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ALL-IN Prediction Not checkable as stated
Calacanis predicts OpenAI will lose its lead and become fourth-ranked AI player
“My most contrarian belief was OpenAI loses its lead, loses its nonprofit to for-profit transition and becomes the number four player in AI. The total collapse of OpenAI is my most contrarian prediction for .”
Jason Calacanis Jan 4, 2025 ▶ 1:11:34 2025 Predictions: Tech, Business, Media, Politics!
ALL-IN Prediction Held up
Calacanis: Nvidia will decline or severely downgrade investment in OpenAI
“I think NVIDIA is not going to take their option to invest in open AI, or they're going to really downgrade at 70, 80%, and they're going to allocate it to other players.”
Jason Calacanis Dec 6, 2025 ▶ 18:35 OpenAI's Code Red, Sacks vs New York Times, New Poverty Line?
ALL-IN Opinion
Calacanis: Mark Zuckerberg is the greatest censor in human history
“His action was to be the greatest censor in the history of humanity. There's no human being who censored more humans than him.”
Jason Calacanis Jan 11, 2025 ▶ 1:08:44 LA's Wildfire Disaster, Zuck Flips on Free Speech, Why Trump Wants Greenland
ALL-IN Prediction Didn’t hold up
Calacanis: Democrats will replace Joe Biden with Gavin Newsom after first debate
“This is why I think Biden's getting hot swapped this month. You heard it here first. He's got, no, Gavin is going to be running for president. It's going to be Trump and Gavin. They are hot-swapping Biden after this first debate. Biden is going to get demolish…”
Jason Calacanis Jun 7, 2024 ▶ 28:25 DOJ targets Nvidia, Meme stock comeback, Trump fundraiser in SF, Apple/OpenAI, Texas stock market
ALL-IN Prediction Not checkable as stated
Calacanis: Trump will attempt to overturn the government again if given the chance
“Guy has no morality, and he would have overturned the government if he had the chance. And he will do it again.”
Jason Calacanis Aug 4, 2023 ▶ 1:18:57 E140: LK-99, Sclerotic establishments, Fitch downgrades US debt, Trump indicted... again
ALL-IN Opinion
Calacanis: FTC Chair Lina Khan is punishing tech for being successful
“I think she is absolutely doing Biden's bidding. With an anti-tech, anti-wealth creation, anti-capitalism, frankly, pro-union punishment. I think this is punishment for tech being too successful.”
Jason Calacanis Jul 14, 2023 ▶ 48:05 E137: Inflation cools, market rips, Ripple/MSFT beat regulators, NATO summit, cocktails of youth
ALL-IN Prediction Partly held up
Calacanis: Microsoft will release an OpenAI search engine impacting Google
“Microsoft, I think is going to release a and there's a prediction as well, a search engine with Open AI, that has a significant impact on Google's franchise.”
Jason Calacanis Dec 24, 2022 ▶ 29:33 E109: 2022 Bestie Awards Live from Twitter HQ
ACQUIRED Opinion
Calacanis: Andreessen Horowitz is a soulless index fund of venture capital
“I think they're just an index adventure. I find it quite soulless, if I'm being honest. Like, I feel like it's a giant index on venture, and I don't think that their hearts are super into it.”
Jason Calacanis Oct 4, 2022 ▶ 2:01:13 ACQ Sessions: Jason Calacanis · Acquired
Calacanis: VCs paid high legal fees specifically to dump tokens
“You set up these structures, you paid all this legal money because you knew you were going to dump. You knew you were going to clear these positions and you knew it was going to be lucrative. That's why you went through the expense instead of just raising mone…”
Jason Calacanis Jul 28, 2022 ▶ 10:33 How To Pick Startup Winners With Jason Calacanis
ALL-IN Opinion
Calacanis: Andreessen Horowitz engaged most in VC token sale flips
“That seems like the firm that did this the most is Andreessen Horowitz.”
