Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: The Secret to Negotiating; Making $50BN for Yahoo on Alibaba | Why Everything You Know About Hiring is Wrong; Domain Knowledge and Past Experience are Dangerous | The Next 10 Years for Fintech; Winners, Losers and Crypto with Jackie Reses, CEO @ Lea About this episode Jackie Reses is the Chair and CEO of Lead Bank, a community bank in Kansas City. Previously, she was the Executive Chairman of Square Financial Services and Capital Lead and Head of the People Team at Block Inc (Square). Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide. Jackie also spent seven years at Goldman Sachs in mergers and acquisitions and the principal investment area. Jackie is on the board of directors of Endeavor, Affirm and Nubank. Previously, she served on the Board of Directors of Alibaba Group. She has been named one of Forbes' “Self Made Women”, Fast Company’s “Most Creative People in Business,” and American Banker “Most Powerful Woman in Finance”. In Today's Episode with Jackie Reses We Discuss: 1. From Humble Beginnings to "Most Powerful Woman in Finance": What is Jackie running from? How did Jackie's upbringing impact her approach to business and management today? What does jackie know now that she wishes she had known when she started her career? 2. Building the Best Teams: Lessons from Square and Yahoo Why does Jackie believe that past experience is BS in hiring candidates for a role? Why does Jackie deliberately not look for domain knowledge when hiring? Why does Jackie believe employers should tell candidates what they suck at in hiring? What does Jackie mean when she says, "you have to invest in people for 20 years"? 3. The Best Deal-Maker in the Business: Secret to Negotiating: What does Jackie believe is the secret to successful negotiations? How did Jackie do the Alibaba deal for Yahoo and make $50BN for them? Why does Jackie believe the Laffonts and Coatue are the best risk managers? What are the biggest mistakes people make in deal-making today? 4. The Next Wave of Fintech: Who wins and who loses in the next wave of fintech? What will happen to the crypto industry? How will crypto be regulated? Why does Jackie believe that financial super apps are BS? Why does Jackie believe that Goldman tried and failed to innovate? Will we see a wave of M&A in fintech over the coming years?
Transcript 10,976 words · 3 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 I focus on what I think the person's innate skills are as a human, not what jobs they've had in the past. Disarm people in an interview by saying, let me tell you what I suck at. I now index away from domain knowledge than I ever did because a lot of what we're creating hasn't been done before.
0:18 Harry Stebbings? This is 20 VC with me, Harry Stebbings, and today's guest has been described as the most powerful woman in finance. She's an OG of the industry and I'm just so thrilled to welcome to the show Jackie Reese's. Jackie is the CEO of Lead Bank, a community bank in Kansas City. And before Lead, she was the Executive Chairman of Square Financial Services. And before Square, had leadership positions at Yahoo and was a partner at Apex Partners. Jackie's also on the board of some incredible companies, including Affirm, New Bank and Endeavor, to name a few. But before we dive into the show, Stacey, you've heard me talk about how Coda is the dock that brings it all together and how it can help your team run smoother and be more efficient. I know this because Coda helps me and 20 VC. So much prep goes into each episode of 20 VC with 10 references for each guest.
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3:35 Speaker 02 You have now arrived at your destination.
3:38 Harry Stebbings? Jackie, I am so excited for this. I loved it when I asked you for people that we had in mutual friendships with. And you mentioned Mickey, you mentioned Guillaume, you mentioned David Velez. Obviously, you did my homework. So first, thank you so much for joining me today.
3:51 Speaker 00 Oh, I'm so happy to be here. I know it's a long time in coming.
3:54 Harry Stebbings? We made it happen in the end, but I want to start with a little bit of an unconventional start, to be honest. I'm fascinated on this one.
3:59 Speaker 00 Aren't they always unconventional?
4:02 Harry Stebbings? No grey story ever started with I had a salad, but a thing back to when you were a child. What did you want to be when you were growing up?
4:08 Speaker 00 All right, now this sounds terrible because it's so trite, but one of my first memories of playing as a kid is playing bank teller Barbie. I had this pink Barbie convertible and David Cassidy, I'm like a 70s kid, so this is like 1976. David Cassidy would pull up as a customer and I was the bank teller. And so I know that sounds totally ridiculous, but it's in fact true. And so I come from an incredibly entrepreneurial family. Everyone in my family started their own companies. I'm the only person to have worked for anyone. I got lucky and then I knew enough to know I didn't know anything. And so I started my career at Goldman Sachs, but then evolved to pretty entrepreneurial components of any company that I worked at,
4:52 Speaker 00 where I was building a team, building a company, building new products. I always stuck with financial services because I loved math. I loved the idea of inventing in a really old industry and I loved building businesses. That's the theme that always exists in my life and total entrepreneurialism.
5:08 Harry Stebbings? It's funny you say about the dreams of being a bank teller there. When I was younger, I always saw like the vaults in movies and they open them up and there's like wads of cash. I wanted to be the bank robber. Yours is slightly more legitimate than mine and yours actually became true. Sadly, I haven't had that moment of cash just like hitting me from a vault.
5:24 Speaker 00 If you come to one of our banks in Kansas City, I run a bank and we actually have physical locations that are pretty gorgeous in Kansas City. And there is a vault in our Lee's Summit, Missouri location that is absolutely stunning. And so you look at it and say, there should be a movie that happens inside this vault because it's pretty cool looking. The door is gigantic and it's old school looking and it makes you feel like you're grounded in a lot of history when you go there.
5:51 Harry Stebbings? How do you know when you were part of the creator economy? When you go, this would be the best TikTok ever if you let me go into the vault?
5:58 Speaker 00 You can go into the vault. We'll put a, we'll put a special place for you in the vault.
6:02 Harry Stebbings? I always believe that we're a function of our histories and I'm secretly an armchair psychologist without the degree, without any degree on that matter. But we're all running from something. What do you think you're running from?
