Jason Calacanis
Founder & CEO, LAUNCH. On 6 shows, 433 appearances, plus 2 compilation re-airs not counted. The Shows tab opens the full record on each.
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Jason Calacanis is an early-stage technology investor who backed companies such as Uber, Robinhood, Calm, and Wealthfront, managing investments through his firm LAUNCH and angel syndicate. He authored the book Angel: How to Invest in Technology Startups and hosts This Week in Startups while moderating the All-In podcast.
6shows
433appearances
1,425statements
555resolved
363supported
58contradicted
65%fully supported
303said about them ↓ Everything Jason Calacanis said on any show that made the record, most notable first. Each card names its show and opens the statement there.
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 .”
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.”
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.”
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…”
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.”
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.”
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.”
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.”
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…”
Calacanis: Andreessen Horowitz engaged most in VC token sale flips
“That seems like the firm that did this the most is Andreessen Horowitz.”
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.”
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.”
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…”
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?”
Calacanis: Tesla's Optimus humanoid robot will be the world's best-selling product
“Optimist will be the best selling. I think product.”
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…”
Calacanis: Anthropic is destroying rare books for AI training data
“Anthropic is destroying rare books to get an edge in training data.”
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”
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.”
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”
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.”
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…”
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.”
The other half of the tape: Jason Calacanis's own voice is left out of every number here. Other people bring the name up 266 times in 82 episodes across the shows. 37 statements on the record name them. every mention, with the transcript →
Who brings them up most Harry Stebbings 57John Coogan 30David Friedberg 24David Rosenthal 17Jordi Hays 16Brad Gerstner 15Sagar Enjeti 8Kevin Hartz 8
Statements about Jason Calacanis, by other people (37)
Calacanis: AI Startups Will Eventually Re-Bloat to Historic Headcounts
“And so even, and so our startups that we're excited about, I think ultimately they will achieve the same historic level of bloat, maybe half the size, but they will get as bloated as they can because they will have much larger, broader product lines.”
Calacanis: Companies will choose spending on AI tokens over humans by year-end
“I really do think by the end of the year, we're going to choose tokens over humans.”
Calacanis: Enterprise AI Buyer Demand Will Drop to 5% Within 24 Months
“They got the price of the vendor right, but the soft costs, the training, the onboarding, the business process change were the highest it's ever been in their lifetimes. They're not going to do that every year. And so we may go back to five percent being in ma…”
Calacanis: AI companies built models by stealing all my copyrighted content
“Just like in the beginning to get these off the ground, we had to trample copyrights and destroy everyone's IP rights. All of my IP is stolen. Everything I've written, all my videos were taken without my consent.”
Critics like Calacanis only changed their tune after Anduril became successful
“And Jason, like many influential people, some of them even in this room, who have treated me like shit for years, suddenly changed their tune as soon as Andrew was on the upswing.”
Media commentators like Jason Calacanis caused Luckey's firing from Oculus
“Jason and the people like him are the reason I was fired from my, from Oculus, my own company.”
Jason Calacanis: Cursor will maim Figma and SaaS incumbents by lowering NRR
“I think the bigger risk for so many vendors is that it maims Figma... HubSpot and box and even anthropic using it, they don't leave, they renew, they don't buy as many seats, right? Because the team is also using cursor, but of course they don't churn. The log…”
Buttigieg says NYC and California tax proposals go further than he would
“I don't know the details of the state and local proposals you just mentioned, but those sound on their face like they're further than I would go.”
Calacanis: Enterprise Buying Window for AI Tools Will Soon Disappear
“They're not going to be in market every year for an AI tool. This will be a window that will disappear.”
Calacanis: Present VC market is the easiest ever for investing
“Yeah, because there's because there's so many entrepreneurs. There's so much change. Change is when you make money, right? Change is when you make money in venture. There's so much change. There's so many great entrepreneurs, and we don't have to worry about g…”
Hays: Jason Calacanis is a bully who ducks charity fight challenges
“Yeah, but he, you know, he is a bully. And it's interesting that as soon as the bully is actually getting invited, saying, step into the ring. He's saying, oh, I, you know, it's, I don't want to do this.”
Sacks: COVID economic recovery will likely be U-shaped or L-shaped
“Jason, I would describe U as a V. I think Chamath is closer to the U, which is the most pessimistic. Sorry, the L is the most pessimistic, and then the U is sort of somewhere in between. And I sort of swing between the U and the L but I also understand the cas…”
Calacanis: Developers would quit if denied their choice of AI model
“I would quit as a developer if you told me I could not use the model of my choice. I would quit.”
Calacanis: Enterprise and developer buyers of frontier AI models are not price-sensitive
“People are not that, no matter what anybody says, we're not that price sensitive today.”
Calacanis: AI apps will consume 1,000x more compute via continuous inference
“Smart folks are going to figure out already how to use a thousand times more inference and compute than we're using today. Because instead of running a little one-off thing, right, or even using lovable for an hour, and then letting the servers with no load go…”
Coogan: Calacanis misses Mount Rushmore of Kleiner, Thiel, Valentine, and Rock
“My Mount Rushmore is, is are those four guys and sorry, Jason you don't make the cut.”
