Microsoft was laughed out of the room when it tried to buy Nintendo
Microsoft did okay in the end though.
Bloomberg has published a sweeping oral history of how Microsoft created the original Xbox, including interviews with heavyweights like Microsoft cofounder Bill Gates and former CEO Steve Ballmer. It includes many amusing anecdotes and misadventures along the way to successfully launching the Xbox brand, including a brief and fruitless effort by Microsoft to buy Nintendo.
At the turn of the 21st century while Microsoft was exploring literally how to build Xbox and which software development partners to bring on board, the company was earnest in acknowledging that it knew little to nothing about game development. It approached the challenge humbly and honestly, which had its ups and downs, and Microsoft faced an overwhelming amount of skepticism. Nowhere was this more apparent than when Microsoft tried to make acquisitions, such as attempting to buy Nintendo.