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Invest Like the Best with Patrick O'Shaughnessy
William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]
01:10:50
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Most software companies try to maximize your time on their app to juice engagement. Ramp does the exact opposite. Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports and checking for policy violations. So they built their tools to give that time back, using AI to automate 85% of expense reviews with 99% accuracy. And since Ramp saves companies 5%, it's no wonder that Shopify runs on Ramp, Stripe runs on Ramp, and my business does too. To see what happens when you eliminate the busy work, check out ramp.com invest Every investor should know about Rogo, because Rogo AI's platform is not just another generic chatbot. Instead, it was designed to support how Wall street bankers and investors actually work, from sourcing diligence and modeling to turning analysis into deliverables. For me, three key things differentiate Rogo first, it connects directly to your system so it can work with your actual data. Second, it understands your workflows, how work really happens across a deal or an investment. And third, it runs end to end and produces real outputs the way the best people do auditable spreadsheets, investment memos, diligence materials, and slide decks that match your standards. This all comes from the fact that Rogo is built by finance professionals for finance professionals, and it's already being adopted by some of the most demanding institutions in the world. To learn more, visit rogo AI/invest, OpenAI cursor, anthropic, perplexity and Vercel all have something in common. They all use Work os and here's why. To achieve enterprise adoption at scale, you have to deliver on core capabilities like sso, scim, RBAC and audit logs. That's where Work OS comes in. Instead of spending months building these mission critical capabilities yourself, you can just use Work OS APIs to gain all of them on day zero. That's why so many of the top AI teams you hear about already run on WorkOS. Work OS is the fastest way to become enterprise ready and stay focused on what matters most, your product. Visit workos.com to get started. Hello and welcome everyone. I'm Patrick O' Shaughnessy and this is Invest. Like the Best, this show is an open ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in depth profiles of the people shaping business and investing. You can find Colossus along with all of our podcasts@colossus.com Patrick O' Shaughnessy is
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the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit Psum VC My
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guest today is William Hockey, the founder of Column. William was also the co founder of Plaid, one of the more famous fintech businesses from the last decade. Column is his second business, which he's built from scratch and funding it entirely himself and building it his way. I think you will find this conversation utterly fascinating, not just because of the incredible quality of the business that he's built, but how maniacal he is about studying and implementing ideas in this specific field. This is a great example of a founder that is winning because he is willing to do everything. My favorite example from our conversation today is that he went and found some obscure book about some ancient bank and found one idea buried in the 2,000 pages that gave him a simple idea for his product. He's willing to do that over and over again and he explains his very different, maybe even heretical views on a lot of what's happening in the world of startups and technology today. He offers a very different way of building that I think will be inspiring and interesting to those that want to build a company. Please enjoy my conversation with William Hockey. Usually I don't start with a description of the company that someone's building, but in your case one I don't think a lot of people are yet familiar with Column and I want to fix that. And it's such an interesting beast in and of itself that it'll be our excuse to talk about many fascinating things in the world. Can you just start by explaining what the business is and does at a high level?
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We are a software company that also owns a bank and what we do is we say, okay, we have this interesting regulatory mode. We have a bank that most other people don't have, and we're going to build just incredible software behind it that nobody else can build because they're not a bank. We started out by serving a lot of software companies that want to get into financial services in the us so with a backend infrastructure that powers the payments, deposits, credit of amazing companies like Bilt, Wise, Ramp, Brex, Mercury, these type of companies, they run on our software than our regulatory rails. Then we also expand that to anybody want to do things with the global dollar. So that could be international fintechs that could be a lot of times global banks or banks in emerging markets that need to transact hold things in the dollar. So in the US you have vertical software people building business software. This is an area that is probably going to get changed as AI kind of rolls through. So people need to go deeper down into the business. Just building software for software's sake is not the case. And so now people actually need to control the underlying finances of business. The Brex ramps of the world have proven that you can actually build enterprise software that also touches the money. But in order to do that, you actually have to control the dollar. You have to control the money whether it be lending money, holding credit, et cetera. And so we just expose a set of primitives and APIs to allow anybody to do that super easily.
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Could you maybe like pick a customer that people might recognize and describe literally what services or products they use and then how they pay you for those products or services? Just really nail it home.
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So maybe I'll use a company out here, that recently relaunched company called Bilt, which is a lot of New Yorkers have, a lot of people in cities have. If you look at the card in the back, it says issued by column. And so we're the one that is actually connecting with the networks, managing the networks and we're actually the regulated entity behind that. And then when you need to go pay your rent or your landlord is going to detect money from your built account, if you look at like oh, the account routing number there. Oh, that's actually a column account routing number. So they build the application, they build the website, they build the consumer marketing. And we're going to handle everything behind the scenes that has to deal with the Federal Reserve or TCH or the card networks or Swift. We're the ones that kind of build the software for that and handle all that complexity. We are technically a bank, but unlike banks, we make 90 plus percent of our money off of software. And so similar to any SaaS company, it's a per API call, it's a pure play tech business. And then we pass most of the economics from the actual bank side of the business down to all of our customers.
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One of the things I love whenever we talk is you've always been somewhere strange and interesting. Kinshasa, I think was the last time we were together.
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I don't know.
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A lot of founders go to Kinshasa very often. Why are you so often in interesting bizarre locales around the world?
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So this is my second company. I started Plaid back in 2012. And it's very easy to stay in Silicon Valley. Quality of life is amazing. There's a lot of money to be had, there's a lot of super smart people. But you can start to get quite isolated and you can start to get very consensus focused. Probably a lot of your listeners read Dan Wang's last letter on China. He has this great and I think accurate, but somewhat harsh criticism where he says the two most consensus societies he's ever been to is San Francisco and Beijing. And I think that's quite accurate, actually. Where San Francisco is probably the most consensus place I've ever been to. And I think that is both a huge clutch for us, but it's also probably our most valuable asset because as a founder, if you're building an AI or like stablecoins or something that San Francisco believes is very consensus but the world does not believe yet, that's actually a great operating environment because you can go and you can have these outlandish ideas that other people are going to believe in that nobody across the world will believe in. And you can build this in a very safe way. And that's why Silicon Valley in San Francisco is so dynamic and we're so up front of the curve. But. But we also have completely lost touch with how the rest of the world operates or everyday American operates. And you've probably seen this smack us in the face over the past decade or two. And so I think it's very important to go to places that don't have that same bias. And I think if you think about emerging markets, specifically the founders who build there, there's the everyday people, they live in this constrained society. They're constrained in a way that like San Francisco and New York isn't. And that breeds a different type of creativity. It breeds a different type of innovation that you really can't get anywhere else. If you go to talk to people in London or Vienna or Mexico City or San Francisco or whatever, people are living to an extent in a world of abundance. And that causes a very specific creation cycle. Why? If you go to Kinsasha, which is a capital, Democratic Republic of Congo, it's going to be the largest city in the world, then in probably five to 10 years, I think it's already larger than most of the megacities. Wow. Probably 95% of people in Silicon Valley couldn't tell you what constraint is a capital of. But tens of millions of people that live in a highly, highly constrained society. And so that breeds a sense of creativity, that breeds ideas, that breeds stuff that you can't really get anywhere else outside of emerging markets. So that's one, I think second for my business. The dollar is fundamentally global and the dollar tends to be strongest in places that one could imagine are relatively dollarized. But places that are dollarized tend to be more emerging markets where they are using the dollar as their main currency, either unofficially or officially, because maybe they can't trust their central bank, maybe they have a history of super bad inflation and the country got implicitly dollarized. And so those places tend to actually need US financial services more than, I don't know, UK and the GBP is pretty strong. Or France. Those places don't need American financial services as much as maybe some parts of the emerging world do.
