The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

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why aren't all 18 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 18 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 2029
Calacanis: Major enterprise customers will abandon OpenAI and Anthropic for open-source
“And I'll make this prediction here, that you're going to see some of the major customers Of Anthropic and major customers of OpenAI. I'm talking about the eight and nine figure customers, people spending fifty million, a hundred million a year. They're leaving…”
Jason Calacanis Jul 30, 2026 ▶ 45:09 Chip Stocks Crash, $20B Fund Margin Called, Frontier Labs: SLOW DOWN AI, Mamdani's Grocery Stores
Prediction Open · timeframe Dec 2026
Sacks: OpenAI forecasts $75 billion in exit ARR by year-end
“I think they were expecting to end the year at sixty billion of ARR. And I think they're forecasting more like seventy five billion of exit ARR.”
David Sacks Jul 24, 2026 ▶ 31:49 The Fight Over Open Source AI, Anthropic's $1.5B Payout, NYC Socialists: Evictions = Violence?
Prediction Open · timeframe Apr 2027
Chamath: Software sector P/E multiples will contract as AI degrades tech moats
“The tech sector PE is going to shrink faster, in my opinion, than the non-tech PE. And the reason is because as these companies come out, the combination of SpaceX, OpenAI, and Anthropic, all three are baking An AI technology that first and foremost will go af…”
Chamath Palihapitiya Apr 3, 2026 ▶ 31:03 SpaceX IPO, Iran War Fallout, Quantum Bitcoin Hack, The Space Opportunity
Prediction Open · timeframe Aug 2029
Chamath: OpenAI could reach a $1.5T valuation within four years
“I would probably put that at like, 500 Dow to be conservative. It's probably doubling every two years. So 500 goes to a 1,000,000,001, billion goes to two in four years, and at two billion Dow, they generate a 1th of Facebook's revenue, just to be very conserv…”
Chamath Palihapitiya Aug 22, 2025 ▶ 35:10 AI Bubble Pops, Zuck Freezes Hiring, Newsom’s 2028 Surge, Russia/Ukraine Endgame
Prediction Open · timeframe Sep 2031
Chamath: Anthropic and OpenAI IPOs will fund over $500B in charity
“The interesting thing that's going to happen post the anthropic and open AI IPOs is if you think about the amount of charitable giving or DAFs that are going to be funded by both of these two IPOs, it's going to be north of half a trillion dollars between the …”
Chamath Palihapitiya Sep 4, 2026 ▶ 41:29 GPT-6 Hits AGI? Tech Euphoria 2.0, SF Mansion Shortage, NYC Bans AI in Schools & Venezuela Oil Deal
Prediction Open · timeframe Jul 2029
Gerstner: SpaceX, Anthropic, and OpenAI will compound revenue at 30%+ annually
“I think all of these companies are gonna compound revenue at well over 30% for the next many years.”
Brad Gerstner Jul 11, 2026 ▶ 13:12 OpenAI vs Anthropic IPOs, Anthropic $3T, Zuck's Price War, China Ends Open Source?, Trump Accounts
Prediction Open · timeframe Apr 2027
Sarah Friar: OpenAI will unveil new hardware in 2026 and sell in 2027
“We're changing into a consumer substrate that I cannot tell you what it is, but by the end of this year, we will unveil it. Early next year we'll be able to buy it.”
Sarah Friar Jun 2, 2026 ▶ 14:57 OpenAI CFO Sarah Friar: IPO, AI Rivalries, New Device, and Spending $100B+ on Compute
Prediction Open · timeframe Oct 2028
Gerstner: AMD could capture $150B incremental revenue from OpenAI deal
“If it works, she's going to get a hundred and fifty billion of incremental revenue just from open AI, right? For building out five gigawatts.”
Brad Gerstner Oct 10, 2025 ▶ 47:35 Trump Brokers Gaza Peace Deal, National Guard in Chicago, OpenAI/AMD, AI Roundtripping, Gold Rally
Assertion Open · timeframe Mar 2027
Sacks: OpenAI likely trained its Sora video model on YouTube data
“I think it's pretty clear that OpenAI trained Sora using, you know, available data on the internet, and that probably included YouTube.”