6:12 Speaker 00 Oh, now we're gonna go deep in psychology because I am absolutely running from my childhood. So I had a very unusual childhood in the sense that I ended up moving out of my house when I was 14, sent myself to boarding school and I got myself out of a household of chaos. So when you're in that kind of environment, you have to stand up for yourself and be independent on your own. And so I was always involved in entrepreneurial endeavors and making sure I could support myself and get myself to a different place in the world. I saw the dreams of building businesses that my parents established, but then also knew that I had to survive on my own. And in order to improve my own life, I was just gonna have to do it on my own. I only went to three years of high school because I needed the work.
6:57 Speaker 00 I needed to put myself through school. I left high school as a junior. I went to college. When I was in college, I ran a bunch of businesses that helped put myself through college. When you're stuck in that kind of environment as a kid, you learn what grit is and you learn what entrepreneurialism is. And I ended up having a drive to succeed, to get myself out of that environment that I think is unending. I wanted to be successful. I wanted to be independent. I wanted to have a lot of things that didn't exist in my family. My entire career is built off of that foundation.
7:29 Harry Stebbings? What do you think grit is?
7:31 Speaker 00 Oh, grit is like an intensity around needing to be independent and needing to drive yourself forward and pick yourself up and just brush yourself off and get back on the train and go. It's one of those things that I try to teach my kids. There is unfortunate a curse of kids growing up in a level of comfort. I try to make sure my kids understand you gotta work. You were independent. You were putting yourself through school. You were gonna have your own jobs. You gotta work to have extra money. They've gotta learn that they've gotta build their own career without the benefits of their parents providing so much comfort that they lose their own self-esteem.
8:10 Harry Stebbings? I totally agree with you. When you're 14, it's so young. My mother, my master when I was like 11, it made me grow up very fast, much faster than I anticipated. But how did you deal with the weight of expectation as a 14 year old is quite unusual.
8:23 Speaker 00 The only expectation I recall from my parents is that around education. They were very education focused and the only place I remember my parents ever talking about was University of Pennsylvania. You're going to go to Wharton and I was a very entrepreneurial kid as I mentioned and my parents just drilled into me that I was going to go to Penn. So I only wanted to go to one school. I went to that school. I applied to that one school. I love that school. I think I owe that school my entire life. That was really the only expectation they had for me. I think everything else I had to build on my own around what I wanted to achieve in my life and who I wanted to spend time with. The other thing that happened to me really young, and again, I think it's a function
9:05 Speaker 00 of reacting to my childhood, was that I met my husband when I was 18 and my husband came from one of these super classy families and he's a very generous family. They were all so erudite and wonderful. His mom studied Shakespeare and his father was like an old school lawyer. He taught me about longevity and relationships and good people. Like you want to spend time with good people. That is a great foundation and a great reaction to my childhood where I met people who had really high integrity and I just wanted to spend time with them and live in a world of excellence. And that's what I saw from him. That was a total reaction from my childhood, which was the exact opposite.
9:48 Harry Stebbings? What did he teach you about longevity of relationships?
9:51 Speaker 00 All of his parents' friends were all married for decades. They had friends for decades and they were true to who they were. They stayed loyal to the people that they associated with and they were all kind of people of high integrity. I love that and I gravitated towards it. It's the same reason why I went to go work at Goldman Sachs when it was a tiny private company, but it stood out amongst Wall Street players as being this high integrity firm that focused on excellence in their clients. My husband's relationships were the same way and I was mesmerized by that as a kid who grew up in a broken home. I wanted to be like those people and I was going to leave behind broken relationships and make sure I put myself in a different world to watch and observe and see what I
10:34 Speaker 00 could glean from people who seem to excel at building trust with other people. And I kind of loved that as a kid.
10:41 Harry Stebbings? Going to get into seeing good in people in the hiring process. I do just want to ask, on your style of leadership first, how do you think about what high performance means in leadership to you?
10:50 Speaker 00 I think there can be a bunch of different dimensions around that where people have incredible raw intelligence and able to actually create outcomes that matter and make a difference to a company. And so I focus on not the work they're doing, but the outcomes they drive and how they drive it as a vehicle for looking at who's an absolute killer. Who has good instincts, who has good judgment, and what do they deliver for us?
11:16 Harry Stebbings? Now, Jackie, you mentioned there are kind of outcomes that people drive. You mentioned being trusting of people. I suck at hiring. I think one of the reasons the show has been successful is because I'm very open, not good at hiring. And I spoke to Mickey before the show and he was like, you've got to talk to her about hiring. I'm just going to ask a very broad question of what have been some of your biggest lessons on hiring and building the best teams?
11:37 Speaker 00 I focus on what I think the person's innate skills are as a human, not what jobs they've had in the past. Someone could be amazing at people skills and you could pull someone from sales and get them to be a recruiter. It doesn't matter that they had a totally different function. That function has a certain level of underlying experiences that attach to it. That often attaches to where someone's true spike is in who they are. That may have nothing to do with their resume. I remember when I was at Square, I ran HR. And people used to look at my background, which was extremely financial, right? I worked in private equity for 20 years. I've always created esoteric financial products.
12:22 Speaker 00 And then I ran HR for a decade at two tech companies. I used to say my best skill was that around understanding the good in people and what they might be good at in their jobs. That had nothing to do with finance. But if you really abstract what private equity is, judgments about people, where you need to place them in their jobs and what levers of growth you give them in order to help them grow a business, that is recruiting and that is leadership and that is HR. And so as much as someone Might look at my background and say, oh, you'd be an amazing CFO. I was like, no, if you truly understand what I'm good at, I'd be an amazing head of HR. I think the most important thing you can do is just understand everything outside of someone's resume.
13:05 Speaker 00 What are they truly good at and what do they suck at? And if you focus them then on a job, that's what matters.
13:11 Harry Stebbings? How do you do that? Because I think sometimes people don't know actually sometimes their biggest strength or their biggest weakness or where their spikes are. How do you detect their spike and do that in reality?
13:22 Speaker 00 So you spend a lot of time with people, both in a personal setting as well as in an interview setting. I like to go through case studies with people and see how they operate in a real world experience. That helps you understand how they operate on the fly and what they're good at and not good at. And then I also spend a lot of time on things that have nothing to do with their resume. And I often start with a question of tell me what your life goals are. Like when you look back at your life 50 years from now, what do you want to have achieved? And then what do you think you're truly amazing at? Please don't give me anything that shows up on your resume. And what do you think you suck at? Disarm people in an interview by saying, let me tell you what I suck at. You might look at what I've done and say, amazing finance.
