OpenAI’s $1.25T Raise, Starlink Mobile & Zuck’s Tax Deal | EP 2354

This Week In Startups is made possible by: Plaud - https://plaud.ai/twist Sentry - https://sentry.io/twist Lightfield - https://lightfield.app Rippling - https://rippling.ai/twist 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): https://www.cnbc.com/2026/10/22/openai-funding-round-uae-investors.html Anthropic investors eye a $2T IPO (Nasdaq): https://www.nasdaq.com/articles/move-over-spacex-anthropic-targets-2-trillion-valuation Uber puts all 30,000 employees on ChatGPT Work (TechCrunch): https://techcrunch.com/2026/10/22/uber-puts-all-30000-employees-on-chatgpt-work/ Telecom stocks fall as SpaceX eyes 80,000 cell sites (Yahoo Finance): https://finance.yahoo.com/markets/stocks/articles/telecom-stocks-fall-spacex-eyes-134838815.html Verizon launches simpler plans and drops activation and upgrade fees (Fox Business): https://foxbusiness.com/markets/verizon-launches-simpler-plans-new-loyalty-program-drops-some-fees Amazon Leo's launch slips past early 2026 (ITdaily): https://itdaily.com/news/network/amazon-leo-faces-delays/ METR and Redwood Research's write-up on red-teaming OpenAI's agent monitoring: https://metr.org/blog/2026-10-22-red-teaming-openai-agent-monitoring/ Open Philanthropy is now Coefficient Giving: https://coefficientgiving.org/research/the-story-behind-our-new-name/ Court documents show the alleged FSU shooter's ChatGPT chats (AOL): https://www.aol.com/news/court-documents-show-florida-state-233829466.html Meta's 8-K filing on the Founder Alignment Agreement (SEC): https://www.sec.gov/Archives/edgar/data/0001326801/000162828026066700/meta-20261019.htm Polymarket: will California's billionaire tax pass?: https://polymarket.com/event/billionaire-one-time-wealth-tax-passes-in-california-election-2026 Mark Cuban vs. Ro Khanna on the billionaire tax (Fortune): https://fortune.com/2026/08/17/mark-cuban-california-billionaires-tax-wealth-ro-khanna/ Elizabeth Holmes: The Theranos Deception (60 Minutes archive): https://cbsnews.com/video/elizabeth-holmes-the-theranos-deception-60-minutes-archive “The Act of Killing” trailer: https://www.youtube.com/watch?v=Q3FcB1UZHlg “Grizzly Man” trailer: https://www.youtube.com/watch?v=uWA7GtDmNFU “Hoop Dreams” trailer: https://www.youtube.com/watch?v=uf9Nq2ju0t0 “The King of Kong” trailer: https://www.youtube.com/watch?v=L5XvArGGIzk “A Short Stay in Hell” by Steven L. Peck: https://www.amazon.com/dp/0983748446 “The Library of Babel” by Jorge Luis Borges [PDF]: https://sites.evergreen.edu/politicalshakespeares/wp-content/uploads/sites/226/2015/12/Borges-The-Library-of-Babel.pdf “The Eureka Machine” by Richard Socher: https://www.amazon.com/dp/154170570X Timestamps: 0:00 Jason’s in SF with the LAUNCH Accelerator 37 cohort 2:40 Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at https://plaud.ai/twist and use code TWIST for 10% off! 6:34 Tactical & Practical talks live at Salesforce Tower 10:21 Using Claude for brainstorming, not writing 19:26 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26 20:42 OpenAI closing $30B at a $1.25T valuation 26:04 Why OpenAI could still lose 30:25 Would you put 30% of your retirement into OpenAI? 32:34 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 https://lightfield.app 34:27 Every Tesla becomes a Starlink hotspot 43:06 What would be the ultimate SpaceX domain name? 45:00 Thanks to our partners at Rippling! Head to https://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. 46:10 Is METR a fair watchdog for OpenAI? 54:03 Jason’s “Know Your Customer” plan for AI models 1:03:34 Meta’s deal to keep Zuckerberg in Cali 1:14:35 Why Jason would raise the minimum wage 1:18:42 Does Nathan Fielder give Liz Holmes a pass? 1:30:59 “A Short Stay in Hell” and “The Eureka Machine” Subscribe to our newsletters on Substack: TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com