Jason Calacanis Jun 24, 2022 ▶ 59:35 E84: Markets update, crypto collapse, Russia/Ukraine endgame, state of the podcast
ALL-IN Prediction Didn’t hold up
Calacanis: Musk will buy Twitter at a lower price by year-end
“My prediction is the Board tries to fight it. Stock collapses. Nobody thinks it's going to get done. Elon lowers his offer, and he wins it by the end of the year, and gives him a lower offer.”
Jason Calacanis Apr 16, 2022 ▶ 55:26 E76: Elon vs. Twitter
ALL-IN Opinion
Calacanis calls the fatal Capitol shooting of Ashli Babbitt a clean shooting
“Coming from a law enforcement family, I can tell you that's a clean shooting.”
Jason Calacanis Jan 8, 2021 ▶ 39:37 E16: Reflecting on the riots at the US Capitol, plus: Georgia runoffs, vaccine distribution & more
Calacanis: Tim Cook should not be CEO of Apple anymore
“If a company is storing a bunch of capital and paying you a dividend, that signals to us that you are not a bold and ambitious founder, and this is one of the big problems I have with Apple and Tim Cook, which, who I don't think should be CEO of that company a…”
Jason Calacanis Apr 14, 2020 ▶ 44:59 #81 Jason Calacanis: Intelligent Risk
20VC Opinion
Calacanis: Y Combinator teaches startup founders to be 'bullshit artists'
“What's happened now is the YC companies have a reputation of kind of being bullshit artists and that the program kind of teaches them to be bullshit artists, right?”
Jason Calacanis Aug 14, 2017 ▶ 27:36 20VC: Jason Calacanis on The 4 Questions Investors Must Ask Founders, Whether YC Have Scaled Their Process Successfully & Why Early Founder Liquidity Is Good Not Bad
ALL-IN Prediction Not checkable as stated
Calacanis: Tesla's Optimus humanoid robot will be the world's best-selling product
“Optimist will be the best selling. I think product.”
Jason Calacanis Aug 29, 2026 ▶ 6:41 Nvidia's Historic Quarter, SaaS Comeback, Bessent vs Druck, America's Debt Crisis, Cancer Vaccine
ALL-IN 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
ALL-IN Assertion Supported
Calacanis: Anthropic is destroying rare books for AI training data
“Anthropic is destroying rare books to get an edge in training data.”
Jason Calacanis Jul 30, 2026 ▶ 1:01:17 Chip Stocks Crash, $20B Fund Margin Called, Frontier Labs: SLOW DOWN AI, Mamdani's Grocery Stores
ALL-IN Assertion Supported
Calacanis: Anthropic paid $1.5B in the largest US copyright settlement
“Obviously last week we saw anthropic paid the largest copyright case in us history, 1.5 billion for seven million books. They allegedly pirated authors get 3000 each lawyers got a hundred million for that one”
Jason Calacanis Jul 30, 2026 ▶ 1:01:59 Chip Stocks Crash, $20B Fund Margin Called, Frontier Labs: SLOW DOWN AI, Mamdani's Grocery Stores
ALL-IN Prediction Not checkable as stated
Calacanis: Margin compression will derail OpenAI and Anthropic IPOs
“I believe that this is going to derail their IPOs. I'm taking it from the top. It's going to derail their IPOs. It's going to be headwinds against it because I think that they're going to have massive margin compression.”
Jason Calacanis Jul 24, 2026 ▶ 35:08 The Fight Over Open Source AI, Anthropic's $1.5B Payout, NYC Socialists: Evictions = Violence?
ALL-IN Opinion
Calacanis: AI companies should pool 10% of revenue to pay content owners
“All the AI companies should get together, take 10% of your revenue, put it in a pool, and keep paying the people and getting permission from them, so you can get updates on the content”
Jason Calacanis Jul 24, 2026 ▶ 1:00:55 The Fight Over Open Source AI, Anthropic's $1.5B Payout, NYC Socialists: Evictions = Violence?
ALL-IN Prediction Not checkable as stated
Calacanis: Frontier AI platforms will absorb their startup partners' businesses
“If you partner with any of these people, they will slit your throat and take your business wholesale.”