14:05 Speaker 00 But in reality, I'm terrible at like accounting and math on the fly. I can't do it in my head. That has never been my skill. But when it comes to like intrinsically understanding what motivates people. I love to just have these questions of curiosity and get to know people and understand what drives them. So I know what job to give them, where to put them in a company. And that's how I spend the time in interviews. Not tell me about how you looked at XYZ company. And I just don't want to know anything that shows up on their resume.
14:34 Harry Stebbings? I think in hiring, you learn a lot from mistakes. When I look at my, I'm learning from you already. When you look at my mistakes, I always looked at the CV, went, oh, they were a tier one fund before. They are a good ambassador. Wrong. Lean land too much on CV, often a common mistake of young founders, I find. When you review your hiring mistakes, what do you think is the most prominent one? And how did you change your approach having made it?
14:59 Speaker 00 I made a lot of mistakes when building some of the functions at Square around hiring for domain knowledge. When we were building out banking and lending at Square, it was a pretty new concept. We were trying to find particular expertise in a product set that really hadn't been done before. Fundamental mistake there. And in reality, I now index away from domain knowledge than I ever did because a lot of what we're creating hasn't been done before, or you want first principles thinking. And I would rather focus on things like raw intelligence, judgment, curiosity, grit, ability to manage ambiguity, rather than looking for things like domain knowledge or operators with prior scale. That's another big mistake where you assume
15:43 Speaker 00 because someone had a lot of zeros around the output that they created at a big company, that means something. And I would rather look for people who are scrappier and have an ability to just manage an ambiguity than I would someone who's been an operator, a high-profile company at scale. I ran HR at Yahoo, and one of the observations from Yahoo, because there's an incredible diaspora at Yahoo, is that anyone who went to Yahoo was grittier than a lot of the people who worked at higher-profile companies that were just minting money. And when you came to Yahoo, you had to work a little harder. And so I find places like that are incredible places to go higher, where people might have a little bit of a chip on their shoulder, they might have to work harder, they might have to be scrappier than places where
16:28 Speaker 00 gold falls from the sky.
16:29 Harry Stebbings? I get in trouble for this, Jackie, but I sound like a real boomer. I feel like our generation is afraid to do the work. The rise of COVID means they don't want to go in in the office at all. They have Friday afternoons off, Monday mornings slower. What happened to the hard work that you did in the 90s, where you remember, what was a personal life? But you were achieving. We are afraid to do the work today.
16:52 Speaker 00 Yeah, I'm a pretty intense 24/7 kind of person. You will get emails and slacks from me at any hour, including in the middle of the nights. But I think it depends on the kind of culture you're building. You have to set up a culture where you don't build entitlements into the way That you operate. And I think that's really important from the first 20 people that you hire to lay out the foundations for the focus, the intensity and the inspiration of what you're trying to build. But you have to be pretty disciplined about your team. Weed out people who are not hitting the goals. And you, as a manager, have the honest to said goals and OKRs that drive the team forward.
17:31 Speaker 00 I had this experience in COVID in developing P and we developed P, this is at Square, in a crisis. And we ended up with a core team of people working on it. And then we literally got the entire company of Square to volunteer for us to be loan reviewers 24/7 during that period of time. And people were inspired by the mission. I'll never forget the discussions with people all over the company and how they were motivated to want to kill themselves in ways that I find incredibly inspiring. Because they knew that they were attached to the mission, they just wanted to change the world. They wanted to see outcomes that were incredible. And so people were willing to roll up their sleeves and do the work.
18:12 Harry Stebbings? I think when hiring people, often people say the best people have people who will follow them. They have a list of people they've worked with before who would join them wherever they move to. I spoke to many of our mutual friends and your old colleagues and they said, her followership is amazing. Everyone would leave wherever they are to do whatever she's doing. What do you think you do to create that loyalty and followership with the people you've worked with?
18:34 Speaker 00 First, I focus on the long game with people. I really care about their career. And it could be someone who is multiple levels down from me. I don't care. If I've built a relationship with someone and I want to help them, I will take a 20-year view of how to build their career and know that they'll show up over time. The second thing I do is I focus on them to my own detriment. And I will send people to business school. I'll send them to other companies. I will want them to go learn something, even if it gets in the way of our roadmap. I'll move them to other departments if I think it's better for their career. I genuinely believe that's the way to build that kind of followership where people trust that you have their best interests at heart. And I have so many examples of this.
19:19 Speaker 00 Where I've sent someone to business school, even though they were my best person in a particular field. And then I pay attention to true, just genuine principles of being a good human around the understanding of who they are, being honest with them, listening to them. I spend a lot of time listening to people I work with. Sometimes they just want to vent and sometimes they need a little bit of respect. Where I'll say, yeah, I got to call bullshit on you. I don't see it that way. And I think people appreciate that honesty and the relationship that drives, because I think they know that I want them to be better as a professional. And then finally, I guess I'd say I hope that I inspire people. I work hard myself. I try to do best for people. I put my heart and head into everything I do.
20:03 Speaker 00 And so hopefully that means something to people and that I'm not just phoning it in. I clean the coffee pot in our office in Sunnyvale because it's dirty. And when I see it's dirty, I'm not above it all. I could do that and then move from that to a meeting at the Federal Reserve. And I have no issues going from one end of that spectrum to the other. I might just try to do whatever needs to get done.
20:25 Harry Stebbings? You mentioned calling bullshit and being direct. I heard that you're one of the master deal makers and negotiators. What have been the biggest lessons on what successful deal making actually is?
20:36 Speaker 00 I don't think of it as a zero sum game. I think there's always ways to be creative in getting an outcome that enables both parties to feel good about something. And that doesn't mean that every point is going to be a love fest where everyone is super happy. But it means that you can make trade offs in what's absolutely the most important things to you and what can you give up? I try to focus on understanding what someone needs, truly understand what's the outcome that they need. Do they need to look good? Do they need a certain economic outcome? When do they need certain economic outcomes? And I think if you're really creative in first understanding what's driving their decision making process, it could yield a lot of optionality in what you negotiate for. I don't see things as black and white as an outcome.
