Looking at Apple today, it can be hard to believe that the corporation was once on the brink of financial ruin. Currently among the largest tech companies in the world in terms of market capitalization, it actually owes a lot from another tech giant

Desperately-Needed Lifeline

You see, Apple was reportedly a mere 90 days away from bankruptcy when its co-founder Steve Jobs returned to the company in 1997 after being forced to take a 12-year hiatus.

Still, people were shocked when the late business magnate announced that Apple entered a five-year deal with Microsoft, which remains to be one of the company’s consistent competitors to this day.

The agreement entailed a couple of cross-licensing of patents. Its most notable stipulation though is that Microsoft’s Internet Explorer would be used as the default browser on the new Macs Apple would produce.

The partnership helped keep Apple afloat as the Bill Gates-headed tech company injected $150 million into it in exchange for Apple stock.

Microsoft’s Investment

Microsoft’s investment bought it 150,000 shares of preferred stock from their competitor. The deal stipulated that Microsoft won’t be able to sell these shares, which were convertible to common stock, for at least three years.

Over the years, Microsoft converted its shares until all of them were common stock in 2001. In total, the company held 18.1 million common shares at the time.

It didn’t waste time holding onto these shares though. Less than two years later, Microsoft has already sold off all of its Apple shares reportedly netting $545 million on their original investment.

What Could’ve Been

Microsoft would’ve gotten back way more than that though had Gates decided to keep his investment longer in Apple.

With Apple’s current stock price, Microsoft’s shares would have been worth a whopping $116.6 billion today. While $545 million is certainly a good return on investment, that’s nothing compared to the billions the company would have gotten had it had a little more faith in its competitor.

These days Apple’s stock is trading for about twice the price Microsoft’s is. The Jobs-led company also achieved the feat of reaching a market cap of $1 trillion ahead of any other American-owned company.

Since then, it has now breached the $2 trillion mark. Safe to say, Jobs left Apple in better shape than ever when he passed away from neuroendocrine cancer in 2011.