Salesforce's stake in Anthropic has grown to approximately $5 billion, up from an initial ~$50 million investment made in early 2023, now representing roughly two-thirds of Salesforce's entire $7.8 billion strategic investment portfolio. The milestone coincides with Anthropic's confidential IPO filing at a $965 billion valuation. Salesforce holds a dual position as both investor and major customer, spending $300 million annually on Anthropic tokens and embedding Claude models across its products including Agentforce. Other early investors like Zoom (25x return) and Accel have also seen massive gains. Risks include Anthropic's legal dispute with the Pentagon, portfolio concentration, and the possibility that the IPO prices below the private valuation.