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.
00:38:45 · Jackie Reses, Molly O'Shea
That was actually a more fun experience than just having one company to run, is like the chaos of having this cousin on the side. That is so wild. Yeah, and they got into so much more trouble than we did. It was like being able to look at your hot mess of a sibling and be like, What are you people doing over there? You're always up to something. And we would be dotting our I's and crossing our T's like the financial nerds that we were. [00:39:14] S1: Yeah, you're silently working at your desk, and then you open the door, you go over there, and everyone's screaming at each other. [00:39:19] S0: Well, silently working, but we're making debit cards and point of sale systems and loan products. They're in the sexy hot mechs of American and global culture. And we're talking about whether our debit card has our logo on the front or the back and how thick the metal is. It was like the contrast couldn't have been more extreme between the two companies. Even our executives, we were such nerds compared to them. They were like the cool kids, a half a block down the street. And even in technical jobs, somehow they always seemed to be much cooler than the Square execs were. [00:40:03] S1: I guess maybe that's a good way to ask. So as you've seen through different tech cycles and through many different lenses of companies, how do you discern through hype and then also durable innovation over time?
00:40:20 · Jackie Reses
[00:40:20] S0: Oh my god, there's so much hype. Interestingly, being involved in the crypto business, because we're one of the most active banks in the crypto industry. We operate in an industry that feels like hype and momentum is kind of the underbelly that has kind of catapulted the industry from 2009 when Satoshi wrote the white paper all the way through to today, where it's a multi trillion dollar established set of industries on a global basis. And I think the characteristic that I look for mostly in crypto products, and I think the discerning kind of framework to look at for hype in general is like, is there a real use case? Like, does this product actually add durable value? There's so many things in my industry where you kind of have to scratch your head and say like, yeah, but I don't understand why that makes something better. Like, is this better? Or is it just like a different version of doing that? Because if it's not making an experience better, a product better, I'm not quite sure why there would be product market fit for that experience. And I think AI is at one end of the spectrum where the mass adoption, I think, makes it so obvious to see where there's value being created and people are using these tools to really change the world. And then crypto is somewhere in the middle where you have big parts of crypto that have lots of hype and momentum attached to it and less of a durable use case. And I think we're really starting to see a breakout between those products and crypto, for example, where there is a use case and durability, and those products which won't stand the test of time. And so I think the framework that I've applied to crypto is probably the same that I'd apply to any other product.