Hey Upper East Siders (and Sand Hill Road dwellers)...

Gossip Girl here, your one and only source into the scandalous lives of Silicon Valley's elite. Grab your oat milk lattes — today's dispatch is dripping with drama.

💰 Spotted: The Biggest Moves on the Block

Stripe just hit $159 billion. You read that right, darlings. The payments juggernaut announced a tender offer for employees and shareholders, and Coatue's Philippe Laffont couldn't help but gush about Stripe being "the default financial layer for the token economy." Thrive Capital and a16z are also at the table. Still private. Still growing. Still making every public fintech CEO sweat through their Patagonia vest. (CNBC)

Thrive Capital raised $10 billion for Fund X — their largest ever, nearly double the last one. When your portfolio includes OpenAI, Stripe, and SpaceX, I suppose LPs just hand you the checkbook. (TechCrunch)

Nvidia is in talks to pour up to $30 billion into OpenAI, valuing Sam's little AI lab at a casual $730 billion pre-money. Jensen Huang told CNBC there's "no question" they'd invest. Sources say this is separate from their $100B infrastructure deal. The plot thickens. (CNBC)

🤫 The Juiciest Funding Rounds

Word on the street: Investor loyalty? In this economy? TechCrunch reports that at least a dozen OpenAI VCs — including Founders Fund, Sequoia, Iconiq, and Insight Partners — also backed Anthropic's monster $30B raise. Sam Altman reportedly gave investors a "don't back my rivals" list in 2024. Clearly, nobody listened. XOXO. (TechCrunch)

Here's who else is cashing checks this week:

• Letter AI — $40M Series B led by Battery Ventures. This YC-backed sales AI startup went from Series A to B in four months. Chicago heat. (Business Insider)
• Jump — $80M Series B from Insight Partners. AI workflow tools for financial advisors. 27,000 advisors onboarded in under two years? That's momentum, darling. (FinTech Futures)
• Render — $100M at a $1.5B valuation. The cloud startup powering AI-built apps. Even OpenAI's Codex deploys on Render. Georgian led the round. (CNBC)
• Freeform — $67M Series B for AI-powered 3D metal printing. They have H200 GPU clusters in-house for manufacturing. Defense-adjacent and very much in vogue. (TechCrunch)
• Mesh Optical Technologies — $50M Series A led by Thrive Capital. Three SpaceX vets building optical transceivers for AI data centers. Thrive really is everywhere. (TechCrunch)
• Circuit — $30M angel round for an Austin AI startup turning technical manuals into step-by-step workflows. Co-founded by former Silicon Labs CEO Tyson Tuttle. (Axios)
• Koah — $20.5M Series A led by Theory Ventures, building "AdSense for AI chatbots." If you're not thinking about how AI monetizes, you're behind. (Adweek)
• VoiceLine — €10M Series A for voice-first AI for enterprise frontline workers, out of Munich. (The Next Web)

Oh, and 17 US-based AI companies have raised $100M+ already in 2026. Including a $480M seed round for humans& and SkildAI's $1.4B Series C at $14B. The numbers are getting absurd, even by our standards. (TechCrunch)

📣 What the VCs Are Saying

You didn't hear it from me, but the VCs have been particularly chatty this week...

Katherine Boyle (@KTmBoyle), GP at a16z, continues to be the beating heart of American Dynamism. Her team's raised over $1.7B across funds backing defense tech, aerospace, and manufacturing startups. She's been highlighting a16z's portfolio company Hadrian (automated manufacturing, $1.6B valuation) and pushing the thesis that "building for America" is venture's next great wave. If defense tech is the new SaaS, Katherine saw it first. (Post)

Grace Isford (@graceisford), Partner at Lux Capital, just helped close Lux's latest $1.5B fund and has been threading brilliantly on AI infrastructure — sharing insights from 50+ conversations with researchers at Hugging Face, Runway ML, and Stanford. She's the quiet powerhouse you want on your cap table. (Post)

Ann Miura-Ko (@annimaniac), Floodgate, is doing what she does best — finding "thunder lizards" at the earliest stages. She recently put out a call for side-project builders to spotlight at Floodgate's Friends & Family event. Remember: this firm only makes 4-6 investments per partner per year. Every signal matters. (Post)

Paul Graham (@paulg) dropped this gem that's been circulating: "Bootstrapping is a proper subset of taking venture funding. Taking venture funding lets a company choose its growth rate." Classic PG — reframing the whole bootstrap-vs-VC debate in one tweet. (Post)

Josh Kopelman (@joshk), First Round Capital, rallied founders around the latest First Round Review — collecting the best company-building advice from builders at Figma, Shopify, Vanta, Webflow, and dozens of others. Required reading for anyone pre-Series A. (Post)

Elad Gil (@eladgil) is staying busy with deals — he personally led a $16M round for Moab, an NYC equipment rental software startup. Also dropped founder meeting prep advice that's been making the rounds: "Come with an agenda so they know you'll make good use of their time." Classic Elad. (Axios)

📊 The Macro Tea

PitchBook's 2026 outlook says SaaS and defense tech are IN, while healthtech and medtech are OUT. SaaS is expected to beat the cross-sector average annualized return of 21%+, while medtech suffers from a "prolonged lack of exits." The reports of SaaS's death were greatly exaggerated. (PitchBook)

Canva is on an acquisition spree — scooping up motion graphics company Cavalry and video ad startup MangoAI while Wall Street punishes software stocks over AI fears. With $4B+ in ARR and a $42B valuation, they're playing offense while everyone else plays defense. (CNBC)

OpenAI launched the "Frontier Alliance" — locking in multi-year partnerships with McKinsey, BCG, Accenture, and Capgemini for its enterprise push. When you need to sell to the Fortune 500, you bring in the consulting cavalry. (TechCrunch)

Cybersecurity VC is skyrocketing — AI security startups closed 144 deals in 2025, with nearly every funded company positioning as "AI-native." (Dark Reading)

The quantum wave is real: Finnish unicorn IQM is going public via SPAC at $1.8B. They join Infleqtion (NYSE debut) and Xanadu (Nasdaq-bound). Europe's quantum darlings are heading stateside. (TechCrunch)

Meanwhile, Egypt launched a $1B Startup Charter at the RiseUp Summit in Cairo — positioning itself as MENA's tech hub with AI, fintech, and digital platforms as core economic drivers. 250+ stakeholders, 15 national entities, and big ambitions. (Forbes)

🔮 One More Thing...

Tara Ghazi, co-founder and CBO of medical imaging startup MALCOVA, published a powerful piece in Forbes about how SBIR funding was critical to advancing their novel diagnostic technology before VC came knocking. A masterclass in non-dilutive funding strategy — and a reminder that the smartest founders use every tool in the toolbox before giving up equity. (Forbes)

And that's the week in VC, darlings. The money is flowing, the mega-rounds are mega-ing, and loyalty is... well, let's just say it's complicated.

Until next time...

You know you love me.

XOXO, Gossip Girl 💋