By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.
Invest Like the BestHow to bet on yourself (without venture capital)
Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.
Transcript
85 min read · 17,063 wordsIntro
Patrick O'Shaughnessy 0:00 My 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 in Japan, and found one idea buried in the two thousand 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 wanna build a company. Please enjoy my conversation with William Hockey. [upbeat music] Usually I don't start with a description of the company that someone's building.
William Hockey 1:16 [laughs]
Patrick O'Shaughnessy 1:17 But in your case, uh, one, I don't think a lot of people are yet familiar with Column, and I wanna fix that, and it's such an interesting beast in and of itself that it'll- it'll be our excuse to talk about many fascinating things in the world.
William Hockey 1:29 Yeah.
Patrick O'Shaughnessy 1:30 Can you just start by explaining what the business is and does?
William Hockey 1:33 At a high level, we are a software company that also owns a bank. And what we do is we say, "Okay, we have this interesting regulatory moat with a bank that most other people don't have, and we're gonna build this 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 wanna get into financial services in the US, so with a backend infrastructure that powers the payments, deposits, credit of amazing companies like Built, Wise, Ramp, Brex, Mercury, these type of companies. They run on our software, then our regulatory rails. And then we also expand that to anybody who wanna 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 holdings in the dollar. So in the US you have, you know, vertical software, people building business software. This is an area that is, you know, probably gonna get changed as AI kinda 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 the business. The Brex, Ramps of, kind 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 through 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.
Patrick O'Shaughnessy 3:00 Could you maybe like pick a customer that people might recognize-
William Hockey 3:03 Yeah
Patrick O'Shaughnessy 3:03 ... and describe literally what services or products they use, and then how they pay you for those products or services-
William Hockey 3:08 Yeah
Patrick O'Shaughnessy 3:08 ... just to like really nail it home?
William Hockey 3:10 So maybe I'll use a, a company out here that recently relaunched, a company called Built, which is... I mean, a lot of New Yorkers have, a lot of people in the cities have. If you look at the card, on the back it says like, you know, like, "Issued by Column." 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 gonna deduct money from your Built account, if you look at like, oh, the account and routing number there. Oh, that's actually a Column account and routing number. So they build the application, they build the website, they build the consumer marketing, and we're gonna handle everything kind of behind the scenes that has to deal with the Federal Reserve or TCH or the card networks or Swift. We're the one that's, uh, that kind of build the software for that and handle all that complexity. We are technically a bank, but unlike banks we make ninety plus percent of our money off of software. And so similar to a, any kind of 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.
Patrick O'Shaughnessy 4:09 One of the things I love whenever we talk is you've always been somewhere strange and interesting.
William Hockey 4:13 Yeah.
Patrick O'Shaughnessy 4:14 Kinshasa I think was the last time-
William Hockey 4:15 Yeah. [laughs]
Patrick O'Shaughnessy 4:15 ... we were together. I don't know a lot of founders going to Kinshasa very often.
William Hockey 4:18 Yeah. Yeah.
Patrick O'Shaughnessy 4:18 Why are you so often in interesting, kind of bizarre locales around the world?
William Hockey 4:23 This is my second company, and I started Plaid back in two thousand and twelve. It's very easy to stay in Silicon Valley. It's like quality of life is amazing. [laughs] Um, 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 o- read Dan Wang's last letter on China, and he has this like great, and I think accurate, but somewhat harsh criticism where he says the two, the two most consensus societies he's ever been to is San Francisco and Beijing, and I think that's like quite accurate actually. Um, 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 in like, I don't know, like AI or like stable coins 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 like outlandish ideas that other people are gonna believe in that nobody across the world will believe in, and you can build this in a very like safe way. I think that's why Silicon Valley and San Francisco is so, is so dynamic and we're so upfront of the curve. But we also have completely lost touch [laughs] with how the rest of the world operates or even like everyday American operates, and you've probably seen this kinda smack us in the face over the past, 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. The constraint 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. Like if you go to talk to people in London or Vienna or Mexico City or San Francisco or whatever, like people are living in, in, to an extent in a world of abundance, and that causes a very like specific creation cycle. Why if you go to Kinshasa, which is the capital of Democratic Republic of Congo, it's gonna be the largest city in the world then in probably 5 to 10 years. I think it's already larger than most of the mega cities.
