TL;DR

OpenAI restructures for IPO; Perplexity AI raises at $14B; Stargate AI infra project delayed.

Highlights

• OpenAI and Microsoft are renegotiating their partnership to support OpenAI’s transition to a public benefit corporation (PBC) and future IPO, with Microsoft seeking post-2030 tech access 1.
• Perplexity AI, backed by Nvidia , is raising $500M at a $14B valuation led by Accel, with strong revenue growth and potential Apple integration 2.
• SoftBank and OpenAI’s $100B Stargate AI infrastructure project faces delays due to tariff-driven cost increases and investor uncertainty 6.
• Google launched the AI Futures Fund, offering capital, early access to Gemini/Veo, and cloud credits to AI startups 7.
• Israeli quantum software startup Classiq raised $110M Series C (total $173M) to expand its hardware-agnostic platform 4.
• Upscale AI and Lovart AI launched new platforms for streaming ads and design, raising early-stage funding 13.
• Saudi Arabia’s PIF launched Humain, a multibillion-dollar AI company focused on Arabic LLMs and AI adoption in the region 3.
• Chegg will lay off 22% of staff and close offices amid declining revenue and AI competition 14.
• KindlyMD shares surged 600% after a $710M merger with Nakamoto to form a public bitcoin treasury vehicle 5.
• American Bitcoin, backed by the Trump family, to go public on Nasdaq via merger, retaining 98% post-merger ownership 8.
• SEC Chair Paul Atkins announced a shift to a rule-based crypto regulatory framework, moving away from enforcement-first tactics 11.
• Senate blocked the GENIUS Act (stablecoin regulation) amid concerns over Trump-linked crypto ventures 12.
• CATL , the world’s largest EV battery maker, will limit US investor participation in its $4B Hong Kong IPO 10.
• XPRIZE Healthspan named top teams for its $101M longevity prize, highlighting biotech and healthy aging innovation 15.
• Epic Games submitted Fortnite for App Store reentry following a favorable court ruling; Spotify also set to return 9.

Commentary

AI remains the primary driver of venture deal flow and valuations. OpenAI’s move to restructure as a PBC and pursue an IPO, while renegotiating with Microsoft for long-term tech access, signals a shift toward more conventional capital structures and exit planning in the sector 1. Perplexity’s $14B valuation and Google ’s AI Futures Fund demonstrate continued investor appetite for both core AI infrastructure and application-layer startups, with capital and strategic support flowing to companies that can show early revenue traction or strong integration prospects 27.

The SoftBank -OpenAI Stargate project’s delays highlight the risks facing large-scale AI infrastructure investments, especially in the current macro environment where tariffs and hardware cost volatility can stall even the most ambitious projects 6. Early-stage investors should be alert to the capital intensity and execution risk in infrastructure-heavy plays, as well as the need for adaptability in the face of shifting policy and technology costs.

Crypto is seeing renewed institutional and public market activity, with KindlyMD and American Bitcoin using mergers and PIPEs to access public capital and scale 58. However, the regulatory backdrop remains fluid: the SEC’s pivot to a rule-based approach may unlock new opportunities, but the Senate’s block of the GENIUS Act and ongoing scrutiny of politically linked crypto ventures suggest continued uncertainty for stablecoin and digital asset startups 1112.

Quantum computing (Classiq) 4, longevity biotech (XPRIZE Healthspan) 15, and creative AI (Upscale, Lovart) 13 are attracting significant venture funding, reflecting growing interest in platform technologies with broad sector impact. Meanwhile, Chegg ’s layoffs and the return of Epic and Spotify to the App Store underscore how incumbents are being pressured by AI disruption and regulatory shifts—creating openings for new entrants 149.

VCs should focus on how regulatory changes, macro headwinds, and partnership realignments are affecting deal structures, capital allocation, and exit windows in AI, crypto, and deep tech. Monitoring capital flows into infrastructure, platform, and application-layer startups will be key to identifying the next wave of scalable opportunities.