more difficult you are to dispense because real time, Thousands, billions of orders are being run in your system, or like mission critical biotech research is being run in your system. The more embedded you are, I think the …”
David Frankel Aug 7, 2026 ▶ 43:30 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Assertion Not checkable as stated
Arora: Over half of AI compute goes to loss-making consumer use
“I think more than half of the compute is going to feed the consumer, which is a fundamentally loss-making entity right now. Like, I don't think any of the frontier models make any money in trying to get you and me to use ChatGPD or, you know, Claude or Gemini …”
Nikesh Arora Jun 22, 2026 ▶ 20:11 Nikesh Arora on the Frontier Model Problem: Breadth vs Depth | The Future of Token Costs · 20VC with Harry Stebbings
Insight
Lindquist: Standalone AI models cannot replace GTM platforms at team scale
“Have you ever tried to like get a hundred people to do something different, to change something, to iterate in the same way that you iterate? Good luck. Because we're still humans, right?”
Becca Lindquist May 2, 2026 ▶ 1:04:47 Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
Opinion
Masad: Frontier AI pricing pressure is low with only two true competitors
“I think part of it is we're living in a world where the true frontier models is actually just between GPT-V and Claude. And so there's no, not a lot of pricing pressure.”
Amjad Masad Apr 25, 2026 ▶ 26:57 Replit CEO: Why the SaaS Apocalypse is Justified & Why Coding Models are Plateauing | Amjad Masad · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: AI labs will throttle subscriptions and hike prices for compute
“You're going to see some compute rationally, people are going to start allocating tokens to the highest, effectively the highest bidder. You're going to see a lot of throttling, like, you're going to see these plans, like, that's why they shot Sora. You're goi…”
Rory O'Driscoll Apr 16, 2026 ▶ 54:11 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Assertion Not checkable as stated
Midha: Claude and Gemini Failed Badly at Physical Science Benchmarks
“About a year ago, as an example, I realized there was a lot of talk about models being good at physical physics and chemistry, AI for science. And I was a visiting scientist at the applied Physics department at Stanford. And we started benchmarking these model…”
Anjney Midha Apr 14, 2026 ▶ 5:36 The Early Days of Anthropic & How 21 of 22 VCs Rejected It | The Four Bottlenecks in AI | Anj Midha · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: Software firms failing to own category AI agents will be maimed
“No, I think just people are going to be maimed even more than they think if they don't own the agents in your category. You've got to own the agents in your category. And whether those agents are owned by a startup, or whether some version of that agent can be…”
Jason Lemkin Feb 26, 2026 ▶ 18:06 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Disclosure
Siemiatkowski: Claude performed a task no single human could do
“This is actually the first time I felt that AI could do something that humans couldn't.”
Sebastian Siemiatkowski Feb 16, 2026 ▶ 1:09:47 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Bolt Outsourced Its AI Agent to Claude and Fell to Third
“So even Bolt, which was the early leader, they're now just at number three, They don't even have an AI agent anymore. They've outsourced it to Claude.”
Jason Lemkin Nov 13, 2025 ▶ 27:45 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Assertion Not checkable as stated
Franceschetti: Eight Sleep spends millions per month on Claude
“No, it's lower than that, but it's still in the millions.”
Matteo Franceschetti Sep 12, 2026 ▶ 19:13 Labour, Engineering, Social Media, GrokBots, Cybercabs: 7 Predictions for How AI Changes the World
Assertion Supported
Katz: Anthropic chose ClickHouse after asking Claude for a recommendation
“If you ask Anthropic how they chose to use ClickHouse, they'll tell you they asked Claude, what technology should we use for this specific observability use case? And Claude suggested ClickHouse.”
Aaron Katz Aug 31, 2026 ▶ 16:34 ClickHouse CEO: AI Margins Need to Improve | Revenue Concentration Should be a Concern
Disclosure
Nitski: Mercor team is shifting away from Figma to Claude
“To be honest, I let the team do whatever is best for them, and this is a trend I've just observed amongst almost everybody, is that cloud design has done a great job. People really like using it, it's easy to use, and we've just had a natural movement towards …”
Osvald Nitski Jul 25, 2026 ▶ 18:01 Mercor Head of Product on Revenue Concentration from Frontier Labs
Assertion Not checkable as stated
Curative Reduced Physician Credentialing Time To 12 Hours Using Claude
“And that used to take us two to three months on average, and cost about 50 dollars. We have now built in-house an agent that runs on, on Claude, that does this end-to-end, and it goes to the website, it verifies the license, it goes and reads the transcripts, …”
Fred Turner Jul 18, 2026 ▶ 42:28 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
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
Assertion Supported
Lemkin: WSJ data shows Claude enterprise share jumped to 48%
“The wall street journal today published the market shares in the enterprise for open AI, Claude, Gemini and Grok. Grok is a rounding error going to the prior conversation, right? It's not making any progress. But everything is so multimodal that it said Gemini…”
Jason Lemkin May 14, 2026 ▶ 15:14 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Assertion Partly supported
Calacanis: Anthropic delayed Claude launch before ChatGPT over safety concerns
“In fact, they refused to release Claude before ChatGPT because he didn't think it was safe. They only released Claude under, under duress.”
