00:29:53 · Molly O'Shea, Jackie Reses
[00:29:53] S1: That's pretty intense. Wow. So in terms of the origins of Square, I know you also leaned into crypto when no one else was doing that. So why did you decide to do that? [00:30:10] S0: So Square leaned into crypto very early on, and that was really Jack's brainchild. He had a vision for Bitcoin trading that he wanted to see executed. And in the way that he and a team started Square Capital, he and a team of three engineers sat down on a Thursday and wouldn't leave the office until Friday night. They coded the system. And I actually sat alongside of them for part of it and did whatever I could to be helpful. And I felt like I was their pizza orderer, their comedy routine, their breath of fresh air, and just someone to coach them and be happy to cheer them along. And so Jack wouldn't leave the office until that product was launched. And so he sat there for a few days and made that happen. [00:31:10] S1: So Square was one of the first fintechs to lean into crypto when it was still a little taboo. Well, it was a little hype y, honestly, [00:31:17] S0: in the crypto world. Yeah. Well, kind of. It was edgy. [00:31:21] S1: It was edgy. [00:31:21] S0: Super edgy. [00:31:23] S1: What was going on there and why
00:31:24 · Jackie Reses
[00:31:24] S0: did you lean into it? I love this story because it's all Jack. The amazing part about Square and its crypto origins is that everything about it was Jack's personality. Jack Dorsey just decided that he wanted to have a crypto product. He wasn't waiting for anyone. He wasn't going to deal with anyone's objections. He was just going to go get the job done. He took three engineers, and he sat at the corner of the 6th Floor at 1455 Market and didn't leave the office for three days. And so everyone sat there, he included, and they coded up the crypto trading platform. And so on Friday night, when they finally were able to trade, it was like the moment that they all left the office. And my space for Square Capital was right next to where they were sitting. I love the group of people who were doing it. It was a very small group that I happened to be close with. I was more than happy to light up the space and keep smiles on their faces. And so I just thought it was the coolest thing that in January 2017, they were gonna launch this crypto product. And then the chaos starts, which is you're a public company and you wanna launch a Bitcoin product, but there weren't really public companies that had Bitcoin. And so you have like accounting implications, which is a really weird thing. You have SEC implications. So you have to take this idea to the SEC, but no one knows how to account for it. And so that is whack a doodle, right? You're trying to go then explain what kind of accounting it should be to your accounting firm. And so we almost got held up that first quarterly earnings period because we couldn't get accountants in the SEC to agree that we were accounting it correctly, and then actually get it in the numbers in order to launch the product. And we weren't gonna wait another quarter to make that happen. We were just anxious to release the product. And so I think everything about that experience just screams Jack Dorsey and his personality on steroids because of the energy and the creativity and the bombastic nature of the way he wanted to go get this product into the world.
00:33:51 · Molly O'Shea
[00:33:51] S1: What are his key leadership traits? I know you just mentioned a few, but like, what
00:33:57 · Jackie Reses
[00:33:57] S0: is Jack Dorsey like? I have no idea. So I loved working with Jack. You know, he's more of a normal person than you would think because people portray him as this iconoclastic, quirky character. And there are elements of his personality that are quite iconoclastic. However, he's deeply thoughtful. He's very caring for his family. He's very healthy. He's very curious and he's an amazing listener. And I think a few of the things that I've loved about him is, when he has an idea, he actually says, like, I kind of want to see this come to fruition, and he just makes it happen. Like how many of us have dreamed about an idea and then you just let it sit and you let it stew in your brain and you do nothing about it. That is not Jack. When Jack has an idea that he thinks is going to change the world, well, of course, we're going to put people behind it and go execute against it. That's just the way he is. And so sometimes he's wrong on timing, but he's never wrong about the idea. And so following his instincts is a great way to follow what to expect in consumer products. His listening skills are unparalleled. He'll sit in meetings and not say a word, like not say a word. And you can either think that is really freaky and you're off put by it, or you kind of watch why he's doing it, what he's synthesizing, what he's capturing, and then realize there's real wisdom in his ability to just zip it. And, that's probably the biggest takeaway I have from my experience working side by side with him for so long is just like, zip it. You know, you don't need to talk. You don't need to put your ideas out there first. Listening really matters and making sure that you're capturing the essence of what people are saying, even when it is a opinion that is divergent from your own. That can drive a lot of value in making your thinking CRISPR.
00:36:13 · Molly O'Shea
[00:36:13] S1: And what was it like with Twitter going on? Was that chaos?
00:36:16 · Jackie Reses
[00:36:16] S0: Oh, it was a disaster. Honestly, the worst job I ever had was being the head of HR at Square. So I ran these financial services products and I ran HR. And the HR job at Square could have been okay, but for the fact that Jack is running Twitter and any time that there was drama at Twitter, which was like every day, you know, people at Square would have a hissy fit about something that was going on at Twitter, but we couldn't do anything about it. Be like, Jack, you know, Laura Loomer locked herself to the office today at Twitter. What are we gonna do? He'd say, what do you mean what are we gonna do? This is Square. He'd be like, I know, but everyone at Square really cares about, like, what's happening a half a block away. And he'd say, like, you know? And so you're literally sitting there with your arms tied behind your back. You don't know what you can say. He won't say anything. And it was almost like, weirdly, Twitter never would be said at Square. And people would talk about some controversy, but we didn't talk about Twitter. And one of the things I found incredibly frustrating was even today, like analysts or reporters will say, Twitter CEO Jack Dorsey reports earnings. And you're like, no, Square reports earnings. You know, Square's CEO or Block now for a long time now. Block's CEO reports earnings, but, like, everyone loved the drama of Twitter. And Twitter was really fun to hang out with in Soho, but Square was where you got the stability and the steady love and the family that, was just steady Eddie over a long period of time. So it was quite the experience, but that conflict of not being able to control what was happening at Twitter was just like an impossible, impossible job. I used to call their head of HR, it was also their CMO, Leslie Berland, who was a friend of mine. Leslie and I would get on the phone on a regular basis and we would have the, oh God, what are we gonna do about this now? And so we had some amazing moments of camaraderie. And the two companies, a lot of the executives thought of ourselves as cousins. So if we would have dinners together, we would have very funny moments of just making fun of Jack because we all considered ourselves like the family. And so that was a really fun experience.