Jason Calacanis
370 statements across 217 episodes · 138 bullish · 122 bearish · 7 people on the record · first statement Mar 19, 2020 by Jason Calacanis · said 60 times in 10 episodes since 2023 · across every show →
On the record as a speaker too: Jason Calacanis's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by David Friedberg (24), Brad Gerstner (14), Sagar Enjeti (8), Donald J. Trump (5), David Sacks (4), Kyle Samani (2), Eric Weinstein (1), Charles Koch (1)
tap a year for its mentions
2026 13 mentions in 3 episodes 4 per episode
- Epstein Deep Dive: Prince Andrew Arrested, Global Network, Mythology, Reid Hoffman Files
- Eric Weinstein: The State of American Science, Breakthrough Coverups, and the Danger of Physics
- How We Grew Koch Industries to $150 Billion Without Going Public: Charles & Chase Koch
- every mention in 2026, scene by scene →
2025 11 mentions in 4 episodes 3 per episode
- Winning the AI Race Part 5: President Trump on the AI Action Plan
- 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
- From Skeptic to Supporter: How This Billionaire Got ‘Red-Pilled’ by Trump
- every mention in 2025, scene by scene →
2024 17 mentions in 2 episodes 9 per episode
Everything said about Jason Calacanis, oldest first
Mar 19, 2020 bearish
Apr 11, 2020 bearish
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…”
Jul 11, 2020 bullish
Sep 9, 2020
Sep 9, 2020 positive
Sep 30, 2020 positive
Oct 3, 2020 neutral
Calacanis: Political discussions are banned on Slack at my companies
“The two companies I run, you could talk about politics. If you want to go for a walk with somebody and have coffee or lunch, and you want to have a two hour discussion about it, go for it. Please do not put this in electronic form, because it's a massive distr…”
Nov 4, 2020 negative
Nov 11, 2020 neutral
Nov 11, 2020 bearish
Calacanis: Mainstream media will be the biggest loser post-2020 election
“Do you know who the biggest loser is going to be coming out of this, I think? Not when you think holistically about the ecosystem. It's going to be the media. Because they have made an absolute fortune over the last four or five years picking aside.”
Nov 25, 2020 bullish
Dec 18, 2020 bullish
Jan 8, 2021 neutral
Jan 8, 2021 negative
Jan 8, 2021 neutral
Jan 8, 2021 negative
Jan 8, 2021 neutral
Jan 11, 2021 negative
Jan 11, 2021 bullish
Calacanis: Peer-to-peer platforms like Mastodon will emerge and prove unbannable
“There is master Don and plenty of other peer to peer software that will be deployed, I predict, and that will put up a competition now for these services, and it will be impossible to ban those peer to peer platforms.”
Jan 30, 2021 positive
Calacanis: VCs must be loyal "ride or die" partners to founders in crisis
“I am trying to work with the company to help them resolve the issues. And I need to be loyal to my founders. And I need to say, Hey, How do we resolve this? How do we get here and work with them? And I'm sorry that I'm ride or die. But that's how I approach th…”
Jan 30, 2021 neutral
Feb 3, 2021
Feb 3, 2021 bullish
Feb 20, 2021 negative
Calacanis: Declaring non-prosecution signals weakness that hard-core criminals exploit
“If you say you are not going to prosecute crime, and you demonstrate to the hardest core faction of criminals that you don't prosecute, they're going to take advantage of that weakness, and that's what's happening.”
Feb 20, 2021 positive
Calacanis: US is reaching COVID-19 herd immunity based on infection and vaccination math
“So if you have thirty million people who've had the vaccine had COVID, you're looking at five times that is a 150, now you have sixty million people who have been vaccinated, we're at two 10, there were three hundred thirty million Americans, seventy million a…”
Feb 20, 2021 bullish
Mar 6, 2021 bearish
Calacanis funds $50,000 grant to investigate San Francisco DA Chesa Boudin
“The GoFundMe page I started, it now has 455 donors and 54,000 dollars in funding. And so I am withdrawing the 54,000 dollars, and I have a meeting with the woman from the Marina Times who's done great coverage of this, and I'm also looking for some data scient…”
Mar 13, 2021
Mar 20, 2021 bullish
Mar 20, 2021 positive
Apr 17, 2021
Apr 23, 2021
Calacanis says investors must guide talented founders to prevent self-destruction
“It's like being Professor X and the X-Men. You could have a Jean Grey or a Wolverine and like everybody's got a different superpower, but you need to teach them how to use that superpower so they don't self-destruct or cause chaos.”
