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. And darlings, today we've got the tea — from sleep tech hitting unicorn status while your mattress overheated during AWS outages, to Palmer Luckey betting $60 billion that defense contractors are the new consumer darlings. Grab your oat milk latte and settle in.

💰 The Freshest Deals on the Block

Eight Sleep — $50M at $1.5B Valuation Spotted: The smart mattress company that literally controls your sleep just raised $50M from Tether Investments at a $1.5 billion valuation. Yes, the same Eight Sleep whose beds stopped working and overheated during last October's AWS outage because they couldn't connect to the cloud. Nothing says "cutting-edge health tech" like your mattress becoming a liability during an internet blip. But CEO Matteo Franceschetti isn't sweating it (pun intended) — the company is free-cash-flow positive, ships to 34 countries, and is now building an FDA-approved sleep apnea system. Sources say they're working on a sleep-focused AI agent that will proactively adjust temperature, elevation, and firmness before you even get into bed. Because apparently your mattress needs to be smarter than you.¹

Anduril — Aiming for $60B Valuation Word on the street: Palmer Luckey's defense tech darling is in the middle of a multibillion-dollar funding round led by Thrive Capital and Andreessen Horowitz that could value the company at $60 billion. That's double the $30.5B valuation from last June's $2.5B Series G. The round comes less than a year after their last raise, and could bring as much as $8 billion into the company. Timing? Chef's kiss. Just as the Pentagon is threatening to blacklist Anthropic over its refusal to fully weaponize Claude, Luckey is out here vocally supporting the government's stance and positioning Anduril as the patriotic alternative. "At the end of the day," he wrote on X, "you have to believe that our imperfect constitutional republic is still good enough to run a country." Translation: we'll take the contracts Anthropic won't. Bold. Calculated. Very on-brand.²

Oxa — $103M Series D (First Close) This UK-based autonomous vehicle company just secured $103M in the first close of its Series D to scale self-driving tech for industrial logistics. Because apparently the future of warehouses is fleets of robots that don't need bathroom breaks or health insurance. Oxa is positioning itself as the infrastructure play for autonomy — selling the software stack rather than building the trucks themselves. Smart pivot, considering how many robotaxi companies have burned through billions trying to do both.³

🎙 What the VCs Are Saying

Buckle up, because the timeline is spicy today.

Jason Lemkin from SaaStr is out here dropping reality checks on AI valuations. His take on why SaaS stocks are tanking? "The market has panicked because it realized the revenue for even public software companies may no longer be durable. And … it may take quite some time to see how that plays out." He's watching hyperscalers drop $650B+ on AI capex while traditional software companies scramble to prove they won't get disrupted into irrelevance. The anxiety is palpable. When even the public markets are repricing based on AI disruption risk, you know the private side is about to get messy.⁴

And if you thought that was dramatic, wait until you hear what he said about growth bars for 2026: The bar for "impressive" ARR growth has officially moved. We're not in 2021 anymore, darlings. Investors want proof that your AI product has actual switching costs and durable revenue, not just a ChatGPT wrapper with a Stripe integration.⁵

Palmer Luckey himself weighed in on the Anthropic drama with a post that's getting all the attention: "At the end of the day, you have to believe that our imperfect constitutional republic is still good enough to run a country without outsourcing the real levers of power to billionaires and corpos and their shadow advisors." Translation: Anthropic's "safety-first" stance is naive, and someone needs to build AI for national defense without the hand-wringing. You didn't hear it from me, but this is Anduril's entire pitch deck in one tweet.⁶

🫖 The Quick Sips

• Fig Security emerged from stealth with $38M to help security teams deal with constant change. Because apparently cybersecurity wasn't hard enough already.⁷

• MyFitnessPal acquired Cal AI, the viral calorie-tracking app built by teens that Gen Z actually wanted to use. When the incumbents start buying the disruptors before they're old enough to drink, you know the category is heating up.⁸

• ChatGPT uninstalls surged 295% after OpenAI's DoD deal announcement. Turns out users have feelings about their AI chatbot working with the military. Who knew?⁹

💭 Parting Thoughts

Here's the tea, darlings: we're living through a moment where the lines are getting redrawn. On one hand, you've got companies like Eight Sleep proving that consumer hardware can still command unicorn valuations if you nail the product and the unit economics. On the other hand, you've got Anduril doubling its valuation in under a year by betting that defense tech is the next frontier — and that being aggressively pro-government is a competitive advantage, not a liability.

Meanwhile, the VCs are quietly panicking. Jason Lemkin's posts aren't just market commentary — they're a memo to founders that the 2021 playbook is dead. Growth-at-all-costs is out. Durable revenue and defensibility are in. And if you can't articulate why your AI product won't get commoditized into oblivion, good luck raising that Series B.

The Anthropic-Pentagon standoff is the canary in the coal mine. It's forcing every AI company to pick a side: do you build for everyone and risk getting blacklisted by the government, or do you build for the government and risk alienating half your users? There's no neutral ground anymore. Palmer Luckey saw that coming years ago, and now he's cashing in.

If you're a founder watching all this unfold, the lesson is clear: know your customer, know your values, and be very sure those two things are compatible. Because in 2026, trying to please everyone is the fastest way to please no one.

Until next time, remember: in the world of venture capital, conviction is currency — but timing is everything.

You know you love me,

XOXO — Gossip Girl 💋