Jason Lemkin Mar 5, 2026 ▶ 3:58 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Assertion Supported
Emberikos: Nearly all AI agents except Claude adopted OpenAI's agents.md standard
“Pretty much every agent except Claude uses agents.md, which is awesome.”
Alexander Emberikos Feb 21, 2026 ▶ 23:15 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: LLMs will become the primary way consumers buy products
“I think we are way under discussing the power of discovery in LLMs. I think this is the way we will buy everything in the future as we are embedded in LLMs. Well, I don't know why I would use anything else other than the best of ChatGBT or Claude or Gemini to …”
Jason Lemkin Jan 22, 2026 ▶ 49:51 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Assertion Not checkable as stated
Alex Schultz: AI chatbot adoption fundamentally changes user search behavior
“When people are using those, their behavior in search changes dramatically.”
Alex Schultz Sep 5, 2025 ▶ 28:18 20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader
Prediction Not checkable as stated
Lemkin: AI platforms like Lovable will build defensible software wrappers
“And so lovable and friends are going to build these thicker and thicker wrappers because they have to do security, right? They have to contain the AI. They're torturing Claude to do things it doesn't want to do. Claude wants to lie and seek out things and shar…”
Jason Lemkin Jul 24, 2025 ▶ 9:34 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Opinion
Flanagan: Claude's app builder is inferior to Lovable and Replit
“I don't see Claude as being as good as Lovable or Repplet. I think it's much more between Repplet and Lovable”
Kieran Flanagan Jul 11, 2025 ▶ 1:11:17 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
Disclosure
Lemkin: I run all legal work for SaaStr through Claude before legal counsel
“Well, all the legal work I do, both for the fund and for Saster Inc., everything, I run through my AI and Claude, and then I run it by my counsel to see if it's correct.”
Jason Lemkin Jun 26, 2025 ▶ 27:59 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Assertion Not checkable as stated
Socher: Anthropic under pressure due to Claude's low consumer market share
“Anthropic has a lot more pressure to keep building the best models because Claude is so much smaller in terms of market share for the consumer app.”
Richard Socher Apr 18, 2025 ▶ 9:58 20VC: Foundation Models: Who Wins & Who Loses | How Economies and Labour Markets Need to Change in a World of AI | China vs the US in an AI Race: What You Need to Know | Rich Socher, Founder @ You.com
Opinion
Nayak: Claude Is Empathetic for Personal Advice, Whereas ChatGPT Is Not
“Claude does. Jatchputi doesn't. It's not as empathetic.”
Aatish Nayak Apr 11, 2025 ▶ 51:01 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
Disclosure
Krieger: Anthropic is actively rebuilding Claude's core user experience
“We have an active effort right now around tearing down some of that and rebuilding the core UX to just feel good. It doesn't feel great right now.”
Mike Krieger Mar 3, 2025 ▶ 54:57 Mike Krieger, Instagram CoFounder & Anthropic CPO: Where Will Value Be Created in an AI World?|E1265 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Levie: Users Will Wire Into Specific AI Models Rather Than Abstracted Selection
“I don't think you're going to have complete commoditization of sort of the personality of the models for the sort of style and the response to the point where then, you know, if you're a user, you know, any given response could come from Gemini, Versus GPT-IV …”
Aaron Levie May 22, 2024 ▶ 5:29 Aaron Levie: How the Business Model of SaaS Changes Forever & Startups vs Incumbents:Who Wins?|E1155 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Franceschetti: Consumers will trust frontier AI bots with payments within two years
“With these bots, it's still a bit, you know, sometimes you feel uncomfortable, but I think in a year or two from now, our bots, particularly bots from frontier models, like from X, OpenAI, and Claude, you will start trusting them soon.”