21:22 Speaker 00 I think it yields good, long term relationships. And I think it yields great economic outcomes.
21:27 Harry Stebbings? What do you think many people get wrong in deals? Deal making and negotiating.
21:30 Speaker 00 Oh, they can be jerks. They think like it's their way or the highway. There's only one way to get to the right answer. And I think sometimes people overplay their hand around leverage. You may have all the leverage in the world, but you got to decide, do you need to have an operating relationship with this person? So having that negotiating leverage is only going to burn the relationship. And I think there are just so many interpersonal relationships in the way that you need to manage these things. And so I think you have to draw that into the components of the discussions you're having. I'll give you an example. I have investors. This is in Lead Bank. And I wanted these investors because I thought they'd make us more disciplined as a group of founders.
22:12 Speaker 00 And the smarter and better they were, I wanted their brain power. I wanted their advice and I wanted them to kick us in the ass. We had a lot of leverage when setting up this company because I was also willing to fund it myself. And the only reason I was taking folks was because I wanted their brain. And when we set the terms for our investing rounds, I was very comfortable letting our investors get a lot of their way on a lot of different components of the transaction because I knew I needed certain things. I needed a structure that was appropriate for a bank holding company. I needed something that was going to get us approved by the Federal Reserve. And speed mattered. That was more important to me
22:53 Speaker 00 than the last percent of economics that I could derive from our investors. And I also didn't want economics to drive the outcome of our deal. It's an upside down way of investing and bringing in investors to a round, but I knew what was important to me. And then I understood what was important to them. I was focused on something very different than them from an outcome point of view. And we were able to negotiate quite easily because I was willing to give them things that they cared about because I wasn't willing to budge on things that were going to make the long-term operations of my business more successful. I didn't want them to have terms that were going to make a bank more complicated to operate over the long duration of our business.
23:37 Speaker 00 And that's the way I negotiated it.
23:39 Harry Stebbings? On review, I'm just too interested. Which is the best deal you've ever made and what's the worst?
23:44 Speaker 00 Economically, some of the best deals I ever made were around Alibaba. And that's a situation where we had no leverage. It probably generated $50 billion worth of economics to Yahoo shareholders. This was while I was at Yahoo. I was on the board of Alibaba. Unfortunately, was a deal that was struck that was selling half of Yahoo's economics back to Alibaba at the IPO. And this is massive economics. I had the goal of trying to get some of those economics back, even though a written transaction was executed and the economics were contractually obligated to be given up at the IPO. I went on a singular mission to get equity back. And I would always say to the Yahoo board, equity is good. Equity is good. I have one goal.
24:29 Speaker 00 And so I went and worked with the Alibaba team. There were pretty bad relationships before my arrival between Yahoo and the Alibaba board and shareholders. I went to rebuild those relationships that we had a foundation for trust in order to renegotiate some of those deals. I worked really hard at that. I spent every other week in China for several years. I showed the shareholders of Alibaba that I was going to put their interests first. So that when I went to negotiate and get equity back, they trusted that I had done right by them for their business. I had let them do things that they felt I didn't have to let them do. And as a result, they were willing to give me back some of the economics on behalf of Yahoo shareholders.
25:10 Speaker 00 So the economic yield of those transactions where we had absolutely zero leverage were extraordinary. And I will forever be proud of it in order to create something out of nothing.
25:22 Harry Stebbings? Oh, Jackie, that is so cool. I'm used to like, oh, I did this, the other day. It was like Alibaba when I was at Yahoo, zero leverage. I'm like, wow, that's impressive.
25:32 Speaker 00 I was involved in dealing with a lot of the financials in managing them between Alibaba and Alipay and the banking licenses at Alipay. And as an American who grew up in Atlantic City, New Jersey, I have to say it was a pretty surreal career experience. The people at Alibaba. Alibaba are extraordinary. As I was watching what was happening in China, there was a lot to learn as an American company with regard to the velocity of invention, the creativity that they had, the way that they were able to deploy financial assets against transactional data. And I know we drew a lot of inspiration from that in what we built at Square because we had seen what was being built at Alipay with firsthand insight
26:15 Speaker 00 and were able to look at that and draw inspiration from it. It was an unusual career experience and an unusual insider's view in being able to draw experiences from Chinese financial services into US products.
26:28 Harry Stebbings? What do you think is the worst deal you've done?
26:30 Speaker 00 Oh, personal deals that I've done. In the last year, I've made some pretty disastrous trades with the changes in the financial market. I can't say that I've done best for myself, not selling quick enough. And I think people usually are great at investing and terrible at selling. And I think I'm guilty of that myself.
26:49 Harry Stebbings? I think this is the biggest lie, actually, that we permeate in venture, which is like, everyone says, oh, lean into your winners. And it's no bullshit, actually. The majority of the best returns are from strategically leaning out of your winners over time in increments and being very thoughtful and deliberate around it. But lean out is also a very successful strategy.
27:07 Speaker 00 Yeah, there's a risk. There's an entire game theory of risk management around exiting. And I think some people are incredible at it. Some people are not. And I think that drives returns in venture and private equity. And there are some folks who are absolutely incredible. Like I think Kotu is an investor of mine. And I look at Philippe Lefont, Thomas Lefont, the way that Kotu manages risk. And I am mesmerized by their ability to understand market dynamics and react to it in really smart ways. They aren't enamored by the companies that they invest in. There's a lot to be learned around watching people like that.
27:46 Harry Stebbings? What do you think they do to manage risk so well? Where are they good?
27:49 Speaker 00 I think they're great at following trends, understanding when they see breakages in the market and not being emotional about the need to sell or the need to. To make different trades. I think they have an intuition and a data science driven expertise that very few people in the world have. I see that with incredible money managers and risk managers. And I think there's a real skill around it.
28:11 Harry Stebbings? You mentioned that their ability to follow trends. We saw over the last few years, the unprecedented investing trend of obviously investing in fintech as ecosystem and space. I'm going to ask the terribly broad question of who will be the big winners and the big losers in the next 10 years of fintech thing, really unfair and broad.
