The Ledger

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why aren't all 112 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 5 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 Not checkable as stated
Ramaswamy: ChatGPT Users Will Not Switch to DeepSeek
“You're not going to switch from ChatGPT to DeepSeq. It's a product. It's not a model.”
Sridhar Ramaswamy Feb 10, 2025 ▶ 0:17 Sridhar Ramaswamy, CEO @Snowflake: Deepseek is Not a Threat to OpenAI & OpenAI Beats Anthropic|E1258 · 20VC with Harry Stebbings
Prediction Not checkable as stated
The era of no-code software is slowly ending due to AI
“The era of no code, of things that we can, humans can do without engineering resources, it's slowly winding down. And if it's in chat, GBT, man, I'm just worried.”
Jason Lemkin Aug 12, 2026 ▶ 10:10 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Prediction Open · timeframe Aug 2029
Anthropic will IPO soon after pulling ahead of OpenAI's ChatGPT
“They will go public because this is peak brass ring moment, and you know, you could argue the trends in 27 are tougher. You've pulled ahead of ChatGPT, so just put a nail in the entropic pit, right? You've pulled ahead of ChatGPT comfortably, OpenAI, to a poin…”
Rory O'Driscoll Aug 12, 2026 ▶ 44:59 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Prediction Not checkable as stated
Zinman: ChatGPT and Claude won't win enterprise AI orchestration
“I don't think that ChatGPT or Gemini on Tropic are going to do it, because going back to my the second theory that we discussed, you know, of course, you know, people are buying a Tropic Claude, they're buying ChatGPT, but it's not a tool where you work with a…”
Eran Zinman Mar 2, 2026 ▶ 32:20 Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman · 20VC with Harry Stebbings
Assertion Supported
Flanagan: ChatGPT scrapes 1,500 web pages for every single referral visit
“Six months ago, it was 250 pieces of content scraped, and they give you one visit back. Today, it's 1500 pieces of content scraped, and they give you one visit back.”
Kieran Flanagan Jul 11, 2025 ▶ 26:31 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
Opinion
O'Driscoll: Legal AI startup Harvey is ChatGPT in a law costume
“Harvey isn't some breakthrough in legal AI. It's chat GPT with a law costume.”
Rory O'Driscoll Jun 26, 2025 ▶ 0:06 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Opinion
Hacker: Many edtech companies are 'homework cheating' businesses hit by ChatGPT
“When ChatGPT came out, one of the first killer use cases for it was homework cheating, for the lack of a better term, okay? So if you were in the homework cheating business, That was devastating. That was really bad. So, so some of our, I'm not going to name t…”
Severin Hacker May 19, 2025 ▶ 29:13 Duolingo Co-Founder, Severin Hacker: How AI Impacts the Future of Work and Education · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2030
Lemkin: Competitors will never catch ChatGPT's revenue lead
“ChatGPT has pulled away. You cannot catch it. No matter what anybody says, you will never catch that revenue.”
Jason Lemkin Apr 24, 2025 ▶ 3:37 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Opinion
Feldman: ChatGPT was a UI invention, not a technical innovation
“ChatGPT was not really a technical innovation. It was a user interface invention.”
Andrew Feldman Mar 24, 2025 ▶ 19:12 Andrew Feldman, Cerebras Co-Founder and CEO: The AI Chip Wars & The Plan to Break Nvidia's Dominance · 20VC with Harry Stebbings
Assertion Partly supported
Osika: Lovable's 85% month-one retention outperforms ChatGPT
“We have month one retention that's better than ChatGPT's month one retention on paying customers, and so it's about 85%.”
Anton Osika Mar 5, 2025 ▶ 32:31 Anton Osika, Co-Founder and CEO @ Lovable: Hitting 85% Day 30 Retention - Better than ChatGPT · 20VC with Harry Stebbings
Opinion
Ramaswamy: Anthropic Lags OpenAI Due to Model-Only Focus
“There's a reason why Anthropic hasn't done as well because it operates sort of at The model level. It's all of the additional things that go into ChatGPD that I think has staying power.”
Sridhar Ramaswamy Feb 10, 2025 ▶ 0:23 Sridhar Ramaswamy, CEO @Snowflake: Deepseek is Not a Threat to OpenAI & OpenAI Beats Anthropic|E1258 · 20VC with Harry Stebbings
Opinion
Sivulka: ChatGPT is a poor product that acts like a calculator
“I don't even think ChatGPT is a really good product. It's like a calculator. It's got the technology in there encapsulated in a very simple form. But it's not a product that, like in Excel, that lets you just build whatever you'd like with it.”