May 1, 2021 negative
May 13, 2021
May 13, 2021
May 22, 2021 positive
May 22, 2021
Calacanis is overpaying for early-stage deals and skipping high-valuation rounds
“I'm going to selectively, you know, overpay compared to what we were paying a year or two ago. You know, if I really love a company, but I will sit out a lot of, I'm sitting out a lot of rounds right now that I just can't get my head around the valuation.”
Jun 25, 2021 negative
Jul 2, 2021
Jul 2, 2021 negative
Jul 2, 2021 bullish
Jul 2, 2021 negative
Jul 3, 2021 bullish
Jul 9, 2021
Jul 9, 2021
Jul 9, 2021 negative
Calacanis: San Francisco DA's office investigated one of my portfolio startups
“The DA's office. You know what they contacted me about? They were investigating a startup that I had invested in. I won't say which one. And they wanted to interview me about my involvement with that startup because that startup had some complaint from a downs…”
Jul 9, 2021
Jul 9, 2021 neutral
Jul 16, 2021 bullish
Jul 30, 2021 bullish
Jul 30, 2021 bullish
Aug 6, 2021
Calacanis: 20% to 30% of promising startup deals fail basic diligence
“Between 20 and 30% of deals that look great, when we get under the covers and look at the diligence, we look at the cap table, we look at the revenue, we look at the accounting, we ask them who's doing their accounting, we ask them for bank statements, we ask …”
Aug 6, 2021 negative
Aug 6, 2021 negative
Aug 6, 2021 positive
Aug 6, 2021 bearish
Aug 28, 2021 positive
Calacanis: Callin syndicate set record with $7M demand for $1M allocation
“It was the absolute record we've ever had for any syndicate. I believe at the end of the day, we had a 150 slots, and we had 950 people apply sacks. We had a million or so in allocation, and I think we had seven million in demand.”
Sep 4, 2021 neutral
Calacanis says his firm tripled diligence and abandons 30% of deals
“We have maybe tripled the amount of time we're putting into diligence now, because I really care about my reputation, and maybe 20, 30% of the companies, we wind up After initially wanting to invest, maybe giving them an offer, getting an allocation in recent …”
Sep 14, 2021
Sep 18, 2021 neutral
Sep 18, 2021 negative
Oct 2, 2021 positive
Oct 2, 2021 negative
Oct 23, 2021 bearish
Oct 23, 2021 bearish
Oct 30, 2021 negative
Calacanis: Developers are crazy to build on Meta's metaverse over decentralized platforms
“I think any developer who puts any amount of their effort into supporting in any way, Zuckerberg's view of the metaverse is crazy when they could do it on a distributed decentralized crypto based open source platform.”
Nov 13, 2021 bearish
Nov 20, 2021 bullish
Dec 4, 2021 negative
Calacanis: Neither Trump nor Biden wants high-skilled immigrant talent in the US
“That was one of the huge failings of the Trump presidency and now going into Biden, who doesn't seem to care about immigration either. Both of these people is huge fails. Both parties do not want to bring intelligent people here.”
Dec 11, 2021 bullish
Dec 17, 2021 neutral
Dec 29, 2021 positive
Jan 8, 2022 bearish
Jan 15, 2022 negative
Calacanis notes human rights groups report up to 1M Uyghurs incarcerated
“That is the numbers that human rights organizations are saying between 300,000 and a million people are incarcerated right now being tortured, raped, and in doing forced sterilization reeducation, and when they're released are being tracked in ghettos.”
Jan 15, 2022 positive
Jan 15, 2022 negative
Calacanis argues VCs should refuse Saudi investment capital over human rights abuses
“When people are involved in torture, murder, rape, and sterilizing people, that there should be economic and disengagement that occurs as a first step. And that that is why when people in our circles, in venture capital, take money from somebody who murdered a…”
Feb 12, 2022 neutral
Mar 5, 2022
Apr 1, 2022 negative
Apr 9, 2022 positive
May 13, 2022
May 26, 2022 negative
Calacanis: Speakers refused to attend All-In Summit due to political lineup
“One of the major challenges I had in this event Was certain people attending the event made some people in that group unwilling to come to the event. No offense, Keith. In other words, like, Keith, Sachs, you know, and then even Glenn Grunwald and... Greenwald…”
May 27, 2022
May 27, 2022 bearish
May 28, 2022 negative
Jun 1, 2022
Jun 3, 2022 negative
Jun 7, 2022
Jun 7, 2022
Jun 23, 2022 negative
Jun 23, 2022 negative
Jun 23, 2022 negative
Jun 23, 2022 negative
Jun 24, 2022 neutral
Chamath: All-In hosts signed agreement as equal 25% partners
“Basically what happened was we had an agreement that it was 25% each. There was a moment where J Cal believed that he deserved more. We had to sort through a lot of the underlying issues that caused them to believe that. We got to a good consensus. We now have…”
Jun 24, 2022 negative
Jun 24, 2022 neutral
Calacanis: All-In Podcast will not host future summits or build a business
“There's not going to be any more summits. There's not going to be any business here. It's just a pod. I have other events I do. I have other pods I do. If I want to get paid, I'll do them over there. And here, it's just a pod that you see every week.”