28:28 Speaker 00 Yeah, fintech is an industry that's driven off of financial services as a whole. And thankfully, from a fintech point of view, most of the market cap in fintech is over 50 years old. It's incredible when you look at the industry and banking as a whole, how old it is and how concentrated it is. There's 23 trillion of assets in the banking system. The top five banks hold 41% of that. And so there's so much room for invention in fintech, starting with that level of control, centralization, and age around the financial products that drive our markets. I think about it from an industry point of view and like a subgrouping within fintech.
29:09 Speaker 00 I think we've spent the last 10 years iterating on revenue within fintech. We've been incredible at top line revenue. You could look at companies like Audi and Square, Stripe, say, wow, they have taken the idea of the inbound of a transaction and made it incredibly frictionless. They have abstracted away all of the pain associated with collecting revenue. The place where we haven't invented nearly as deeply is that around expenses. It's much harder because the fractionalization of that market is much deeper. And so I see the next 10 years of interesting companies being developed around expenses, expense management, and then infrastructure.
29:51 Harry Stebbings? What have we not done in expense management? Because as a VC, I get expense management every single day. What do you mean by the fractionalization of expense management? And where does that go?
30:00 Speaker 00 So within expense management, right now, when you want to manage your entire P and L,
30:09 Speaker 00 The components of how things get paid go out in very different ways. You track it in different ways, you pay it in different ways. You get invoices, you have to manage it differently. You have to pay out people differently. You have to pay out people in different countries. You have to pay out in different companies. You have to pay out people, again, people are in different countries, different states. And so the complexity around every component of that stack is extraordinary. And there really aren't companies that have made it easy that are operating at scale. If you think about a company like Square, all of the innovation has been around taking in the inbound transaction. Right? We've made the actual transaction at the countertop super easy. Great, that's revenue.
30:54 Speaker 00 Everything below that in how you manage your P and L is still a hot mess. There isn't an organized way to do that. You might think of accounting software, but accounting software is the tip of the iceberg on a ledger. It's not the management of are you sending out checks? Are you sending out invoices? Are you sending out credit cards? And you have the same amount inbound. And so all of that is going to get abstracted away by companies who are able to streamline how that P and L is managed from an expense point of view. That's what I mean by expense management.
31:24 Harry Stebbings? Why has that not been done? That seems like, given the size of the problem and the magnitude, an obvious problem to go after. There is incredible talent looking for it. Why has no one done that?
31:35 Speaker 00 If you think back to fintech, it's not that old of an industry. When Jack created Square was 2009. So we're in a market that is 15 years old. And so I think the first batch of invention was really around the first and easiest part to tackle around revenue. And in the last few years, companies are starting to build creativity around expense management. Melio is one of these companies that I love. Tapulti is one of these companies that I love that are really just starting to invent around that market. And then I think there's also investment around infrastructure. And you needed the infrastructure to be more sophisticated in order to really get to these underlying components that are now getting more and more sophisticated. Both of those markets are things that I think will
32:19 Speaker 00 Be really interesting in the next 10 years.
32:21 Harry Stebbings? Why do incumbents not do it? Why is Square not going, hey, we can integrate this into a future product suite?
32:27 Speaker 00 You can ask that question to every bank in the United States and in the world. Why didn't JP Morgan create Square? I think in some ways they have so much embedded infrastructure and benefits associated with the system that they run that in many cases they don't decide to disrupt themselves. And I think these companies will be incredibly disruptive to lots of incumbents who have lots of tentacles into the ecosystem of how money is paid out.
32:54 Harry Stebbings? Who will be the losers in the next 10 years?
32:56 Speaker 00 Old school infrastructure companies, large financial services companies have understood that they need to innovate. I think the question is, can they do it? And they all need to disrupt their own products and set up teams around their own disruption. And I think if you're willing to do that, they have the chance at being able to build the next stage of products that are inventive. If they decide that they just want to manage their business for cash flow, they will die a long-term death.
33:24 Harry Stebbings? Who do you think does it best?
33:26 Speaker 00 Companies like PayPal, Square, Audian and Stripe are kind of incumbents. Like you can't say that these companies at the scale they operate in aren't incumbents. And I do think you see different levels of invention at companies like Square that still manages to build many multi-billion dollar products within its own organic infrastructure, Stripe as well. And I think there's a magic to the way that they do that, that I think is very important to learn. And I think those kinds of companies will continue to innovate. I think Goldman tried to disrupt themselves, but they did it in a market that they weren't good at, which is consumer finance. They just had to restructure that business. And I think they're learning some important lessons about focusing on things and don't focus on something that you have no insight into.
34:10 Speaker 00 They're learning some tough lessons right now.
34:12 Harry Stebbings? You said like focus on something you have insight into. I always believe really in investing that defensibility is bluntly a bit of BS and that actually anyone can copy your products. And this is very specific on segments, so we'll have a caveat. But like actually bluntly, it's speed of execution, quality of thought, quality of team that determine outcome and ability. That's not actually true with banks. How do you think about bluntly the importance of defensibility? How that plays out in buying banks?
34:38 Speaker 00 So there's always room for someone to innovate on what you're doing. And if you are not disrupting yourself, someone else will. I think no matter who you are, there's always room for your product to be disruptive. I look at what's happening right now with AI and a company like Google, which I consider to be one of the most interesting scientific companies ever created. And out of the blue comes ChatGPT. Like, it's incredible. I think you always have to be willing to disrupt yourself. Two of the things I like to do that are really important in a culture of disruption is making sure that you have ICs who are well regarded. And if someone is a star and the highest performer can be an IC,
35:22 Speaker 00 you don't have to be a manager in order to be considered amazing. That's super, super important because this idea that you need to like keep growing teams in order to become more powerful in a company is like a culture killer on invention. You could have people who are incredible, who are just incredible operators in their own, and they need to be rewarded. The second thing that you need to do is to take people out of jobs that they have succeeded in and give them an idea. And if you can do that in a company and a person is rewarded for coming out of this huge job and starting over, that is incredibly powerful. Because there is this historic convention that power grows with the number of headcount
36:05 Speaker 00 that you have underneath you, and that absolutely is a cancer in a company. And so when people get rewarded for invention and creation, starting small and being entrepreneurial around teams, that is absolutely magic in a culture or company, no matter how big it is.