Jason Calacanis Jul 3, 2026 ▶ 20:22 AI Sovereignty Wars, Palantir-Nvidia Deal, SCOTUS Birthright Ruling, Newsom’s CA Budget Lie
ALL-IN Prediction Open · timeframe Jul 2036
Calacanis: Humans will no longer sort or deliver packages in 10 years
“What Optimus is going to do when Bezos and Andy Jassy unleash Optimus inside of the Amazon factories is it's going to get rid of every, let me state this very clearly, every single package sorting, every single package delivery will not be done by humans in 10…”
Jason Calacanis Jul 3, 2026 ▶ 47:35 AI Sovereignty Wars, Palantir-Nvidia Deal, SCOTUS Birthright Ruling, Newsom’s CA Budget Lie
ALL-IN Assertion Supported
Calacanis: Anthropic secretly downgraded users training competing AI models
“If Fable five detects you're doing frontier AI research, in other words, using their model to make a better model, competitive model, they were downgrading you, but they weren't telling you, and this was buried deep in a 319 page documents.”
Jason Calacanis Jun 13, 2026 ▶ 1:34 Anthropic's Fable Backlash, Nationalizing AI, Inflation Heats Up & California’s Broken Elections
ALL-IN Prediction Open · timeframe May 2036
Calacanis: All cab, truck, and package sorting jobs eliminated within 10 years
“Every cab driver's losing their job. Every truck driver's losing their job in the next 10 years. Anybody sorting packages is losing a job.”
Jason Calacanis May 29, 2026 ▶ 1:12:11 Anthropic's Digital God, Pope vs AI, Job Loss Narrative Flips, Open Source Crackdown Coming?
ALL-IN Prediction Not checkable as stated
Calacanis predicts open-source AI will capture 90% of total LLM token usage
“I believe open source is going to win the day on the large language models and take 90% of the token usage, and I think the entire frontier model space could be undercut by open source”
Jason Calacanis Apr 10, 2026 ▶ 30:54 Anthropic’s $30B Ramp, Mythos Doomsday, OpenClaw Ankled, Iran War Ceasefire, Israel's Influence
ALL-IN Prediction Not checkable as stated
Calacanis: 90% to 95% of AI compute jobs will move to local hardware
“What's going to happen is 90% or 95% of our jobs are going to go to this local hardware.”
Jason Calacanis Jan 31, 2026 ▶ 1:02:21 ICE Chaos in Minneapolis, Clawdbot Takeover, Why the Dollar is Dropping
ALL-IN Prediction Not checkable as stated
Calacanis: Tesla will produce 1B Optimus robots and won't be remembered for cars
“I can tell you now, nobody will remember that Tesla ever made a car. They will only remember the Optimus and that he is going to make a billion of those.”
Jason Calacanis Jan 14, 2026 ▶ 39:13 Why AI will dwarf every tech revolution before it: robots, manufacturing, AR glasses from CES 2026
ALL-IN Prediction Not checkable as stated
Calacanis: Young white-collar workers will be 2026's biggest business losers
“And I went with Young white collar workers in America. I think they're going to be the biggest business loser. I think it's getting really hard for them to get entry level jobs. I'm seeing that all over the place because companies are having an easier job just…”
Jason Calacanis Jan 10, 2026 ▶ 45:28 All-In's 2026 Predictions
ALL-IN Prediction Not checkable as stated
Calacanis: US-China standoff and Taiwan issues will be largely resolved under Trump
“I think the standoff with China is going to be largely resolved. And I think president Trump's, when he makes his visit there, I don't know if you're going to go on that one. Sax, but I think it should be included in it, obviously because of the AI race. I do …”
Jason Calacanis Jan 10, 2026 ▶ 1:02:35 All-In's 2026 Predictions
ALL-IN Assertion Supported
Calacanis: 82 of 92 Minnesota feeding fraud defendants are Somali
“So, starting with that feeding our futures fraud in 2022, 82 of 92 people charged have been Somalian.”