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So sticking with Kinshasa as an example, so you go there, what are you doing there? What are you discovering? Say more about the constraints you encounter there. Teach us a bit about. I've never been to Kinshasa.
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They operate in a world where there's actually like relatively large markets. Zrc, that's an example, is one of the largest exporters, not the largest exporter of some critical minerals in the world. So there is a lot of money flowing through there. It's a massive exporter. It's a place where there's a lot of Chinese investment. Africa broadly has had more Chinese investment than anywhere else in the world outside of Pakistan. And so there is money and there's a lot of people doing things. And the population growth is absolutely bananas. I mean the population growth in Africa is probably larger than Western Europe, North America and parts of Asia combined. And so why they may be GDP per capita quite small. There's still a lot of going on where there is. There are founders that are building super cool things. The large companies actually tend to be quite innovative. And I can talk about that in a second. I talk to them, I meet a ton of people. I'm meeting CEOs of largest multinational companies there. I'm meeting founders on the ground and I'm talking them through, like, what are you building? What is your perception of America? What is your perception of American financial services? How can we be helpful? Honestly, I spent a lot of my time walking around, ideating, just taking in the scenes. And sometimes quarter of the time I come up with a really interesting idea that ends up building us a cool product. Or is it a good market?
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What's an example of that?
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I've had 90% of my ideas either in the shower or like walking around random emerging markets, country. It kind of expands your senses a Little bit. If I'm walking down the Marina Green, I'm walking through the Mission in San Francisco. The only thing I'm thinking about is, oh my gosh, how is AI going to change things? Because you can't walk around San Francisco and just not get like completely hit with AI FOMO 24. 7. But there's other stuff we need to do in order to get people up to like, mobile penetration. Take DRC. Like, mobile phone penetration is still less than 25%. Banking penetration is still less than 5%. There's stuff we need to do before we think about embedding LLM in everybody's brain.
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If that penetration is that low, will you and your business naturally benefit from that going up based on the products that you're building? Is that how you think about some of these opportunities where it's much lower hanging and just no one's paying attention?
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The leapfrogging that happened in Asia is obviously quite well known. Trying to skip the laptop went straight to the mobile phone. Most famously, we shipped, you know, online E commerce and went straight to social commerce in China. There's going to be leapfrogging as well. And you're going to see the same thing in financial services. Financial services tend to be most innovative and most progressive in their worst countries. You can see this in Argentina, you can see this in Iran, you can see this in other places. The Iranian financial system, say what you will, it's complicated. They have to deal with a lot of incredible constraints and thus they've built a lot of bespoke stuff just for themselves because they do not have access to global financial markets. And when you get to design things from scratch, you end up actually building things a little bit differently. And that's actually quite interesting. If you look at these emerging markets, Africa, for example, they were the first ones to do mobile payments and M Pesa decades ago, well before Venmo. If you talk to them, they are actually quite a bit more open. They are used to this. Their category being somewhat disrupted. An interesting thing is they have a bit of an access to differentiated capital, which is differentiated talent. If you're in the U.S. pardon the banks that I should on here, but you do not have access to the top talent. The top talents go into anthropic. They're going to Google, et cetera. But if you believe that brains are distributed equally, you are Congress. Some proportion of equally smart people as there are in France, there's no anthropic to go to. They don't have the ability to move to London and go to DeepMind. But there's still like a pretty decent talent pool there. They're going to go to where there is job safety and where there is money. That tends to be in a lot of emerging markets like the breweries and the banks. That's where the money is. And so the talent I'd say at the middle level and top can actually be quite a bit higher than people. Then I'd say you take you like emerging markets, bank executive team, their hands down is way better than I think probably what you see in the western world. They also have the ability to verticalize much better than they do in the US because we already have amazing software, amazing retail experiences down the entire stack. In most emerging markets or in developed countries everybody has a bank account. A lot of the people who have a phone have a bank account so they can actually cross sell there effectively. You and I talked about this before but I think one of the most interesting companies out there is Caspi in Kazakhstan.
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Fascinating. Can you explain it?
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They started out by buying a bank and then they just built, did everything, did everything. The largest E commerce company, the largest bank. You pay your taxes on Caspi. You don't like renew your driver's license, it's on Caspi. Because what they realize is where people start is people, okay maybe people start in social media but they also start in financial services. And so if we acquire financial services we can cross sell and we can distribute products there. The largest bank in Congo's bank called RAR bank, highly sophisticated, download the mobile app, it's way better than we have here in the US you can upgrade your TV subscription on it. Imagine JP Morgan doing that or bank of America doing that, or Wells Fargo doing that or Candle even like US Fintechs doing that. Even if they could build that, there's no market for that. And so their ability to land and expand is fundamentally different. And you know the good thing for us is in all these countries the main currency is a dollar. And so our ability to kind of innovate with them is much more akin to what a fintech looks like in the US than maybe a large traditional
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bank do you end up earning similar amounts of revenue from outside the US as you do inside because of these potential relationships.
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The US market is so good and fintech is so developed. One of our theses is fintech is probably going to be like the last E area that is somewhat maybe disrupted by AI. I think what you'll see is you'll see a collapse in domestic fintech. And enterprise software. And you're already seeing this with the rams and stuff of the world as they go deeper into the workflow management side. Good thing for us some of our customers are growing just so quickly, but the rest of the world is also. It's a big part of our revenue. It's something that we're super excited about as well. It could be both, like Western Europe or emerging markets.
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Can you say more about this comment that the Silicon Valley along with Beijing is the most consensus place? Because you traips around California, what strikes you as the strangest? Like you're building something so different, you spend so much more of your time away from there, you're able to get outside perspective. Despite being of that place originally, what would you say stands out as the strangest elements of it and its culture today?
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I'm a product of Silicon Valley. I've been there since I was 21, started some of the top companies in Silicon Valley. I am a product of that. But I think as you get older and as you travel more, you think you have the ability to probably look back and be more retrospective on the society you grew up in. And SF and Silicon Valley, it's an elite dominated society, whether we like it or not. It's probably more akin to Wall street in the 1990s than it is to what we want it to be, which is research lab in Cambridge in like the 1950s, maybe that was Silicon Valley in the 90s, but it's not anymore. And what that happens is elites end up building software for elites. And I think that has somewhat made sense because if you look at consumer buying patterns, people buy something that's aspirational and then it moves down market. But when you do that, you can start to drink your own Kool Aid a little bit too much. And I think that has probably happened in Silicon Valley because we talk to each other, we build for each other, and we think that the market is each other, but we don't actually look broader than that. And the companies that figure that out, they do really well. If you look at AI, our research labs are doing fantastic because that's a consensus oriented problem. If you take a bunch of people that are super smart and you pretty much lined off everything from you, and you can all talk and you can all share ideas and that's like a fantastic research place. And we are going to win on that alone. But as you think about applicability to people's everyday lives, people in Silicon Valley don't live everybody else's lives. They don't live the lives of like Americans. They don't live the lives of like other people outside the world. And so our ability to actually build software or have ideas or perspectives that resonate is probably the low point in the entire time I've been here. Silicon Valley is not a popular place. I think we tend to forget that we think we're on the top of the world. But I don't know what our approval ratings are, but I think they're probably pretty dang low. And I think that's for good reason. I think it's something that I at least try to focus on a lot because I have to build software and I have to build products that are applicable to outside the walls of San Francisco, New York. But that's probably less than less the case.
