The Ledger

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why aren't all 32 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 3 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 Open · timeframe Jul 2027
SpaceX, Anthropic, and OpenAI IPOs will exceed all past tech IPOs combined
“We're going to see three trillion dollar plus IPOs over the coming months. It's never happened before. The value of SpaceX plus Anthropic plus OpenAI will be more than all the other tech IPOs combined ever.”
Jason Lemkin Jul 8, 2026 ▶ 45:45 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
Prediction Not checkable as stated
Lemkin: Four Upcoming Tech Mega-IPOs Will Eclipse All IPOs Since 2000
“SpaceX, Anthropic, OpenAI, we'll add in Databricks, we'll have Arsan, one of the co-founders here in about half an hour after this. That's going to create more market value, more value, and more wealth than every other IPO since 2000.”
Jason Lemkin Jun 11, 2026 ▶ 13:41 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
Prediction Held up
Lemkin: Anthropic Will Reach $50B in Revenue in Four Years
“Anthropics revenue is like nothing we've ever seen. Okay. It'll be at fifty billion in less than four years or four years plus or minus.”
Jason Lemkin Jun 11, 2026 ▶ 27:35 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
Prediction Not checkable as stated
Ripabelli: 99.9% of OpenAI and Anthropic users will not stay on DeepSeek
“But I think in two months, I think, 99.9% of the people who are using Anthropic and OpenAI today is going to go back to using their products, not DeepSeek's model.”
Victor Riparbelli Jan 31, 2025 ▶ 13:54 The Future of AI in B2B SaaS: Insights from Synthesia and Theory Ventures. Hosted by Jason Lemkin
Prediction Open · timeframe Dec 2032
O'Driscoll: OpenAI and Anthropic Revenues Won't Match AI CapEx Until 2031-2032
“The stunning thing is it takes until 2031 or 2032 before The revenue from those two companies surpasses the total capex.”
Rory O'Driscoll Jul 15, 2026 ▶ 6:56 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Prediction Not checkable as stated
O'Driscoll: Foundation model makers will probably continue capturing the delta value
“The truth is they are the apex predator of this distribution. They are the guys who have taken the value, the delta value, and probably will continue to do so under those forecasts.”
Rory O'Driscoll Jul 15, 2026 ▶ 11:26 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Insight
O'Driscoll: VCs Are Hedging Between Foundation Models and SaaS
“No one knows the answer and most VCs are betting both ways. They're chucking a bunch of money in at a modest 300 or six hundred billion pre at Antropic. And at the same time, they're doing a whole bunch of investments that only make sense if in fact there is r…”
Rory O'Driscoll Jul 15, 2026 ▶ 14:46 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Opinion
Masad: Replit's memory compaction algorithm beats Claude's
“We actually think ours is much better than Claude and many others on the market.”
Amjad Masad Jun 9, 2026 ▶ 6:24 What Agents That Actually Work Look Like Right Now with Replit's CEO and Founder
Assertion Not checkable as stated
Dorfman: Self-serve drives 54 percent of new Anthropic enterprise logos
“54. 54% of our new enterprise logos have come through the self-serve funnel in 2026.”
Eleanor Dorfman May 20, 2026 ▶ 7:29 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Prediction Open · timeframe Jan 2031
Lemkin: Anthropic and OpenAI Will Reach Trillion-Dollar Valuations
“Anthropic isn't topping out at a billion. OpenAI isn't topping at a billion. They're topping at a trillion.”
Jason Lemkin Jan 2, 2026 ▶ 14:04 AI + B2B in 2026: Find the Tailwinds or Get Left Behind | Jason Lemkin
Disclosure
Anthropic Uses Shadow Targets Instead of Traditional Sales Quotas
“No quotas at Anthropic today. That might change. Everything in this space, I feel like as soon as you say it, it's already outdated, but just shadow targets today.”
