May’s venture landscape remained crowded by familiar names, but it shifted toward fewer, larger rounds. Crunchbase’s tally shows U.S. startup investors deploying more capital than ever, yet the number of deals edged down as lead backers concentrated their firepower on marquee opportunities. Andreessen Horowitz, General Catalyst, and Y Combinator dominated May’s activity, often co-leading rounds alongside other big funds. Notably, Anduril’s $5 billion Series H and Cognition’s $1 billion Series D highlighted a preference for mega rounds anchored by proven investors. Anthropic’s massive $50 billion Series H led by multiple top firms underscored the ongoing appetite for high-profile AI bets. In aggregate, Lightspeed Venture Partners, Upfront Ventures, and Index Ventures also ranked among the most active in leading or co-leading rounds. When ranking by value, the largest rounds were led by backers in Anthropic’s financing, which drew co-lead participation from Sequoia Capital, Altimeter Capital, Dragoneer, Greenoaks, Capital Group, Coatue, D1 Capital Partners, GIC, Iconiq Capital, and a few others. May’s activity reaffirmed that a small set of marquee funds continues to shape the funding agenda, particularly around AI-related startups. The pattern suggests that the market remains optimistic about AI, even as deal flow tightens and terms may tilt toward the lead investors and their co-lead partners. For founders and portfolio managers, the takeaway is clear: align with top-tier backers, be prepared for larger rounds, and sweat the details of governance and control when negotiating with co-leads.