On June 9, 2026, OpenAI (the San Francisco–based AI firm behind ChatGPT) filed confidentially with the SEC for an initial public offering. This is a bet that public markets will underwrite a business losing more cash than it generates for at least four more years.
The timing is brutal. OpenAI recently missed internal targets for new users and revenue, according to The Wall Street Journal. Its CFO has reportedly raised concerns that the company may not be able to support its massive data center spending. In late March, OpenAI secured $122 billion in the largest funding round in Silicon Valley history — $3 billion of which came directly from retail investors via bank channels. Yet the firm expects to spend roughly that same amount on computing power for AI research alone in 2028, and projects burning $85 billion that year even after doubling sales from the year prior.
The confidential filing allows OpenAI to prepare for a public offering without disclosing detailed financial information or business risks yet. Secondary markets provide a glimpse into what investors are willing to pay. Anthropic (OpenAI’s main rival, also filing to go public) recently surged to a $1 trillion valuation on Forge Global (a retail secondary market platform), surpassing OpenAI’s $880 billion mark in April. David Shapiro, founder and CEO of OpenVC, which oversees the NYSE OpenVC 500 Index tracking the largest public and private companies in the U.S., notes that Anthropic’s rate of appreciation far exceeds OpenAI this year — 123% year-to-date versus OpenAI’s 11.3%.
The race to get to the public markets first is a real concern. Experts say whoever makes their debut first will likely nab more of what is becoming increasingly scarce capital for AI companies, much of which will have already gone to SpaceX, expected to IPO first among the three at a $1.75 trillion valuation. Additionally, Anthropic’s filing disclosures will set a valuation comp that constrains how OpenAI can price its own offering when it files, according to a recent PitchBook report that viewed OpenAI as overvalued relative to its fundamentals. OpenAI was founded in 2015 as a nonprofit research lab and disrupted the world of AI when it released ChatGPT in 2022. The company has built real scale, with around 900 million weekly active users.
Waymo Buys Apple’s Desert Test Track — For $220 Million
On June 5, 2026, Waymo (the Alphabet-owned autonomous vehicle company) acquired a 4,500-acre proving ground in Wittman, Arizona, for $220 million. This is the largest closed test course purchase by any self-driving company to date.
The property was previously owned by Route 14 Investment Partners LLC, a Delaware shell company associated with Apple. Apple purchased the facility in 2021 for $125 million after renting access to it for years. The site had been used as a test facility for Fiat Chrysler, featuring different road surfaces, a high-speed oval, and hot-weather testing capabilities. Apple used it to put prototype vehicles through their paces as the tech company oscillated through different variations of its car project — known as Project Titan — which was ultimately scuttled in early 2024 after Apple had spent billions of dollars on it.
Waymo confirmed the sale to TechCrunch. The Arizona location includes a 115-acre city course, a 35-acre vehicle dynamics area, a 4-mile oval track, and a freeway course purpose-built for autonomous vehicle testing. A Waymo spokesperson said the facility will be used to simulate driving scenarios in a controlled environment to continuously test and improve the performance of its self-driving system. Specifically, the company will support rider-only testing, motion control testing, operational training workflows, and future testing expansion over time.
Waymo is in the middle of a dramatic expansion of its fleet, which currently stands at close to 4,000 vehicles. The company recently started offering the first rides in its new van, which is made by Zeekr. Waymo has said it wants to make tens of thousands of robotaxis per year, including the Zeekr van and the Hyundai Ioniq 5. The purchase rounds out Waymo’s already robust network of closed test courses. The company still uses the Castle Proving Ground in California as well as the Transportation Research Center in Ohio. Both of these are dwarfed by the Arizona location.
Pentagon Adds Baidu, BYD, Unitree — To China Military List
On June 9, 2026, the U.S. Department of Defense added Chinese search giant Baidu, EV-maker BYD, and buzzy robotics company Unitree to a list of entities it says support the Chinese military. This is likely to further strain tension between the U.S. and Chinese governments.
The list — known as the 1260H list, for the specific section of the 2021 National Defense Authorization Act that created it — is just one tool that the U.S. has used to place restrictions on Chinese tech. President Donald Trump has used tariffs in both of his terms to put pressure on China, including a 100% tax on imported Chinese EVs. This particular update to the 1260H list was briefly published in February, before being pulled from the Federal Register for unexplained reasons, as Bloomberg News notes. The expansion of the list increases the chance that the Department of Defense could make it harder for U.S. companies to do business with these entities.
Most of China’s biggest artificial intelligence players are now on the list, with Tencent added last year. This comes as Trump has said he’s weighing whether the U.S. should take equity stakes in the country’s top AI companies. The updated list now includes 188 companies. The Pentagon added a handful of automotive industry players to the list this year. In addition to BYD, trendy EV company Nio and battery companies CALB Group and EVE Energy were added. RoboSense, one of China’s leading makers of lidar sensors, has joined its rival Hesai on the list, too. Baidu is also one of China’s leaders in autonomous vehicles.
Apple Revamps Siri — With Google Gemini and a Stand-Alone App
At WWDC 2026, Apple announced a major revamp of Siri that makes the smartphone voice assistant more helpful, attuned to iPhone users’ personal data, and action-oriented. This is Apple’s attempt to catch up with the generative AI revolution that has raged around it for years.
A major aspect of this Siri revamp is a partnership with Google Gemini to help power the AI tool’s underlying model as part of Apple Intelligence. After extended delays, Apple is moving forward with a dynamic repositioning of Siri that changes how the voice assistant appears on iPhones and gives people a new way to access it: a stand-alone Siri app. This revamp is expected to roll out to consumers later this year. Soon, users will also be able to have chatbot-style interactions with Siri and access past conversations, similar to the user experience on ChatGPT. Siri will also be able to use personal information stored on your phone — including what’s currently on your screen — when answering questions.
Before this announcement, Siri had stayed relatively static while the generative AI revolution raged around it. Other voice assistants — Google’s Gemini, Anthropic’s Claude, and OpenAI’s ChatGPT — were able to eclipse Apple’s efforts in a short time. This new Siri can simply do more. If you want help composing an email, the revamped Siri can pull in contextual information from your Apple devices, details tucked away in your Notes app, to generate a response for you. It can even compose draft texts to send to your group chats. Siri is following a similar pitch set forth by other hot assistants in 2026: Give the AI tool more personal info so it can be a better helper. Despite the company’s early success with Siri, is Apple too late here to succeed alongside the next generation of AI assistants? That doesn’t seem to be the case, based on the company’s history.
The capital markets are no longer pricing AI companies on revenue multiples alone — they’re pricing them on the gap between cash consumed and cash generated. OpenAI’s filing makes that explicit: a business that won’t break even until at least 2030, asking public investors to bridge $85 billion in annual burn by 2028. That’s not a growth story. That’s a bailout dressed up as an IPO. Waymo’s $220 million land grab and Apple’s Siri reboot both signal the same thing — the infrastructure arms race for AI is entering its most capital-intensive phase, and the companies that can’t raise at these nosebleed valuations will either partner, get acquired, or disappear. If you’re allocating capital in 2026, the question isn’t whether AI is overhyped. It’s whether you’re prepared to fund businesses that won’t generate positive cash flow until the next recession.
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AI Ludens — a creator who works with AI as if it were play.
“Ludens” is Latin for “the one who plays,”
borrowed from Johan Huizinga’s Homo Ludens.
I believe creation alongside AI is meaningful play.
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