The Exchanges

Q a lot to talk about. I know there's a lot of stories. I want to start with one of the stories that we talked about beforehand that caught my eye and I was Just flabbergasted by it. I just don't, I don't know how this happened. So you were on the Alibaba board. You were sitting there with Jack Ma, Joe Tsai, Masa's son, and yourself. How did that happen?

A That's a crazy group of people. It was, honestly, it was one of the most fascinating experiences of my life. I went to Yahoo to be the chief development officer, and once there I was asked to join the board of Alibaba. Because Yahoo was the largest shareholder. They had the most contentious relationship. If you remember, there was this dynamic where Carol Bartz had been in this contentious fight with Jack Ma that was widely chronicled, and the two companies stopped talking to each other, even though Yahoo owned 40% of Alibaba. And so I came in and was asked to help clean it up. And so what did that mean? There was like hedge funds and activists trying to force Yahoo to sell their stock, and agreements that were going to cost Yahoo tens of billions of dollars, and so I go into this situation having never been to China, and I show up in Hangzhou, and I met Joe and Jack, and Work to start to build a relationship to try to bridge these two fractured companies. I mean, this is like an unbelievable relationship, an unbelievable value capture for Yahoo and Yahoo shareholders, yet to not actually have a relationship with the CEO and founders of the other company is unprecedented, let alone the scale of the dollars we were talking about at the time. And so I went to China You know, as often as I could, multiple times in a month, I spent a lot of time with the principals there, and Joe a…

AI assessment note: “I went to Yahoo to be the chief development officer, and once there I was asked”

Q How does this then lead you to Square and Jack Dorsey?

A Jack's the best. So, you know, I was working at Yahoo, and out of the blue one day I get a phone call from Jack Who said, I've heard about you, and I understand you run HR at Yahoo. Can you explain that to me? I was like, I don't understand this phone call. It was so funny to just get a phone call and ask about my job, and so we talked multiple times about what it was like to run HR as an operating person and not a traditional HR person, and that was a model that hadn't been Use that much within Silicon Valley. And he was really curious about it because he thought that HR should have more of an operational bent to it than a lot of traditional HR leaders deployed. And I think he also trusted the function as an advisor. You know, at the time I called, when I ended up going there eventually, I felt like I was more of an advisor than a business advisor, than You know, what a traditional HR person would do, and so he asked me whether I would come to Square, and at the time it was before the Alibaba IPO, and I didn't think I could leave before the Alibaba IPO, and so I felt like my job wasn't done at Yahoo. So I waited for the Alibaba IPO. It was amazing. Then we reconnected, and I ended up Where I was in the middle of this huge tax transaction for Yahoo. There was a massive capital gains tax bill, and I was tasked with trying to solve how to manage that. And the complexity of that, …

AI assessment note: “out of the blue one day I get a phone call from Jack”

Q Wow. And all referrals. Can you list out some of your clients?

A It is all referrals, but, and honestly, I, our clients are really our sales team, and between our clients or me, um, that's sales. And so, you know, our first client was actually Ramp, and at the time, I was at a KOTU conference, and I was with Eric, and I pitched him on what we were building, and he was like, I'm in. And we ended up working on one product with them, and his philosophy was you can be no worse than the traditional banks that we use, and given the roadmap that you're going to build and the technologists that you're working with, um, you'll be incredible. And so I'm willing to wait the six months when you go build out your tech, uh, and advance your technology in such a way that We're willing to wait, and I know you won't be worse than what we work with, and so we got very lucky to have such a high quality client, and so, um, that was our first client, and then Atlas was one of our other clients, and they had just had a situation where another bank, um, ran into trouble, and Atlas had to come off their rails along with a handful of other clients, so they immediately came to us in an emergency and said, can you take us? We hadn't even closed the deal when I said, like, you have to go talk to the team before we own the company, but if they onboard you, we will absolutely deploy our technology to your products, and so we ended up onboarding Atlas as our second client…

AI assessment note: “our first client was actually Ramp... Atlas... Stripe, Walmart's OnePay, Affirm, Flex, Self”

Q What are his key leadership traits? I know you just mentioned a few, but like, like, What is, what is Jack Dorsey like? I have no idea.

A So I loved working with Jack. You know, he's, he's more of a normal person than you, ah, 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, um, 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. Um, his, his listening skills are unparalleled. You know, he'll sit in meetings and not say a word. Like, not say a word. And you can either think that he's really freaky, and you're like, you know, 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 h…

AI assessment note: “he's deeply thoughtful. He's very caring for his family. He's very healthy.”

Q What do you think the biggest misconception is about working with the government?

A They can't actually have a conversation. I think the more honest and open you are and square about what your agenda is, the more you can have a conversation that actually provides advice or listens to a perspective about what they're trying to achieve. Like there's so many things that need to be changed to update the world for the AI age. And I don't think the experts are going to be in the government at all. Therefore, the people who are the experts need to show up in droves and actually provide their insights to the government so that they then can distill the best framework for judgment To build laws. Like, I think lawmakers are good at figuring out what level to, to write those frameworks in, but they're not going to be able to do it in AI based on their insight and knowledge and experience. They have zero of it. And so I think all of us who have specialized knowledge, mine around crypto, financial services, building out digital rails, many on the AI side, probably our lead, many of us are experts on what regulatory framework It's need to be changed for Agenda Commerce. But like true AI legislation on the core of the technology, I think, you know, it behooves all of those executives to just show up in droves.

AI assessment note: “They can't actually have a conversation.”

Q mean, I think it's pretty incredible. You were at Goldman Sachs for that long, and then you went to Apex where you stood up their TMT practice and you led that. And then from there you go to Yahoo. And so you get into Yahoo and you're chief of HR. So how did you get into that role? And then how did you maneuver that role into the other role?

A Yeah. So Goldman was amazing. And I had A few twists and turns at Goldman. I invested at Goldman, which was super fun. I worked in equity capital markets for a stint for this legendary executive and management committee member named Eric Dobkin. And, you know, I had just such an amazing experience there, but I wanted to invest on my own. I was always really entrepreneurial. So, like, my fear with Goldman was that if I stayed there, I'd never leave. Like, at the time, it was private, and it was an amazing place to work, but, you know, I had to go pursue this entrepreneurial dream, and so I ended up at Apex, and I founded the media group, and there were great investors there, like Oren Zev, who's actually one of my current investors in my company, who led the tech group, and We went and tried to build, you know, a media technology practice, and so at least I had this entrepreneurial opportunity within the context of a broader private equity firm. I think private equity at the time was interesting, but didn't satisfy the itch, and I really was entrepreneurial in my entire life. I just really wanted to own my own Like, I always had this dream that I wanted to, like, own the wire hanger company or the box company. Like, something that no one really knows. I mean, I guess I own a bank now, so maybe I've achieved that.

AI assessment note: “Yeah. So Goldman was amazing. And I had A few twists and turns at Goldman.”