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I started Plaid and I did the standard Silicon Valley playbook. You have to like id. You have to build stuff and then Put a deck together and you go to like these 80 venture capital firms and hopefully one of them gives you money. And then every year you move up the Alphabet. And I think that worked. And Plaza, a very successful company. I'm very lucky to have started it. But the things that Silicon Valley sometimes gets confused by is okay, either like a venture funded company and if that's the case, you're like ambitious and you're going to build amazing software and you can like these like amazing products, or you're like a bootstrapper and you're going to like thought pieces on Twitter, but you're going to subscale people and you're going to grow small amounts. It's going to be like a cute lifestyle business. And I think you can actually be highly ambitious and you can hire like the world's best talent. You can build like a massive doubling company without actually being able to be addicted to venture money. What we do is we say, okay, we are going to grow by our earnings. We're going to make sure that 100% of employees and myself own the company for the foreseeable future. It makes it a lot harder. It does definitely put some constraints on your business, but not only for the net worth of myself and my employees, but also culturally it's actually quite a bit more effective because being long termism is probably a little like a trite saying, but I think it does actually help us do that. Yes, Silicon Valley companies are probably more long term oriented than your average business in the us But I think the hamster wheel of VC doesn't actually allow us to be long term because if you are having to spend a lot of money for employees and you're burning a rate of you have to raise every year, year and a half, you end up optimizing for that next fundraiser and you say, okay, stablecoins are like cool this year, so I need a StableCoin strategy. Okay, AI is cool this year because I need an AI strategy. And so your business, maybe it's going the general direction, but it's definitely taken a pretty windy way to get there because you need capital. And so I think it's very rational what you are doing, but that's not going to be the straightest line to your goal. I sometimes make this joke like VC money is kind of heroin feels good, it's amazing. But like you gotta keep shooting up. It gets very challenging at all. I know very few people that have like tried heroin once. Yeah, like once. And they're like, wow, that was awesome. I'm off right? It's like how many people you know have like raised like a hundred million dollars Series A and then they're like I'm done, it just doesn't happen. And I kind of think that man, you raise a hundred million dollars, you should be able to build a couple billion dollar business after that. Why do you need to keep raising it? And there's a lot of structural reasons for that. And the fact that San Francisco is a bit like a factory, like is by design, I think it can be like quite effective. But, but I think for the, the ambitious founder, I actually don't think it's the right thing. And for us I can invest in things that I think are going to have like a 10 year payback. I'm totally fine with it. If we grow 80% versus 110% then it doesn't really matter that much as long as we're profitable as we're building the software we want. And as long as we're growing at the rate that we want, I just don't have the same constraints. And that is I think freeing in a way that most companies can't operate.
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What's an example of something that you've done or made a long term investment in that you think you wouldn't have done if you had been venture backed?
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We bought a regulated bank when we were early, that's probably like a little bit cooler now in this new administration. But we bought a regulated bank during the first Biden administration and that required us not grow or like not focus on revenue for two, three years and do a bunch of stuff that inherently didn't scale. Buying a bank is not a software defined problem. That's not like a great use of venture capital dollars that you expect to grow A relatively non consensus bet at the time. There's just no way that could have happened. There's no way somebody would have been like oh we want to buy, right? We want you to do stablecoins, we want to do AI. That's just not a fundable bang. So I think and then able to just invest behind that for a multi year period before we actually take on clients. People think they're long term focus, but it's just not. I think we're able to weird stuff with employees that doesn't scale like what we pay employees, like here's $2,000 a month to go to your rent or mortgage if you live two miles of the office. Well like that doesn't inherently scale but it's massive because now I can get people who Live close to the office. They feel great because they're getting like a huge part of all of their housing stipend in San Francisco subsidized. But like is that going to be a good use of venture capital? Probably not. So we can just do all this stuff from an employee perspective, from a retention perspective. What we do every single year, we take 25% of our earnings and we just buy back our shares with employees. So we just run our own tender every single year. It's been great for retention. Able to actually get liquidity to employees when they need it. And it allows people to believe that we're like in this venture grand business. But if you're in a VC business, you're like, hey, you should be using like 100% of that money for growth. We say, well actually we don't necessarily think that we're quite profitable so we can afford it, so we can invest in growth, but we can also invest in employees.
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That's a really good example. So maybe just to pull it apart a bit more, are you granting equity to people in a similar way that a normal startup would? Investing over some period of time and then just every year saying we'll buy back some portion of that to provide. That's how it works. Literally.
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Structurally we look exactly the same as like a high growth startup, right? We grow up to the same people, we have all the same perks, if not more so. We operate very much like a high growth Silicon Valley startup. We happen just also be like quite profitable. What I tell people is our profits every year. Imagine that's like our funding round each year, like on January 1st, we raise a massive round each year. That's how we view it. There's part of it that's going to be used as like a tender that we're going to buy back company shares and the rest of it we're going to put to growth. Oh, by the way, you also haven't diluted at all. By the way, you also don't have any prep stack. By the way, like we get to make our own decisions. That's super compelling. So I can hire someone to say over a 10 year period you're not going to be diluted. I think what some people forget is if you're early stage founder, you're going to lose probably 50 to 75% of your equity value due to dilution alone. You may lose 10 to 15, 80% of your upside by the preference stack. These are like weird economic things that people don't really understand until they've Been doing this for like 5, 6, 7, 8, 9, 10 years or seen an exit. Like with us, we say, hey, just don't worry about that stuff. What I give you is what you're going to have. And by the way, you have liquidity on a yearly basis going forward. That's like super compelling to people.
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How have you honed the communication of that idea to a new employee so that they get it? Because I think so often people just say, oh, I got this many shares and this is the valuation and if it goes to this valuation I can just do the math. But that's not actually the math of what they'll take come. How do you frame it to people?
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We're far from perfect. I think one of the things we do is we target people that this is their second company. We are probably not the best place for a new grad to land because new grad to land, they're going to go through this calculation of where are all of my friends going? What is the number one company on hacker news? I read all the time. What's all like the thought fluencers talking about on Twitter? It's like actually like not a bad strategy. Like if you're a new grad, that's probably relatively fair, but you aren't really going to be thinking about some of this kind of nuance and it's honestly not as hard as you think. It's actually like quite refreshing. We go to people and we're like, hey, we like are super fast growing but we provide you liquidity. Oh, by the way, here's some very basic math on preference and dilution and here's why you can actually make way more money for the same equity value. It's a hard story for 21 year old. It's actually a pretty easy story for a 25 year old that's been through six rounds and four pivots at their previous company and don't have anything to show for it.
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Does this empirically show up in employee retention numbers versus Silicon Valley norms?
