Once upon a time roughly about twenty years ago, Microsoft tried to buy the Seattle indie label Sub Pop. No, really. Once grunge died out in 1994, Warner Bros. paid $20 million to own 49% of the label, which is a deal that still holds up today. The person who made that deal happen was Dana Giacchetto who was a rockstar in the broker world, throwing crazy parties with Leonardo DiCaprio. Eventually he landed himself in jail for fraud, and in a new profile on Billboard he looks back on his career and sheds some previously unheard details, including that Microsoft offer.

"I can now reveal that Universal was the top bidder, $25 million, but it wasn’t the right creative fit. Sony Music bid $5 million. David Geffen bid $8 million — I told him his bid was way too fucking low — and Microsoft bid a paltry $4 million, frankly insulting. Bill Gates, who at the time considered himself to be ’the future of entertainment,’ couldn’t have been a more dull character. It definitely would have made Microsoft a bit more hip, which in hindsight might have actually made Microsoft a player in entertainment. They’re still not.”