Patrick O'Shaughnessy 6:31 Wow.
William Hockey 6:31 Probably 95% of people in Silicon Valley couldn't tell you what Kinshasa is the capital of. But, like, you know, just 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, like the dollar is fundamentally global, and the dollar tends to be strongest in places that one could imagine are relatively dollarized. 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 like 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, you know, UK and the GBP's pretty strong or, you know, France. Those places don't need American financial services as much as maybe some parts of the emerging world do.
Patrick O'Shaughnessy 7:25 So sticking with Kinshasa as the example.
William Hockey 7:28 Yeah, yeah.
Patrick O'Shaughnessy 7:28 So you go there, what are you doing there? What are you discovering? Say more about like the cons- the constraints you encounter there.
William Hockey 7:34 Yeah.
Patrick O'Shaughnessy 7:34 Like teach us a bit about... I've never been to Kinshasa.
William Hockey 7:36 They operate in a world where there's actually like relatively large markets. You know, DRC, take that as an example, is, you know, one of the largest exporters, if not the largest exporter of some critical metals in the world, right? So there is a lot of money flowing through there. It's a massive exporter. It's a place where, um, there's a lot of Chinese investment. You know, 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. While they may be, you know, GDP per capita quite small, there's still a lot of going on. And where there is, there are founders that are building super cool things. The large companies actually tend to be quite innovative, and I can kind of talk about that in a second. And so you just... I talk to them, I meet a ton of people. I'm meeting CEOs of the largest like multinational companies there. I'm meeting kind of 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? Like, how can we be helpful?" And you just... Honestly, like I spend a lot of my time just like walking around, kind of ideating, just like taking in the scenes and sometimes, you know, quarter of the time I come up with like a really interesting idea that ends up building us like a cool product or just a good market.
Patrick O'Shaughnessy 8:51 What's an example of that?
William Hockey 8:52 I put 90% of my ideas either in the shower or like walking around in like a random emerging markets country. It kind of expands your senses a little bit. If I'm like walking down the Marina Green, I'm like walking to the Mission in San Francisco, like kind of the only thing I'm thinking about is like, "Oh my gosh, like how is AI gonna change things?" Because you can't walk around [laughs] 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.
Emerging Markets
William Hockey 9:19 Like take DRC, like mobile phone penetration is still less than 25%. You know, banking penetration is like still less than 5%.
Patrick O'Shaughnessy 9:25 That's crazy.
William Hockey 9:25 There's like stuff we need to do before we think about like embedding LLM in everybody's brain.
Patrick O'Shaughnessy 9:30 If that penetration is that low-
William Hockey 9:32 Yeah
Patrick O'Shaughnessy 9:32 ... will you and your business naturally benefit from that going up based on the products that you're building? Like is that how you think about some of these opportunities where it's much lower hanging and just no one's paying attention?
William Hockey 9:41 The leapfrogging that happened in Asia i- is obviously quite well known, right? Like trying to skip the laptop, went straight to the mobile phone. Most famously, uh, you know, we strip- we, we, we shipped, you know, online e-commerce and like went str- straight to, straight to social commerce in China. Like there's gonna be leapfrogging as well, and you're gonna see the same thing in financial services. Like financial services tend to be most innovative and most progressive in like the worst countries. You can see this in Argentina, you can see this in Iran, you can see this in other places. Like the Iranian financial system, like say what you will, like it's complicated. They have to deal with a lot of incredible constraints, and thus they have 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, you know, a little bit differently, and that's actually quite interesting. If you look at these emerging markets, take, you know, like Africa for example, they were the first ones to do mobile payments and M-PESA like decades ago. Well before like, you know, Venmo. And if you talk to them, they are actually like quite a bit more open and they are quite more... Like they are used to this, their, their category being somewhat disrupted. They also have a, like an interesting thing is they have a, a bit of a access to differentiated capital, which is if... uh, differentiated talent. If you are... And if you're in the US, like, you know, pardon, pardon the banks I'll, I'll kind of shit on here, but you do not have access to the top talent. The top talent's going to, they're going to Anthropic, they're going to Google, et cetera. But if you believe that, you know, brains are distributed equally, you go to, you go to Congo and there's gonna be like some proportion of like equally smart people as there are in France. There are like, there's no like Anthropic to go to. They don't have the ability to move to, move to London and go to DeepMind. But there's a, still like a pretty decent talent pool there. They're gonna go to where there is job safety [laughs] and where there is money. That tends to be in a lot of emerging markets. What? Like the breweries and the banks.
