Salesforce's Anthropic Bet Likely Worth 'Tens of Billions' — And Benioff Plans to Cash In

Marc Benioff has a plan for the most profitable investment Salesforce, Inc. (NYSE:CRM) ever made: sell it and retire debt. Speaking to a gathering at Dreamforce this week, the Salesforce CEO said the company spent hundreds of millions of dollars on Anthropic stock, a position he expects will likely be worth tens of billions, according to CNBC. CRM stock is moving. See the chart and price action here. “We’ll end up probably selling it,” Benioff said, adding that proceeds would pay off the accelerated share repurchase debt Salesforce took on earlier this year. “So it’ll be a good trade for us.” The Math Behind the Bet Salesforce Ventures first backed Anthropic in early 2023. Since then, the AI lab’s valuation has gone vertical. Anthropic closed a $30 billion round in February at a $380 billion post-money valuation. By late May, a $65 billion Series H pushed the figure to $965 billion, vaulting Anthropic past OpenAI as the world’s most valuable AI startup. The markups have reshaped Salesforce’s income statement. Last quarter’s profit was boosted by a $2.6 billion gain on strategic investments tied to the Anthropic bet, and the stock jumped almost 23% — its best day since 2020. Read Also: 'This Selloff Makes Zero Sense': An Analysis from WallStreetBets Why the Debt Matters Benioff’s exit logic ties back to March, when Salesforce funded a $25 billion accelerated share repurchase — it’s largest on record — with newly issued debt. The buyback retired roughly 103 million shares immediately, lifting per-share earnings while loading the balance sheet with obligations that did not exist a year ago. Selling a private stake to extinguish that debt would close the loop neatly. Two paper gains become one cash event. Timing remains the open question. Anthropic is still private, so any sale depends on a secondary transaction or an eventual public listing, and Benioff offered no calendar. Salesforce is simultaneously one of Anthropic’s largest customers, with Benioff projecting roughly $300 million in token spending this year, mostly on coding workloads. Unwinding equity in a critical supplier carries its own strategic wrinkles. See More: Top Momentum Stocks What it Means for Investors Gains on strategic investments have been dismissed as non-cash noise, and skeptics noted that most of last quarter’s earnings beat came from the markup rather than software sales. Benioff’s remarks suggest management views the position as a funding source and not an accounting artifact. A sale would also strip a volatile input from Salesforce’s future quarters as Anthropic’s swings currently move Salesforce earnings by hundreds of millions. CRM Stock Price Activity: Salesforcestock was down 2.13% at $245.21 at the time of publication Thursday, according to data from Benzinga Pro. Read Also: These 10 Stocks Are Squeeze Candidates Waiting to Happen Photo: Thrive Studios ID / Shutterstock