Founder of LAUNCH, LAUNCH
Jason Calacanis CNBC SquawkAlley 5/24: Amazon opens store; Uber corrects; which tech giant to drop
.@jason on @CNBC @SquawkAlley: @amazon all-time high, opens bookstore & on-ramp retail; @uber corrects; which tech giant would you drop?-PT1
About Jason Calacanis
Jason Calacanis, co-host of the All-In podcast and founder of LAUNCH, has been active on his podcast and at events discussing investment strategy, the technology industry, and political dynamics. In October 2024, he outlined his investing philosophy, emphasizing backing a team's vision over hype and dollar-cost averaging into companies one believes in. He described Elon Musk as having a gift for pursuing multiple visions concurrently and argued that criticism of valuation hand-wringing stems from an inability to tolerate ambiguity across multiple business lines. In mid-2026, Calacanis moderated the All-In Liquidity Summit in Napa Valley, describing it as an event for the "top 0.1%" of the podcast's audience, with 550 capital allocators representing $7 trillion in capital present. He stated that the event was part of a broader community-building effort and that his philosophy for events is that attendees return if they make a great contact, have a great experience, or learn something. Calacanis has also commented on the current tech boom, which he attributed to AI, noting that companies like xAI, OpenAI, and Anthropic are going public. He described seeing "a Cambrian explosion in startups" and said he personally invests in roughly 100 new companies per year through his fund LAUNCH and a program called Founder University. In a May 2026 appearance on the Bulwark Podcast, Calacanis discussed why some in Silicon Valley have been reluctant to criticize President Trump, arguing that access to the administration to shape policy is preferable to not having one's phone calls returned. He also described former President Trump's handling of Iran as "an unmitigated disaster" and said he believed it would "kill his presidency." Additionally, Calacanis has been publicly critical of Mark Zuckerberg, stating that the Meta CEO has "damaged the reputation of the industry" by repeatedly prioritizing self-interest over what Calacanis described as the right thing for humanity, including in matters of privacy and content moderation.
Transcript (16 segments)
✨ AI-enhanced transcript with speaker attribution
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Host0:00
Jason Calacanis, inside.com founder, also joins us. Lots of discussion coming up. Yeah, let's talk about Amazon as you just mentioned. Shares hitting all-time highs this morning, third record in a row. This CEO Jeff Bezos speaking at the company shareholder meeting yesterday says now is not the time for complacency. The exact quote: 'There's no rest, we cannot rest on our laurels.' Adding the competition is as fierce and challenging as ever. Speaking of not resting, Amazon plans to open the doors of a brand new bookstore in Midtown Manhattan right on the site of what was once a Borders bookstore. Farad, one of the questions is: Are they trying to make money? Are they trying to rub it into these book sellers that they helped put out of business? What's the goal here?
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Jason Calacanis0:46
I don't think they're trying to rub it in. I mean, I think they're trying to make money. That's what they do. Sometimes I think they're testing it out. They're seeing if stores are good for some things like discovery, looking at electronics. They could try out lots of experimental things with the checkout-less store they're trying out in Seattle. So those kinds of things, they could try out a lot of things. They have a lot of money. And the thing about Amazon is they're the most experimental of the big companies and the most willing to surprise. This is another one of those surprises. I wouldn't have guessed a few years ago that they would have opened a huge retail operation, and they are so... I'm looking forward to seeing what happens.
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Farad1:38
Jason, this can't be about selling books, right? Because if it were about selling into some category, wouldn't they be selling clothes or something? Isn't this about the ecosystem, showing you can buy an Echo, you can buy a Kindle, look at all the stuff that you can do when you tie it all together?
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Jason Calacanis1:54
Yeah, Farad's wrong that this is an experiment. This is a deliberate, very specific program. It's on-ramp retail. What they're doing is, there's a large number of people who maybe haven't become a Prime member yet, maybe they haven't played with a Kindle. This is Amazon's way to do on-ramp retail and also relationship retail. If you look at what Apple did with their stores, you come in, hit the Genius Bar, you don't know how to use iCloud, you don't know how to use photos, you're not sure what Apple TV is, and they educate you. It services the people who are fans of your product and deepens that relationship, but it also serves as an on-ramp to your entire ecosystem. If you look at Amazon Prime, if they could onboard two or three dozen people per day in that store, they could do that by offering discounts on books. You're talking about generating tens of millions of dollars per store if you could convert 50 people to Amazon Prime, because the LTV of an Amazon Prime member is thousands of dollars. So this is really about on-ramping. And consumers are embracing physical books again, which is a counter-trend to the social media cacophony of idiots. People want substance in their lives, so they're buying books. Farad, you know this is also an occasion for a lot of people to remind everyone that Sears started out as a mail-order thing and became nothing but physical. Obviously we don't think that's the case, but it is a reminder that even though it looks like an exception in the retail strategy, Amazon as a company has massive amounts of physical assets: huge warehouses. It's not exactly a little virtual business that just runs on software alone.
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Farad3:48
Oh yeah. I mean, Amazon is a huge software company, but it is a massive presence in the world physically in a way that Google is not and Facebook is not, and even Microsoft is not. They have real stuff in the real world and they know how to manage those operations.
I mostly agree with Jason. I guess the reason I call it an experiment is because a lot of things that Amazon starts out as experiments. They try stuff out and they're willing to shut things down. I'm not convinced they're going to have hundreds of stores at this point. I think it's still at a point where they're testing out dozens of stores and seeing how it works. It could end up huge like AWS, or it could be like Amazon Fresh, which they've run in select cities but haven't made a huge thing at this point. It'll be really interesting to see if they can beat some of these brick and mortar stores at their own game.
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Host4:43
Do want to move on though, guys. Mention another rough morning for Uber. Just unbelievable. The company now says it plans to repay millions of dollars to New York drivers due to a calculation error that had to do with taxes. Another key executive exited the company, the seventh one in recent months. This time it was Uber's general counsel for Europe, the Middle East, and Africa, saying he's leaving for personal reasons. And then there's this: Hamish Douglas, the co-founder of Australian Mellen Financial Group with some $37 billion under management, says he thinks the ride-hailing service has less than 1% chance of surviving over the next decade. From his comments at the annual stockholders and financial advisers conference in Sydney: 'It's constantly losing money and its capital raising strategy is a Ponzi scheme.' We've reached out to Uber for comment. So Jason, this one's going to go to you. A Ponzi scheme for investors?
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Jason Calacanis5:33
Yeah, respond. I think it's kind of laughable. If he would like to make a long bet with me for $10 million, I'll bet my entire net worth that Uber will be here and thriving in 10 years. So it's a silly comment. I'll replace Uber in his statements with Amazon or Google or Facebook and I think that will be as laughable. On the issue of New York drivers, I put this in the bucket of good news for Uber. In that instance, Uber made a mistake in calculating the tax in one market on one service, and they are quickly making it right. I put this in the bucket of good corporate citizenship, owning a problem, being transparent, and working quickly to solve it. But a company that has reached tens of billions of dollars in bookings, it's laughable to say that's not a real company. Obviously this is a very real company, and the millions of people who take Ubers this week and the hundreds of thousands of drivers who collect checks this week would differ from our friend from Down Under.
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Host6:55
Farad, it's getting close to the point where Uber's taking so many hits, and it's not yet that I'm starting to think maybe this is good for the company. I mean, we just had LinkedIn on last week saying people really want to work at Uber despite all these negative headlines. The alternative is Lyft, and Lyft certainly hasn't overtaken Uber despite the negative headlines. I mean, do you buy this or do you think Uber's really in this for the long haul?
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Farad7:17
I mean, it's in this for the long haul. The question is whether riders and drivers stick with them. I think Jason could be right, this could be a completely innocent mistake in New York. In fact, I'm inclined to believe it's an innocent mistake. But the trouble for Uber is that no one is willing to give it the benefit of the doubt anymore. There's no massive goodwill for Uber. That's the difference between Uber and Amazon, Google, and Facebook. We all know these companies are big and make mistakes, but generally we give them the benefit of the doubt. They are well regarded by customers. I don't recall another tech company as big as Uber that is so vilified, even loyal customers feel kind of icky about using it sometimes.
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Jason Calacanis8:16
I think it's fair that they've had a rough year. When you have this much bad news, people are piling on now. But what it's doing is making the management team more resilient and more focused, and it's created a massive culture evolution at the company. Based on my knowledge, as an early investor, I am more bullish on the company than I've ever been and more bullish on the management than I've ever been. When you have this kind of microscope on you, it really makes you focused. If you look at Facebook, they went through some really tumultuous times including the largest fine in the history of the FTC and a 20-year audit. This isn't unprecedented. Microsoft was the most hated company on the planet for a period during their antitrust. What's important is how the management team responds, and they're getting there. I think they're really getting there and making progress. So I'm super, super bullish, and obviously massively conflicted.
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Host9:17
Yes, thank you for reminding viewers and listeners about your investment in Uber. Farad, finally, you had an interesting column the other day on what you call the Frightful Five tech companies. We call it FANG, but Alphabet, Amazon, Facebook, Apple, and Microsoft. Asking readers if you had to, which tech giant would you drop, and in which order? So we wanted to indulge you. What did you learn from this exercise?
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Farad9:39
I learned that a lot of people would drop Facebook first. I'm not sure whether to believe them, but in our poll, I think about 60% said they would drop Facebook first. I wonder if they're just saying that and they're completely addicted to Instagram, WhatsApp, and Facebook. Then a lot of people said Google was the one they would drop last. Google and Apple and Amazon were pretty close. I can believe that. I would drop Google first as a matter of fact because Google has the most analogs to something else I can use. Maybe not quite as good, but I can use other stuff. Probably the last one I would drop is Apple because you love your consumer product.
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Host10:29
Yeah, Jason, what about you?
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Jason Calacanis10:33
Yeah, so John's right that Google has Microsoft and Apple contemporaries that have duplicate product lines, so it's very easy to give up Google. When I hear that the majority of people say they would give up Facebook, that's like Lena Dunham or Rosie O'Donnell saying they're going to move to Canada if Trump is elected president. No chance. Completely fake news. Farad, I don't know about Microsoft. Maybe I could get another Word document, but in a corporate environment, Microsoft's pretty indispensable. Yeah, it has to be a bracket: the next one, do a bracket where you put them heads up. Would you give up Amazon or Facebook? You obviously give up Facebook to Amazon. Google versus Amazon, you give up Google. So I think Amazon wins the day in a bracket system because they have the most unique product in the world. For me, they're the last ones. I'd find it the hardest to give up Amazon.
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Host11:30
Yes, Amazon. We have no way to get toilet paper, guys. We've got to leave it there. Thank you, Farad. Jason Calacanis, always a pleasure.