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We have almost close to no regretted attrition, which means people that we like to stay end up staying. There's a couple reasons for that I think. One is second time around it's a lot easier. I think I learned from a lot of mistakes at Plaid and I know where to spend time and where not to. And so I think generally it's probably a more mature company than your average Silicon Valley startup. And so I think a that helpful. We're probably better at picking talent but also I think we Know what matters to people? I think sometimes as like founders or VCs, we think that people join companies because they want to become billionaires. Maybe that's true up to a point, but a majority of people join companies because they hit into like their late 20s or the early 30s. And like what are they optimizing for? I want to send my kids like a good school and private school. I want to not live with roommates and like a one bedroom apartment up until like I'm 35. How is it in education? That's super important. You can't feed that on illiquid stock. So how do you think about optimizing for that? Basic things like team culture, all that stuff. Like people want to work for somebody who feels like they are taken care of. Not just a 20 year period where like, here's your path to being a Deca millionaire. Do they understand my short term needs? Can you take care of me in the short, medium and long term? And I think sometimes we are maybe too long term oriented sometimes, hey, yes, of course, come with me, we'll work on this for 20 years and you're going to be a decimal after that. That resonates with a certain type of person, but it doesn't resonate with everybody. And so building a company, building a culture that actually optimizes for every single point of an employee's journey, an employee's life that's actually quite unique and that actually can lead to really good numbers.
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How much of this was just possible because you were already rich at the start and had money to fund something like this? Is this portable advice? Could someone else that hadn't had the experience you had with plaid do something like this without taking outside money?
- [28:57]
B
I think it's hard. I think it was definitely successful at first. But what I would say is, without kind of going too much details, yes, I started a very large company. I think I was probably less liquid and less rich than probably everybody thought at the time. When I started this plaza, funny story, we attempted to sell it to visa for $5 billion. And that's the point. When I left to go start something, it didn't go through. We got blocked by the doj and I did not sell my company. Thus I did not have any money. And so my liquidity versus paper wealth was pretty extreme. And so I think I got a lot of credibility from people being like, oh, this guy's like, he's. For this guy to say, yeah, easy, yeah. But I did not have any money. Is that kind of going too much of the details of it, like I pretty much funded the entire company with debt, went to a bunch of banks and I said, here's a bunch of plaid shares, please give me money. And the best I got was like a SOFR plus 10% loan at 5% LTV. And so I pledged over a billion dollars of stock to get 70 million. Wow. And I bought the bank for 70 million. I haven't had a lot of money in my bank account for a long period of time. And yes, and I ended up, business became profitable. I got to pay off that loan a period of time. But in the process I probably got margin called three times and almost went bankrupt multiple times.
- [30:06]
A
Talk about that stress. Let us in the room. I mean the first three years were
- [30:09]
B
definitely the most stress in my life because I had a fundamental thesis that we could pull this off and we could build a business that 100% of employees and my cell phone. But to do that in a world where you need to invest and not make money for multiple years is very, very challenging. And at the regulatory climate at the time and the building, it was intense. And I have this loan I have to pay off. It was probably the most intense period of my life. And as a founder, you have to shelter that from everybody. You need to be transparent. You need to bring people in, but you also need to like not bring people all the ways in. I had pretty extreme conviction myself and I thought I knew a hundred percent over a multi decade period. I can pull this off. But there's that quasic quote of markets can stay irrational longer than you can stay solvent. And it's true. And I look at that quote and I'm like, which side of that equation am I on in my day? And we ended up making it through and I got an amazing place now we have a big company that I own. But I think the idea of like, oh like you know, billionaire buys thing and still funds it, it's probably a little further from the truth than people think.
- [31:11]
A
What's it like getting margin called? What is the literal thing happening? How do you manage through that surface
- [31:16]
B
to say you owe bank a million dollars, they owe you, you owe bank a billion dollars like you own them. Like I think that's a little bit same is true. I mean there's a reason that like margin lending in private companies is not a great business. Because when you want to take collateral that stock, that's usually the exact time when you do not want to hold that private stock. I have like immense appreciation for the people that did it for Me, I'm not quite sure they got like a great deal out of it, and I'm not quite sure I would definitely be in that business.
- [31:44]
A
The reason I feel the story is important to tell is that it's these things where so much of the value gets created. The extreme entrepreneurial risks, the act itself, but also the psychology behind it. And I'd love you to just riff one bit more what the psychology was like and how your mind is different after that three year experience than it was before. Even though I know you'd already been through the entrepreneurial wringer with Plaid. What changed about your mind, your perspective on the world? How did that experience affect you?
- [32:12]
B
I think that the good founders bet on themselves and take an extreme amount of risk to do that. And I think the extreme amount of risk part is something that we no longer have. But when there's literally only one door in front of you, you don't have a choice. You have to go in. And that fear and that innate desire creates, that's another part of you. It creates creativity, it creates inspiration. It's extremely valuable part of the founder journey. And in many ways, I think in Silicon Valley, we've actually removed that. Do you think about most founders these days? I talk all the time like, hey, you talk to a 23 year old. I'm like, you know what? I'm thinking about going to be like the 12th employee at this company or starting a company for myself. And I don't know, I'm kind of like mixed. And we've created this incredible environment in Silicon Valley that it's really safe to start a company. And there's like a playbook. And you go through YC and assuming you're moderately competent and went to the right high school and college, you're going to get like a $3 million seed round. And worst case scenario, you can go work at a great company as an engineer. You'll have a founder on your resume. Life is good. And that has created a lot of value, but I'm not quite sure it's created a lot of great founders and a lot of great companies, because there is no risk in that proposition. And if you go back to even pre 2008 or something like that, you're on the edge of the knife. And I think that creates just so much intensity and creativity and fear. That is such a critical part of the founder journey. And I don't know why we don't talk about it more. We don't create environments where a founder has to bet themselves. And I Think if we did that, I think we'd actually be in a slightly different place. I always am somewhat perplexed by I'm a second time founder, but I'm not alone. Like there's a lot of great founders I shall not name that you know, have made a bunch of money. And you go dig in, they're like, oh, here's my second company, the third company. And you dig into that of the a hundred million dollars they've made, they're putting like a million dollars of the capital risk and they've raised $500 million. And I'm always like, why? If you believe in this so much, if you're going to dedicate your life to it, why the fuck aren't you going all in? And if I'm an employee, I look at them, I'm like you asking me to go all in. But you can't go on. Because the weird thing is an early stage employee takes way more risk than early stage founder.
- [34:26]
A
Explain that.
- [34:27]
B
So let's talk to an example here. So I'm a 24 year old, I'm making TTC perspective 400k, 500k at Google and Meta or something like that. Okay. And I'm going to go to an early stage company and I'm going to go get 1% of this company and I'm going to make $90,000. Well, I've now changed the trajectory of my life. I can no longer buy a house, I can no longer go on the vacations I want. So I'm making like a four to five year trade off where I'm saying I'm going to make pretty much no money over the next four or five years. But maybe in five, six years I'm going to make like millions of dollars that I couldn't make at Google and Meta. That's actually a lot of risk. Say I'm going to live with my friends instead of living by myself. Like I'm making massive, massive changes to my life. But as a founder you're not. It's a much higher likelihood at the next round, regardless of your company, you'll be able to sell some secondary. You know that if it shuts down, you can go get employed at a great company. You have a CEO on your resume. That first employee, they have first employee, like a failing company, that's actually not a great resume line item. And so we've de risked the founder, but we haven't de risked the early stage employee. And I don't think we should actually de risk the early stage employee. For what it's worth, I just think we need to increase the risk for founders. I think we need to make failure much more expensive. I think we need to say, hey, you're a second time founder, you have liquidity, put all of your money into that. If you're going to be asking this of employees, you're asking for yourself. And I don't think we're having that conversation enough. And I think starting companies is just too fucking safe and it's caused a lot of companies to be just super safe. Companies like hey, we're going to pivot to AI wrap, open, AI rap, anthropic, whatever. Like that's not bold, that's not ambitious. And it's because we are attracting founders that actually maybe want to be employees. They don't actually think about the long term. They actually don't think say hey, if I don't pull this off, I'm going to become bankrupt, my life is over. And I think that's pretty healthy. That's when you bring out the rawness of humanity and I don't see that very much anymore.
