Jason Calacanis

Ben Horowitz says Andreessen Horowitz holds a lot more stock in OpenAI, and that the firm is philosophically long both OpenAI and Anthropic. Jason Calacanis asks how a firm ends up on the number one and number two player at once. Ben Horowitz says many investors are in both, because these companies are no longer venture rounds. At tens of billions of dollars a company needs everyone's money, so long as the money is green.

He separates that from a real conflict. Owning two Series A companies that do the same thing is still a problem. OpenAI and Anthropic, at a scale people discuss around 2 trillion dollars, are not. He traces the setup to regulatory changes in the late 1990s and early 2000s

Jason Calacanis says Anthropic's investor day hit the AI trade in the same week as the CoreWeave selloff. Anthropic is planning to go public around Thanksgiving. Polymarket puts the chance of a listing this year at 74 percent, down from 95 percent in early September. The figures he walks through, secondhand from investors, include 16.8 billion dollars of third-quarter revenue, already more than 5 billion dollars a month, and net revenue retention of 900 percent, meaning customers spent nine times what they spent last year.

The company also described itself as free-cash-flow positive, with an adjusted gross margin of 85 percent and an adjusted operating margin of 11 percent. He notes that no

Jason Calacanis says Bill Gates retired because becoming the world's richest man made him the most hated man on the planet. The hatred got in his head. Then Gates had an antitrust investigation. He felt all the pressure from the antitrust investigation and from being the most hated man, and he decided he had to be loved.

The move Jason Calacanis calls based was to stay CEO and keep building the greatest company in the world. Gates instead asked how he was going to be loved. His answer was to get rid of polio, give all his money away, and do the giving pledge. Once the job is gone, Jason Calacanis says, the worry gets in the head. There is too much time, and the spiral starts. The worry turn

Jason Calacanis argues the CoreWeave crash is market volatility, not a fundamental break. Underwriting multi-trillion dollar outcomes on exponential rates of growth makes the market super sensitive to present-day data points, so the swings get exaggerated. He does not think something fundamental has changed.

Demand for compute keeps growing by leaps and bounds. The biggest model companies say they are compute constrained. Startups are asking venture capitalists for help getting compute, and some venture capitalists are trying to buy compute as a competitive edge for their startups. One accelerator bought compute and used it to get people to apply. Older chips, the H100s and the A100s, sever

Jason Calacanis says the biggest neoclouds got crushed after CoreWeave's bonds started to sell off. He calls the selloff a possible canary in the coal mine and says the week may have been an AI bubble, if one exists, popping or deflating a little.

On Tuesday, people on X, including Chamath Palihapitiya, pointed out that the yield on some of CoreWeave's debt had hit 15%. Yields rose because bond traders are worried about CoreWeave's ability to generate enough cash to support its debt and want a higher rate of return. Elon Musk added one word, yikes, headlines followed, and everything tanked. CoreWeave, IREN, and Nebius were down about 20% as publicly traded companies. On Wednesday, CoreWeave

Jason Calacanis told Geek at Sea that a COVID-19 lockdown has effects you miss if you count only the first one. People who lose jobs may skip the doctor, lose insurance, drink, use opioids, become depressed, or go bankrupt, and some of those paths end in suicide. He put the same question to student-debt cancellation and to business aid: a grant, equity, or a loan, and if a loan, at zero interest or at a rate that gives savers a reason to save. He did not claim to know the answer. In Silicon Valley, asking out loud is normal. Outside it, the habit looks like evasion. Anyone who got rich fast and now affects other lives should expect the questions.

It all depends on your aspirations. If you desire to start a billion-dollar venture backed high-growth company, you are going to have to work harder. If you are satisfied with a small business that just makes money to live off, chance are you won't work as hard.

Jason Calacanis told Geek at Sea that by 2020 a hiring manager should take the person who can do the work, degree or not. In the early 1990s, he said, MIT, NYU, and a city college meant three salaries, about $100,000, $75,000, and $50,000, and the diploma decided who got in the door. He would choose an Uber driver who finished the open courseware at night over an MIT student in the same AI classes, if the work matched. The night student spent about nothing and showed more grit than someone who spent a quarter of a million dollars and four years. The same test applies to founders. Bootstrap to $10,000 a month and write to him at jasoncalacanis.com.

Jason speculates that we are now living in a society where surviving has gotten so easy that it removes the edge and fear.

On the other hand, work, entrepreneurship, and capital has become portable, and you are now competing with anyone who can do your work, around the world. It could be demoralizing.

"Bootstrappers are my people." ~ Jason.

There are two groups of people in the world: people who write checks and people who are so good at what they do, the are so resourceful, they build it themselves.

Jason loves to invest in people who were able to elevate themselves without a handout.

Jason Calacanis told Geek at Sea to reach 60 or 70 percent on many skills and to be truly good at one or two. At his magazine he was neither photographer nor designer. A few classes let him shoot the issue, then talk about framing, type, and cropping with the people who did it for a living. Cross-field people, the subject of the book Range, carry a method from one job to another. Enterprise sellers learn a funnel. Consumer apps learn invites. Slack took Twitter and Facebook's virality and let anyone in a workspace invite a colleague. There is more than one way to cook chicken, and more than one road from New York to California.

When faced with a challenge, the most successful people in the valley ask questions, they immediately start collecting data about the world and process and debate it. They theorize and look for answers.

The most successful founders are opportunistic and take control of the world. They never feel victimized.

Who you hang out with changes how you think about the world.

"It's not even necessary money over people, because that would be like looking at it in the most first order, you know, superficial way. It's if a large number people lose their jobs cannot afford health care. Stop going to Dr Start abusing opioids or alcohol. Ah, full into depression commits suicide because they go bankrupt like you can actually track these things.

It just takes a moment of taking a deep breath and saying, Oh, there are second order effects and buried water effects of every action, and we have to think holistically when we do things in different systems in the world. So for every time you put an incentive out there, it could have dire consequences that you didn't expect th

Jason Calacanis told Geek at Sea he would be massively active during the crisis and after it. Support founders and inspire innovation is the mission he stated for Launch, his investment firm, and he also thought other investors would freeze, which would make the deals better. A company doing $10,000, $20,000, or $30,000 a month that could not raise should call him. He was no longer a Sequoia Scout. The checks would come from his own fund and from thesyndicate.com, the group of about 4,000 investors he set up after leaving AngelList. That syndicate, he said, was doing about 30 deals a year and gathering $250,000 to $2.5 million for each one.

Jason Calacanis told Geek at Sea he had stopped investing as a Sequoia Scout. He has his own fund and thesyndicate.com. AngelList taught him the model, and he left to build his own team, with no grudge against theirs. It is not a rival marketplace. It is one syndicate of about 4,000 accredited investors, which he called the largest individual syndicate. They do about 30 deals a year. He writes a memo, the founder does a webinar, and the group puts in $250,000 to $2.5 million. A member can write a check for $2,000, write one for $200,000, or write nothing and only read the memos. Some put $2,000 into every deal and call that a portfolio.

"Brian Alvey would come over, he came over, I think 29 times on I would do about two or 3000 words. He would come over. He'd edit them real quick, and then we talk about it. Then we go for a walk. We'll get some Mexican. True, both, Like Mexican food.

Then we walked back to my house and talk about it a bit more. And what other topics you want to do? This. I'd say I got about 80 70 or 80% of it done in those 30 days on."

They were going to write more chapters, but the editor read it and said it was the perfect time to publish!

YouTube! Open YouTube and look up how to do whatever it is that you need to do. There is a video out there for mostly everything.

Jason and family are big on Montessori and Reggio activities, tools and techniques which center around the child. Anything the child can do, let them do it.

His 3 year olds cut food, while the 10 year old bakes their dinner. They know how to do it, and it's really rewarding to see your kids take care of themselves independently.

When you practice martial arts or you learn how to use a firearm, you learn how fragile you are. You learn how dangerous the world is and how to avoid those situations.

Being able to assess a situation, and to get through it on their own, without help, is what would give kids their confidence.