TL;DR

OpenAI eyes $500B secondary sale; AI startups dominate 2025 VC; Bullish upsizes $990M IPO.

Highlights

• OpenAI is considering a secondary share sale at a $500B valuation (up from $300B in its recent primary round), with IPO restructuring under review and revenue run-rate now ~$12B 1.
• AI startups captured a record share of 2025 VC/PE capital: 41% of U.S. venture dollars YTD went to just 10 AI firms; 498 AI unicorns now valued at $2.7T 10.
• Ex-OpenAI researcher Leopold Aschenbrenner raised $1.5B for new AI hedge fund Situational Awareness, which returned 47% in H1 2025 11.
• Musk’s xAI made Grok 4 free, driving it to top App Store rankings globally 12; OpenAI restored GPT-4o access after GPT-5 backlash and doubled GPT-5 rate limits 13.
• Thiel-backed Bullish upsized its NYSE IPO to $990M amid oversubscription, implying a $4.8B valuation 4.
• Heritage Distilling (CASK ) launched a $360M IP token reserve, backed by a $220M PIPE (a16z, Cantor Fitzgerald), making IP tokens its primary reserve asset 6.
• ALT5 Sigma raised $1.5B via equity and WLFI tokens (Trump-linked), embedding WLFI as a core balance sheet asset and appointing new crypto-linked board members 2.
• Paxos applied for a U.S. national trust bank charter, joining Circle and Ripple as stablecoin regulation advances post-GENIUS Act 9.
• Rumble is in advanced talks to acquire Germany’s Northern Data (AI cloud) for $1.17B in stock; Tether (X:USDTUSD ) supports the deal 5.
• Vulcan Elements raised $65M Series A (Altimeter Capital) to build a U.S. rare-earth magnet plant, targeting domestic supply for EVs, AI, and defense 7.
• Western Union will acquire Intermex for $500M to expand in Latin American remittances, adding 6M customers 14.
• Revel exited NYC ride-hailing to focus on EV charging infrastructure, targeting 400+ stalls by 2026 and 2,000 by 2030 15.

Commentary

AI remains the central focus for both venture and institutional capital, with OpenAI’s potential $500B secondary sale and record VC/PE allocations to AI startups highlighting ongoing capital concentration 110. The pace of value creation is notable: 41% of U.S. VC dollars in 2025 have gone to just 10 AI firms, and the number of AI unicorns has surged to 498 globally 10. This concentration is mirrored in hedge fund activity, as seen with Situational Awareness’s rapid $1.5B raise and strong returns, suggesting LPs are willing to back new managers with deep technical expertise 11.

The generative AI platform race is driving rapid product cycles and aggressive user acquisition tactics. OpenAI’s quick reversal on GPT-4o 13 and Musk’s move to make Grok 4 free 12 reflect an environment where user retention and engagement are critical, and competitive pressure is forcing incumbents to adapt quickly. For VCs, this raises the bar for product-market fit and defensibility in AI, while also increasing the likelihood of secondary sales and strategic M&A as preferred exit paths.

Institutional adoption of crypto and token-based assets is accelerating. Bullish’s upsized IPO 4, Heritage Distilling’s (CASK ) PIPE-backed IP token reserve 6, and ALT5 Sigma’s WLFI treasury 2 all point to public companies and major investors diversifying into altcoins and tokenized assets. Paxos’s application for a national trust bank charter, alongside similar moves by Circle and Ripple, signals greater regulatory clarity and could facilitate further VC activity and M&A in crypto infrastructure 9.

Strategic pivots and consolidation continue in mobility and infrastructure. Revel’s shift from ride-hailing to EV charging 15, Vulcan Elements’ domestic rare-earth magnet push 7, and Western Union ’s acquisition of Intermex 14 all reflect a focus on building scale and defensibility in sectors with policy support and supply chain considerations. Rumble ’s bid for Northern Data underscores ongoing convergence between cloud, AI, and crypto infrastructure 5.

VCs should closely monitor late-stage AI deal pricing, the durability of institutional demand for token-based treasuries, regulatory developments in digital assets, and consolidation opportunities in critical infrastructure sectors.