- [36:21]
A
How have you felt that in yourself? So how has your behavior changed or your perspective changed or like just the ways that you show up that are different now than prior to this pretty extreme three year period?
- [36:31]
B
I am not the most diversified person on the planet. I own two things. I own column and plaid. That's it. I don't even own a majority of my house. That is truly it. Those are the only two things and that's motivating to me at some point in my life. I have a six month old son and I do need to probably diversify and so that is a goal for me at some point. As a 36 year old you should probably not be this concentrated. But it's also that's what makes building companies unique. There's probably a lot of people that look at me and they're like, oh man, billionaire, amazing. I think that's what makes it special. I think that's what drives me every day which is if you don't have something you are driving towards, such as for me like solvency, it's really hard to be motivated every day.
- [37:12]
A
The other thing though too is that very often the thing you own and control and are building might be your best investment. And getting money out of something is costly from a tax standpoint and other things. So you're in some ways you're just continue to be all in on what you're building.
- [37:25]
B
Bet on yourself. I'm sure every Fancy executive has probably told you that, but I think it is somewhat true. Compounding on yourself is probably the best investment to make. I'm not a generalist, I'm a specialist. I'm probably the best in the world. A couple small boring stuff. I'm really good at creating really confusing, boring sounding companies. That's really hard to explain on podcasts. And I think that's like my expertise, that's like my niche. I feel pretty confident in my business because I do not think in my business you want to compete with me. I mean, I'm hungry and I know my little niche space better than anybody in the entire world. And if I'm investing or doing something else, there's a me on the other side of that trade. I don't want to do that. I'm a builder. I think sometimes there's a trap where builders ain't their investors and investors ain't their builders. There are rare cases when you can do both. But in a world where it's increasingly competitive, I do think the world for builders is the world of specialists. And you have to go extremely, extremely deep into your area. And that's where you find value. I probably have read more about the history of MySpace, the history of financial services. I studied banks in Japan in like the 1800s. I read like a very boring 2000 page book on the history of banking in China in the 19th century. And there's stuff I got out of that.
- [38:46]
A
What's something that book. But like what's something you get out of that degree of extreme study?
- [38:51]
B
The hard part about this is you probably get like one small thing in a 2,000 page book.
- [38:55]
A
Yeah.
- [38:55]
B
And so it's probably not efficient unless you own a thing that happens to
- [38:59]
A
be crazy leverage on that.
- [39:01]
B
And that like one little thing can create millions of dollars of value to these and it's creates like hundreds of millions of dollars of value. And so without kind of going too much into detail on it, that's where you find your leverage. And I'm pretty good at that.
- [39:12]
A
This notion of being the best in the world at the thing you do is really interesting to me. It seems the environment today makes that harder than ever because there's so much distraction.
- [39:22]
B
Totally.
- [39:22]
A
And there's such a high rate and ease of comparison, which is certainly the thief of joy. But it's really hard to ignore people doing other stuff. Spending a 30 year day reading about anthropic or whatever. It's exciting. What have you learned about how to become apart from reading obscure 19th century Chinese banking books. What else have you learned about how to become the best in the world at what you do? Assuming that there's lots of people interested in that mission or that idea.
- [39:48]
B
I think one of the best determiners for success of founders is can they find the most boring thing humanly possible interesting and can they find that interesting over a multi decade period? Who doesn't find AI interesting? Yes, Geopolitics, fantastically interesting. There's all these like general topics that are quite broad, that is very mass market interesting and that's what makes Twitter so fascinating. That's why podcasts so fascinating is because people like to feel that they are really smart across a broad swath of categories. But that doesn't really align to company building. So many people right now are thinking about and are have a lot of knowledge around how AI is going to disrupt software, how AI is going to disrupt vertical software, how AI is going to be the next XC round. These are like generalist topics that I can probably find a thousand people that have interesting, compelling ideas and can go pretty deep on that. But you can't create value there. You can create value if you're like, I'm the number one person in the entire world at this little niche thing and I think this niche thing can generate billions of dollars from ever over time. But the problem is is those places are really boring. The fun ones like food and like surfing in Thailand or whatever, like those are solved categories. Yes. I would also love to be an expert on hospitality in Thailand and Southeast Asia. Like that's a fun problem. I could imagine one going niche on that for almost a decade period. But that solved problems. But I think finding the extremely boring thing that requires you to read hundreds of thousands of pages that you cannot gemini deep research your way through, that's where value is. But it's fucking boring for a lot of people. You have to suffer in silence for a huge amount of time. And if you can find that super fascinating, you can like love to learn that, then I think you'll be successful. But I think it's a minority of people. My partner gives me shit all the time. But like how on earth do you find that book interesting? What is wrong with you? And I was like, well like if I don't, you and I are going to be super poor.
- [41:47]
A
You said earlier that building a company for the second time is a lot easier than the first time. Yeah. What are the most extreme ways that that's true? What are the things that you've done the most differently this time than the first time experience is valuable.
- [41:58]
B
I started plaid right out of college and I think Zach, who was my absolutely incredible co founder, we both said like man, if we have just worked at a company for like nine months, we're going to learn a lot. We probably saved like three years. Because the amazing thing about working at a company, especially an early stage company, is you just fail forward all the time. And that's incredible. That's incredible lesson. But like when you fail forward as a founder, that's a lot of dilution, that's a lot of time, that's a lot of like wasted resources. And if you could do that on somebody else's dime, amazing. Now I think it's like a little bit easier because everybody's YouTube videos on YC Startup School and there's some PDF for everything and you can probably like Gemini your way through the early stage part of a company. But experiences matter a lot.
- [42:39]
A
What about picking talent? What things do you optimize for now that have been honed because of your prior experience?
- [42:47]
B
When people always think about employees and it's like a kind missionary mercenary framework, you have to look into employee, like what do you want to do? There's like the mercenary type which is okay, super smart, probably super pedigreed and really what they're doing is they are using your company as a launchpad for something else. They're using their company to collect a bunch of two year vested options from like the top five companies and hoping one of them goes up. That can be a valuable employee. But you have to have a very specific type of company that is used to that churn and burn in order to take advantage of them. Then you have the missionaries which is this person is very mission focused. Inspiration is super important to them and if you get that right, they will go to like the ends of the earth for you regardless of like their short term benefits. People also have some downsides as well, which is the moment maybe you want to be a little bit more commercially oriented and the moment you have to maybe make trade offs on your mission or something like that. That can cause a lot of societal unrest inside of your company. Then there's like the third category of employees which are generally what I think are probably like the best, which is like the combination of everything. But really what they care about is they care about, yeah, we want a ton of upside, but we also want stability. We also want people that hey, I like to be friends with my coworkers, I like to be in an environment that is like warm and welcoming but also gives me like the near term and long term financial value. And I'm will to like work really hard to get there. Everybody has personality types, everybody has different styles. And you have to figure out what is right for your business. But I think it's very challenging to tell that on LinkedIn. Everybody's like, okay, cool, you went to the right New York prep school, thus you went to like the right Ivy League school. That happens at like this good engineering program. And then you have these couple LinkedIn things that are like, good for me and boom, done. That can be super successful. But that is also not the right for everything. And so just getting that hone for talent is super important.
