A few small mentions of Square are in the talk, and Jack discusses Square with a little more detail at around the 1:20 mark in the Podcast. The conversation mostly revolves around Twitter and it’s impact in the world.
https://www.theringer.com/the-bill-simmons-podcast/2019/1/23…
He also just did an interview with Rolling Stone. Most of it definitely focused on Twitter, but there were a few mentions of Square:
By all accounts, Square runs more smoothly than Twitter.
It has to, though. Yeah, you’re dealing with people’s money. I mean, it’s extremely emotional. If you lose 140 characters, people are like, “Eh.” If you lose $140 or even $1.40, it’s important. We knew the severity, and we knew how emotional this was to people. We’re impacting their livelihoods, so we had to get every single thing right. There’s a lot of regulation around payments. If you do something wrong, you go to jail.
And
Did you come away from Twitter to Square with a newfound world-conquering ambition?
No, I don’t want to conquer the world.
Some people say you were motivated by revenge or, more pleasantly, to show them that they were wrong.
Definitely, when I started Square, I needed to prove a lot to myself. I was put in a position to do something, and I thought it was going quite well. I was surprised to learn that it wasn’t. Then I was out. I spent months trying to figure out what happened. The only way I know how to figure out what happened is just to do it again.
Read the whole thing at https://www.rollingstone.com/culture/culture-features/twitte…
Matt
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