OpenAI’s $1.25T Raise, Starlink Mobile & Zuck’s Tax Deal

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Today’s show:

Is OpenAI finally priced correctly? Jason argues that the reported $30 billion raise at a $1.25 trillion valuation is finally “right-sized.” He also says that he’d put money in at that price, while walking through the risks that could still sink the investment.

It’s a Friday all-news episode with Jason and Lon, covering OpenAI’s latest round, SpaceX’s push to become America’s fourth major carrier, Zuck and Meta’s creative move around the proposed California billionaire tax, and some of Lon and Jason’s favorite documentaries.

Plus we’re asking the timely question: who watches the AI watchdogs?

Relevant Links

OpenAI nears up to $30B round at $1.25T valuation, led by UAE investors (CNBC):cnbc.com/2026/10/22/openai-funding-round-uae-i…

Anthropic investors eye a $2T IPO (Nasdaq):nasdaq.com/articles/move-over-spacex-anthropic…

Uber puts all 30,000 employees on ChatGPT Work (TechCrunch):techcrunch.com/2026/10/22/uber-puts-all-30000-…

Telecom stocks fall as SpaceX eyes 80,000 cell sites (Yahoo Finance):finance.yahoo.com/markets/stocks/articles/tele…

Verizon launches simpler plans and drops activation and upgrade fees (Fox Business):foxbusiness.com/markets/verizon-launches-simpl…

Amazon Leo's launch slips past early 2026 (ITdaily):itdaily.com/news/network/amazon-leo-faces-delays

METR and Redwood Research's write-up on red-teaming OpenAI's agent monitoring:metr.org/blog/2026-10-22-red-teaming-openai-ag…

Open Philanthropy is now Coefficient Giving:coefficientgiving.org/research/the-story-behin…

Court documents show the alleged FSU shooter's ChatGPT chats (AOL):aol.com/news/court-documents-show-florida-stat…

Meta's 8-K filing on the Founder Alignment Agreement (SEC):sec.gov/Archives/edgar/data/0001326801/0001628…

Polymarket: will California's billionaire tax pass?:polymarket.com/event/billionaire-one-time-weal…

Mark Cuban vs. Ro Khanna on the billionaire tax (Fortune):fortune.com/2026/08/17/mark-cuban-california-b…

Elizabeth Holmes: The Theranos Deception (60 Minutes archive):cbsnews.com/video/elizabeth-holmes-the-therano…

“The Act of Killing” trailer:youtube.com/watch?v=Q3FcB1UZHlg

“Grizzly Man” trailer:youtube.com/watch?v=uWA7GtDmNFU

“Hoop Dreams” trailer:youtube.com/watch?v=uf9Nq2ju0t0

“The King of Kong” trailer:youtube.com/watch?v=L5XvArGGIzk

“A Short Stay in Hell” by Steven L. Peck:amazon.com/dp/0983748446

“The Library of Babel” by Jorge Luis Borges [PDF]:sites.evergreen.edu/politicalshakespeares/wp-c…

“The Eureka Machine” by Richard Socher:amazon.com/dp/154170570X

Timestamps:

Jason’s in SF with the LAUNCH Accelerator 37 cohort

Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at plaud.ai/twist and use code TWIST for 10% off!

Tactical & Practical talks live at Salesforce Tower

Using Claude for brainstorming, not writing

Sentry - New users can get $240 in free credits when they go to sentry.io/twist and use the code TWIST26

OpenAI closing $30B at a $1.25T valuation

Why OpenAI could still lose

Would you put 30% of your retirement into OpenAI?

Lightfield - Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you - it even prospects and books your meetings. Used by thousands of startups. Free at lightfield.app

Every Tesla becomes a Starlink hotspot

What would be the ultimate SpaceX domain name?

Thanks to our partners at Rippling! Head to rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business.

Is METR a fair watchdog for OpenAI?

Jason’s “Know Your Customer” plan for AI models

Meta’s deal to keep Zuckerberg in Cali

Why Jason would raise the minimum wage

Does Nathan Fielder give Liz Holmes a pass?

“A Short Stay in Hell” and “The Eureka Machine”

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