Opinion
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…”
Insight
Calacanis: Work-life balance advocates do not understand how startups work
“These businesses take a level of focus and commitment that is otherworldly. Like, the fact that people are Even talking about life work balance, and oh, you know, you can have life work balance, and that's what's important in life, like, these are people who d…”
Opinion
A startup could reach $100M in revenue using entirely no-code tools
“Like Airbnb, if it's being built today, could be built on Bubble, Webflow, one of these tools, Squarespace, Zapier, Slack, Airtable. You could glue all this stuff together and do it without a developer and probably get to 10 to a hundred million in revenue wit…”
Opinion
Calacanis: Accredited investor rules harm poor people by blocking high-upside bets
“The accreditation rules and the fact that our economic system is designed to protect people who are poor by not letting them take risk. That's noble, but it's wrong in today's society. The people who need to take risks and make bets That could have 200 X outco…”
Insight
Calacanis: Waiting for Real Customer Traction Cuts Angel Risk by 90%
“What people don't realize is if they just waited six months until the product was in market, then they could talk to a customer, and when the customer says, I love this product, and the customer's not the founder's cousin or former sorority sister or fraternit…”
Opinion
Calacanis: Hanging Investment Decisions on Market Size Is Cowardice
“So you have to, I think, if you're going to be great at this, not try to be a coward and hang your hat on the market size. I think that's what cowards do.”
Prediction Open · timeframe Apr 2025
Calacanis: US rules will let non-accredited gig workers invest in startups
“We're going to see some regulation in the United States where people are going to be able to be sophisticated investors, In other words, maybe they don't have the accreditation benchmark of whatever it is, a 152 100,000 a year in revenue of, in you know, incom…”
Assertion Not checkable as stated
Calacanis was invited to Molly Bloom's celebrity poker games in Los Angeles
“I was invited to all the Molly, Molly's games in LA, because I was living there at the time, and she used to invite me to all these games, and be like, at the Four Seasons, oh, Leo's here, and Toby's here, and they really want to see you, and I was like, they …”
Insight
Calacanis: Founders Quitting Is the Top Reason Startups Fail
“That is the number one killer of startups, is people quitting. If you are betting on somebody to take on a major, majorly difficult task, the number one killer is that they give up. At some point, they tap out. And most people think it's because the company ru…”
Insight
Calacanis: Founders with side projects will not succeed in their primary startup
“If you ask a founder, like, what else you're working on? Like, oh, I have a nonprofit and I'm doing a conference and my podcast and this and that. It's like, okay, well, they're not going to be successful at what they're doing. I mean, unless it's a podcasting…”
Assertion Supported
Calacanis: Asana Has Built a Much Bigger Business Than Basecamp
“I forgot the name of it because it's no longer the biggest player in that space. Like there's other people like Asana who've built like much bigger businesses, but you know, they decided they wanted to build a profitable lifestyle business.”
Opinion
Calacanis: Employers Value Self-Taught Candidates Over University Graduates
“People would value you more if you hacked the system and didn't pay them and did it on your own than if you actually went to the school.”
Prediction Didn’t hold up
Calacanis predicts Masayoshi Son will deliver very good returns for LPs
“Masayoshi-san is the last person in, and I think he'll ultimately wind up looking smart, because he picked some good companies, and I think he'll ultimately wind up having a very good return for his LPs”
Prediction Not checkable as stated
Calacanis: No-code tools will enable 20% of people to build products
“I think we're going to see the pool of people who can build a product go from like, call it low single digits, four or five percent of the country. Or even the world, young people starting companies, old people starting companies, I think it's going to grow to…”
Insight
Calacanis: Raising stakes breaks opponents' composure, making them predictably tight
“And that's why you'll see the really good players try to kick up the stakes constantly because at a certain point, people's brains, you know, like kind of tick over and break and they're like, oh my God, this is a lot of money. And once you have somebody think…”
Insight
Calacanis: Degenerate Gamblers Find Recovering Losses More Rewarding Than New Gains
“There are people who, if they're down a 100,000 dollars and they come back to zero, that's more rewarding to them than getting a 100,000 dollars up from zero. So let me say that again, like digging themselves out of a hole is a better feeling, more rewarding t…”
Assertion Supported
Calacanis: Uber Seed Round Paid Off 4,000x to 5,000x
“So an outlier like an Uber, for the people who are in the seed round, paid off somewhere in the range of 4000 to 5000 X, not percent, X.”
Prediction Not checkable as stated
Calacanis: Probable He Hits Another 300x to 1,000x Return
“Now, will I ever hit another one? It's probable that I will not. But will I hit another 300 X, 500 X, 1000 X? It's probable I will if I keep up at this pace.”
Insight
Calacanis: Seed Startups Are Experiments Until Hitting $500K Revenue
“And because I changed my perception of investing at the earliest stage, you know, I'm talking when the company's two, three, four, five people, and they've got the product in market for two, three, four weeks or months, I look at these as experiments. When the…”
Assertion Partly supported
Calacanis: 70% to 80% of Angel Investments Go to Zero
“70, 80% of these investments go to zero.”
Insight
Calacanis: Novice Angels Should Make Small Bets and Concentrate on Follow-Ons
“You know, in the same analogy of 500,000 dollar bankroll, I would make 25, 2000 dollar bets, put 50,000 to work, and then out of those 25, look at the top five and then say, okay, I'm going to allocate 25 to 50 to a 100,000 dollars into the top five based on t…”
Insight
Calacanis: Investing in underrepresented founders provides an edge due to lower competition
“The reason we're doing it is it's actually good business. A lot of these founders have incredible insights, and there, there's not competition for these deals because People are not making space for them to come to them and say, here's my idea, here's my busin…”
Assertion Supported
Calacanis: Three of 21 Angel Investors Backed Uber at Open Angel Forum
“Uber pitched out one of those, and three of the 21 people at that event invested.”
Disclosure
Calacanis: Launch Gets Higher-Traction Startups at Decade-Old Seed Valuations
“So we're finding ourselves investing later in the companies at the same price that we paid 10 years ago for companies that had not yet launched or had less traction, and frankly, maybe didn't look on the outside as polished.”
Jason Calacanis