36:20 Harry Stebbings? I just had Toby from Shopify on the show and we had a little nice debate. He said that micromanagement is absolutely a productive way to manage teams. And actually that you are always involved in processes as a founder, that you shouldn't extrapolate yourself from. I vehemently disagreed, obviously with absolutely no credentials to back up my disbelief. Agreement, but do you agree with him on that aspect of the importance of micromanagement?
36:45 Speaker 00 I don't agree with micromanaging at all, unless there's someone who needs to be micromanaged because there's a particular performance issue. I am a believer in setting direction as a leader and that you hope that you're hiring the right people who know how to get the job done in their own way. I don't focus on the inputs of how they do it. I focus on the outputs of what gets done. I am not a micromanager, maybe to a fault. People I work with, I absolutely trust, but I like to hire certain kinds of entrepreneurial people and let them run. And so I don't ascribe to the theory of micromanagement.
37:22 Harry Stebbings? You mentioned pushing people and like in positive ways. You mentioned also earlier about taking investors that push you in positive ways. Miki asked the question before, how does the entire crypto winter affect you and how do you assess it? I thought this was a really interesting one that I wanted to give Miki credit for.
37:39 Speaker 00 Yeah, what's happening in the crypto market has been an important moment because I think it's causing everyone to step back and take, take a moment to think about what real models are in the business that are going to drive real businesses and real outcomes. What is a product of a bull market? And I think we're going to revisit on first principles, businesses that are going to change the way financial services take place. And so I think the air comes out of the balloon and you go back to first principles thinking, you go back to constraint and you get disciplined about what you're going to operate. There are some components for us as a bank that are also interesting. We understand how to assess risk in the crypto
38:24 Speaker 00 market and we have been able to onboard those crypto companies that are super high quality companies that are getting unbanked. We have benefited out of the de-risking in the market and we have been a net beneficiary of the scrutiny in crypto. And fundamentally, I'm a long-term believer that we will find use cases that have benefit over the long term. I don't think we're there yet. On any use case, frankly, that I think will have longevity in the market. But I do think the underlying technology is super important to experiment with and to explore new ways of building financial rails. I think it's worth the investment.
39:02 Harry Stebbings? I just don't understand how central banks give up fiscal and monetary controls with the rise of crypto in mainstream consumer finance. It seems completely impossible to me that they would let it become what many believe it will become because of the lack of controls around it.
39:18 Speaker 00 We're absolutely suffering in the United States as a result of that. And you have heard the leaders of the largest crypto companies call for more regulatory oversight because the place that we're in today is really challenging. You don't know whether you are going to be governed by the SEC or another regulatory body coming in and saying, oh, you can't do that. Sorry, we didn't have a rule for it, but we're going to stop you right now. And that kind of compliance doesn't work for companies that are trying to build within guardrails and rules. And so I do think regulatory clarity is probably the most important thing for the crypto industry today. And what we're seeing is the politics amongst the multiple regulatory bodies that operate
40:01 Speaker 00 in the financial services system, trying to figure out first what the genuine nature of what each of these products are, and then second, who should regulate it, and then how. I do think they let it get to a scale with no regulation, and I am eagerly looking forward to regulatory oversight that provides clarity to the industry.
40:20 Harry Stebbings? Speaking of regulators, I think one aspect where we're going to see a lot of reduction more broadly is M and A activity with, I think, increased scrutiny and regulation around a lot of potential M and A transactions. Do you think we will see this kind of consolidation wave of M and A, or we just see shutdowns and companies going bust?
40:36 Speaker 00 So I think we see it already. Companies that were funded in 2020, 2021 have done everything they can to streamline their cash flow burn, and they have used 2022 to try to achieve product market fit. They are now suffering the consequences, in many cases, of upside down cap tables. And so where you have environment Where they've raised more than their company is worth, they need to do another round that is upside down for current investors. In many cases, they will choose to pursue M and A exits and try to yield an outcome to investors that can be positive. And a positive outcome in some cases can be a shutdown, it could be a sale.
41:18 Speaker 00 But all of those yield a rationalizing of the market. And given the increase in funding that happens, I think there's a 10x increase in funding over the last few years. You will see the rationalizing of this market with companies that just haven't achieved product market fit. I know we look at a lot of M and A opportunities for Lead Bank. We love to buy some technologies that we haven't built yet. Where we can find that in companies that haven't been able to succeed, we would love to bring those founders into our company. So we're always opportunistic to look at it. And I don't think we're alone as someone who is a well-funded, highly profitable company in fintech. It's a really interesting market to be able to look at startups like that that just haven't been successful.
42:00 Harry Stebbings? No, I think you are entirely, you need to be a highly profitable company in fintech, Jackie. I don't know if you've seen most fintechs, I have done. You mentioned the increase in funding going from ventured to obviously new fintech startups. Like what trend in terms of investor hype did you go, oh no, over the last few years? Was it could be debit cards, it could be verticalization of neo banks?
42:21 Speaker 00 I do think it's really hard to build a consumer facing neo bank if you don't truly have an advantage or a use case that is differentiated. Like today debit cards are a dime a dozen. They're a table stakes for any fintech at this point. And there are only so many beautiful designs. That is a really tough business model to try to gain users, particularly after Apple changed their ad models. I think if you're solely operating in the digital ad market, you really need to have a unique product that stands out amongst your peers. And so I do think there are many where I just don't see the differentiation in the product to truly stand the time. Or their features, they're not companies.
43:04 Speaker 00 They should be integrated into other products that can help build LTV. I do think we ended up where people built companies out of features. And I think those will disappear over time.
43:15 Harry Stebbings? I see the unbundling of actually consumer banks into student banks, into immigrant centric banks, into construction worker banks. Because we all have such specific and individual needs that actually lending facilities are very different. Product expectations are very different. Service requirements are very different. And actually, for you at Lead to cater to this homogeneous group of people is so difficult. What I want is so different to what my mother wants and what my brother wants. And do we see that as a unbundling of consumer banking?