Patrick O'Shaughnessy 11:32 Mm.
William Hockey 11:32 That's where the money is. And so the talent, I'd say the mid-level and top, can actually be like quite a bit higher than people, than people think. I'd say you take your like emerging markets bank executive team, they're hands down just way better [laughs] than I think probably what you see i, in, in the Western world. They also have the ability to, 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 a developed country, like everybody has like a bank account. Well, a lot of people who have a phone have a bank account, so they can actually cross-sell there effectively. Like you and I talked about this before, but I think one of the most interesting companies out there is Kaspi in Kazakhstan.
Patrick O'Shaughnessy 12:14 Fascinating. Can you explain it?
William Hockey 12:15 They started out by, by buying a bank, and then they just kind of built-
Patrick O'Shaughnessy 12:20 Did everything
William Hockey 12:20 ... did everything. Like they're like the largest like e-commerce company, the largest bank. Like you pay your taxes on Kaspi. You know, like renew your driver's license, it's on Kaspi. Because what they realized is like where people start is people... Okay, maybe people start on social media, but they also start in financial services. And so if we require financial services- We can cross-sell and we can distribute products there. The largest bank in, in, in Congo has been called Raw Bank. Highly sophisticated, download the mobile app, it's way better than anything we have here in the US. You can, like, upgrade, like, your TV subscription on it. Imagine, like, JP Morgan doing that, or Bank of America doing that, or Wells Fargo doing that. Or can't believe in, 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, you know, these countries, the main currency is the dollar. Um, and so our ability to kinda innovate with them is, is much more akin to what a Fintech looks like in the US than maybe a large traditional bank.
Patrick O'Shaughnessy 13:16 Do you end up earning similar amounts of revenue from outside the US as you do inside because of these potential relationships?
William Hockey 13:23 The US market is so good and, and Fintech is so developed. And, and I do think, you know, like, one of our theses is, like, Fintech is probably gonna be, like, the last area that is somewhat maybe disrupted by AI. I think what you'll see is you'll see a collapsing of, like, domestic Fintech and enterprise software. And you already see in this with, like, the ramps and stuff of the world as they go kind of, like, deeper into the workflow management side. Good thing for us, like, some of our customers are growing just, like, so quickly. But the rest of the world is also... It's, it's a, 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.
Patrick O'Shaughnessy 13:52 Can you say more about this comment that the Silicon Valley, along with Beijing, is the most consensus place? Like, as you traipse around California, what strikes you as the strangest? Like, you're building something so different.
Silicon Valley's Elite Consensus Problem
Patrick O'Shaughnessy 14:03 You spend so much more of your time away from there. Uh, you're able to kinda get outside perspective despite being kind of of that place originally. What would you say is, like, str- stands out as the strangest elements of it, it, and its culture today?
William Hockey 14:14 I'm a product of Silicon Valley, right? I, I, I've been there since I was 21. Started kinda, like, some of the top companies in Silicon Valley. I am, like, 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. SF and Silicon Valley, like, 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, like, you know, a research lab in Cambridge in, like, the 1950s. Like, maybe that was Silicon Valley in the '90s, but it's not anymore. And what that happens is, like, you know, elites end up building software for elites. And I think that has somewhat made sense because if you look at, like, 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, like, 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, like, our research labs are, are doing fantastic because that's, like, a consensus-oriented problem. It's you take a bunch of people that are super smart, and you, like, pretty much, like, blind off everything from the 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, like, applicability to people's, like, everyday lives, people in Silicon Valley don't live everybody else's lives. They don't live in the lives of, like, Americans. They don't live the lives of, like, other people outside the world. And so our ability to, I think, actually build software or have ideas or perspectives that really resonate is probably, like, at a low point in the entire time I've been here. Like, Silicon Valley is not a popular place, and I think we, we tend to forget that. Like, 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
Rejecting the VC Hamster Wheel
William Hockey 16:03 that, you know, 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, like, outside the walls of, of, of San Francisco and New York, but that's probably less and less the case.