Jun 30, 2022 bearish
Jul 14, 2022 bearish
Jul 22, 2022
Calacanis: Deposited a couple million dollars to actively trade public stocks
“So I put a couple million bucks into an account, and I'm just trying to actively figure out how does value work there? And, you know, I'm just starting to make trades that I want to hold for 10 or 20 years, and we'll see if I can beat the market.”
Aug 26, 2022 positive
Sep 1, 2022 bearish
Sep 10, 2022 negative
Sep 10, 2022 neutral
Nov 5, 2022
Calacanis: Many journalists would choose to publish without bylines to avoid harassment
“One of the problems with journalism today is even if you're doing reporting in good faith, Chamath, and you put your byline on there, harassment, you know, threats, et cetera, can become very acute if you're just covering certain topics. And so I actually thin…”
Nov 12, 2022 bearish
Nov 19, 2022 neutral
Calacanis: Tech will divide into aggressive startups and lifestyle companies
“I think we're going to have a cultural divide here. There are going to be a series of companies that say, this is classic Silicon Valley. We're going to crush it. We're going to work aggressively. We're going to put in. 50, 60, 70 hours a week, and we're all g…”
Dec 3, 2022
Dec 10, 2022 negative
Dec 16, 2022 neutral
Calacanis: Coordinated tech bans dramatically reduce individual reach
“When they got banned across all systems, it was dramatic in terms of the reach of the that information. So because of the size and scale of YouTube, Facebook, Twitter, etc, when they act in coordination, They can, ah, have a dramatic impact.”
Dec 24, 2022 bullish
Dec 24, 2022 negative
Calacanis: Twitter management previously held back ready-to-ship features
“What we found over and over again was that there were great features that were ready to be released that were being held back by management. And there were brilliant people with all the ideas that you think should have been released. And they just weren't allo…”
Dec 24, 2022 bullish
Jan 6, 2023 neutral
Jan 6, 2023 bullish
Calacanis: Seed stage venture capital will be 2023's best-performing asset class
“I'm going with C stage investing again. I don't think people want to get into these toxic cap tables at the late stage, as Chamath pointed out. So I go with seed stage and, you know, end up to series A, the people brave enough to place bets, the founders brave…”
Jan 13, 2023 neutral
Jan 13, 2023 neutral
Jan 13, 2023
Jan 20, 2023 positive
Jan 20, 2023
Calacanis warns startups must implement austerity to maintain balance sheet strength
“Freebrick, I'm dealing this with startups I have right now, and I tell them, the balance sheet is how you compete. If your balance sheet is flipped upside down, and you're going to be out of business in nine months, you're not competing with these two other co…”
Jan 20, 2023 negative
Calacanis: World Economic Forum charged $40,000 fee for Young Global Leaders
“They recruited me to be part of their world leaders, 15 years ago, after I had sold my second company, and I met Claus, the guy who runs it, at some New York Four Seasons event, and then I got the bill, and to be a world leader, Was 40 fucking thousand dollars…”
Feb 4, 2023 bullish
Feb 11, 2023 negative
Calacanis asserts AI web scraping for derivative answers violates fair use
“It's not fair use because in fair use, you have the ability to create derivative works on future platforms. And you are taking this person, the original content owner's ability to exploit that And you are co-opting it and you're doing it at scale. And that is …”
Feb 11, 2023 bullish
Feb 11, 2023 bullish
Feb 17, 2023
Feb 24, 2023 positive
Mar 3, 2023 bullish
Calacanis invested $500K for 10 percent in a ChatGPT wrapper startup
“Serial founder and team that we've backed for that had an exit said, can I show you something? I said, yeah, got on the zoom, showed me a little proof of concept using chat GPT. And he said, this is my idea. This is the vertical. And I just said, okay, what do…”
Mar 11, 2023 neutral
Mar 17, 2023 neutral
Mar 24, 2023 neutral
Mar 24, 2023 positive
Apr 7, 2023 negative
Apr 21, 2023 bearish
Apr 21, 2023 bullish
Apr 21, 2023
Apr 28, 2023 negative
May 12, 2023 neutral
Jun 2, 2023 positive
Calacanis: Presidential meetings with foreign leaders are not endorsements
“I think there's a part of this military industrial complex that believes a meeting with the president is a reward or an endorsement of the worst things anybody's ever done. It's not, it's a meeting to try to make the world safer or to try to build common groun…”
Jun 2, 2023 positive
Jun 10, 2023 bullish
Jun 16, 2023 bullish
Jason Calacanis notes 80% of LAUNCH startups are actively implementing AI
“Four out of five startups that we've invested in and the majority of them that we're being pitched on right now are not only talking about AI, which they were all talking about it three years ago. They're actually implementing it now because the tool sets are …”
Jun 24, 2023 negative
Jul 1, 2023 bearish
Jul 14, 2023 positive
Jul 14, 2023 positive
Jul 14, 2023 bullish
Calacanis discloses stock purchases in Disney, Warner Bros Discovery, and Netflix
“I bought the stock and it's the one thing in my J trading portfolio I've gotten crushed on that and Warner Brothers Discovery. I made two entertainment bets and what I think are the two best companies. I also did Netflix, but one out of three ain't good.”