David Sacks Mar 16, 2024 ▶ 27:29 E170: Tech's Vibe Shift, TikTok ban debate, Vertical AI boom, Florida bans lab-grown meat & more
Prediction Open · timeframe Mar 2029
Calacanis: OpenAI will face severe IRS scrutiny over its corporate structure
“And I think this is where OpenAI is going to get super tripped up. And I think the IRS is going to have a field day here.”
Jason Calacanis Mar 8, 2024 ▶ 14:51 E169: Elon sues OpenAI, Apple's decline, TikTok ban, Bitcoin $100K?, Science corner: Microplastics
Prediction Open · timeframe Jan 2029
Calacanis: OpenAI will pay a nine-figure settlement to New York Times
“I think it's going to be a nine figure settlement for previous stuff, and then an ongoing licensing fee in order to have the New York Times in their training data.”
Jason Calacanis Jan 6, 2024 ▶ 26:38 E160: 2024 Predictions! Markets, tech, politics, and more
Prediction Open · timeframe Apr 2028
Friar: OpenAI won't get compute from Michigan data center until late 2027 or 2028
“Like that Michigan data center in Saline, I don't think we will be getting compute out of it until probably end of 27, early 28.”
Sarah Friar Jun 2, 2026 ▶ 19:08 OpenAI CFO Sarah Friar: IPO, AI Rivalries, New Device, and Spending $100B+ on Compute
Prediction Open · timeframe Dec 2026
OpenAI aims to execute an IPO later in 2026
“OpenAI wants to IPO later this year.”
Jason Calacanis May 1, 2026 ▶ 4:10 OpenAI Misses Targets, Codex vs Claude, Elon vs Sam Trial, Big Hyperscaler Beats, Peptide Craze
Prediction Open · timeframe Apr 2029
Chamath predicts OpenAI and Anthropic must build their own data centers
“I don't see any path except they're going to have to do it themselves, and Anthropic will have to do it themselves.”
Chamath Palihapitiya Apr 17, 2026 ▶ 29:31 OpenAI's Identity Crisis, Datacenter Wars, Market Up on Iran News, Mamdani's First Tax, Swalwell Out
Prediction Open · timeframe Dec 2026
Calacanis: At least two major tech unicorns will file IPOs in 2026
“Anticipate one of the following two will file. SpaceX, Android, Stripe, Anthropic, and OpenAI. I think two of those file, and it is going to be gangbusters.”
Jason Calacanis Jan 10, 2026 ▶ 1:20:27 All-In's 2026 Predictions
Prediction Open · timeframe May 2030
Sacks: OpenAI will release a hardware device like an AI phone or pendant
“On a serious note, what I would say is maybe what this deal indicates is, I mean, obviously is that open AI is going to do something with hardware. It could be a new kind of phone that is AI first, as opposed to the wall of applications, or maybe it's like som…”
David Sacks May 24, 2025 ▶ 53:46 Bond crisis looming? GOP abandons DOGE, Google disrupts Search with AI, OpenAI buys Jony Ive's IO
Assertion Open · timeframe May 2028
Calacanis: OpenAI plans to charge $2k-$20k monthly for AI agents
“Open AI is planning to charge between two and 20 K a month for different levels of AI agencies would be basically cron jobs.”
Jason Calacanis May 3, 2025 ▶ 1:04:15 Trump's First 100 Days, Tariffs Impact Trade, AI Agents, Amazon Backs Down
Prediction Not yet assessed · timeframe Mar 2031
Chamath: OpenAI and Anthropic will adopt normalized metrics by IPO
“And by the time it goes public, both of these two businesses will have a very clean, and I suspect normalized way of telling a story so that you can actually compare.”
Chamath Palihapitiya Mar 27, 2026 ▶ 11:53 Anthropic's Generational Run, OpenAI Panics, AI Moats, Meta Loses Major Lawsuits
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