Kelly Loftus Sep 5, 2025 ▶ 12:34 Anthropic, Cursor, FaL & Bessemer Venture Partners: The Realities of Scaling AI
Insight
Tamir: Direct OpenAI or Anthropic APIs outperform cloud intermediary platforms
“Using a first party solution with say OpenAI or with Anthropic is going to have different performance, different latency than if you do it via an intermediary, like a cloud. So you maybe get some simplicity by not having to onboard different vendors and differ…”
Mike Tamir Apr 26, 2024 ▶ 14:53 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Opinion
O'Driscoll: OpenAI and Anthropic Prove Software Is Not Dead
“What they don't mean is software dead because OpenAI and Entropic are software, and they are most definitely not dead.”
Rory O'Driscoll Jul 15, 2026 ▶ 14:13 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Disclosure
Dorfman: Anthropic sales forecasts are largely run by Claude
“What's most important is forecasts are being largely run by Claude and then inspected and reviewed by managers.”
Eleanor Dorfman May 20, 2026 ▶ 12:53 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Opinion
Lemkin: Top AI Companies Rely on Traditional SaaS GTM Leaders
“If you look at who is running go-to-market at some of the hottest AI companies from open AI to anthropic on down, you'll see folks that spoke at Saster in the past few years. You will see the exact same people essentially running the same playbooks they ran be…”
Jason Lemkin Oct 5, 2025 ▶ 3:09 Is The Classic GTM Playbook Really Dead? with SaaStr CEO and Founder Jason Lemkin
Assertion Supported
Dholakia: Dario Amodei Revealed Model Coding Abilities Were Emergent, Not Designed
“Dario said on that panel, That they discovered that the models could code. Like it wasn't a design requirement. It wasn't an intentional, the model. It had the capability. It figured out how to do it.”
Sameer Dholakia Oct 11, 2024 ▶ 13:40 State of the Cloud: The Cloud AI Era with Bessemer Venture Partners
Disclosure
Anthropic encoded top rep behaviors into five Claude skills for AEs
“And we built a sales plugin that documented what our top reps do and turned them into five skills that we included in Claude that every rep uses every single day.”
Eleanor Dorfman May 20, 2026 ▶ 20:57 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Insight
Dorfman: Rapidly scaling sales headcount cannot absorb sudden vertical demand
“Even if we were prepared to hire an onboard and three X or four X or five X the sales team, You simply can't absorb that number of bodies at the pace that we needed to absorb them in order to deliver against the demand and in order to deliver a positive custom…”
Eleanor Dorfman May 20, 2026 ▶ 1:16 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Assertion Not checkable as stated
Anthropic's enterprise demand went vertical after Claude Opus 4.6 launch
“And it wasn't until December of 20, 25, when things really took off. The launch of Opus 4.6 in December was a bit of a sea change for us. And we came back from what was in hindsight, An incredibly restful winter break to demand going vertical.”
Eleanor Dorfman May 20, 2026 ▶ 0:39 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Disclosure
Anthropic sales reps feed Gong transcripts into Claude Code for prototypes
“Some of our reps like to take gone calls when they've had a really good discovery call and drop them into Claude code so that Claude code can build a prototype”
Eleanor Dorfman May 20, 2026 ▶ 26:17 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Assertion Supported
Anthropic, Figma, and Cursor Use Clay for Inbound Qualification
“And this is, by the way, workflows that Anthropic, Figma, Cursor are all using play to power.”
Varun Anand Feb 11, 2026 ▶ 20:14 Going From Blobs to Billions. Clay's Co-Founder Breaks Down Inbound, Outbound, and AI-Powered Sales.
Disclosure
Anthropic Has Scaled to 1,300 Employees and 150 Go-To-Market Staff
“About 1300 at Anthropic, probably a 150 or so on the go-to-market team. So crazy scaling over the last year and a half.”
