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's tea is *scorching*. We're talking the biggest funding round in venture history, a former GitHub CEO making a grand return, and VCs trying to make sense of it all. Buckle up — it's going to be a wild ride. --- ## 💰 The Freshest Deals on the Block **OpenAI — $110 BILLION (Yes, You Read That Right)** Word on the street: OpenAI just closed the largest private funding round in *history* — a jaw-dropping $110 billion at a $730 billion pre-money valuation (that's $840 billion post-money, for those keeping score at home). Amazon is throwing in $50 billion — their biggest investment *ever* in any company. Nvidia and SoftBank each contributed $30 billion. [^1] But wait, there's more! This isn't just a cash infusion — it's a full-on strategic partnership. OpenAI committed to spending an additional $100 billion on AWS over the next eight years, will use Amazon's custom AI chips (Tranium), and is building a custom model for Amazon's consumer products. Meanwhile, Microsoft issued a separate statement saying their partnership remains "unchanged." Classic love triangle energy. [^2] Sources say OpenAI is now targeting roughly $600 billion in total compute spend by 2030. The company has over 900 million weekly active users and 50 million paid subscribers. You didn't hear it from me, but when you're raising more than most countries' GDPs, maybe — *just maybe* — the AI race has gotten slightly out of hand? [^3] **Basis — $100M Series B at $1.15B Valuation** Spotted: This AI accounting platform just became a unicorn, and not in the cute, furry animal way. Basis raised $100 million in Series B funding led by Accel and Google Ventures (GV), with former Goldman Sachs CEO Lloyd Blankfein also jumping in. [^4] The startup uses AI agents to automate complex accounting workflows — think tax preparation, audit, and reconciliation. Currently, about 30% of the Top 25 accounting firms are using Basis. The accounting industry is facing a massive talent shortage, and AI is stepping in to fill the gap. Because nothing says "future of work" like having robots do your taxes. [^5] **Temporal — $300M Series D at $5B Valuation** Word on the street: This AI reliability startup just secured $300 million in Series D funding, doubling its valuation from $2.5B to $5B in just four months. Andreessen Horowitz led the round, with participation from Lightspeed, Sapphire Ventures, and Sequoia. [^6] Here's why this matters: Temporal solves AI's "reliability problem." As AI systems move from generating responses to executing real-world tasks, they need durable execution — the ability to recover from failures without custom recovery logic. The company reports 380% year-over-year revenue growth and processes 130 billion actions monthly. Clients include OpenAI, Netflix, Snap, and JPMorgan Chase. When the AI infrastructure players start raising this kind of cash, you know the agentic AI boom is for real. [^7] **Entire (Formerly EntireHQ) — $60M Seed at $300M Valuation** Sources say this is the biggest seed round of the year so far. Why? Because it was founded by Thomas Dohmke, the former CEO of GitHub. He raised $60 million in seed funding at a $300M valuation from Felicis, Madrona, Microsoft's M12, and Datadog CEO Olivier Pomel. [^8] The startup is building open-source developer tools to manage AI-generated code — because apparently, there's now *so much* AI code that humans can't keep track of it all. Their first product, Checkpoints, allows developers to track and review AI-generated code in context. When even the former GitHub CEO says we need new tools for AI code, maybe we should pay attention. [^9] **Inhouse — $5M Seed** Direct-to-business legal AI startup just raised $5 million in seed funding. The company uses a combination of AI and human lawyers to provide legal services to small and midsize businesses. Legal tech continues to be one of those "boring but essential" categories that VCs apparently love. [^10] --- ## 🎙️ What the VCs Are Saying Buckle up, because the timeline is *delicious* today. **Endowment Eddie** is back with his annual 10 VC predictions for 2026. Key takeaways: US VCs will raise $80 billion (steady as she goes), deal value hits $350 billion (approaching 2021 peaks), but early-stage remains brutal. His hot take? "AI is inflationary, not deflationary" — CEOs are reticent to lay off staff because they don't fully trust AI yet, so humans and AI end up duplicating efforts. The man has seen