OpenAI’s $1.25T Raise, Starlink Mobile & Zuck’s Tax Deal | EP 2354
October 24, 2026 · 1 h 33 min
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DEBRIEFWritten and voiced by AI from the episode's audio
Jason Calacanis and Lon Harris cover three major tech stories on This Week in Startups: OpenAI's valuation at $1.25 trillion for a $30 billion raise (down from $1.4T), Elon Musk's Starlink Mobile plans to become a fourth nationwide wireless carrier using satellites and 80,000 cell towers, and Mark Zuckerberg's board deal allowing him to sell stock quarterly without losing voting control as California considers a billionaire wealth tax. The episode explores the implications of each: whether OpenAI is finally fairly priced despite competition from Claude and open-source models, how Starlink could disrupt wireless pricing for consumers, and whether the Zuckerberg arrangement signals that even billionaires can't escape California's tax pressure. Jason argues these are net-positive developments for competition and entrepreneurship, while both hosts debate regulatory concerns around AI safety audits and wealth taxation policy.
🎧 AI Debrief
Show notes
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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): 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):