Kelly Loftus Sep 5, 2025 ▶ 11:21 Anthropic, Cursor, FaL & Bessemer Venture Partners: The Realities of Scaling AI
Insight
Mann: Knowledge Extraction Is Low-Risk AI Compared to Tool Use
“Take a portfolio approach, try some less risky use cases, like where knowledge extraction or summarization might be involved. And maybe some more risky use cases like tool use, where it's using that company's tooling, function calling.”
Ben Mann Jan 17, 2024 ▶ 7:55 How Enterprise Companies are Buying AI (or Not) with ContextualAI, Anthropic, and Glean
Assertion Not checkable as stated
Dorfman: Claude 3's coding proficiency sparked Anthropic's commercial sales acceleration
“We've had a commercial product for the last three years, but it wasn't until the Claude III family of models, when Claude started getting really good at coding, that things started to accelerate.”
Eleanor Dorfman May 20, 2026 ▶ 0:27 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Disclosure
Dorfman details the exact tech stack behind Anthropic's sales operations
“We use lean data for routing. We use clay for enrichment. Salesforce is our system of record and source of truth. We use Jira for tickets intercoms fin product. We use for Custer's customer support, as well as for sales support. I joke with the ironclad team t…”
Eleanor Dorfman May 20, 2026 ▶ 3:02 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Disclosure
Anthropic uses Claude via Slack to triage internal sales support tickets
“So we made Slack the front door. Slack comes in, tick it out. Claude does the triaging. So Claude actually co-work now does a lot of this. And that's changed for us probably in the last week since I made these slides, but co-work can check your emails and can …”
Eleanor Dorfman May 20, 2026 ▶ 18:49 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Disclosure
Anthropic uses Claude to surface six dynamic weekly coaching moments
“Every week Claude surfaces six coaching moments. And this isn't a static set of coaching based on a methodology. This is dynamic based on how the needs of our business evolve month over month.”
Eleanor Dorfman May 20, 2026 ▶ 14:34 How Anthropic's Head of Industries Built an AI-Native Sales Org from Scratch
Disclosure
Persson: Snowflake internal agents run on Cortex with Anthropic and OpenAI
“These are proprietary models based, you know, using Snowflake. Cortex, and then we're using various large language models to build these agents. That could be, you know, it could be anthropic, you know, it could be, you know, OpenAI, you know, and other models…”
Denise Persson Oct 16, 2025 ▶ 18:38 Snowflake's AI Revolution in Sales, Marketing and GTM with Snowflake‘s CMO and Founding CRO
Disclosure
Anthropic uses Claude in Slack to answer employee questions and onboard staff
“Across both the technical and non-technical org, one of the favorite use cases is the Slack channel that we spun up, and what this Slack channel does is employees can go in, ask questions. Claude is on the back end and uses to go search over our internal knowl…”
Kelly Loftus Sep 5, 2025 ▶ 18:59 Anthropic, Cursor, FaL & Bessemer Venture Partners: The Realities of Scaling AI
Assertion Not checkable as stated
Cursor Receives Pre-Release Access to Anthropic Models to Provide Coding Feedback
“Cursor has given us feedback on our models in the coding area and had access to our models before we released them and been able to actually give us feedback to meaningfully improve the user experience on both of our ends.”
Kelly Loftus Sep 5, 2025 ▶ 23:11 Anthropic, Cursor, FaL & Bessemer Venture Partners: The Realities of Scaling AI
Assertion Supported
Jensen: Intuit uses Anthropic to explain taxes to customers
“Intuit is using Anthropic to help explain what taxes you actually paid and why.”
Kate Jensen Oct 11, 2024 ▶ 19:12 State of the Cloud: The Cloud AI Era with Bessemer Venture Partners
Assertion Not checkable as stated
Mann: Large Bank Identified 500 LLM Use Cases Across Company
“One large bank that we were talking to, they said, they came to us and they said, we've, Talk to everybody in our company, and we have 500 different use cases that we want to apply large language models to.”
Ben Mann Jan 17, 2024 ▶ 4:04 How Enterprise Companies are Buying AI (or Not) with ContextualAI, Anthropic, and Glean
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