Jason Calacanis Dec 31, 2025 ▶ 2:44 Massive Somali Fraud in Minnesota with Nick Shirley, California Asset Seizure, $20B Groq-Nvidia Deal
ALL-IN Opinion
Calacanis: Elon Musk was 100% right about government waste and fraud
“Elon was a hundred percent right. Everybody who attacked him, they may not have liked his tactics, and how fast he was going, and locking doors, and turning off credit cards. His techniques they may not have liked, but we as Americans can all get behind not al…”
Jason Calacanis Dec 31, 2025 ▶ 29:31 Massive Somali Fraud in Minnesota with Nick Shirley, California Asset Seizure, $20B Groq-Nvidia Deal
ALL-IN Prediction Not checkable as stated
Jason Calacanis predicts Google will eventually kill ChatGPT
“Hey, ChatGPT is probably gonna get killed by Google, ah, so.”
Jason Calacanis Dec 24, 2025 ▶ 51:43 All-In x Kill Tony: A Hilarious Holiday Special
ALL-IN Opinion
Jason Calacanis says Apple's best innovation in 10 years is thin iPhone
“My biggest business loser was Apple. This company has unlimited distribution and unlimited capital, and the most impressive thing they've done in the last 10 years is a thin iPhone.”
Jason Calacanis Dec 24, 2025 ▶ 57:57 All-In x Kill Tony: A Hilarious Holiday Special
ALL-IN Prediction Open · timeframe Dec 2030
Calacanis: AI will eliminate millions of entry-level jobs within five years
“We will have massive job displacement. Destruction, whatever term you prefer in entry level jobs already happening in, you know, what I'll call chores like dishes and driving cars, entry level jobs. Those are going away and they're going to go away in the mill…”
Jason Calacanis Dec 13, 2025 ▶ 57:20 Tucker Carlson: Rise of Nick Fuentes, Paramount vs Netflix, Anti-AI Sentiment, Hottest Takes
ALL-IN Prediction Held up
Calacanis predicts US youth unemployment will reach 14% due to AI
“Nine percent in January, now 10 and a half percent. I think this chart's going right up to 14%, just my prediction, and I think it's because of AI.”
Jason Calacanis Dec 13, 2025 ▶ 1:20:06 Tucker Carlson: Rise of Nick Fuentes, Paramount vs Netflix, Anti-AI Sentiment, Hottest Takes
ALL-IN Prediction Open · timeframe Dec 2030
Calacanis: Google will make top Gemini models free for life
“They're going to make Gemini free for life for the best models. That's my prediction for Google, and I think Meta will be right behind them.”
Jason Calacanis Dec 6, 2025 ▶ 15:33 OpenAI's Code Red, Sacks vs New York Times, New Poverty Line?
ALL-IN Prediction Not checkable as stated
Calacanis: Consumer paid subscriptions for AI chat will fall to zero
“Right now, 80% of the revenue comes from 20 dollar subscriptions. That's going to get decimated to zero. I don't think consumers are going to pay For this product, just like they won't pay for search, and they won't pay for a browser, because Google and Meta w…”
Jason Calacanis Dec 6, 2025 ▶ 16:08 OpenAI's Code Red, Sacks vs New York Times, New Poverty Line?
ALL-IN Prediction Not checkable as stated
Calacanis predicts Epstein release will reveal involvement of an intelligence agency
“We're gonna find out that some intelligence agency was somehow involved in this, and that's why it's being covered up, and that's why it's so toxic.”
Jason Calacanis Nov 22, 2025 ▶ 11:56 Epstein Files Fallout, Nvidia Risks, Burry's Bad Bet, Google's Breakthrough, Tether's Boom
ALL-IN Prediction Not checkable as stated
Calacanis: Google search will grow, while OpenAI will lose market share
“I think the search franchise is going to grow, and that Google is not going to lose to ChatGPT, and I think the big loser in all this is going to be OpenAI, because they started with a hundred percent of the market, and they're only going down, and they're fac…”
Jason Calacanis Nov 22, 2025 ▶ 38:21 Epstein Files Fallout, Nvidia Risks, Burry's Bad Bet, Google's Breakthrough, Tether's Boom
ALL-IN Opinion
Calacanis: US government should auction half of all H-1B visas
“And the brilliant thing to do is to take the 100,000 and make it an auction. I would auction off half of these to the highest bidder.”