Patrick O'Shaughnessy 16:13 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 eighty-five percent of expense reviews with ninety-nine percent accuracy. And since Ramp saves companies five percent, 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 WorkOS, 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 WorkOS comes in. Instead of spending months building these mission-critical capabilities yourself, you can just use WorkOS 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. WorkOS is the fastest way to become enterprise-ready and stay focused on what matters most: your product. Visit workos.com to get started. One of the things that you've done that's so unique is not raise money.
William Hockey 18:08 Yeah. [laughs]
Patrick O'Shaughnessy 18:08 Uh, but, but built at a, a pace and a scale that looks as though you raised a ton of money. Suffice to say it's, it's huge. Talk about that decision. W- what, what building a company where you and the employees basically own the whole thing-
William Hockey 18:21 Yeah
Patrick O'Shaughnessy 18:21 ... feels like relative to having built, you know, a marquee company that was venture backed? And just like, I wanna go into all the various lessons-
William Hockey 18:28 Yeah, yeah
Patrick O'Shaughnessy 18:28 ... that you've learned.
William Hockey 18:29 Yeah.
Patrick O'Shaughnessy 18:29 We'll spend a lot of time in this section. But at a high level, like, why did you choose to do it this way, uh, in the first place?
William Hockey 18:34 I started Plaid, and I kinda did, like, the, the standard Silicon Valley playbook, where, like, you have to, like, ideate, you have to build stuff, and then you, like, put a deck together and you go to, like, these, like, 80 venture capital firms, and, like, hopefully one of them gives you money. And then, like, every year you, like, move up the alphabet. And I think that worked and, you know, Plaid's a, a very successful company. I'm very lucky to have started it. But the things that Silicon Valley c- sometimes gets confused by is they're like, okay, you're either, like, a venture-funded company, and if that's the case you're, like, ambitious and you're gonna build amazing software and you can, like, amaze, like, amazing products. Or you're, like, a, like, a bootstrapper and you're gonna, like, write a lot of thought pieces on Twitter, but you're gonna, like, hire [laughs] like subscale people, and you're gonna, like, grow small amounts as, like, a cute lifestyle business. And I think you can actually be highly ambitious, and you can hire, like, the world's best talent, and you can build, like, a massive doubling company without actually be, being able to be addicted to, to venture money. What we do is we say, "Okay, like, we are going to grow by our earnings. We're gonna make sure that 100% of employees and myself, like, like, 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, you know, the net worth of, like, myself and my employees, but also culturally it's actually quite a bit more effective. Because, you know, being longtermism is, is probably a little bit of a trite saying. Um, but I think it does actually help us do that. I think, yes, Silicon Valley companies are probably, like, 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, you're burning at a rate of you have to raise every, like, year, year and a half, you end up optimizing for that next fundraise. And you say, "Okay, stable coins are, like, cool this year, so I need a stable coin strategy. Okay, AI is cool this year because, like, I need a AI strategy." And so your business, maybe it's, like, kinda going in 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 gonna be the straightest line to your goal. I sometimes make this joke, maybe not appropriate, but like, like, VC money's kinda like heroin. It, like, feels good, it's amazing, but, like, you gotta keep shooting up. Like, it's very challenging to get off. Like, I, I know very few people that have, like-
Patrick O'Shaughnessy 20:49 Tried heroin once. [laughs]
William Hockey 20:50 Yeah. Like, who tried heroin once and they're like, "Oh, that was awesome. I'm off," right?
Patrick O'Shaughnessy 20:53 Yeah.