Jul 21, 2023 negative
Jul 27, 2023 bullish
Calacanis: Holds Disney stock, sees potential asset sales or acquisition
“Right now I'm going to ride it out. I think their IP collection is amazing. I think there's a chance that, you know, depending on how the FTC winds up being run over the long term, that Disney could be selling pieces of that business, and I think that it could…”
Jul 27, 2023 positive
Aug 4, 2023 neutral
Aug 18, 2023 positive
Aug 26, 2023 positive
Calacanis: 2024 election could be a tipping point for podcasts
“What we're witnessing right now is the transition from traditional media and the establishment defining who the great candidates are to the public and the people on podcasts and social media who are the tip of the spear on the vanguard. They're going to pick t…”
Sep 8, 2023 bearish
Sep 19, 2023 bullish
Sep 22, 2023 neutral
Sep 22, 2023
Calacanis: Two-thirds of LPs in meetings are cutting VC fund commitments
“And I'd say, two thirds of the meetings I'm having, people are saying, we're not adding managers, we're cutting managers, and we're cutting commitments to managers, but we'd love to meet, you know, just to start the relationship, you know.”
Sep 22, 2023 bearish
Sep 28, 2023 negative
Oct 2, 2023 neutral
Oct 7, 2023 positive
Oct 7, 2023 negative
Oct 13, 2023 positive
Calacanis: Conflict will ultimately renew commitment to Middle East peace
“I actually think that in some ways this is going to create a climate where people are going to really fight to try to resolve this situation, or at least contain the situation. Two States Illusion, the Abraham Accords, and I think they're, this is going to ren…”
Oct 20, 2023 positive
Oct 27, 2023 bearish
Dec 8, 2023 bullish
Dec 16, 2023 negative
Dec 16, 2023 negative
Calacanis: Tech DEI consultants ran a grift charging attacked firms for allyship
“I tweeted today about the absolute, ah, grift that was going on in tech not long ago, ah, which was call out a company, venture firm, whatever it is, for their DEI stats. Then quietly contact them after you've done this brigadooning of them and say, hey, we ca…”
Dec 16, 2023 negative
Dec 16, 2023 negative
Dec 29, 2023 positive
Dec 29, 2023 positive
Jan 6, 2024 bullish
Jan 6, 2024 bullish
Calacanis: TikTok or ByteDance will go public or spin out in 2024
“I'm gonna say this year that I think TikTok goes public, and they'll be under pressure from different political factions to get the CCP off the board. So I'm going to go with by dance taking, going public or tick tock spinning out and going public.”