Matteo Franceschetti Sep 12, 2026 ▶ 30:30 Labour, Engineering, Social Media, GrokBots, Cybercabs: 7 Predictions for How AI Changes the World
Insight
Foody: AI data training requires domain experts who are AI power users
“And it's more about people that actually are very acclimated to the frontier of AI, because it's the people that understand, that both have the expertise in oncology, but also are power users of ChatGPT or Claude that are able to find where the model makes mis…”
Brendan Foody Jun 1, 2026 ▶ 26:03 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: SaaStr will not switch internal AI apps from Claude to OpenAI
“It runs on Sonnet three. I mean sorry, four, seven, and maybe a little bit of Opus. There is no way we're going to switch the model. This is dialed in. It works. Now we're going to have to deal with QA when it goes to four, eight and five. There's a little bit…”
Jason Lemkin Mar 26, 2026 ▶ 12:06 Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
Assertion Supported
Green: Most regulated companies block access to Claude and ChatGPT
“Most big companies that are, like, financially regulated, you can't even go on to Claude or ChatGPT. Like, you can't even, like, get on the system to do work.”
Mitchell Green Mar 7, 2026 ▶ 19:51 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Opinion
Siemiatkowski: Claude serves as an unbiased advisor rather than a user-pleaser
“Claude to me is very different. Claude is like my intelligent advisor and I am trying to push and I say to Antropic all the time, like, I don't want an AI that tell me you're so great, man. Like, I understand that that's, like, a nice experience, and some peop…”
Sebastian Siemiatkowski Feb 16, 2026 ▶ 56:34 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
Prediction Not checkable as stated
O'Driscoll: AI agent activity could boost Claude's Q1 run rate by $200M
“This is probably good for, this is probably good for a couple of hundred million on Claude's run rate for Q one.”
Rory O'Driscoll Feb 5, 2026 ▶ 1:30:40 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Disclosure
Lemkin: Conducts Vendor Discovery on Claude Rather Than Google
“I do my vendor discovery on Claude and a little bit on Google. That's when I want to find a new tool or a new product, that's where I start. I start with LLMs”
Jason Lemkin Jan 22, 2026 ▶ 46:37 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Disclosure
Bendov: Gong operates 40 to 50 proprietary AI models alongside Claude and OpenAI
“First, like we have a lot of our own models. We have probably 40 or 50 Gong models. And then we use, like, Claude, we use, like or Sonnet, we use, like OpenAI.”
Amit Bendov Sep 12, 2025 ▶ 27:20 20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong
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 Supported
Mollick: Claude can design and iterate playable app prototypes in one prompt
“You could tell Claude come up with 30 ideas for a product to serve, you know, market X, then rate them all on quality and feasibility level. Then create, this is one prompt, by the way, then create a playable prototype of the interface for the application. The…”
Ethan Mollick Jul 31, 2024 ▶ 40:50 Ethan Mollick: Why OpenAl Abandons Products, The Biggest Opportunities They Have Not Taken | E1184 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Jain: Glean combines ChatGPT, Claude, and Gemini into one product
“Today the way to think about Glean is that first, it's a super set of JetGPD, Cloud, Gemini, All of those combined into one product experience.”
Arvind Jain Jul 11, 2026 ▶ 2:55 ⁠Why OpenAI and Anthropic Won't Win the App Layer | Glean Founder · 20VC with Harry Stebbings
Assertion Supported
Yamashita: Figma Make explicitly uses Anthropic's Claude AI model
“Today, like, if you take a screenshot of Figma Make, you see, like, oh, it's being powered by Claude, and it's like, okay, like, no questions. You know exactly where the code is being generated from.”
Yuhki Yamashita May 16, 2025 ▶ 30:05 20Product: Figma CPO on How Figma Builds Products: What Works, What Does Not | How Figma Does Testing and Product Reviews | The Future of Design, Engineering and Product with Yuhki Yamashita
Disclosure
Nayak: Uses Claude and Replit Agent Mode for Rapid Prototyping
“I currently use actually Claude for prototyping because I actually don't want to deal too much with the very nuanced stuff that Windsor for Cursor has. And so I ended up using Claude and then I've actually been using also Replit agent mode. The reason being is…”
Aatish Nayak Apr 11, 2025 ▶ 47:10 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
Disclosure
Rangan trained AI on 16 quarters of HubSpot earnings transcripts
“And I've literally fed it with the last 16 quarters of earnings script.”
Yamini Rangan Mar 17, 2025 ▶ 42:47 Yamini Rangan, CEO @ HubSpot: How HubSpot Competes Against Salesforce · 20VC with Harry Stebbings
Disclosure
Osika: Anthropic's Claude is Lovable's main workhorse for code generation
“We use all of OpenAI's models, Google, Gemini, and the main workhorse is Anthropic's cloud model for writing the code.”
Anton Osika Mar 5, 2025 ▶ 36:23 Anton Osika, Co-Founder and CEO @ Lovable: Hitting 85% Day 30 Retention - Better than ChatGPT · 20VC with Harry Stebbings
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