George Sivulka Jan 22, 2025 ▶ 10:53 George Sivulka, Co-Founder & CEO @Hebbia: The Future of Foundation Models | E1250 · 20VC with Harry Stebbings
Insight
Shulman: Empty text box UI is wrong for most AI products
“They did every AI company a huge disservice because everybody thinks that just like empty text box is now the right interface, and it is for ChatGPT, and it is incorrect for basically everything else.”
Mikey Shulman Jan 10, 2025 ▶ 39:11 Mikey Shulman, CEO @Suno: The Future of Music, What is Gonna Happen? | E1244 · 20VC with Harry Stebbings
Prediction Open · timeframe Aug 2034
Cahn: ChatGPT Is Now a $3.4 Billion Revenue Business
“Definitely OpenAI. I mean, OpenAI has a brand, it has consumer distribution, it has product market fit with ChatGBT, which is a 3.4 billion dollar revenue business now. I think ChatGBT will definitely be around. Yeah, I think a bunch of the others will too for…”
David Cahn Aug 5, 2024 ▶ 1:11:13 David Cahn: Why Servers, Steel and Power Are the Pillars Powering the Future of AI | E1186 · 20VC with Harry Stebbings
Assertion Open
Uber president's biggest fear is ChatGPT routing rides purely by price
“I just interviewed the president of Uber. What is his single biggest fear? It's actually the disaggregation of UI or the removal of UI where you say, I want a car, and ChatGPT automatically routes you to Lyft, Uber or another provider based on price.”
Harry Stebbings Aug 12, 2026 ▶ 13:56 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Prediction Not checkable as stated
Nitski: Robotics adoption will scale like driverless cars, not ChatGPT
“Yeah, I think so, but I think it might play out similar to driverless cars, where it's really hard to scale physical things as opposed to software, so it might be more of a, more of like a Waymo robo-taxi-cruise type moment than a ChatGPT moment, but I think t…”
Osvald Nitski Jul 25, 2026 ▶ 1:01:56 Mercor Head of Product on Revenue Concentration from Frontier Labs
Opinion
Stebbings: ChatGPT Is Already Better Than the Majority of Doctors
“I think OpenAI and ChatGPT is a lot better than the majority of doctors at this point, actually.”
Harry Stebbings Jul 13, 2026 ▶ 45:12 Wix Founder: Will Base44 Win the Vibe-Coding Wars? | The Truth About the Economics of Vibe-Coding · 20VC with Harry Stebbings
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
Assertion Supported
Acharya: 75% of public SaaS companies raised prices post-ChatGPT
“I looked at the data this morning, and if you look at SaaS, public market SaaS companies, 75% have raised prices since ChatGPT was released.”
Anish Acharya Feb 9, 2026 ▶ 5:36 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Opinion
O'Driscoll: Advertising is inevitable for ChatGPT to fund free users
“And the only way consumers get free stuff is if you want ads. So there's no choice. So I think it's kind of a, it's inevitable.”
Rory O'Driscoll Jan 22, 2026 ▶ 46:08 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Prediction Didn’t hold up
O'Driscoll: OpenAI Will Capture All Ad-Buying Value Natively Without Ad-Tech
“So I think for the paid ads, all the value that's going to be captured is going to be captured by OpenAI, and there's not going to be a optimization engine.”
Rory O'Driscoll Jan 22, 2026 ▶ 57:40 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Assertion Supported
Stebbings: ChatGPT usage dropped 22% after Google released new Gemini models
“Since the new Gemini models came out, you've had a 22% drop in ChatGPT usage.”
Harry Stebbings Jan 15, 2026 ▶ 24:28 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Assertion Supported
Calacanis: ChatGPT monthly user growth has slowed to single digits
“If you look at the numbers, the growth is down to single digits. Like, it's just, it is empirically true on any source. The growth is down to single digits on monthly growth.”
Jason Lemkin Dec 18, 2025 ▶ 16:35 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
Prediction Held up
Rory O'Driscoll: ChatGPT will succeed without destroying Google Search
“The likely outcome for me is ChatGP continues to build this compelling consumer product, can command differentiated market, while at the same time Google search does not quote unquote go to zero.”
Rory O'Driscoll Nov 27, 2025 ▶ 30:30 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Prediction Not checkable as stated
Randle: ChatGPT will be the dominant consumer app for 5 years
“Like there's just no way that it's not going to be the most important kind of consumer destination over the next five years and consumer app over the next five years.”