Hays: Calacanis deserves a spot on angel investing's Mount Rushmore
“If there was a Mount Rushmore of angel investors, he certainly would be on it with the Uber.”
Jason Calacanis invested in three Swell AI competitors that will all fail
“Jason Calacanis has invested in like three companies that are like exact competitors of us. And we're just laughing because I was like how many tap bats can you get with this? It's not going to work.”
Stebbings: Jason Calacanis bet $100K that IPO market returns H2 2024
“And he's got a hundred K bet with me on it being the back half for next year. One a week for the back half for next year.”
David Sacks claims co-hosts are the stars and Jason Calacanis merely moderates
“We're the stars of the podcast, you're just the moderator.”
Sacks: Epstein asked Jason Calacanis for intros to Bitcoin founders in 2011
“What happened was that Jason hosted an episode of This Week in Startups, roughly, I think, in 2011 with a couple of the Bitcoin core founders, and then Epstein reached out to him for an introduction to those people.”
Calacanis: UiPath NRR dropped from 140% at IPO to 107%
“Come, 1.8 billion in ARR, but he's got 98% GRR and a 107% NRR. Okay. So mathematically one problem is his NRR has fallen from the 140% peak at the IPO because people aren't buying that much more for UiPath, but he's got 98% GRR, 98% retention.”
Calacanis: One-year equity cliffs hinder poaching talent in competitive markets
“And so on the one hand, it seems like a dumb idea, like you're creating mercenaries and perhaps you are, but in the age and you're asking someone that's 18 months into somebody else to leave and wait 12 months to make a dollar. That can be a tough sell in, in,…”
Every mention by year
tap a year for its mentions
20VC 109
TBPN 66
All-In 60
Acquired 20
the Startup Ideas Podcast 10
the Knowledge Project 1
2026 47 mentions in 13 episodes 4 per episode
- Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
- Epstein Deep Dive: Prince Andrew Arrested, Global Network, Mythology, Reid Hoffman Files
- Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
- FULL INTERVIEW: Uber Founder Travis Kalanick is Back with a New AI Startup
- Moltbook goes viral, $100B OpenAI-Nvidia deal stalled, SpaceX merges with xAI | Diet TBPN
- Cerebras IPO, Warsh Confirmed Fed Chair, Musk-OpenAI Trial Nears End | Diet TBPN
- FULL INTERVIEW: Anjney Midha on Fixing AI’s Biggest Bottleneck
- Eric Weinstein: The State of American Science, Breakthrough Coverups, and the Danger of Physics
- 5 more episodes that year, every mention in 2026 →
2025 56 mentions in 15 episodes 4 per episode
- Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
- Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
- What's Happening at SONOS (Total Disaster)
- Winning the AI Race Part 5: President Trump on the AI Action Plan
- Weekly Recap: Tesla Robotaxi, Mr. Beast's AI Tool, Yacine, The Social Network 2, Neuralink Update
- Trump Rally or Bessent Put? Elon Back at Tesla, Google's Gemini Problem, China's Thorium Discovery
- Multicoin Capital’s Kyle Samani on Internet Capital Markets
- The Businesses Making $$$ off Disaster Relief
- 7 more episodes that year, every mention in 2025 →
2024 64 mentions in 16 episodes 4 per episode
- E174: Inflation stays hot, AI disclosure bill, Drone warfare, defense startups & more
- How BILLIONAIRES dress for XMAS (ep17)
- Kevin Hartz: "How I Lost Airbnb at Seed Because of an Exploding Term Sheet" | E1180 · 20VC with Harry Stebbings
- Kamala surges, Trump at NABJ, recession fears, Middle East escalation, Ackman postpones IPO
- Election Betting Gone WRONG (ep15)
- The Secret Billionaire Party (ep6)
- CHRISTIANITY: Why it's making a comeback (ep23)
- Inside JD Vance's Portfolio (ep8)
- 8 more episodes that year, every mention in 2024 →
2023 29 mentions in 6 episodes 5 per episode
- E136: Hacking the pod, Threads launches, Fed minutes, immigration, balloon farce, heart health
- Beezer Clarkson: Are LPs Open for Business & Why Do LP Incentive Mechanisms Need to Change? | E1073 · 20VC with Harry Stebbings
- Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings
- How To Make Money As A Creator | Nathan Barry (ConvertKit)
- Tim Urban: How "Wait But Why" Grew to 600k Readers; AI's Revolutionary Impact on Media | E1048 · 20VC with Harry Stebbings
- Uber CEO Dara Khosrowshahi · Acquired
- every mention in 2023, scene by scene →
2022 26 mentions in 9 episodes 3 per episode
- Benchmark Part I · Acquired
- Holiday Special 2022 · Acquired
- Enron · Acquired
- Money, Wealth, and Personal Holding Companies with Michael Karnjanaprakorn
- Altimeter (with Brad Gerstner) · Acquired