William Hockey 20:53 It's like, how many people do you know have, like, raised, like, $100 million series A and then they're like, "I'm done"? It just doesn't happen. And, and I kinda think that, man, like, if you raise $100 million, you should be able to raise, like, you should be able to build a couple billion dollar business after that. Why, why do you need to keep raising it? And there's a lot of structural reasons for that, and, and the fact that San Francisco's a bit like a factory, like, is by design, and I think that is, it can be, like, quite effective. But I think for the, like, the ambitious founder, I actually don't think it's, it's, it's the right thing. And for us, you know, I can, I can, I can invest in things that I think are gonna have, like, a 10-year payback, and I'm, like, totally fine with it. If we grow 80% versus, like, 110%, like, it doesn't really matter that much. Like, as long as we're profitable, as long 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.
Patrick O'Shaughnessy 21:41 What's an example of something that you've done or made a long-term
Equity and Liquidity
Patrick O'Shaughnessy 21:45 investment in that you think you wouldn't have done if you had been venture-backed?
William Hockey 21:49 I mean, like, like, we bought a regulated bank when we were early. I think that's, like, you know, it's probably, like, a little bit cooler now in this new administration, but we bought a regulated bank during the, the first Biden administration. And that required us to, like, not grow or, like, not focus on revenue for, like, two, three years and do a bunch of stuff that inherently didn't scale. Like, it's not ... Like, buying a bank is not a software-defined problem. That's not, like, a great use of, like, venture capital dollars that you expect to grow. And that was a relatively non-consensus bet at the time. Like, I ... There's just no way that could've happened. There's no way somebody would've been like, "Oh, we want to buy this money-losing company."
Patrick O'Shaughnessy 22:20 Here's a software company, right?
William Hockey 22:21 We want you to do stable coins. We want you to do AI. That's just not a, that's not a fundable thing. So I think ... And, and then able to just kind of invest behind that for a multi-year period before we actually take on clients. Like, people think they're long-term focused, but it's just not. I think we're able to also do, like, weird stuff with employees that doesn't scale.
Patrick O'Shaughnessy 22:36 Like what?
William Hockey 22:37 We, like, pay employees, like, you, "Here's $2,000 a month to go to a rent or mortgage if you live two miles from the office." Well, like, that doesn't inherently scale, but it's, like, massive, 'cause now I can get people who live close to the office. They feel great because they're getting, like, a huge part of, like, all of their housing and stipend in San Francisco subsidized. But, like, I don't know. Is that gonna, like ... Is that gonna be, like, a good use of, like, venture capital money? Like, probably not. So we can just do all this stuff from an employee perspective, from a retention perspective. You know, what we do every single year, we take 25% of our earnings and we just buy back our shares with employees.
Patrick O'Shaughnessy 23:11 Mm.
William Hockey 23:11 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, like, "Hey, believe that we're, like, in this venture growing business." But if you're, if, you know, you're in a VC business, you're like, "Hey, you should be using, like, 100% of that money for growth."
Patrick O'Shaughnessy 23:27 Mm.
William Hockey 23:28 And we say, "Well, actually, we don't necessarily think that. Like, we're quite profitable, so we can afford it, so we can invest in growth, but we can also invest in employees."
Patrick O'Shaughnessy 23:35 That's a really good example.
William Hockey 23:36 Yeah.
Patrick O'Shaughnessy 23:36 So maybe just to, uh-
William Hockey 23:37 Yeah
Patrick O'Shaughnessy 23:37 ... pull it apart a bit more. Are you vest- are you granting equity to people in a similar way that a normal startup would, ve- vesting over some period of time and then just every year saying, "We'll buy back some portion of that to provide"... That's how, that's how it works literally?
