I know this wasn't the top question from votes, but it's probably my favorite, so kudos to the author.

Two answers:

1. Hal Varian: I had the chance to hang out with him briefly when I was at Google and he's one of those homies that just understands economics in the age of the internet. Would love to chat with him about how he simplified and then expanded the ad rank algorithm.

2. Adam Smith: I know it's old school (and a bit generic), but I think there's a fascinating conversation to be had with Smith on what's happening with subscription and the internet in general. He'd likely bring it all back to fundamentals, because he'd have very little context on all the quibbles we worry about, which would be very refreshing and provide a ton of context on the things I'm/we're trying to solve at ProfitWell.

Bonus: I kind of want to sit down with anyone with an economics tint that's doing actual research in the world of subscriptions. There aren't a lot of us, so there's a good summit/dinner to be had.