00:00:00 · Jackie Reses, Molly O'Shea
[00:00:00] S0: I don't believe there was deep banking. I think it's a crack of shit. There's 5,000 banks in The United States. We're one of the most active banks in the crypto industry. Our last year's revenue was about $280,000,000 and about 31,000,000 of net income. It is all referrals, but honestly, our clients are really our sales team. [00:00:18] S1: You were on the Alibaba board. Yes. You were sitting there with Jack Ma, [00:00:22] S0: Joe Tsai, Masa's son, and yourself. Yahoo owns 40% of Alibaba, and the two companies stopped talking to each other. So I came in and was asked to help clean it up. And what I ended up doing was executing a deal between Alibaba and Alipay that helped pull back tens of millions of dollars of value back to Alibaba shareholders. [00:00:41] S1: I don't know how to describe you. You're like a Swiss army knife. You're kind of like a b two bomber. You're kind of like an f 22. You're very stealth, and you accomplish the mission every time. [00:00:51] S0: When faced with something pretty unprecedented and hairy, like, I run straight into that fire. [00:01:06] S1: Jackie Riesis, welcome to Sorcery. Hello. Well, thanks for joining us here in LA. [00:01:12] S0: Oh, I'm happy to. It's so great.
00:01:12 · Jackie Reses, Molly O'Shea
[00:01:12] S0: Oh, I'm happy to. It's so great. [00:01:14] S1: It's such a pleasure. I'm so excited to get into this conversation because I mean, we were talking about this beforehand. I was like, I don't know how to describe you. You're like, you're kind of like a Swiss army knife. You're kind of like a b two bomber. You're kind of like an f 22. You're very stealth, and you accomplish the mission every time. [00:01:33] S0: I I hope so. [00:01:34] S1: We'll see. I'm still well on my way. So I wanna lay out, because this is wild, your experience. So you're currently the CEO and founder of LeadBank. Absolutely. You raised a $180,000,000 last valued at 1,500,000,000. You're currently on the boards of Affirm and NewBank. Your previous boards include Alibaba, Pershing Square, Taunting Holdings, Endeavor with Ari Emanuel, and your previous roles include exec chair at Square, head of lending, head of Square Capital at Square, and chief development officer at Yahoo, which you started as an entry role of chief HR officer. We're gonna talk about that. [00:02:18] S0: Random. We're gonna talk about that for [00:02:19] S1: sure. On top of that, you started TMT at Apex. You were an M and A at Goldman Sachs for about [00:02:27] S0: seven Seven years.
00:02:27 · Jackie Reses, Molly O'Shea
[00:02:27] S0: seven Seven years. [00:02:29] S1: Yeah, okay. So this is a lot to talk about. I know there's a lot of stories. I wanna start with one of the stories that we talked about beforehand that caught my eye, and I was just flabbergasted by. 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, Josai, Masa's son, and yourself.
00:02:56 · Jackie Reses
[00:02:56] S0: How did that happen? 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 gonna 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 and 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 and Jack, and Masa too, but I spent the most time with Joe, ended up to be wonderful people that I build a relationship with, and ended up doing a bunch of deals with them as a board member of Yahoo in order to continue to grow the company, take the company public, and then do transactions between Alibaba and Alipay, where Yahoo ended up yielding a lot of value back from the Alipay transaction that had been seeded through mechanisms related to the way the Chinese government operates. And so it was a pretty surreal and unprecedented learning experience, that's for sure. You were one of the only Americans ever to
00:05:27 · Molly O'Shea
[00:05:27] S1: be on the Chinese board. What was that dynamic like? So
00:05:33 · Jackie Reses
[00:05:33] S0: it is a very weird dynamic to think how unusual it is to have the experience going deep into Chinese companies. But thankfully they had a broad enough shareholder base that they understood both Eastern and Western values. And Joe in particular was someone who I regarded as like an incredible deal guy, easy partner to work with. A lot of the team there was incredible. And so he helped bridge the cultural dynamics of operating in China. There was a moment in time I remember where they asked me whether I would speak at an entrepreneurialism convention for them, where they were presenting to female entrepreneurs in China. And you're like, okay, this will be interesting. And then you realize it's like a convention center of women. It's like a stadium. And what they're talking about is that they are working to change the middle class system in China, to build entrepreneurship in China. And I'm like looking out at this stadium and I am like, oh, this is not like an ordinary course, 500 person event. This is like a gigantic deal in China. And they had this mission to just change the number of people that evolved into the middle class in China. And to do that meant elevating female entrepreneurs. And so it was like this incredible experience because the scale of China was just daunting, and the values and the conception that they're just gonna try to change an entire classism because of this concept of entrepreneurialism was something I hadn't thought about in advance of being invited to this event. Like, the company changed the country. And that is a pretty surreal dynamic. I mean, I think we're seeing that now with a lot of AI companies, fast forward fifteen years. But at the time when you think about like, what's the impact of a company like Alibaba and Alipay to the country of China, it's a pretty surreal experience to be a part of. And so as a board member, I loved every minute of it. I mean, there were a lot of times that weren't so happy and lots of discussions, particularly around taking the company public. But for the most part, it was a very well run company, well governed company, which I think a lot of Americans just have this belief that a Chinese company wouldn't be well governed. It was an exceptionally well run company. And so you watched excellence at its best, at a scale that is pretty unprecedented.