Big Regret? How Bill Gates' Microsoft Missed Out On $159 Billion By Selling Apple Stock Too Early (2024)

Bill Gates and Steve Jobs are two names that separately led the paradigm-shifting boom of personal computers starting in the 1990s, one with Microsoft and the other with Apple.

But the paths of the two tech giants directly crossed in 1997, when Apple was on the brink of bankruptcy.

Microsoft Saved Apple From Bankruptcy

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On August 6, 1997, Bill Gates led Microsoft invested $150 million in Apple in exchange for shares in the company. Apple's share price at that time was just about $0.2–$0.3.

So, Microsoft received 150,000 shares of preferred stock in exchange for its $150 million investment. These shares could be converted into common shares of Apple stock at a price of $8.25 and were redeemable after three years, as per US-based financial news website Benzinga’s report.

Microsoft converted all of its shares into common stock by 2001, giving it roughly 18.1 million shares of Apple.

And by the year 2003, Microsoft had sold its entire stake in Apple for $550 million.

Also Read: ISRO & Microsoft Announce Tie-Up To Support Space-Tech Startups

What If Microsoft Had Not Sold Apple Shares

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But what if Microsoft had still held on to its Apple shares? How much would they be worth today?

Well, Apple stock reportedly split on a 2-for-1 basis once since the lock-up period ended, on a 7-for-1 split in 2014, and on a 4-for-1 split in 2020.

The first split would have given the company 36.2 million shares. The second would’ve netted 253.4 million shares. The third, 1.031 billion shares.

Apple stock is trading at $157.4 right now; if Microsoft held its position until today, it would be worth around $159 billion.

The Agreement Between Microsoft & Apple

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Also Read: Apple Earns Nearly Rs 1.5 Lakh Profit Every Second, Says Research

During those days, the two tech giants were well known for publicly ridiculing and reprimanding one another, and they even had a string of continuing legal disputes along the way.

During the height of the browser wars with Netscape, Microsoft promoted Internet Explorer, triggering an antitrust lawsuit by the Justice Department, as per the report. Microsoft was also embroiled in an ongoing legal dispute with Apple over claims that Microsoft stole the macOS look for Windows.

Apple’s lawsuit was subsequently dropped following Microsoft’s cash injection.

But amidst the legal wrangling, there were areas of agreement, including Steve Jobs' promise to make Internet Explorer the default browser and include it in the next Mac software versions. Bill Gates, meanwhile, promised not to sell Microsoft's non-voting Apple shares for three years.

In recent years, one of the world's greatest investors, Warren Buffett, has mentioned that Apple is one of his company Berkshire Hathaway's "four giants". Also, did you know that it was a lost iPhone that led Buffett to invest in Apple? Click here to read about it.

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