Jan 6, 2024 bearish
Calacanis predicts LLM startup valuations will fall 50% to 80% in 2024
“My worst performing asset in 2024 is LLM startups. I believe they've been massively overvalued, and I believe open source is making an incredible run at them, and I think they're going to hit parity, and there's too many players... I think they're all going to…”
Jan 13, 2024 neutral
Calacanis: LAUNCH invests strictly on startup merit to avoid lawsuits
“What I did in our company was I said, hey, if we don't feel we're getting enough applicants for the programs, Founding University, the accelerator, we could have, you know efforts to increase the number of applicants, but we can't make investment decisions bas…”
Jan 26, 2024 bearish
Jan 26, 2024 negative
Calacanis: Border strategy could backfire on Democrats as immigrants favor Republicans
“I think this could blow up in Democrats' faces if it is their strategy, because a lot of people who are coming here, immigrants, don't want to be part of the Democratic and the liberal woke Democratic Party. They want to be part of the Republican hardworking p…”
Feb 2, 2024 negative
Mar 1, 2024 negative
Calacanis: News industry could have forced Google payouts through a federation
“This is why the news industry should have always had a federation, because they could have just said to Google, hey, we're going to de-index ourselves from the Google search engine, and so you won't have the New York Times, Washington Post, LA Times, you're ju…”
Mar 16, 2024
Mar 29, 2024 bearish
Mar 29, 2024 bearish
Mar 29, 2024 negative
Apr 9, 2024 positive
MrBeast says audiences enjoy watching large cash and gift giveaways
“No, not really, to be honest. Most people think it's cool, because it's like, it's kind of fun to watch someone receive, you know, 10,000 dollars, or a Lamborghini, or a house, or, I think, like, the last thing we did was I ordered pizza and tipped the guy a h…”
Apr 19, 2024
Calacanis starts $100 monthly Robinhood investment club for his daughter
“With my 14 year old, I'm doing an allowance, and then I decided to do an investment club. And so I'm putting a hundred dollars every month into like a Robinhood account. And we're gonna do like two meetings every month, one to buy a new stock and one to examin…”
Apr 19, 2024 positive
Apr 26, 2024 bullish
Apr 26, 2024 positive
Apr 26, 2024 negative
May 10, 2024 positive
May 17, 2024 bullish
May 17, 2024 negative
Calacanis passed on early Twitter investment at single-digit million valuation
“I had the opportunity to invest in Twitter when it was like a single digit millions company. And I just thought, you know what? This thing is only like the headline. And I told that like, it's the headline. It's not like the entire blog post. It's going to be …”
May 17, 2024 bullish
May 17, 2024 neutral
May 17, 2024 positive
May 24, 2024 neutral
May 31, 2024 negative
Jun 14, 2024 bearish
Jun 14, 2024 neutral
Jun 20, 2024 positive
Jun 25, 2024
Calacanis: Found illegal activity in two startups across 400 investments
“Over 400 investments we've done. You had maybe two instances where people were Doing things that would be illegal. And we had to, in both cases, I had to sit with the founders and said, listen, I can't be on the board of this company if you're going to do this…”
Jun 29, 2024 negative
Jun 29, 2024 negative
Jul 4, 2024 neutral
Jul 10, 2024
Calacanis requires his kids to match screen time hour-for-hour with creative projects
“If they want to do screen time, I tell them, great come up with a creative project and one hour of creative project. You can do one hour of TV or one hour of iPad or something. So I just do one for one with them.”
Jul 10, 2024 negative
Calacanis: TikTok's black-box AI algorithm is more pernicious than earlier gamified social media
“So you had the gamification of Twitter and Facebook, which was likes. Retweets, follower count, Instagram, and then now it's transitioned into something even more pernicious, which is some black box on, in TikTok knows this is going to maximize the dopamine hi…”
Jul 12, 2024 bullish
Jul 12, 2024 bullish
Jul 23, 2024 negative
Jul 23, 2024 bullish
Jul 26, 2024 negative
Calacanis: Y Combinator bullies rivals and falsely claims exclusive founder-friendliness
“Y Combinator does circle the wagons. They do bully people. And they do put out a presentation that we are the only people in Silicon Valley who are founder friendly, you know, even though they're getting seven percent for a 125 K like we do in our accelerator,…”
Aug 16, 2024 bearish
Aug 16, 2024 neutral
Aug 16, 2024 negative
Aug 30, 2024 negative
Sep 27, 2024 bullish
Nov 6, 2024 negative
Nov 8, 2024
Nov 16, 2024 bearish
Calacanis: Combined 2022–2024 VC distributions total less than 2019 alone
“If you look at the distributions from 2022 through 2024, those three years combined, it's been around two hundred billion, which is less than 2019 in total. And with this year projected to be about a hundred billion in distributions, that's about 14% of the pe…”
Nov 16, 2024 negative
Nov 16, 2024 positive
Dec 20, 2024 negative
Dec 25, 2024
Sacks admits he grew annoyed co-hosting the podcast with Jason Calacanis
“I mean, to be honest, I was starting to feel really annoyed with you, Jcal, on the pod. I wasn't sure how much longer I could put up with it, to be perfectly frank, but, you know, tonight, you kind of remind me why it's fun to do this.”
