Microsoft vs. Salesforce: A $10,000 Bet Five Years Later
As seen on the 24/7 Wall St. homepage on August 27, 2026.
Five years ago $10,000 split between these two enterprise software rivals: Microsoft turned it into $17,527, while Salesforce handed back $9,598, still under water. A near $8,000 gap from the same starting line.
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An equal split of $10,000 between Microsoft and Salesforce in late August 2021 produced two very different outcomes over five years. The Microsoft half returned 75.3% while the Salesforce half finished below the original stake.
The gap between the two positions matters because both companies compete for enterprise software budgets and were widely regarded as comparable bets on cloud adoption at the start of the period.
Microsoft's position dipped well below its starting value at various points across the five years. Investors who stayed through those drawdowns saw it recover and push past its prior highs.
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Salesforce fell to the mid-$5,000s at its lowest point and staged partial recoveries that briefly brought it back near the original stake. It finished the five years still underwater.
Two companies selling to the same buyers can produce dramatically different shareholder outcomes over the same holding period, a 75.3% gain for Microsoft against a 4% loss for Salesforce.