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As the owner of ideal type of venue for artists who are too big for a club but can’t fill an arena or NFL stadium, Live Nation has a lot of power over artists who want to play to growing crowds.

"As there's no one ideal type of grassland, we always have to weigh up the pros and cons. We have to ask ourselves: Who's benefiting the most from what kind of management and in what location?"

Fink, who chairs a newly created music industry program at UCLA, said he sees Swift as a “kind of ideal type”: the artist-entrepreneur who controls her career.

And Wilson might be the ideal type of player to gamble on in this area.

“When you feel like it’s a combination of it all, that’s when you feel like you kind of hit the jackpot in terms of this is the ideal type of interview, and that was one that I have consistently said I came out of feeling that way regardless of how it ended up.”