- [44:33]
A
How much do you care about mission? This is an interesting part of the equation.
- [44:37]
B
You need a mission. Otherwise people just go work at hedge funds. You need to say, like, hey, we are building something bigger. And I think we absolutely are. But I think mission can actually be a little bit distracting. I think a lot of times people focus a ton on, hey, what are like the values of my company? What good are we doing? And I think that's like an important part of the equation. But I think it's on a list of five things most important. I think it's probably on the bottom end of that five list. And I think a lot of times we can be kind of distracted by that. That, that's because when you're pitching investors, investors want to feel like they are part of something. They want to feel that, man, I'm not just recycling pension fund money into other capitalists. And that's what we do. Like, we want to feel like it's bigger than that. And so I think we've taught people that, man, you need to focus on the millennia journey. You need to focus on the impact that we're doing. And like, yes, numbers go up, but like, numbers go up is only one part of the equation. And I think that's important for employees. But I think it's, it's sometimes not the best. In the end, what do you want to do? You want to convince somebody to buy your product and you deliver them enough of an experience that they can't build it themselves and they're going to pay a lot of their hard earned money to you. That's the goal. And that person doesn't give a flying fuck about what your mission is. They just care about, does this product create value for me and am I willing to pay for it? That's it. And if you start to drink your own Kool Aid too much, you Kind of forget that.
- [45:52]
A
It makes me smile to think about your earnings and cash flows. It's such a novelty that a company like yours would have a bunch of this so young in its life. And at this scale. How do you pick your margins? How do you think about how profitable to be and why? You mentioned earlier that it's like having a funding round every year. Does that imply that you're actually spending it so you're not paying taxes so that you can spend it on growth? How do you think about earnings in a high growth technology business?
- [46:19]
B
Our customers pay us for safety and our companies pay us for longevity. It's a unique thing around financial services where I'm going to look at you as a customer. I like I'm going to be your best partner over like a 10 to 15 year period. Switching costs are really high and they are putting a lot of your customer trust and risk in you. So I am playing a longevity and a risk game just as much for me as my customers. I take that extraordinarily seriously. And I think earnings and being profitable and sustainable and not relying on somebody else's decision making framework is extremely critical for our customers. And that's extremely important to me as well. I tell people the risk falls on me. I can't pass my risk to some other venture fund or like their LPs or something like that. I want you to be successful. I want you to be successful. If we're not like, I'm the one who takes the pain here. That's quite unique in Silicon Valley because at some point your critical vendor could get like acquired or maybe the founder could get like a $20 million offer from Anthropic. It's the rational decision for them to do that. In many ways, we aren't competing with other Silicon Valley companies. We're competing against maybe them doing it themselves, or maybe competing with them trying like build a patchwork of software vendors on top of a legacy bank or something like that. And so I have to show that I am more sustainable than you. And I think that earnings is a critical part of that. And I think people are like, oh, your margins, My opportunity type thing. And my argument would be like, you run this business at a lot lower margins. You're going to be dependent on somebody else that you probably don't want to be dependent on. You also have to be introspective about your business. Is my business the type of business that if I raise a bunch of money or I have a ton of earnings, I can throw all of that back on growth. And I think a lot of times enterprise software companies, they cannot ingest like a huge amount of capital. Like if you give me like a billion dollars right now, I don't know if I grow it a thousand times faster than I am right now. And I don't necessarily think I should. And so what we do is we say, okay, of this earnings, what goes to employees, what's going to go to growth, and what's going to go to capital, which is pretty much in case something goes wrong or we have a bad couple of years. Nbd, we good. Let's keep moving down to the extent of now. We're like, hey, if something goes wrong for 10 years, how are we? Like, we're good. There's a lot of societal change going on. There's a lot of crazy stuff going on in the environment. I can totally paint you a picture where like the markets gets insane for the next 10 years. How do I make sure I can survive that? Even with a lot of our companies go up or the economies are no changes that goes back to that or chest because markets go like this sometimes. Like, yes, the line through it goes like this.
- [48:49]
A
You forget it when you're one of the good ones.
- [48:51]
B
Yes, exactly. And we look at slope. But a lot of times, like we have down years and you need to be able to weather through those down years. And there's so many incredible companies that just couldn't survive a couple bad periods. And you really want to make sure you're not one of those.
- [49:05]
A
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- [50:27]
B
I actually feel pretty lucky. Where at Plaid in the early days actually had a pretty hard time fundraising. First of all, I think we probably chatted with like 80, 90 investors and we got rejected. Sometimes I think I have a reputation being oh like William's like someone anti vc. It's actually like not for this one. The truth. Plaid would not exist without VCs straight up. I just don't necessarily think the VC model is perfect for every single type of company. Or maybe DC owns like 10% of your company or 20% of your company and maybe the employees yourself own like 80%. There are different cuts of this you can make. But I think for me picking investors is important. I don't think there's a lot of transparency in the environment on like when investors are 7 year timelines, which ones are 10 year timelines or which ones are actually truly super long term oriented. So I think figuring that out. But I think the most important thing you should do is say okay, realistically what is my margin profile look like? What is my revenue growth over time? How should I find a capital structure that matches that? And am I actually going to grow at a consistent enough period? Do I want liquidity in 10 years that the venture model makes sense for me? Because the thing that people forget is yes, growing 100% on a $10 million base or $20 million base or $30 million base. It's not like that hard. Every like shares these graphs, not LinkedIn, like we're the fastest company to get to $100 million of all time. That's, that's awesome. But you know what's like much harder growing above 30% a year off of a billion dollar revenue base. That is 99 times harder than going to 0,900 million in three years. However, the venture model only works if you can grow above 30% off of a billion $2 billion base. And you have to like really look inside yourself and be like does my model make sense for that? And can I do that in a way that I can ingest hundreds of millions if not billions of dollars of capital on the way and put really good use to that? Because I think sometimes businesses grow at the rate of the market or businesses grow differently than just dollar and dollar out. And the venture model is built off a fact of you can make a company like an atm, which is you put in a dollar, you get a $30 back. That's not the case with most markets. And so I think you have to look really intensely at yourself and your business to make sure that works. And there's so many amazing tech companies that works for why that venture is a really good asset class. And Silicon Valley is probably like the best place to accumulate capital of anywhere in the entire world probably throughout all history. But that's not every single business. And you have to look really intensely at yourself in order to do that.
- [52:54]
A
Given your unique perch, what have you learned about how the world works through the lens of this dollar focus, this demand for dollars being the operating system for the global dollar system through the lens of the dollar, what are your takes on the ways the world works or interest you that might surprise people?