William Hockey 23:48 Yeah, I mean, like, structurally, we look exactly the same as, like, a high-growth startup, right? We go after the same people. We have, like, all the same perks if not more. So we operate very much like a high-growth Silicon Valley startup. We happen to just also be, like, quite profitable. So, like, what I kinda tell people is, "Okay, I'm at, like, our profits every year is, like, imagine that's, like, our funding round." Like, each year, like, on January 1st, we, like, raise a massive round each year. [laughs] That's the way we view it. There's part of it that's gonna be used as, like, a tender, that we're gonna, like, buy back company shares, and the rest of it we're gonna put to growth. Oh, by the way, you also haven't diluted at all. By the way, you also don't have any pref stack. By the way, like, we get to make our own decisions. That's super compelling. So I can hire someone and say, "Over a 10-year period, you're not gonna be diluted." I think what sometimes people kind of forget is if you're an early-stage founder, like you're gonna lose probably 50 to 75% of your equity value due to dilution alone. You may lose 10 to 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 five, six, seven, eight, nine, 10 years or have seen an exit. Like with us, we say, "Hey, like just don't worry about that stuff. Like what I give you is what you're gonna have, and by the way, you have liquidity. You'll have liquidity on a yearly basis going forward." That's like super compelling to people.
Patrick O'Shaughnessy 25:01 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 like-
William Hockey 25:09 Yeah
Patrick O'Shaughnessy 25:09 ... "This is the, you know, this is the valuation, and if it goes to this valuation I can just do the mult- I can do the math."
William Hockey 25:13 Yeah. Yeah.
Patrick O'Shaughnessy 25:13 But that's not actually the math of what like they'll take home. So how do you, how do you frame it to people?
William Hockey 25:17 We're far from perfect. Um, I think one of the things we do is we target people that this is their second company. Like, we are, um, like we are not, we are probably like not the best place for a new grad to land, 'cause a new grad to land, they're gonna, they're gonna go through this calculation of, "Where are all of my friends going? What is the, like what is the number one company on Hacker News I read all the time? What's all like the thoughtfluencers talking about on Twitter?" And 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 gonna be thinking about some of this, some of this kind of nuance. And it's honestly not as like hard as you, as you'd think. It's actually like quite refreshing.
Patrick O'Shaughnessy 25:51 Mm.
William Hockey 25:51 We go to people and we're like, "Hey, we like are super fast-growing, but we provide you yearly liquidity. Oh, by the way, here's like some very basic math on preference and dilution, and here's why you can actually make way more money for the same equity
Funding a Bank
William Hockey 26:03 value." It's a hard story for a 21-year-old. It's actually a pretty easy s- story for a 25-year-old that's been through like six rounds and four pivots at their previous company and don't have anything to show for it.
Patrick O'Shaughnessy 26:13 Does this empirically show up in employee retention numbers versus like Silicon Valley norms?
William Hockey 26:18 We have almost, almost close to no, no regretted attrition, which means kind of people that we like to stay end up, end up staying. I think there's probably a couple... There's a couple reasons for that. I think one is second time around, it's a lot easier. [laughs] You know, like I think I learned from a lot of mistakes at Plaid and I, I know where to spend time and where not to. And so I think generally we're like a, it's like a, a probably more mature company than your average Silicon Valley startup, 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, like we think that people join companies because they want to become billionaires, and I think maybe that's true up to a point, but a majority of people join companies because, you know, they hit into like their late 20s or their early 30s and like what are they optimizing for? They're like, "Okay, I wanna like send my kid to like a good school and private school. I want to like maybe not live with roommates in like a one-bedroom apartment up until like I'm 35." Like housing and education, that's super important. You can't feed that on illiquid stock. So how do you think about optimizing for that? Think about like 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 over like a 20-year period or like, "Here's your path to being like a decamillionaire." They'll say like, "Do people, 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 like too long-term oriented sometimes. Say, "Hey, yes, of course, come with me, work on this for 20 years, and you're going to be like a decamillionaire 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.
Patrick O'Shaughnessy 27:59 How much of this was just possible because you were already rich at the start and had money to fund something like this? Like is this, is this portable advice? Like could someone else that hadn't had the experience you had with Plaid do something like this without taking outside money?
William Hockey 28:15 I think it's hard. I think it was definitely successful at first, but what I would say is, you know, I, without kind of going into too much details, like I, uh, yes, I started a very large company. I think I was probably less liquid and less rich than probably everybody, everybody thought at the time.