43:43 Speaker 00 I think we go through these cycles of bundling and then unbundling. You attack a horizontal, and I'll use Square as an example. Square attacked a horizontal, point of sale. It went all the way across every industry and they were going to serve customers with the same product set. And then from that grew a whole series of verticalized solutions. Shopify is one, Stripe is one, Toast is one. And you started to get verticalized products that went after the horizontals. But then you find that the verticals aren't broad enough from an LTV point of view in order to serve a market. And again, you start to go into this bundling phase where now, as you see people talking about killer apps, like we're going to have one consumer app is like many people's obsession. They're obsessed because they're trying to build LTV,
44:28 Speaker 00 particularly in a rising interest rate market where the cost of a lot of products and financial services has gotten more expensive. So you have this idea, once we get a customer in, we're going to sell them a whole series of product and build this super app. And you go through these movements of bundling and bungling across the market.
44:44 Harry Stebbings? Is the super app idea bullshit? Because I have so many founders come on the show and they're like, super app of travel expenses. Super app of, I'm like, oh, it sounds very good. Very nice.
44:54 Speaker 00 First of all, I think you have to start in a place where you have the right to have those products. Not every verticalized solution has the right to be a broad-based financial services ecosystem. And so depending on where you start, I think you'll have an easier or harder time building out multiple products that your customer base wants to use. I don't see a broad market for super apps. I think there are. A few players out there who have shown that they could build multiple use cases around their product. I got to go back to Square because I know it so well. Cash App is, to me, the most brilliant example of that. Cash App at least has shown that they have multiple verticals that people want to use with a broad-based consumer ecosystem. Nubank in Brazil is another one.
45:39 Speaker 00 Broad-based ecosystem of products that consumers want to use. I do think there are certain companies who've shown an ability to do this, but they're few and far between. And I am not betting on many of these companies starting up today from very narrow vertical solutions to be able to achieve that.
45:56 Harry Stebbings? What are the, sorry, what are the characteristics of those that enable those to versus those that don't? Is it purely David and Jack and you name the great people? Or is it the market themselves, the intricacies of them? What is it that enables those to expand versus those not to?
46:12 Speaker 00 You know, you mentioned two great founders who have incredible consumer instinct, seeing what consumers want and maniacally focusing on it and going after it. I remember in 2017, yeah, it was end of 2016 when Jack wanted to put Bitcoin into Cash App. And he, two engineers, sat on the sixth floor of 1455 Market and wouldn't leave the office until they were able to build that product. It was inspiring to watch, like he had a point of view about what the future was going to look like with Bitcoin as a part of that and the power of what that could achieve for consumers. No matter how many naysayers thought it was crazy at the time,
46:55 Speaker 00 he wasn't leaving the office, and I do mean that literally, until that product was built. I think there's a power to that kind of conviction in having a hypothesis and building back to it. One of the things I love to do is take a point of view about, okay, so what will the future look like? This is something that we did a lot of at Square. I have a hypothesis about what the future is. This is what I believe to be true. And if that is true, what does that mean today? And what does that mean that I need to build? And if you have that type of thinking embedded in your product development cycles, I think it helps. You add conviction and execution to creative ideas around how you see the future unfolding. Super important to do. You could live in a world where you're shoda koda wada,
47:40 Speaker 00 or you take those ideas and you actually put execution resources against them.
47:45 Harry Stebbings? Very upset that I never got to invest, Jackie. But anyway, I had absolutely fine. Listen, I could talk to you all day. I would love to move into a quickfire answer. I say a short statement, you give me your immediate thoughts. Does that sound okay?
47:56 Speaker 00 Yeah, that sounds great.
47:57 Harry Stebbings? What's your biggest regret?
47:59 Speaker 00 I don't really have any regrets, to be honest. I look at everything I did wrong as a learning experience. I just look at it as a battle scar. I could regret stupid things that I've done, like I can remember stupid things I did over my career where I'm embarrassed about my own behavior. I pissed someone off, I said something dumb, I really did something misguided. I think they're all really minor in the grand scheme of a life. You have to look at the totality of your behavior and just make sure you get better every year. There are so many things I've done with my kids that I regret, but like fundamentally, do I believe I'm a good parent? Yes.
48:37 Harry Stebbings? What have you changed your mind on in the last 12 months?
48:40 Speaker 00 I've changed my mind on my willingness to try psychedelic drugs. I am so squeaky clean. I think my biggest vice is my obsession with carbohydrates. And I read Michael Pollan's book and I am truly inspired by his exploration of psychedelic drugs. And I have not gotten up the courage to really go out there in the way that he did, but I really would like to. Like I look at what's happening with PTSD, with veterans, with people who have depression. And I really want to learn more. And as I said, I'm always someone who wants to learn and do something that's new. And that is something that I would really like to try. And because I've lived in a very constrained, controlled way,
49:25 Speaker 00 and not intentionally, but I have, I'm like a Girl Scout. That's the one area of my life that I really would like to explore.
49:32 Harry Stebbings? Jackie, I'm with you. I'm, I've never tried any form of drugs ever. And I'm, everyone's like, oh, it's great, the creativity, it's better for you than. And cigarettes. I'm like, oh, mom would still kill me. Not that I'm not a mature adult, obviously. Tell me crypto does more harm to income inequality than help. Agree or disagree?
49:49 Speaker 00 I don't think we've seen any use case where it has benefited or created a detriment for income inequality. Today, the use case that you've seen most prevalent is that around investment speculation. I have yet to see it really move the needle for societies, even in places like El Salvador, where you've seen governments adopt it as a currency. It really has not created an environment where it is used day in, day out as a core tender type. And I think what crypto means is that around access. And I do think access will create dynamics where it will reduce the number of underbanked people around the world. But access can be created in lots of different ways, even outside of the crypto market.
50:34 Harry Stebbings? December 2024, will we be in a better or worse place, kind of fraternally?