- [53:11]
B
What the dollar does, it connects countries. Very interesting ways that I think in the US when you can pretty much just build an incredible company by the US alone, you lose that perspective. If you look at the official stats, most economies spend less than 10% of their GDP trading with their neighbors. And that's been a big focus point of the OECD over the while. But when you actually dig into it, the unofficial trade that's going on over government rails, it's actually closer to 90%. It just shows like how trade and how money and how lots of like really connects these cultures and connects these societies. And I find that like super fascinating. We can talk about how that's impactful in a lot of ways, but that is something that we don't really get in the US because the US has this very unique luxury of we can almost somewhat sustain ourselves. Like you can sustain businesses only building for yourself. US market is just so fantastic. I am so long the US As I'm sure anybody building you can sustain yourself. You become a billionaire by like never truly ever leaving America or never interact with anybody outside of America. And that's what makes America so unique. I don't think we get like how much of a luxury that is, but outside of the world it is not. And that comes down to trade. That comes to like financial connectivity that is so impactful and it's so important. I think you also forget how reliant the world is on the US financial system. So let's take two insanely developed countries. Let's take Qatar and let's take Switzerland. Okay, you're shipping gas from Qatar to Switzerland. I would argue right now neither one of These countries love America like a ton. That trade is denominated in dollars. The money that's moving from Switzerland to Qatar, Glencore to Qatar. The Qatari gas company crosses through U.S. financial institutions. It's crazy to think about. Let's think about boom. Maybe our two enemies like China, Russia. China is a big importer of Russian gas and oil. It's kind of crazy to think about that trade is still denominated for a vast majority in the US dollar. That's mind boggling. That's a luxury. And that's such an insane national security strategy that nobody else has. Russia doesn't want Chinese currency. China definitely doesn't want the ruble. They barely have access to it. They almost hate each other as much as they hate us. And the fact that they then choose a dollar is still so critical. Then you could argue that maybe dollar is eroding over time, stuff like that. But still in the vast majority, it's like 75% of global trade still is in the dollar. That's crazy. And we don't recognize that the soft power the American has or even the hard power the American has with that, that is so fundamental to our life and the fact that we have such a strong economy.
- [55:59]
A
Do you talk to your team as though this is part of the mission that almost like national security is part of the mission because of the importance of the $100.
- [56:08]
B
One of the best shifts I think Silicon Valley has done is we now are like Silicon Valley. We take an active role in the national security of the country. We didn't six, seven years ago. Even though American society, American GDP growth growth is even more than ever completely indexed on the success of Silicon Valley, probably too much and it's way too levered in that regard. But now Silicon Valley, whether it be social media, whether it be defense or whether it be software or whatever, we're starting to recognize our world in the world. And financial services is probably the most important component of that. You know, that's any general I have, they want to use a sanction before there's a missile. The great thing about a sanction, the great thing about the dollar, you can enforce American dominance without putting boots on the ground, without putting anybody at risk. And sometimes you're shown in Venezuela you kind of need both. The reason we were able to go to Venezuela is because we had fundamentally destroyed the economy before. How? Sanctions. We had completely collapsed their ability to export oil. We completely collapsed our ability to actually trade with other people. That friction is real. And so when we went in there, Venezuelan People were probably like, yeah, okay, we good? We're maybe not going to troubleshoot these helicopters from the sky. We're pretty happy here. That is fundamentally so amazing. If France wants to shut down another country in order to go like enforce their will, they have an option, they have two options, which is don't drink our wine and here's some missiles. Okay, the missiles can enforce their will. They have a strong military, they're strong special forces, they can go do that. But their lives, the special forces on the ground, they're gonna have a much harder time because they haven't in many ways control that economy before. And that is so, so unique to the US And I think China's obviously developing this with trade and exports. One of the things that China can do is they can start to enforce their will by shutting down a country from exports. That is real. And so I think China has definitely this increasing might, but the strength of the dollar and that is so fundamental for national security. And in many ways we don't talk about it because it's a little bit uncomfortable truth. The global bank doesn't want to sit up and say we're part of the national security strategy because if the government tells us to, we're going to collapse this economy. That's not like a fun narrative that people want, but I think there's a way to tell that narrative that says we are a weapon that can be used like when our citizens come to harm, when we need to do something that is like super important for the U.S. interest. And we are part of that strategy just in the same way that Palantir is part of that strategy, Lockheed Martin's part of that strategy, Boeing's part of that strategy, and financial services is a key pillar. You can argue that financial services is like the first end to war torn country. We start with sanctions, we start cutting them off from the US trade, we start with that before we put boots on the ground.
- [58:43]
A
What do you then hope is the future of global financial services? Obviously you're actively building the technology backbone for it. But if you think big picture, how do you hope the system changes? What would be best for it?
- [58:55]
B
I still hope it's very US bound and I think we sometimes want to believe this world where there's a lot of people in Silicon Valley that I fundamentally disagree with, that want to put the power of financial services outside of the US and the US has a lot of problems that we can spend spent hours talking about. I still think we're the greatest country in the world and we have Change of power. Every four years we change our mind on stuff. Yes, there are some problems, but we are still the best place to be. And I think we are the ones that. We should still have the nuclear weapons. We should still have the nuclear weapons of financial services, which is. We control the world's trade. And I hope that continues to exist. And I think if we don't, I think if it just hands in the power of other people, I think that's a scary place. And I don't think people have really thought through the ramifications of that. If you look at most countries, financial services is still power, but it ends up just accumulating to government officials. It ended up just accumulating the power of a very small elite. And say what you will about the US and there's probably way too much power concentration in certain industries. Financial services is actually quite fragmented. JP Morgan is the largest financial services country in the us but it's not that dominant. It's still pretty diversified. Take Canada, 95% of Canadians have four banks. Take Australia, it's even more concentrated. You go to most countries, it's been more concentrated than that. We do have a little bit of financial services today. A relatively decentralized financial services system is. You still keep fragmenting, right? We should still disperse the financial power throughout. Multiple US corporations, multiple US people. We need to do a better job there. But we're actually starting from a pretty good baseline. The other thing I tell people is there's this narrative like, oh, financial services is fundamentally broken. Our institutions are actually pretty damn good. There's this narrative. Sometimes people talk about like, oh, U.S. financial Services. It's like built on like cobalt and stuff like this. It's just not. It's like a Fun talking point. IraqMyran hardware at the Federal Reserve and all these like places. There's no cobalt in a lot of these places. It's actually pretty good. I would go on the record talking about this. The Fed is a pretty good tech team. Their systems are actually like pretty good. If you think about the US right now through the Fed has the capability to move money and to clear money throughout all these institutions 24. 7 faster than stablecoins, faster than crypto right now as we speak. We've had that for decades. Systems are very good, extremely reliant. They're fantastic. I think it's very challenging for Silicon Valley to build something better. The problem isn't in the fundamental infrastructure. It's in our implementation of it. The reason why community banks can't send money 247 isn't because the technology doesn't exist at the Fed. It's because there are constraints in those business models that make it very challenging with them to do. Give an example, if you can send money out of your community bank 24 7, well, that bank could run on a weekend. I don't know if you guys have ever been to a rural community, the community bank with 50 people, you can't get people to work on the weekends. If you're JP Morgan, if you're Stripe, yeah, you can manage 247 liquidity, but if you're a small community bank, you can't have that. And so I think people can fleet. We don't have something, we don't have access to something with. We don't have the fundamentally ability to do that. But actually the reason is implementation, not the underlying infrastructure.