Patrick O'Shaughnessy 28:27 [laughs]
William Hockey 28:27 Um, you know, when I started this, [laughs] Plaid's a funny story. You know, we, we attempted to sell to Visa for like $5 billion, and that's kind of 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. [laughs]
Patrick O'Shaughnessy 28:44 [laughs]
William Hockey 28:44 And so I had like, you know, my, maybe like my liquidity ver- p- versus paper wealth was, you know, pretty, pretty extreme. And so I think I got a lot of credibility from people being like, "Oh, this guy's like rich."
Patrick O'Shaughnessy 28:54 Easy for this guy to say.
William Hockey 28:55 Yeah, easy, yeah. But like, I did not have any money.
Patrick O'Shaughnessy 28:57 [laughs]
William Hockey 28:57 Without kind of going into too much of the details of it, like I pretty much funded the entire company with debt. I went to a bunch of banks and I said, "Here's a bunch of Plaid shares. Like please give me money." You know, I got like a... The best I got was like a SOFR plus 10% loan at like 5% LTV. And so, you know, I pledged over a billion dollars of stock to get $70 million. I bought the bank for $70 million. [laughs] I haven't had a lot of money in my bank account for a long period of time. And um, and yes, and I ended up, you know, the business became profitable and I got to pay off that loan in a period of time, but in the process I probably got margin called three times and almost went bankrupt multiple times.
Patrick O'Shaughnessy 29:31 Talk about that stress. Like you gotta like let us in the room on that.
William Hockey 29:34 Yeah. The first three years were definitely the most stressful of my life because I, I had a fundamental thesis that we could pull this off and we could build a, a business that 100% of employees and myself owned. But
The Necessity of Extreme Founder Risk
William Hockey 29:45 to do that in a world where you need to invest and not make money for multiple years is very, very challenging. And with the regulatory climate at the time and to build a com- like that, it was, it was intense and, you know, I have this loan I have to pay off. It was, 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 like pretty extreme conviction in myself and I thought, I like knew 100% over a multi-decade period I can, I can pull this off, but there's that crazy quote of, you know, markets, markets can stay, you know, irrational longer than you can stay solvent, and it's It's kind of true. And, you know, I look at that quote and I'm like, "Which side of that equation am I on every day?" [laughs]
Patrick O'Shaughnessy 30:31 [laughs]
William Hockey 30:32 And, um, you know, we ended up making it through. But I think the, the idea of like, oh, like, you know, billionaire buys a thing and self-funds it is probably a little farther from the truth than people think.
Patrick O'Shaughnessy 30:40 What's it like getting margin called in the... Like, what are you... Like, what is the literal thing happening? How do you manage through that?
William Hockey 30:46 Surface to say, you know, you own a, you know, you owe a bank a million dollars, like, you know, they owe you. You owe a bank a billion dollars, like you owe them. Like, I think that's a little bit, I think that's a little bit true.
Patrick O'Shaughnessy 30:56 That saying is true. [laughs]
William Hockey 30:57 I mean, there's a reason that, like, margin lending in private companies is not, um, is, is, like, not a great business because when you wanna take collateral of that stock, that's usually the exact time when you do not wanna hold that private stock. I have, like, immense appreciation for the people that did it for me. Uh, 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.
Patrick O'Shaughnessy 31:18 The reason I feel the, the story is important to tell is that it's these things where so much of the value gets created, like the, the extreme entrepreneurial risks. The, the act itself, but also the psychology behind it. And I'd love you to just riff, like, 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 you... I know you'd already been through the entrepreneurial wringer with Plaid. What changed about your mind, your perspective on the world? Like, how did that experience affect you?