Dec 25, 2024
Dec 25, 2024 positive
Calacanis names Trump's post-assassination attempt fist pump the moment of 2024
“I thought the moment of the year for me was not the assassination attempt at Trump, obviously, but his reaction to it. When he got up and he pumped his fist and he said, fight, fight, fight, I think you got an idea of his character and that he wasn't going to …”
Jan 4, 2025 bullish
Jan 11, 2025 negative
Jan 11, 2025 positive
Calacanis: I flipped to supporting Trump because of his executive appointments
“This is why I've changed my position on rooting for Trump now. I was a never Trumper. Everybody knows that. But he put executives around him this time around, and I am rooting for those executives to do what's right for the American people and solve big proble…”
Jan 11, 2025 negative
Jan 11, 2025
Jan 18, 2025 bullish
Jason Calacanis: Google Gemini Deep Research outperforms multi-million-dollar consulting firm reports
“They designed it to basically be one of these, like, million dollar or five million dollar reports you pay for from these consulting firms. That MBA's right. And it does a better job. It's more accurate. It's done in five to 10 minutes.”
Jan 18, 2025 positive
Chamath Palihapitiya hires a Philippine executive assistant for $3,000 monthly
“Now I use Jason's service called Athena, and I have a guy that works with me in the Philippines, and it's about 3000 a month, and I can honestly tell you this guy is the single most effective administrative support I've ever had”
Jan 18, 2025 positive
Jan 18, 2025 negative
Jason Calacanis: LA wildfire damage is estimated at $135B to $150B
“The estimates right now of damage are between a hundred and thirty five billion and a hundred fifty billion dollars. This is some of the most Expensive real estate on the planet. It's 10 times more costly than any other wildfire in history, according to report…”
Jan 18, 2025
Jan 20, 2025 negative
Jan 20, 2025 negative
Jan 20, 2025 negative
Jason Calacanis criticizes Democratic Party's stance on entrepreneurs and 2024 primary
“I'll just leave it at that, that you didn't have a speed run primary, that Biden was put up when he was clearly in cognitive decline, and I'm absolutely disgusted by the Democratic Party's hatred of successful entrepreneurs in this country.”
Jan 20, 2025 positive
Calacanis advocates for a sophisticated investor test for crypto retail buyers
“I think there should be a sophisticated investor test where people learn About things like diversification. They learn who owns 80% of the coins that have just been dumped on retail, and under what circumstance they can sell them.”
Jan 20, 2025 neutral
Jan 20, 2025
Jan 20, 2025 positive
Jan 25, 2025
Jan 25, 2025 positive
Feb 22, 2025 negative
Mar 1, 2025 positive
Mar 1, 2025
Mar 1, 2025 bullish
Calacanis: Stripe could generate $10B-$20B profit via stablecoins in 5 years
“I do think Stripe's main business could be, if we're sitting here in five years, Chamath, could be sitting on three hundred billion dollars and getting whatever it is, three, four or five percent on some coupon, right? They could be making 10, twenty billion d…”
Mar 1, 2025
Mar 8, 2025
Mar 15, 2025 neutral
Mar 15, 2025 negative
Mar 19, 2025 neutral
Mar 20, 2025 bullish
Mar 29, 2025 neutral
Mar 29, 2025 bearish
Apr 3, 2025
Calacanis says he helped Sam Harris start his podcast
“I remember I had him on my podcast, and he said, what's podcasting? And I explained it to him, and he said, well, how do I do it? And I said, well, you get two microphones and a guest. And he's like, then what? I'm like, well, then we hit the record button, an…”
Apr 3, 2025
Apr 3, 2025 positive
Apr 3, 2025 negative
Calacanis: $800 online courses provide more job value than college degrees
“People go to school, they go 50,250 thousand dollars in debt, and then what I hear from young people all the time is they go take a course afterwards, and that course for 800 dollars does more from them in the marketplace and getting jobs than the degree did”
Apr 3, 2025 bullish
Calacanis: Everyone should allocate a low single-digit percentage to Bitcoin
“We own a decent amount of Bitcoin, and, ah, I think everybody should own, like, a low single digit percentage. It's not an investment price. I think, like, a low single digit in Bitcoin, if you lose it, so be it. If it a hundred X's from here, anything's possi…”
Apr 3, 2025 negative
Apr 3, 2025
Apr 3, 2025 positive
Apr 3, 2025 bullish
Apr 4, 2025 negative
Apr 4, 2025 neutral
Apr 4, 2025 neutral
Apr 19, 2025 negative
May 3, 2025 positive
Calacanis: Launch built AI agent processing 20,000 startup applications yearly
“We have 20,000 applications a year, and we have updates coming in from investments. We are now taking those sacks, Aaron, and we are having an agent sort them and then look for competitors and compare them to the last update. And we're looking into our notion,…”
May 31, 2025 bullish
Jun 13, 2025 negative
Jun 21, 2025 neutral
Calacanis predicts Microsoft's headcount will stay flat near 225,000 to 250,000
“I think they'll have just about two 50 plus or -10%. I don't think if I could pick push as the answer, I would pick push, which is they're going to get 10% better every year with AI, 20% more efficient. Therefore, they don't need to add people, but I also don'…”
Jun 28, 2025
Calacanis predicts AI models will require publisher subscription authentication for search outputs
“And then ChatGPT and the New York Times should do a deal, and I predict they will do this, or with another language model that's smart enough to do it, where when you go to ChatGPT and you do a search from the New York Times, you say, what does the New York Ti…”
Jun 28, 2025
Aug 1, 2025 neutral
Calacanis: Trump term will focus on AI, crypto, immigration, tariffs
“This presidency, this term is going to be earmarked, I think, by four key initiatives, AI, crypto, immigration, and tariffs. I think that feels like what they're locking into as what's important for the next three and a half years.”
