APPLE:

The Deal: $150 million

The deal happened when Apple was not so famous and Microsoft was the lone rulers in the tech world. In 1997, Microsoft invested $150 million in a struggling Apple. The deal spoke of Microsoft’s commitments in making software for the still unpopular Mac. But later, the whole scene went upside down as both the companies started arguing on the patent, eventually saving Apple from a massive downfall. This deal also can be regarded as an agreement that Microsoft is willing to forget because later we know Apple was able to surpass Microsoft in terms of revenue and profit.

COMCAST

The Deal: $1 billion

Another billion dollar deal from Microsoft, this time grabbing the stocks of cable provider Comcast Corp in 1997. Deal was to build a high speed data and video services, concreting Bill Gates idea of connecting PC and TV. But 12 years later, Microsoft had to sell the stake for better benefits.

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