Everett Randle Nov 10, 2025 ▶ 14:59 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Contradicted
O'Driscoll: ChatGPT ended the 2022 VC market correction within a year
“In the context of anyone playing this business from 2010 on, there has never been a period of longer than a year where there's been a substantive correction or a curtailment of capital. The only year would have been 22, twenty-three-ish, and God bless ChatGPT …”
Rory O'Driscoll Oct 23, 2025 ▶ 1:10:20 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Insight
O'Driscoll: LLMs face higher regulatory liability than social platforms
“We didn't write the content. We're just trans, you know, we're just a connection mechanism. It's other people's content. And what's super clear on chat GPT is you are writing the content. So for things like, you know, advice that goes wrong, medical stuff, may…”
Rory O'Driscoll Oct 23, 2025 ▶ 1:18:30 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Opinion
Lloyd: Google faces a classic innovator's dilemma in AI
“I think Google's a risk. Like, I would never have said that five, 10 years ago. I find myself using ChatGPT more and more, and so I think they have big innovators dilemma problem.”
Zach Lloyd Oct 17, 2025 ▶ 7:36 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
Insight
O'Driscoll: ChatGPT's real threat to Meta is stealing user attention
“The big picture comment is if you spend two hours a day on chat GPT, that's two hours a day that you are not spending on Facebook and we live and die on our attention.”
Rory O'Driscoll Oct 2, 2025 ▶ 56:59 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
Insight
O'Driscoll: AI search threatens media sites, not product companies
“In fairness, the kind of, the SEO, I think you have to distinguish between people like Canva where they have a product to sell and they're totally happy to sell it via ChatGPT, and then media companies where the only product they have is their content, where i…”
Rory O'Driscoll Sep 4, 2025 ▶ 1:04:07 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: ChatGPT generates 70% to 80% of OpenAI's revenue
“ChatGPT, which is, you know, 70, 80% of the revenue dollars when they shipped, they didn't even think it was a major release.”
Rory O'Driscoll Aug 14, 2025 ▶ 6:21 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Disclosure
Stebbings invested $12M in Lovable, citing consumer brand leadership
“Why did I write a twelve million dollar check into Lovable? I think very much in the same way that ChatGPT owns the consumer brand for that front end OS for the modern consumer, I think Lovable's reached escape velocity with the consumer brand in this space”
Harry Stebbings Jul 17, 2025 ▶ 45:18 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: xAI will fail to displace ChatGPT's dominant consumer mindshare
“The market's already been taken and maybe it gets some share of it, but I don't think, yeah, I don't think you can build as big a thing. I don't think you can build, I don't think you can displace ChatGPT at scale in the minds of the consumer, which is 80, 90%…”
Rory O'Driscoll Jul 17, 2025 ▶ 1:09:50 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Partly supported
Lemkin: ChatGPT Holds 85% Market Share and Continues Growing
“And listen, I mean, open, I mean, chat GBT has like 85% market share, right? And growing, right?”
Jason Lemkin May 15, 2025 ▶ 45:02 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinda: OpenAI and horizontal LLMs will dominate most AI model categories
“At the fundamental LLM level, I think the horizontal, you know, GPT may just win most categories. The same way that Google won search reasonably read large, except maybe kayak for travel. I suspect, I think OpenAI and JGPD win most of the LLM type categories”
Fabrice Grinda May 1, 2025 ▶ 41:39 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
Opinion
Socher: Other consumer LLM apps are rounding errors compared to ChatGPT
“Consumers, once you're really famous and you cross that threshold of just like being well known, being the default for a lot of people, all the other LM apps companies are almost rounding errors to ChatGPT.”
Richard Socher Apr 18, 2025 ▶ 10:10 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
Assertion Supported
Lazarte: U.S. is winning the AI race against China by all measures
“I think by all, like, I think by all measures, like the U.S. Is winning. If you look at, like, all the AI products, like, ChatCPT is the most used, ah, AI assistant in the world, and sure, you can talk about, like, oh, how about DeepSeq and this and that, but …”
Victor Lazarte Apr 14, 2025 ▶ 44:39 Benchmark GP, Victor Lazarte: The 3 Traits All the Best Founders Have · 20VC with Harry Stebbings
Prediction Held up
Ramaswamy: ChatGPT Will Remain the Primary Consumer AI Entry Point
“On the consumer side, I know you disagree, I think ChatGPT is getting to be that entry point, and so if I were a betting person on the consumer side, To the extent that there are variations in models and specializations I think that'll include to the incumbent…”
Sridhar Ramaswamy Feb 10, 2025 ▶ 46:57 Sridhar Ramaswamy, CEO @Snowflake: Deepseek is Not a Threat to OpenAI & OpenAI Beats Anthropic|E1258 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Riparbelli: OpenAI's next GPT release won't match ChatGPT's cultural impact
“I think it'll come out and it'll be like, good. It'll be definitely better than the previous things. But I think most people will not like care that much because the bar for someone to really care that much is incredibly high, right?”
