TL;DR

Rippling raises $450M at $16.8B; xAI seeks $120B valuation; OpenAI acquires Windsurf, restructures Microsoft deal.

Highlights

• Rippling raises $450M Series G at $16.8B valuation, launches $200M employee tender; annualized revenue hits $570M 1.
• xAI seeks new funding at up to $120B valuation after $33B merger with X (Twitter) 2.
• OpenAI to reduce Microsoft revenue share by 50% by 2030; acquires Windsurf for $3B; 2029 revenue forecast raised to $125B 3.
• CoreWeave seeks $1.5B in unsecured debt after a scaled-down IPO; has borrowed $12.9B at 11–15% rates 4.
• Coinbase Q1 revenue falls to $2B, net income drops to $66M; announces $2.9B Deribit acquisition to expand derivatives trading 5.
• Robinhood to enable 24/7 trading of tokenized U.S. securities in Europe; SEC considers DLT platform exemptions 7.
• Meta Platforms, Inc. Class A Common Stock explores stablecoin payouts and crypto wallets for 3B users; hires crypto-focused product VP 8.
• SEC and Ripple settle XRP lawsuit for $50M, pending court approval; appeals to be dropped 10.
• Nvidia Corp to launch downgraded H20 AI chip in China by July to comply with U.S. export restrictions 6.
• China to implement first private economy law, supporting 3T yuan in projects and offering new legal protections 13.
• SBI and Indian banks sell 20% of Yes Bank to Japan’s SMBC for ₹13,482 crore (~$1.6B), making SMBC largest shareholder 14.
• Mass General Brigham’s AI tool FaceAge predicts cancer survival with 80% accuracy, outperforming clinicians 15.

Commentary

Late-stage capital continues to concentrate in AI and SaaS, with Rippling’s $450M round at a $16.8B valuation and xAI’s rapid escalation to a potential $120B valuation following its merger with X. Rippling’s $200M employee tender reflects growing secondary liquidity options for talent retention at scale, while xAI’s fundraising signals ongoing investor demand for differentiated AI platforms with ecosystem potential 12. OpenAI’s $3B acquisition of Windsurf and its renegotiated revenue split with Microsoft further highlight the sector’s focus on vertical integration and margin optimization, as well as the growing importance of enterprise AI tooling 3.

In fintech and crypto, regulatory developments are starting to open new paths. Robinhood’s move to tokenize U.S. securities for European 24/7 trading coincides with the SEC’s consideration of exemptions for DLT-based platforms, which could accelerate the emergence of tokenized asset markets 7. Meta Platforms, Inc. Class A Common Stock ’s renewed crypto push and the Ripple-SEC settlement further suggest a thawing U.S. regulatory climate, though Coinbase ’s weak Q1 and pivot to derivatives via the Deribit acquisition underscore the continued volatility and need for diversification in digital asset platforms 5810.

Cloud infrastructure and hardware remain capital intensive and exposed to market and policy shifts. CoreWeave’s pursuit of unsecured debt after a disappointing IPO, and Nvidia Corp ’s compliance-driven chip launch in China, both illustrate the financing and regulatory hurdles facing scale-up infrastructure players 46. Meanwhile, China’s new private economy law and the Yes Bank transaction highlight ongoing cross-border capital flows and policy-driven openings in Asia, which may create new partnership and exit opportunities for growth-stage companies 1314.

Healthcare AI continues to show commercial promise, with Mass General Brigham’s FaceAge tool outperforming clinicians in cancer survival prediction—demonstrating tangible value for AI in clinical workflows and potential for venture-backed healthtech startups 15.

VCs should track secondary liquidity trends in late-stage SaaS, regulatory shifts in tokenization and digital assets, and the evolving capital stack for infrastructure and AI hardware. Deal flow remains robust in favored sectors, but financing is tightening elsewhere.