Jason Calacanis

Jason Calacanis says Google lost about $500 billion of market cap on Thursday, falling 10 to 15 percent, after Q3 earnings missed search revenue for two straight quarters. Searches are growing massively, but the people clicking the ads are not. Free cash flow is negative even while cloud doubled year to year to $30.7 billion. Overall revenue is still growing 25 percent year over year. Search, the business that pays for everything, grew 12 percent, down from 17 percent.

David Friedberg says the core Google ad business is a real challenge. The company trades at roughly 21 times operating income. Google Cloud operating income for this quarter went from three and a half billion dollars last yea

Jason Calacanis says Gallup still has frequent and daily AI use at work at about 10% and 20%. Frequent use means a few times a week, and daily users are about 10% of people. Adoption is nascent because a lot of top enterprises will not let employees use AI without limits.

Those companies are not letting employees connect email, knowledge bases, Notion, or Slack. Big corporations block the full power of AI because they are scared about cyber risk. Once that cyber threat is mitigated, daily users go from 10% of people to 60, 70, or 80%. A lot of growth is left for the point when every employee has an agent. Uber bought ChatGPT for every employee just last week.

Jason Calacanis says Anthropic's S-1 targets a $100 billion public offering, large enough to pass SpaceX and rank as the largest ever. The target date is November 16, and the ticker will be ANT. Anthropic raised $85 billion in June. Polymarket puts a 78% chance on a raise of at least $95 billion, and the valuation runs from $1.5 trillion to $2 trillion. Polymarket's leading range is $1.75 trillion to $2 trillion at 31%, so the working assumption is a market cap slightly under $2 trillion.

Revenue was $16.3 billion in the first half of 2026, 14 times the first half of 2025. The second quarter is $11.6 billion, a 30 times jump over the last five quarters and almost as much as the first half.

Jason Calacanis says Anthropic's targets put revenue at 100 billion dollars, then 300 billion, and eventually 600 billion.

Anthropic is already at about 100 billion in revenue for the year, roughly a third of Google and a quarter of Apple. He compared cumulative revenue across the first seven years of the iPhone, Google cost-per-click search, and Amazon as a seller of books and other retail goods. AWS stays out of the early Amazon total, and adding AWS in later years makes the historical picture even more striking. It is possible Anthropic's business is bigger than the iPhone, Google cost-per-click search, and Amazon books and retail put together.

A franchise of that size has never shown u

Will Ahmed says WHOOP stood up a travel team for its AI coach because travel is a common use, and the coach is a large part of the product's future after years of work. A Japan trip comes up in the conversation: sleep on the first half of the flight, and skip caffeine at a set time after landing. The audience he describes is aspiring people, a serious athlete, someone already fit, or someone who wants more energy for family, work, and a longer life.

The coach sits on more than the wrist sensor. Advanced labs, blood tests, and medical records come in beside the physiology, and the journal is the other large set. Just over 50 percent of members journal every day. The WHOOP Journal is 100 plus

Will Ahmed says a GLP-1 is a meaningful shift for the body, and typically about 50% of the weight someone loses is fat and 50% is muscle. The muscle share is how people can sometimes end up quite frail even after losing a considerable amount of weight.

Knowing someone is on a GLP-1 lets Whoop push activity and a little strength training, even if it is only body weight, so the person does not end up losing weight. The right diet includes protein, and anecdotal success around creatine while on a GLP-1 is treated as super important.

Jason Calacanis added a GLP on a mirrored phone. The plan called for 9,800 steps, two strength activities a week, hydration, protein seven days a week, and a chec

Jason Calacanis says France just saw its worst riots in decades. Protests that started because high schools were dilapidated and underfunded have turned into civil unrest, and they have spread to Italy, Spain, and Albania. More than half a million people have taken part.

Jason Calacanis says more than 3,000 businesses have been damaged, with hundreds of millions in losses. More than 1,000 police officers have been injured, and 2,500 people have been arrested, 70% of them adult men. A 143-year-old city hall in Limoges, 250 miles south of Paris, burned down. He says President Trump and Vice President Vance called this a third world immigration and welfare state issue. France's justice ministe

Jason Calacanis says AI found two critical exploits, nicknamed PHP to shell, in PHP, the open source language that powers about 70% of websites, including WordPress and Wikipedia. The PHP security team rated them 9.2 out of 10.

The plan was one major patch on October 22, the day of the recording. The details leaked, so PHP moved the release up to Wednesday, October 21. Jason Calacanis says AWS then reported a jump in hacking activity, and the Cloudflare CEO said they saw millions of hacking attempts. Governments in France, Germany, Netherlands, Denmark, and Finland started taking websites down. Wikipedia took some systems down to patch them. In the United States, the NSA and the FBI put out

Jason Calacanis says President Trump's approval is so low because the president no longer talks about the bottom half of the country. President Trump talks about data centers, crypto, and a golden age, while people are waiting to hear about the minimum wage, housing, and inflation.

On his tweet about how President Trump could save the second term, Jason Calacanis says the president has to talk about housing as much as he talks about data centers. Raising the federal minimum wage is only a nice gesture, because it impacts 10 to 15 million people. Jason Calacanis says the president signs executive orders for the tech industry and large businesses, and people in the bottom half do not see the

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.