A new report from Billboard Magazine revealed that Microsoft once tried to buy into Sub Pop Records but the deal never came through.

This comes from their interview with Dana Giacchetto, a former stock broker who went to jail for a time for fraud. He gave the details of the deal with Warner Brothers and Sub Pop, how they paid the company $20 million for a 49% stake. Others who tried to get in were Universal Music, Sony, Geffen, and Microsoft.

Bill Gates wanted to improve the image of his company and make them more hip, thinking that getting in with Sub Pop would have done it. It may have worked and would definitely have given Microsoft music to feature in PCs and advertising, but they had the lowest offer of anyone that was seriously interested at just $4 million. Giacchetto was helping Sub Pop make their deal happen but considered the Microsoft offering to be insulting.

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You can read the full Billboard article on Dana Giacchetto here.