Aug 1, 2025 positive
Aug 1, 2025 neutral
Aug 1, 2025 bullish
Aug 1, 2025 positive
Aug 9, 2025 bullish
Aug 15, 2025 negative
Aug 21, 2025 positive
Aug 21, 2025 neutral
Aug 22, 2025 positive
Aug 29, 2025 positive
Calacanis: Founder University expanding to Riyadh in November with Sanabil
“We just sort of soft launched that we're going to be bringing Founder University. It's one of the things I do in my day job is invest in startups. So we created this Founder University. We do it here in the United States. But we had a lot of interest to bring …”
Sep 4, 2025 negative
Sep 7, 2025 neutral
Sep 7, 2025 positive
Sep 7, 2025 neutral
Sep 15, 2025 positive
Sep 15, 2025 bullish
Sep 19, 2025 negative
Sep 19, 2025 positive
Oct 6, 2025 bullish
Oct 9, 2025 positive
Oct 10, 2025 bullish
Oct 10, 2025 neutral
Oct 10, 2025 positive
Oct 18, 2025 bearish
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.”
Oct 30, 2025 negative
Oct 31, 2025 negative
Nov 7, 2025
Nov 14, 2025 positive
Nov 22, 2025 positive
Nov 22, 2025 bullish
Nov 22, 2025
Nov 26, 2025
Jason Calacanis declined Molly Bloom's poker invite over $50,000 stakes
“I remember you invited me and you said, Toby's gonna be there, Leo's gonna be there, whatever, and they'd love to see you, and I said, they would love to see me lose 50,000 dollars. There's no way I'm going to this game, because I was playing in a five 10 game”
Nov 29, 2025
Calacanis: Fans crowdfunded $2,000 to replace Phil Hellmuth's fraying tracksuit
“Help fund a new tracksuit for Phil Humming that I took a picture of his fraying, you know, classic Adidas tracksuit, and instantly, 2000 dollars comes in from the poker community. Wow. 50 different people were like, absolutely, that tracksuit smells.”
Dec 6, 2025 bearish
Dec 13, 2025 bearish
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…”
Dec 13, 2025
Dec 19, 2025 neutral
Jan 10, 2026 bullish
Jan 10, 2026 bearish
Calacanis: US dollar will perform poorly in 2026 due to growing national debt
“I went with the U.S. Dollar in different permutations of how you can buy it because our debt continues to grow unabated and, you know. I just think it's gonna be hard for, you know, the USD because we're talking about, we've been adding, I think we're gonna ad…”
Jan 23, 2026 positive
Jan 23, 2026 positive
Jan 24, 2026 negative
Calacanis: Twitter was paying for software subscriptions that were never used
“And, so we sit there and we're like, yeah, cancel the cards. Immediately, I get three back channels from software companies who are like, hey I know you're helping Elon. I saw a story in the New York Times. Our bill stopped getting paid. Can we come in? And I'…”
Jan 24, 2026 negative
Feb 7, 2026 bullish
Feb 7, 2026 negative
Feb 7, 2026
Calacanis: Team uses recursive AI bots to optimize YouTube headlines
“We are doing it internally Saks. Like we have a bot that is going and saying, go search Reddit X, Message boards, hacker news, and find out what the latest way to do headlines and marketing of YouTube videos is, and then incorporate that into a skill, then sav…”
Feb 13, 2026 bullish
Feb 13, 2026 bullish
Feb 13, 2026 bullish
Calacanis commits to investing in 10 to 20 OpenClaw startups
“I'm investing in. 10 startups in open claw space, a 125 K each to come to the accelerator. If you're doing work on this, openclaw at launch.co, email me what you're doing, because we want to invest in at least a 10 or 20 of these companies right now.”