Jason Calacanis Nov 14, 2025 ▶ 40:46 Home Affordability Crisis, Palantir's Advantage, Big Short on AI, H-1B Abuse, Solar Storm Hits Earth
ALL-IN Assertion Supported
Calacanis: San Francisco spends $52,000 per homeless person annually
“High estimate, like, eight hundred million, lower estimate, seven hundred million, and low estimate for homeless people is like 8000 high estimates, like, 20, if we cut in between these two, they're spending 52,000 dollars a year per homeless person.”
Jason Calacanis Oct 18, 2025 ▶ 19:53 Trump: Send National Guard to SF, China Rare Earths Trade War, AI's PR Crisis
ALL-IN Prediction Not checkable as stated
Calacanis: Driving, delivery, and warehouse jobs will inevitably be automated away
“If you think about the average American citizen, you know, they have somebody in their family who drives for Uber or DoorDash, they have truck drivers, they have Amazon factory workers, and all those jobs are going away. It's just a matter of when.”
Jason Calacanis Oct 18, 2025 ▶ 57:32 Trump: Send National Guard to SF, China Rare Earths Trade War, AI's PR Crisis
ALL-IN Prediction Not checkable as stated
Calacanis: Democrats will shellack Republicans in midterms if tactics continue
“The Democrats are going to shellack the Republicans in the midterms if this continues.”
Jason Calacanis Oct 10, 2025 ▶ 28:57 Trump Brokers Gaza Peace Deal, National Guard in Chicago, OpenAI/AMD, AI Roundtripping, Gold Rally
ALL-IN What-if
Calacanis: Trump administration pressure caused late-night show cancellations
“I think they would have let both of their contracts run out, renegotiate them for smaller dollar amounts, and reset the economics of those shows, if not for the pressure put on them by the 47th administration.”
Jason Calacanis Sep 19, 2025 ▶ 43:08 Charlie Kirk Murder, Assassination Culture in America, Jimmy Kimmel Suspended, Ellison Media Empire
ALL-IN Assertion Supported
Calacanis: RFK Jr. withdrew federal mRNA funding and altered CDC guidelines
“RFK withdrew federal funding for MRNA vaccine development, and he removed the COVID vaccine from the CDC recommendations for healthy children and pregnant women.”
Jason Calacanis Aug 29, 2025 ▶ 1:23:22 Trump Takes On the Fed, US-Intel Deal, Why Bankruptcies Are Up, OpenAI's Longevity Breakthrough
ALL-IN Prediction Not checkable as stated
Calacanis: EU and Germany will never buy Russian oil again
“These people are never going to buy his oil again. Not after what happened here.”
Jason Calacanis Aug 22, 2025 ▶ 1:04:26 AI Bubble Pops, Zuck Freezes Hiring, Newsom’s 2028 Surge, Russia/Ukraine Endgame
ALL-IN Insight
Calacanis: Biden administration used FTC and censorship requests to pressure Big Tech
“They also put Lena Kahn in. Now Zuckerberg is a cutthroat business executive. He likes to buy companies. That's his thing. And Twitter was known for buying a lot of companies. So now you got Lena Kahn saying, We're gonna come down hard on you, not let you buy …”
Jason Calacanis Aug 21, 2025 ▶ 9:30 Senator Eric Schmitt: Exposing the Biggest Censorship Scandal in US History
ALL-IN Prediction Not checkable as stated
Calacanis: Publisher AI content licensing deal values will rise
“I will guarantee that this will be the beginning of the deals and the deals will go up from here.”
Jason Calacanis Aug 1, 2025 ▶ 43:50 Trump AI Speech & Action Plan, DC Summit Recap, Hot GDP Print, Trade Deals, Altman Warns No Privacy
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