Victor Riparbelli Jan 15, 2025 ▶ 36:19 Victor Riparbelli, CEO @Synthesia: OpenAI vs Anthropic vs X.ai - Who Wins and Why | E1246 · 20VC with Harry Stebbings
Opinion
Taylor: ChatGPT is the most important tech product of the past decade
“At least my understanding why it has a sort of a goofy name is it was a research preview that turned out to be the most important product of the past decade, you know, and I think that, you know, one of the things I think about is, wow, what an important mecha…”
Bret Taylor Oct 2, 2024 ▶ 30:29 Bret Taylor: Why Pre-Training is for Morons & Companies Will Build Their Own Software | E1209 · 20VC with Harry Stebbings
Insight
Gomez: AI Value Currently Accrues at the Chip and Application Layers
“Value is accruing beneath, like at the chip layer, because everyone is spending insane amounts of money on chips to build these models in the first place, and then above, at the application layer, where you see stuff like let's say ChatGPT, which is charged on…”
Aidan Gomez Aug 19, 2024 ▶ 15:10 Aidan Gomez: What No One Understands About Foundation Models | E1191 · 20VC with Harry Stebbings
Opinion
Luan: Chatbots and AI Agents Are Becoming Distinct Technology Species
“I kind of think that chat bots like chat GPT and stuff and agents are kind of becoming different species of technology a little bit, right? Like I think they'll be useful in very different ways and what they need to be used for super different, right?”
David Luan Jun 24, 2024 ▶ 15:11 David Luan: Why Nvidia Will Enter the Model Space & Models Will Enter the Chip Space | E1169 · 20VC with Harry Stebbings
Assertion Supported
ChatGPT's Release Forced Google Onto Red Alert After Delaying Transformers
“Google Brain invents the kind of transformer and publishes it, and it's kind of bouncing around as kind of a research project, and it takes OpenAI developing it, scaling it, and releasing it as ChatGPT for Google to go on red alert and go, oh my god, we should…”
Reid Hoffman Jun 10, 2024 ▶ 32:02 Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Srinivas: In two years, Perplexity's differentiation from ChatGPT will be obvious
“And there's like some competition for mindshare and users, but even that will like be pretty clear, like two years from now, you're not going to keep asking how is perplexity different from chat GPT. Today you are, but two years from now, I don't think so.”
Aravind Srinivas Jun 5, 2024 ▶ 52:12 Aravind Srinivas:Will Foundation Models Commoditise & Diminishing Returns in Model Performance|E1161 · 20VC with Harry Stebbings
Prediction Open · timeframe May 2029
Levie: ChatGPT will not replace dedicated language tutoring apps like Duolingo
“I don't think ChatGPT itself is going to become a language tutor. I think it'll have the full capability to be a language tutor at the model level.”
Aaron Levie May 22, 2024 ▶ 28:00 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
Mathrubootham: Generative engine optimization will replace SEO for software marketing
“Now we have generative engine optimization, right? Like if a lot of people are going to go to ChatGPT and ask about, hey which software should I use? How do we make sure that the AI models are trained to tell customers that Freshworks is a great product? So, s…”
Girish Mathrubootham Apr 19, 2024 ▶ 13:32 Girish Mathrubootham: Biggest Product and Pricing Lessons from Scaling to $597M in ARR | E1142 · 20VC with Harry Stebbings
Opinion
Bastian Lehmann: OpenAI may struggle to build successful products beyond ChatGPT
“It's a fantastic research company is how I would describe OpenAI. I think it remains to be seen if they can launch extremely successful products other than a chat based a chat GPT.”
Bastian Lehmann Apr 8, 2024 ▶ 1:00:12 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Insight
Will Wu: Prompt engineering AI startups lack long-term defensibility
“I do think the hype is warranted, but I'll caveat by saying I wouldn't just invest in every single generative AI based company that comes across my radar. I think there's a lot of entrepreneurs right now who have a great idea maybe for how to apply Something l…”
Will Wu Feb 2, 2024 ▶ 48:10 Will Wu: Top Five Product Lessons from Creating Snapchat "Discover" and "Chat" | E1111 · 20VC with Harry Stebbings
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