- [62:12]
A
I feel like because of your unique setup as a business and your unique focus on the boring problem as you described, you have such interesting perspective on so many things. Is there anything that we haven't covered either about company building or the way that the world works that you think is interesting that we've missed?
- [62:29]
B
One of the things that I think about AI is here we're probably much closer to ASI than people think. And it's going to be on the tidal wave through the economy. You have to think about what's the implications of your business. And I think in my perspective, if you're not a researcher, if you're not a lab, how do you play? I actually don't think, quote, unquote, AI companies are very set up for success. That's actually probably not where value is going to accrue. The value is going to accrue, like in two areas. Most important area, I think, do you have massive distribution? Because if you have massive distribution, if you have massive costs, AI is going to be a massive bin for you. And so the thing I think a lot about is how do you think about not just from a software perspective, but from a distribution perspective and a brand perspective that you would best capture to utilize AI? Because I think people talk a lot about the railroads. Yes, the value accrued to the railroads. Yes, the value accrued to the ISPs, yes, the value accrued to the people like building the mobile phones, but the value actually accrued to the people that could harness that the best. The value in railroads accrued to the oil company companies. That's a little bit hard to fundamentally understand. The Standard Oil is the biggest beneficiary, biggest boon for Ray. Railroads by an order of magnitude what is the equivalent area for AI? And I sometimes don't think we're focused on that enough. Hot take here. I think like the biggest, fattest, most inefficient brands are even the best beneficiary of AI because brands have a massive moat and man, there's a lot of cost to cut there.
- [63:54]
A
How do you think AI will most affect financial services specifically? Maybe even just your own products and services?
- [64:01]
B
Financial services, especially at large banks, they suffer from the fact that the business model is too good. Banks are pretty profitable financial services. It's like you like own a bank and you aren't profitable. Like that's a problem. You've clearly done something wrong. Like the business model fundamentally is what I get. That's made them laggards in a lot of ways. But that also I think makes their massive opportunity where I think financial services and legacy banks tend to be the largest inefficiencies out there. They also are very hard to take over. There's not a lot of private equity activity in financial services because it's highly regulated. And so I think the large banks that can actually effectively harness that are going to be some of the largest beneficiaries. Because banks don't have a lot of physical assets. Places have massive capex and physical assets. It's hard to tell a good AI story there. How's AI going to make railroads more efficient if 99% of your money is spent on fuel track maintenance and people like the human cost in railroads is like de minimis. You take conductors down from a thousand to five hundred doesn't like change the equation at all. But if you think about attritional bank it's pretty headcount focused and it's pretty technology focused. That's where majority of the money goes to the actual physical branch infrastructure is such a minority of your balance sheet. I do think they will be either the most disrupted or probably actually like the largest beneficiaries. It's like the banks that are like most effectively run have the largest distribution of the largest cost structure, are going to be the largest beneficiaries. I think the UX of financial services will change a lot because people think oh my gosh, my bank is hard to use, my bank is hard to move money. It's like slow to move money. That's actually a feature, not a bug. I think what fintechs sometimes start with is they start with hey, we're going to make it like super easy to like super free to move money. All over the place, it actually starts to slow down. The reason it slows down is because fraud is like super expensive. And if you make it like really easy for your grandma to send money to somebody in Nigeria, yes, that's great for remittances, but that's like really bad for romance scams. That's really bad for fraud. But I do think with AI we can actually build those detection models like a lot better. And so it's probably less likely your grandma is going to fall prey to elder abuse. And if the banks don't have to optimize so much for that and it comes a little bit for free, we can actually make the UX better for everybody else because we have the technology right now to make financial services almost entirely instant and like entirely friction free. All the friction is actually built to protect the 5 to 10% of consumers that can get hurt. People forget that. But I think if we can build models that are just as good a human at detecting that stuff and that can happen instantly, we can actually take that tail away and it actually is massively beneficial for everybody else.
- [66:35]
A
Do you think it's a good time to be a new entrepreneur in financial services?
- [66:39]
B
Anybody who tells you that it's a bad time to be an entrepreneur, that probably means it's a good time to be an entrepreneur. If you look at there's all these stats on Twitter that I'm sure people have seen where the best companies are created in the worst environments. And I think that's generally true. It is cheaper than ever to be an entrepreneur. It's probably the least risky time to be an entrepreneur. It's also pretty crowded, but you probably look at like the last YC batch. I'm sure like my 90 plus percent of them were like AI related. So yeah, I think it's actually probably a pretty good time to be a founder in a non AI related place right now because there's less competition, less smart people. If you want to be successful, you can go look at every single industry and you can say, okay, who is the dumbest people and what makes the most money? And if you go attack that area, probably pretty good space. The problem is sometimes Silicon Valley or founders, you look and say like, hey, we're all the smartest people. That's maybe like a cool space that's probably like the most crowded with the smartest people. And so your ability to compete, your competition's pretty intense sense. YC puts out this request for startups. My recommendation is like that should be a list of startups you should not start because by the time that gets so consensus that this is a good area or super interesting, the amount of capital and the amount of smart people, it's like moth delight. I would almost go the opposite way. Hey, YC I love you guys. Please continue to fund our customers. You guys are amazing, but as a founder, I would maybe be a little bit skeptical.
- [68:11]
A
I think your perspective is so unique and interesting. I always love talking to you. I always find it very inspirational on the dimensions of just really going your own way, but also just the willingness to fall in love with some part of the world and get devoted to it and just out learn everybody and stick with it. I love your diversification strategy of illiquid plaid and illiquid column. I think you know my traditional closing question. What is the kindest thing that anyone's
- [68:34]
B
ever done for you? I've had a lot of kind people in my life, but. But I think it's challenging to not look back and be like, oh, like your mom and dad are like the kindest people. My mom and dad did not have the most, like, straightforward life and not the easiest. And my childhood could have been a lot more difficult than it was because I think they insulated me from a lot of things that were going on. I had a lovely childhood and I feel super lucky for that. And I think we've talked about a little bit. As a founder, you have to be willing to take on risk. And if you grew up in an environment of fear, if you grew up in an environment where like, you were constantly de risking when you're a little kid, it's very challenging to feel comfortable going up the risk spectrum as you grow an adult. And I feel very lucky. My mom and dad did that. They also taught us, like, it's okay to fall. It's like, okay to get punched in the face. Like, see these? They're all fake. The amount of time I got punched in the face and I've like lost teeth is honestly crazy. It's like embarrassing. But I'm like, you know, I was pretty good at getting punched in the face. And you can only teach that as a little kid. You can only have that childhood that makes that comfortable in a very specific environment. I have a six month old and as I look at my peers and look at everybody else, we are quite obsessed with creating this perfect environment for our children. We send them to the best schools. They have the nicest people in their lives, and that is valuable. But we may be creating children that can do linear algebra at 7 and I guess it's going to be great AI researchers, but is that what we're going to need in 20 years from now? Or do you want kids that are going to be pretty good at taking risks, that are going to be pretty good at being punched in the face? And I think my parents did a really good job at that and I feel very lucky for that. If I copy all of my peers, I don't know if that's the path we're going to go down. And I think the fact that I am pretty damn resilient is a complete product of my parents and I think that's a huge gift and I feel super lucky for them every day. A beautiful place to close.
- [70:26]
A
Thank you for your time.
- [70:27]
B
Thank you.
- [70:28]
A
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