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.”
Prediction Not checkable as stated
Calacanis: California will be damaged for a decade or two
“I think Austin's kind of the future. I think California's gonna be damaged for a decade or two. So I think for the rest of our adult lives, this town.”
Prediction Not checkable as stated
Calacanis: Andreessen Horowitz's long-term returns won't match Benchmark or Sequoia
“I think in the arc, it will not be comparable to benchmark at Sequoia.”
Opinion
Calacanis: Bezos dunked on Sanders and Warren via Amazon's internal policies
“He took the platform that you could never actually enact. And he enacted it inside of Amazon. If it's not perfectly clear what just happened, literally he's dunking on you. You wanted free college and couldn't get it done, he gave it to Amazon employees. You w…”
Assertion Not checkable as stated
Calacanis: My syndicate is the world's largest, deploying $50M annually
“The angel syndicate is now the largest syndicate in the world. I've deployed, like, one hundred eighty-five million dollars in my career as an angel investor. I'm doing fifty million a year now.”
Opinion
Calacanis: The All-In podcast is worth $50M to $100M
“It's worth fifty million, to answer your question. 50 to a hundred million. I mean, as a top 40 podcast, it's worth at least fifty million.”
Assertion Supported
Calacanis: Chamath Palihapitiya invented 'growth hacking' at Facebook
“There is no equivalent of growth. That was, the idea of growth hacking didn't exist as a term until Chamath did what he did.”
Disclosure
Calacanis: I premeditated character arcs on All-In and created 'Sultan of Science'
“In all honesty, I did craft with All In. I was very premeditated in creating some character. I've never really talked about this. But I crafted some character kind of arcs. I, The fights are all real. Trust me, there's nothing scripted about that. But I did sa…”
Assertion Not checkable as stated
Calacanis: Only ~5% of my 350 portfolio founders attended Stanford
“I've invested in 350 companies. Like, maybe five percent of the founders went to Stanford.”
Opinion
Calacanis: Journalists only have between 5% and 35% of any story
“I, now looking back on it, I think we had between five and 35% of a story, and I know that's, like, probably triggering to a lot of journalists that they have that little information.”
Opinion
Calacanis: I did not change Uber or Robinhood's trajectory
“A, that is not the case with Uber or Robinhood. I was along for the ride, let's be honest. I did not change the trajectory of those companies.”
Assertion Partly supported
Calacanis: AOL paid $30M for Weblogs Inc with only $200K in revenue
“And when I sold weblogs to AOL, people were like, oh my God, these people are idiots. They gave thirty million dollars to, you know, for weblogs Inc. They've only got 200 K in revenue.”
Insight
Calacanis: Best M&A deals seem overpriced initially, underpriced five years later
“And that's the best M&A. Is when you look like you robbed the bank. And then five years later, it looks like you robbed the founder.”
Opinion
Calacanis: I am on the Mount Rushmore of angel investors
“I know I'm Mount Rushmore for angels.”
Disclosure
Calacanis: Sequoia offered a 50/50 carry split on early scout deals
“It was like you know, at the time, they carried fifty-fifty. Fifty-fifty at the time. They dropped it down after that.”
Prediction Open · timeframe Oct 2027
Calacanis: SEC accreditation rules will soon allow test- or course-based qualification
“I believe that we're going to have a test For accreditation. And you'll be able to be sophisticated if you take a course. So I think that's coming in the coming years.”
Assertion Not checkable as stated
Calacanis: Top endowments cited solo GP status as blocker
“If, you know, I've met with all the top endowments in the world over the years, and they're very kind to me, but it's always been like, solo GP is a blocker, no track record.”
Assertion Supported
Calacanis: Calm raised at $4M then bootstrapped to $250M valuation
“They had, it was four million dollars, we put 378 K in on six percent, and they didn't raise any money. Until it was a two hundred fifty million dollar valuation, so no dilution.”
Disclosure
Calacanis: My initial Uber investment was Sequoia's money as a scout
“That was Sequoia's money.”
Assertion Supported
Calacanis: SoftBank and J.P. Morgan each backed half of Flatiron Partners
“They were half of it, and Masayoshi-san, Softbank, was the other half.”
Assertion Not checkable as stated
Calacanis bootstrapped Silicon Alley Reporter to $10M revenue by age 27
“I grew that business to ten million dollars in revenue off my credit cards and Had a, 75 to a hundred people working for me when I was 27 years old, and I didn't know anything about how to run a magazine, how to run Edsels.”
Disclosure
Calacanis: Only one producer works on an episode of All-In
“Producer Nick, that's it.”
Disclosure
Calacanis: Inaugural All-In Summit generated millions and turned a small profit
“In the event, did a couple million dollars, had a small profit. But it was the number one tech event of the year by far.”
Assertion Supported
Calacanis: Mark Cuban invested $300K in Weblogs, Inc.
“Mark Cuban was our big investor and by big investor, he put 300 K in for five percent. So that was a great outcome for him.”
Jason Calacanis