Jack Dorsey

“The good news is the companies are not conflicting in any way, so there's no chance of him having some kind of awkward situation where he feels he's on the fence because he sort of has two different companies to deliver value to.”

“I think that idea has well and truly been replaced in the U S where it's okay to do that if you want to do that, but it's also okay to stay in charge. So you have, you know, very, very prominent cases like someone like Mark Zuckerberg, for example, or Jack Dor…”

“I don't know how he can do it. I don't know. I just don't know how anyone can run two companies, especially two massive prominent companies as a single person.”

“I remember seeing Jack Dorsey's pitch for squares series a, and he literally started with like, these are 75 things that could kill this company in the short term.”

“I don't know that it was offered to me, but Square, when Jack Dorsey was walking out in the hallways at a conference with a dongle, and I thought I was too busy.”

“I mean, my first one was square and I had looked into payments a bit for Microsoft because, you know, we had so much cash in the balance sheet that one of the things we could have done was become a bank. And we could have gone after digital currencies and stuf…”

“So when Jack was starting square and we met with him, he said, well, you know, if you thought Twitter was expensive, this is going to be even more expensive. And his first round was at a 40 pre and we learned our lesson and we were fortunate enough to be the S…”

“You know, I think when we invested in the Series A of Square, I think it was around a thirty million dollar valuation. It was Jack and Jim in a PowerPoint.”

“There will be many moments in a company where you're, as a leader, you will be an island, and you will need to make a decision that you think is best, and you will expect your team to disagree and commit.”

“There was a committee of the board that was trying to find somebody else, and they weren't able to find anyone better than Jack.”

“What I did when I came in is, is Jack and I hammered out a purpose statement for Twitter. The answer to the question, why do we exist? Because before that, if we asked around at the company, you know, what's the purpose of Twitter's existence? People would say…”

“Instagram came to me. Kevin Systrom literally said, I want three angels, you, Adam D'Angelo, and Jack Dorsey.”

“Another one that's very similar, and it wasn't me, it was a different partner, but I don't think I was helpful, was Jack That brought Square to us on the A.”

“Instagram came to me, but like Kevin Systrom literally said, I want three angels, you, Adam D'Angelo and Jack Dorsey. And so he pitched me. I literally was not seeking photos. I, it sounds fucking hilarious, but I thought it was spent. I thought it was done. A…”

“I remember in 2017, maybe, yeah, it was end of 20 16 when Jack wanted to put Bitcoin into Cash App. And he, ah, two engineers sat, ah, on the sixth floor of 14 55 market and wouldn't leave the office until they were able to build that product.”

“You know when you're editing or when you're actually writing, and you want to be editing people's work as the CEO. You don't want to be writing, and if you feel like you're using a lot of red lines consistently in the same area of a company, that's a really ba…”

“Like I remember when I was talking with Jack Dorsey before he invested, one piece of advice he gave me was that we should stay private as long as possible.”

“Twitter could have been infinitely a more interesting company, but VCs got involved and created politics, and they fired Jack Dorsey early, and I don't know if that was right or wrong, but they created issues, and the company was pretty messed up.”

“I would say the best technical CEO, Larry Page, the best growth-centric CEO, Mark Zuckerberg, The best design-centric CEO, Jack Dorsey, and the best physical world operational CEO, the most likely to be Jeff Bezos next, Tony Xu.”