qinbafrank|May 16, 2026 13:05
Here’s another version of the story: When Microsoft went public in 1986, Bill Gates held about 45% of the shares (some sources say it briefly reached 48%-49% on the IPO day but later stabilized at around 45% after selling some shares). Over the years, he gradually reduced his stake, with his holdings decreasing year by year. Currently, his personal stake is below 1%, and the Gates Foundation has completely sold off its shares. If Bill Gates had held onto those shares until now, they’d be worth close to $1.5 trillion, a figure that would likely remain unmatched for many years to come.
Here’s another version: In the late 1990s, Microsoft’s stock price skyrocketed, and Bill Gates’ wealth ballooned along with it. Warren Buffett once gave Gates a very simple piece of advice: don’t put all your wealth into just one company, even if it’s Microsoft. According to Buffett’s logic, a founder’s wealth should gradually be diversified across different asset classes to reduce risk. In the following years, Gates began consistently selling Microsoft shares and reallocating the funds into a broader range of investments.
Of course, from a mathematical perspective, this kind of calculation isn’t necessarily wrong. But from an investment logic standpoint, what we’re really talking about here is a classic case of “survivorship bias.” No one could have been certain that Microsoft would maintain its dominant position for the next 30 years—not even Gates himself.
This story reminds us that even founders who are deeply committed to their own companies find it incredibly challenging to hold onto their shares for the long term. Holding on with conviction is far harder than buying or selling.
To all of us who often sell too early and can’t hold on—let’s learn to make peace with ourselves.
Be Water!
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