I know this is out of order, so bear with me; I just forgot about it!
I was living in San Leandro, commuting to Apple, about a 50 mile commute each way. Things weren’t going terribly well at Apple, so I was open to looking for another position.
A really good friend of mine who lived in San Diego called and wanted to meet me for dinner; he was in town and had an idea he wanted to float by me.
His idea was to provide a music streaming service (keep in mind, there were very few if any existing). It would play radio stations, but would have a “buy me” button that would instantly allow you to purchase a tune from iTunes (probably?) as you were listening to it. His first thought was that he would enlist terrestrial radio stations and simulcast them, and then add machinery to for the purchasing. He wanted to start a company. He had a friend who was a startup CEO-for-hire; he wanted to know if I wanted to head up Engineering. He had some prototype streaming Java code in a web server, but the company would need more developers.
I told him I was intrigued. He said, “OK. I would like you to meet my partner. And I want you to show him your elaborate usage patterns of iTunes, iPods, and the Apple Music Store, and talk about your frustrations with listening to music.” I said sure.
A few weeks later, the two of them came by the house. We talked about the proposed company. They asked where the best place to setup an office was, and I said San Francisco “since there are many vacant office after the Dot Com bubble burst” and there are engineers there. Plus good network.
They said that they were going to go try to get Round A Funding, and that if they got it, they would come by and we could negotiate about an offer.
Another few weeks later, my friend called. They were changing the offer to be a pure streaming service (once again, there were few to none), but the VC’s were balking because they were not convinced that they could get access to any catalog from record companies worth streaming.
After a few months, he gave up. He called me and said that they had pitched the idea to 65 venture capital firms, including some in Los Angeles, Austin, and New York.
Oh, well. Would have been nice to have beat Spotify to the market.