Marc Benioff, co-founder of Salesforce Inc., has adopted a unique and strategic stock selling approach, gradually cashing out at a rate of $3 million a day. Since July, Benioff has consistently sold 15,000 shares of Salesforce’s stock daily, totaling over $475 million in more than 170 transactions. This method, initiated shortly after Salesforce’s 2004 initial public offering, has contributed to Benioff’s growing cash pile, funding charitable initiatives such as donations to pediatric hospitals, public schools, and medical research.
Benioff emphasized the transformative potential of business as a platform for positive change, aligning with his commitment to improving the world through philanthropy. In addition to his stock sales, Benioff highlighted his ownership of Time magazine, acquired for $190 million in 2018.

While CEO stock sales can sometimes signal investor concerns or pose legal risks, Benioff’s gradual approach is considered one of the “safest” methods. According to Alan Jagolinzer, a professor at Cambridge University’s Judge Business School, the risk is mitigated by trading daily, subjecting the sales to normal price movements.
Other billionaires employ varying approaches to stock liquidation, ranging from disposing of large blocks to taking breaks from selling. Notable examples include Mark Zuckerberg, who recently sold $185 million worth of Meta Platforms Inc. shares after a two-year hiatus, and Jeff Bezos, who has not sold any Amazon.com Inc. shares since 2021.
Benioff’s consistent daily selling stands out among billionaire super-sellers, surpassing the frequency of Joe Mansueto of Morningstar Inc. and Joe Gebbia, co-founder of Airbnb Inc. Benioff’s strategy involves more than 2,800 transactions over the years, supporting the notion of diversification and risk mitigation.
Many executives utilize 10b5-1 trading plans to pre-schedule share sales and certify that these transactions aren’t based on nonpublic information. While these plans offer predictability, Daniel Taylor, a professor at the University of Pennsylvania’s Wharton School, notes the downside of potential discounts if stock prices decline.
Despite this, Benioff’s strategic approach, adjusting the daily shares sold based on market conditions, has been praised as an intelligently designed system. Nejat Seyhun, a finance professor at the University of Michigan’s Ross School of Business, commended the strategy for helping Benioff sell stock at above-average prices while avoiding legal entanglements.
In 2023, Benioff’s fortune has grown by over 55%, reaching $9.3 billion according to the Bloomberg wealth index. With approximately 2.5% ownership of Salesforce, Benioff’s wealth is distributed between the company and other assets, reflecting a successful blend of strategic stock management and philanthropic endeavors.