- Brad Gerstner: How I Pick Companies; Lessons from Warren Buffet; Chamath vs Gurley | E935 · 20VC with Harry Stebbings
- Logan Bartlett: WTF is Happening at Growth Stage Investing? | 20VC #920 · 20VC with Harry Stebbings
- Henri Pierre-Jacques: How I Founded Harlem Capital; Our $134M Fund | 20VC #901 · 20VC with Harry Stebbings
- 1 more episode that year, every mention in 2022 →
2021 1 mention in 1 episode
2020 5 mentions in 3 episodes 2 per episode
- 20VC: Calm Founder Alex Tew on What It Takes To Build Viral Products Today, The Current State of Customer Acquisition Costs, What Makes The Best Brands
- 20VC: Moxxie Ventures' Katie Stanton on What It Takes To Raise A First Time Fund As A Solo GP, The Entrance of Multi-Stage Funds Into Seed Rounds and The Inverse Relationship of Those That Fund Diverse Managers and Those That Say They Do
- 20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means
- every mention in 2020, scene by scene →
2018 10 mentions in 3 episodes 3 per episode
- 20VC: Lessons From 2x $Bn Exits in Trulia and lastminute.com, 3 Leading Indicators That Suggest Potential Marketplace Success & Why We Are Going To See A Fundamental Change To The World of VC with Pete Flint, Managing Partner @ NFX
- 20VC: Thumbtack's Marco Zappacosta on The 3 Core Elements To All Board Meetings, Raising $250m from Sequoia and Why You Have To Win Supply Side Acquisition First For Marketplace Success
- 20VC: The Mindset The Best Investors Assume When Assessing Opportunities, Why So Many Hardware Startups Fail Today & The Right Way To Think About Employee Retention with Andrew Farah, Founder & CEO @ Density
- every mention in 2018, scene by scene →
2017 2 mentions in 2 episodes 1 per episode
- 20VC: Why Not Every Element of A Scalable Business Has To Scale, Why You Should Be Bearish on Retail & Why Fewer Businesses Are Getting Started Today Since The Great Depression with Brad Hargreaves, Founder & CEO @ Common
- 20VC: The 7 Requirements For Startup Scaling, Why VCs Must Approach Every Conversation with A Yes Mentality & Why We Will See The Humanisation of Technology with Renata Quintini, Partner @ Lux Capital
- every mention in 2017, scene by scene →
2016 8 mentions in 7 episodes 1 per episode
- 20VC: Why Every Employee Should Re-Apply For Their Job Every Year & The Strategies To Prepare For A Successful Fundraise with Kyle Hill, Founder & CEO @ HomeHero
- 20VC: Investing Lessons From Fred Wilson & Brad Feld and Why Fundraising Is An Art & Not Everyone Can Be An Artist with Howard Lindzon Founder @ Stocktwits & Managing Partner @ Social Leverage
- 20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing
- 20VC: Creating A Competitive Process Between VCs & Having Bill Gurley As A Board Member with Aaron Hirschhorn, Founder & CEO @ DogVacay
- 20VC: Sprig's Gagan Biyani on The 3 Principles Of Fundraising and Building The World's Largest Restaurant
- 20 VC: Niccolo De Masi @ Glu Mobile on Private Market Valuations, Being A Public Market CEO & The Trends Of Mobile Gaming
- 20VC FF 028: Where To Start Your Startup and Single Founder vs Co-Founder Model with Richard Hanson, Co-Founder & CEO @ HiringScreen
- every mention in 2016, scene by scene →
2015 18 mentions in 7 episodes 3 per episode
- FF 011: 'The Savviest Investors Don't Ask What If' with Ben Nader, CEO & Founder @ Butterfleye
- 20 VC FF 018: Brian Wong, Founder @ Kiip on Raising $30m in VC Funding by 24
- 20 VC FF 026: Ryan Hoover, Founder @ ProductHunt on Relationship Building, Habit Forming and The Vision for ProductHunt
- 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
- 20 VC 079: BETAWORKS WEEK: East vs West Coast Investing with Peter Rojas, EIR @ Betaworks, Co-Founder @ Weblogs & Engadget
- 20 VC 071: Pre-Seed Investing, Why Now Is The Best Time with Nicholas Chirls @ Notation Capital
- James Altucher: Ideas, Investing and Entrepreneurs
- every mention in 2015, scene by scene →
One line per show, most statements first. The link opens Jason's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| ALL-INLEDGER | Founder & CEO, LAUNCHhost | 428 | 1,301 | 65% 349/536 | full record on All-In → |
| 20VCLEDGER | Founder & CEO, LAUNCH | 2 | 51 | 75% 6/8 | full record on 20VC → |
| KNOWLEDGE PROJECTLEDGER | Founder & CEO, LAUNCH | 1 | 30 | 60% 3/5 | full record on the Knowledge Project → |
| ACQUIREDLEDGER | Founder & CEO, LAUNCH | 1 | 24 | 80% 4/5 | full record on Acquired → |
| STARTUP IDEASLEDGER | Founder & CEO, LAUNCH | 1 | 18 | 100% 1/1 | full record on the Startup Ideas Podcast → |
| TBPNLEDGER | Founder & CEO, LAUNCH | 0 +2 | 1 | — | full record on TBPN → |