things. [^11] **Jesse Cohen** dropped some numbers that'll make you spit out your latte: The MAG7 companies are pouring $650 billion into AI in 2026 alone — Amazon ($200B), Alphabet ($185B), Meta ($135B), Microsoft ($105B), and Tesla ($20B). That's more than most countries spend on their militaries. The level of investment is unmatched this century. [^12] **Hemant Mohapatra** from Lightspeed India is giving founders the real talk on avoiding fundraising mistakes: "Don't wing it verbally — use a deck." He advises prepping 10-15 "rude questions" about your product, market, and competition. Be concise. Read the room. And for the love of all that is holy, "don't sell" — stop using jargon, brushing off genuine questions, and falling back on meaningless TAM comps. This is must-read advice for anyone raising in 2026. [^13] **Jackie B** compiled the ultimate list of 2026 incubator and accelerator options. From VC-backed programs like Greylock Edge ($500K+), Sequoia's Arc ($500K-$1M), and a16z Speedrun ($500K-$1M), to traditional players like Y Combinator ($500K for 10%), to pre-idea options like Southpk Commons (up to $1M). If you're an early-stage founder and need capital without destroying your cap table, this thread is your bible. [^14] --- ## 🫖 The Quick Sips - **Plaid** reportedly hit an $8 billion valuation in a latest funding round focused on employee liquidity. The open banking giant now has over 900 employees facilitating data sharing across financial services. [^15] - **Zap Africa**, a Nigerian crypto startup, cut 44% of its workforce in February as the company pivots to a leaner, automation-driven model. OTC transactions are now filling the revenue gap left by declining in-app activity. [^16] - **Crypto startups** raised $883 million in February 2026, down 13% year-over-year. Investors are placing greater emphasis on revenue and user bases. [^17] --- ## 💭 Parting Thoughts Here's the tea, darlings: The AI arms race just hit a new level. OpenAI's $110 billion isn't just a funding round — it's a declaration of war against anyone who thought they could compete in the infrastructure layer. Amazon's $50 billion bet tells you everything you need to know about where Big Tech sees the future. But here's what's fascinating: While the mega-rounds keep getting bigger, the early-stage market is *struggling*. Endowment Eddie's point about bifurcation is spot on — capital concentrates at the top and bottom, leaving the middle (Series A/B) in a chasm. If you're a founder raising now, the lesson is clear: be so good they can't ignore you, or find a niche that the mega-funds overlook. The VCs are scrambling to figure out what value they provide beyond capital. The answer? Distribution, signal, governance, and service. Pick one. Excel at it. Make yourself indispensable. Until next time, remember: in the world of venture capital, the only constant is that everyone thinks they know what's coming next — and almost everyone is wrong. You know you love me, **XOXO — Gossip Girl** 💋 [^1]: https://www.bloomberg.com/news/articles/2026-02-27/openai-finalizes-110-billion-funding-at-730-billion-valuation [^2]: https://www.axios.com/2026/02/27/openai-funding-nvidia-amazon [^3]: https://techcrunch.com/2026/02/27/openai-raises-110b-in-one-of-the-largest-private-funding-rounds-in-history/ [^4]: https://www.indexbox.io/blog/basis-ai-accounting-startup-hits-115b-valuation-with-100m-series-b/ [^5]: https://www.getbasis.ai/blogs/basis-raises-100m-series-b-led-by-accel-and-google-ventures [^6]: https://temporal.io/news/temporal-raises-300m-to-make-agentic-ai-real-for-companies [^7]: https://www.businesswire.com/news/home/20260217453156/en/Temporal-Raises-%24300M-Series-D-to-Make-Agentic-AI-Real-for-Companies [^8]: https://venturecapital.com/news/technology/former-github-ceo-thomas-dohmke-raises-record-seed-round-for-ai-code-management-startup-v1 [^9]: https://pureai.com/articles/2026/02/10/dohmke-launches-startup.aspx [^10]: https://www.law.com/legaltechnews/2026/02/27/the-evolving-boundary-of-ai-and-legal-privilege/ [^11]: https://x.com/endowment_eddie/status/2005307864689021146 [^12]: https://x.com/JesseCohenInv/status/2019764141674676563 [^13]: https://x.com/MohapatraHemant/status/2005280687528755393 [^14]: https://x.com/jackieberardo/status/2008225216451797188 [^15]: https://www.fintechfutures.com/venture-capital-funding/plaid-reportedly-hits-8bn-valuation-after-latest-funding-round [^16]: https://techcabal.com/2026/02/28/zap-africa-layoffs/ [^17]: