Travis Kalanick: OpenAI's Identity Crisis, Datacenter Wars, Market Up on Iran News, Mamdani's First Tax, Swalwell Out

The episode opens with banter about the panel's locations. It then moves to a proposed New York City tax on pieds-à-terre, meaning homes that are not the owner's primary residence. The rate had not been released. The figure the panel had seen in speculation was 3.9% a year, and they stressed that it was not final. As described on the show, the tax would apply every year to second homes worth more than $5,000,000 within 15 miles of Midtown Manhattan.

The panel's main economic objection was that the tax targets the most elastic buyers: people who do not live in New York and who could buy a second or third home anywhere. The prediction was that demand for second homes would fall sharply and drag down the wider market. One participant suggested this could, oddly, help housing affordability. Another rejected that idea because lower prices would remove the incentive to build. A third added that luxury penthouses were never going to become low-income housing.

The panel also worked through the cost to a buyer. Because the uncertain rate could keep rising, one speaker argued that no prospective buyer would go ahead now. Another estimated that, with interest and inflation, the tax would nearly double a unit's effective price over a decade. On that estimate, a $10,000,000 unit would need a $20,000,000 resale price to break even after about ten or eleven years. A further point was that the tax would also hit rental units that are not the renter's primary residence, from one-week stays to five-year leases. That led to the remark that the policy might mainly benefit hotels.

The panel disagreed about a video in which the mayor pointed at a property owned by Ken Griffin. One participant called it doxing. Another disagreed: the purchase and the unit had been widely known and marketed for years, and Griffin does not live there. This speaker said the case would be different if it were a private primary residence. The first speaker accepted that this case was more tenuous but called the video a "dog whistle." The speaker said it had been seen by tens of millions of people and tied it to the shooting of the UnitedHealthcare CEO. The speaker also cited that week's attack on Sam Altman's house, which they said involved a Molotov cocktail and a bullet.

The same speaker tested the argument by reversing the parties, imagining a Republican standing outside Bernie Sanders' second home. They condemned political violence against anyone:

you can feel however you want about him, but nobody deserves to have their house fire bombed or shot at, period. Full stop.

Not everyone defended second homes. One participant said they own one house, dislike the multiple-home lifestyle and "go to a hotel" on vacation. This speaker pointed to London, where wealthy people used real estate to store assets and parts of the city were hollowed out. Their description of areas like Chelsea was that "it's not as if it was unlivable. It's just that it was unlived." They said those streets felt like a ghost town on Thursday or Friday nights. Another speaker agreed that this "land banking" is a real issue.

The broader housing debate then turned to supply. Panelists cited Austin, where they said rents and housing prices fell three years in a row while net migration rose. They also said the city had roughly doubled over the past decade while one- and two-bedroom rents went down. Their conclusion was that allowing building to meet demand solves the problem. They blamed Democratic cities and NIMBY opposition for blocking construction, and contrasted this with a Texas approach summed up as "It's your land. You have the right to develop it." These comparisons were offered as assertions; no sources were cited for the figures.

London came up again as a warning. One speaker said the high end of London's market had "basically turned over and collapsed" after the stamp tax, which they compared to the New York proposal. Another argued that wealthy people park money in a few world-class cities because those cities have the rule of law and are expected to keep appreciating. On this view, arbitrary new taxes would push that capital elsewhere, which is bad for the city and, more broadly, for the country.

Several arguments framed absentee owners as a net gain for cities. They already pay property tax but rarely use city services, so they are "profitable to the city." One speaker guessed that Griffin "must be paying 3 or 4,000,000 in taxes every year." The panel also described a development argument. A price-insensitive "whale" willing to overpay per square foot for a top floor can make a whole project financially viable. On this argument, removing that part of the market would cause development to "dry up to a large degree."

The UK case was raised again with its restrictions on non-dom status. One speaker said wealthy residents moved to Zurich, Lugano and Milan. This speaker had met with the UK government the day before. Officials there did not yet see a measurable enough impact to treat it as a crisis. The speaker's open question was whether the effect is a slow bleed that becomes hard to reverse because no single dramatic moment ever forces a policy change.

Panelists compared this with existing transfer taxes. Los Angeles has a 5% mansion tax covering most areas, though not Beverly Hills. In San Francisco, as described, an extra transfer tax starts on properties above $5,000,000 and rises to 6% above $25,000,000. With brokerage commissions, a speaker put the total cost of selling at 13%. Another linked LA's tax to transaction volume that had "completely dried up." This speaker said San Francisco's tax was imposed retroactively and concluded:

your property is not safe in blue states.

The main topic was OpenAI's apparent identity crisis. The host described a four-page memo to employees from chief revenue officer Denise Dresser, which leaked immediately. As relayed on the show, the memo said a $30,000,000,000 run rate was inflated by $8,000,000,000 because of a revenue share and accounting with AI model providers. The pronoun in the transcript is ambiguous, but later discussion applies this point to Anthropic. The memo also reportedly described Anthropic's story as built on fear, restriction and the idea that a small group of elites should control AI. It said OpenAI is going hard after business customers and wants to win the agent platform layer. The host's view was that such memos are written to reach the press and to undercut Anthropic's valuation.

The host added context. OpenAI hired Peter Steinberger, the architect of the open-source OpenClaw project, without acquiring the project itself. Perplexity Computer had reportedly quadrupled its revenue. A Polymarket market put a 75% chance on OpenAI releasing its new model, SPUD, the following week. The FT cited anonymous OpenAI investors frustrated by the company's lack of focus:

you have ChatGPT, a 1,000,000,000 user business growing 50 to a 100% a year. What are you doing talking about enterprise and code? It's a deeply unfocused company.

The host also said ChatGPT's market share is falling even as its user count rises, because Gemini and Claude are gaining. Meta had just released its first proprietary model, and Apple has users but no product in market yet.