Feb 13, 2026 negative
Feb 13, 2026
Calacanis: Construction and hospitality employ 2.5M undocumented workers in US
“The top two areas where illegal aliens are working in the United States. Most people don't know this construction number one, and the second one is leisure and hospitality. So you got two and a half million people working in those two categories”
Feb 20, 2026 neutral
Feb 28, 2026 bullish
Feb 28, 2026 bearish
Calacanis predicts Donald Trump will lose the midterms
“I think Trump's gonna lose the midterms, and we're gonna get to more chaos again, and it, we might as well start this reconciliation process of these two sides stopping their law for against each other and working together for the American people on the import…”
Mar 11, 2026
Mar 13, 2026 negative
Mar 13, 2026 bullish
Mar 23, 2026 bullish
Mar 27, 2026 positive
Mar 27, 2026 neutral
Apr 3, 2026 bullish
Apr 10, 2026 neutral
Apr 17, 2026 positive
May 1, 2026 negative
Calacanis: AI agent on Cursor wiped Pocket OS live database and backups
“He was using Opus 4.6 through Cursor's AI platform, their coding platform. And You know, which is like the most expensive tier. And he said he configured it with enough safety rules, but the agent was working on a routine task. They saw some sort of credential…”
May 15, 2026 positive
May 15, 2026 bullish
May 29, 2026 neutral
May 29, 2026 bearish
May 29, 2026
Jun 7, 2026 positive
Jun 7, 2026 positive
Calacanis: Launch sells secondary shares alongside founders at $500M valuations
“We are now pari pursue selling into every chance we get because our average investment is at 10 to twenty million dollar valuations. When they hit five hundred million, I tell the founder, you're going to start selling at five hundred million. I'm going to sel…”
Jun 8, 2026
Calacanis: Cut SaaS spending 90% using Claude and Slack integrations
“We had an instance with a SAS product with 20 seats. Nobody was logging in and using it, but the data was there. So we created like three accounts, got rid of 17, connected it to Slack, connected it to Claude. And now everybody can interface it through a natur…”
Jun 13, 2026 positive
Jun 13, 2026 negative
Jun 13, 2026 bullish
Jun 29, 2026 neutral
Jason Calacanis: Heritage Foundation data shows voter fraud cannot flip elections
“They have a lot of people trying to figure out where fraud exists, investigating it, and it's de minimis. It's a couple of thousands of cases they can find. So even if you extrapolated them, 10 X or 20 X, pick your multiple, it would never swing a major electi…”
Jul 3, 2026 positive
Calacanis defines intelligence sovereignty as preventing AI from dictating human thought
“The intelligent sovereignty is different than privacy. Privacy is, oh, you can't see my photos, you can't peek into my notes app and what I wrote there in my journal. Intelligent sovereignty is, you can't tell me what to think. You can't use your AI to analyze…”
Jul 10, 2026 positive
Jul 10, 2026 positive
Jul 11, 2026 positive
Jul 11, 2026 bullish
Jul 21, 2026 positive
Jul 24, 2026 positive
Jul 24, 2026 bearish
Jul 24, 2026 negative
Aug 7, 2026 negative
Aug 12, 2026 positive
Aug 13, 2026 bullish
Calacanis: US AI spend will hit $1T as companies adopt tokens
“There is no world in which I don't see corporations and people in the economy spending five or 10% of the salaries of their employees on the equivalent in tokens. In other words, somebody makes 80,000 dollars a year on average, they're gonna, you will spend 80…”
Aug 13, 2026 neutral
Calacanis: Unnamed hyperscaler pivoted a nine-figure AI strategy to open source
“One of the hyperscalers told me they just did a nine figure Double Lindy reverse, where they went from doing a frontier model on 100 billion dollars in infrastructure, and they're like, bing, it's gonna be open source, not frontier.”
Sep 4, 2026
Calacanis: Founders should raise large cash cushions during market euphoria
“Companies with hundreds of millions or billions of dollars in the cash have optionality, and if things do collapse or there's a big retreat, you'll survive through it, like DoubleClick, Amazon, Google, and countless other companies did. You take the money when…”