50:39 Speaker 00 By the end of 2024, I think we'll be in a better place. We're in a bit of a market of volatility and uncertainty because we have this tail of inflation that has really plagued us for the last few years. And the Federal Reserve trying to control that with a dramatically different raise in interest rates and the way that they have ever done. The slope of the interest rate raise has been extraordinary. And interestingly, we are at a 50-year mark on unemployment. And so there's this odd moment of uncertainty where Larry Summers predicted that you needed to have unemployment being at a 5% or 6% for a persistent number of years
51:23 Speaker 00 in order to bring down inflation. Yet we're at this weird inflection point in the market where that's not happening, yet inflation is coming down. So I think 2023, we're still suffering through the uncertainty about whether there's going to be a recession, how deep that recession will be. And once we get the uncertainty out of the market of the next two quarters around unemployment, around inflation levels, I think that will start to create a more even market. That there's less uncertainty out there for players in the market.
51:53 Harry Stebbings? My management styles, I ask incredibly smart people, are you worried? If you're worried, I'm worried. If you're not worried, I'm not worried. Are you worried?
52:00 Speaker 00 I am not worried about this state of the economy today. Unemployment is an incredibly successful marker today to watch. And we still have such strong numbers that underpins the success of the economy. There are notes in the market that show weakness. It could be total credit card balances. It could be savings rate levels. It could be auto defaults and things that are starting to mark more debt. But I don't see widespread fear in the same way that I did a year ago when we were sitting last December, that I actually was truly worried about the state of the market because of the signals around inflation. When the Fed was signaling that inflation was going to be temporary,
52:43 Speaker 00 I think you had to sit there and look at what was going on in the economy and just scratch your head. I feel like, really? I don't know how that could be, but I think we're in a much better place today.
52:51 Harry Stebbings? The ultimate one, what's your biggest lesson from working with Jack for many years?
52:55 Speaker 00 What I took away from Jack was the power of listening. He is the most extraordinary listener I've ever seen. And he can sit through meetings and just listen and then synthesize in his own way what he heard or his own point of view in such a simple and powerful way. And I really appreciated that. I think he also has such dignity in the way that he operates. I find it so impressive, the way he treats people, even that he disagrees with. I think he's a truly remarkable person and I will always be inspired by how he lives his life, what he's built, and I love spending time with him.
53:33 Harry Stebbings? The final one, 2028, me and you sit down for another conversation. Where are you then and where do you want Lead Bank to be then?
53:41 Speaker 00 I think Lead Bank will be one of the biggest innovators in fintech infrastructure in the world. And I'm excited about what we're building across banking products. I'm excited about the customers that we work with. They are A++ players in the fintech and crypto market. I think we're going to continue to change the way banking is operated in the United States. I'd love to be multi-country. I'd love to be deep in compliance products, even beyond core banking products, so that people could come to us for a full slate of banking services that when they want to onboard into the banking system in multiple countries, they could come to us and have it be really easy and know that they are
54:23 Speaker 00 working with a partner who will help them build at scale in a way that is existentially safe and sound for their business.
54:32 Harry Stebbings? Jackie, 20VC clearly lost my naming with this show. I so love doing this. Thank you so much for putting up with so many of my off-schedule questions. You've been amazing. So huge thank you, Jackie.
54:43 Speaker 00 Oh, thank you. Thank you. I'm so happy to be here.
54:48 Harry Stebbings? I just loved that with Jackie. What a fantastic conversation. If you want to see more from us, of course, you can on YouTube by searching for 20VC or heading over to 20vc.com. But before we leave you today, you've heard me talk about how Coda is the doc that brings it all together and how it can help your team run smoother and be more efficient. I know this because Coda helps me and 20VC. So much prep goes into each episode of 20VC with 10 references for each guest. And with Coda, multiple of my team members can work together on the research, find commonalities, differences, comment on each other's work, and just be so much more efficient. And so by putting all of their work in one centralized location, regardless of the format, Coda eliminates roadblocks that can stop your team in their tracks. So with Coda, you'll never ask, where
55:33 Harry Stebbings? are the latest project updates? Anyone know where the performance stats are? This is what slows down productivity and collaboration. And with Coda, your team can operate on the same information and collaborate in one place to get projects across the finish line faster. Help your team run more smoothly, more efficiently with Coda. Get started today for free. Head over to coda.io/20vc. That's coda.io and get started for free. Coda.io/20vc. And speaking of tools we cannot live without, you probably know Brax. Brax was the first corporate card for startups, but Brax has grown a lot since then to scale up right along With its customers. Now 90% of Y Combinator grads trust Brex as their all-in-one financial stack.
56:15 Harry Stebbings? I get to speak to founders all day and I know how important having the right financial stack is to their success. With Brex, you get fast access to high-yield business accounts, high-limit cards, and rewards like cash back and billboards to fuel your growth. Beyond that, Brex has the venture debt, financial modeling, and spend management solutions you need to run your startup globally and well. So are you ready to make your future CFO proud? Learn more at brex.com/20vc. That's brex.com/20vc. And finally, if coder and Brex make your team work more efficiently, Intercom makes modern customer service software that really redefines how businesses support their customers.
56:57 Harry Stebbings? And their platform connects businesses directly to customers using powerful messaging and automation. Intercom enables teams to scale support without investing more resources, leading to happier customers and more efficient support teams. And Intercom is used to send over 500 million messages per month and enables interactions with over 600 million monthly active end users, trusted by customer service teams at more than 25,000 global organizations, including Atlassian, Amazon, and Lyft Business. Check out this amazing offer. Eligible startups get advanced Intercom features at a 95% discount. So do not miss out. Head over to intercom.com/20vc to find out more.
57:41 Harry Stebbings? As always, I so appreciate all your support and I can't wait to bring you an incredible episode with Toby and Shopify on Monday.
Previous 20Product: Nubank's CPO on Why Product is 90% Science and 10% Art, Why Execution is Overrated and Strategic Clarity is Under-Appreciated, Why You Should Never Fall in Love With Your Own Ideas & Nubank's Biggest Product Challenges Scaling to 80M Users Next 20VC: Shopify Founder Tobi Lütke on Why Micromanagement is Good | Why You Will Learn More From Studying World of Warcraft Guilds Than You Will Companies | Why Happiness is BS; Lessons on Marriage, Fatherhood & Decision-Making Quality Page updated September 29, 2026 · transcript and summary are machine-generated