William Hockey 31:49 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, like, when there's, like, literally only one door in front of you, you don't have a choice. You have to go in. And that, in that fear, in that, like, in- innate desire creates, like, another part of you. It creates creativity, it creates inspiration. Like, it's extremely valuable part of the founder journey. And in many ways, I think in Silicon Valley, we've actually removed that. If you think about most founders these days, like, like, you know, I talk all the time, like, "Hey," you talk to a 23-year-old and they're like, "You know what? I'm thinking about go- going to be, like, the 12th employee at this company or starting a company between... for myself. And I don't know, I'm, like, kinda, like, mixed." And we've created this, like, 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, like, moderately competent and went to the right high school and college, you're gonna get, like, a $3 million seed round. And worst case scenario, you can, like, you know, you can go work at, like, a great company as an engineer and, like, you'll be, like, have a founder on your resume and, like, 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, like, you know, pre-2008 or something like that, like, you're, like, on... You're on the edge of the knife, and I think that creates just-
Patrick O'Shaughnessy 33:19 Yeah
William Hockey 33:19 ... 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. Like, we don't create environments where a founder has to bet themselves, and I think if we did that, like, I think we'd actually be in a slightly different place. I always am somewhat perplexed by... You know, like, 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 into, like... They're like, "Oh, here's my, like, second company or third company," and you dig into that and, like, of the $100 million they've made, they're putting, like, a million dollars of the capital at risk and they've raised, like, $500 million. And I'm always like, "Why?" Like, if you believe in this, if you believe in this so much, if you're gonna dedicate your life to it, like, why the fuck aren't you going all in? And if I'm an employee, I look at them, I'm like, "You're asking me to go all in, but you can't go all in." 'Cause the, the weird thing is an early stage employee takes way more risks than an early stage founder.
Patrick O'Shaughnessy 34:14 Explain that.
William Hockey 34:15 Kinda messed up. Yeah. So let's talk through an example here. So I'm a, I'm a 24-year-old. I'm making TTC perspective 400K, 500K at Google or Meta or something like that, okay? And I'm gonna go to an early stage company and I'm gonna go get 1% of this company and I'm gonna make, like, $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 gonna make pretty much no money over the next four or five years. But maybe in five, six years I'm gonna make, like, millions of dollars that I couldn't make at Google or Meta." That's, like, that's actually a lot of risk. I'm now going to now, like, say I'm gonna live with my, my friends instead of living by myself. Like, I'm making massive, massive changes to my life. But as a founder, like, you're not. Like, you know, like, it's a much higher likelihood the next round, regardless of your company, you'll be able to sell some secondary. You know that you'll be able to, like, if it, if it shuts down, you can go be an employee at a great company and have a CEO on your resume. That first employee, they have, like, first employee at, 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.
Patrick O'Shaughnessy 35:29 Yeah.
William Hockey 35:29 I just think we need to... I think we need to increase the, the, 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. Like, put all of your money into that. Like, if you're gonna be asking this of employees, you should ask it for yourself." I don't think we're having that conversation enough, and I think starting companies is just... It's too, it's too fucking safe.
Patrick O'Shaughnessy 35:48 Yeah.
William Hockey 35:49 And I think it's caused a lot of companies to be just super safe companies. Like, "Hey, we're gonna, like, pivot to AI and, like, wrap OpenAI or wrap Anthropic, whatever." Like, that's not bold. That's not ambitious. And it's because we're attracting founders that actually may be just, like, wanna 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, like, I'm gonna become bankrupt. My life is over." Um, and I think that's, that's pretty healthy. That's when you bring out, like, the raw, the rawness of humanity, and I don't see that very much anymore.
Patrick O'Shaughnessy 36:21 How have you felt that in yourself? Like, 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- [laughs]
William Hockey 36:29 Yeah
Patrick O'Shaughnessy 36:30 ... pretty extreme-
William Hockey 36:30 [laughs]
Patrick O'Shaughnessy 36:31 ... you know, extreme three-year period?
William Hockey 36:32 You know, I am not the most diversified person on the planet. I own two things. I own Column and Plaid. That's it. Like, I don't even own a majority of my house. Um, that is, that is truly it. That, those are the only two things, and, and that's, and that's motivating to me. Like, yeah, like at s- at some point in my life, you know, I, I have a, I have a six-month-old son and, um, I, I, I do need to probably diversify, and so that, like, is, you know, a, a, a, a goal for me at some point. As a 36-year-old, you should probably not be this concentrated. Um, but it's also, like, that's, that's what makes c- building companies unique. Like, yes, like I... There's probably a lot of people that look at me and they're like, "Oh, man," like, you know, "billionaire, amazing." Maybe California would look at me and be like, "Oh, yeah, billionaire, amazing."
Patrick O'Shaughnessy 37:14 [laughs]
William Hockey 37:15 But, um, it's probably a little bit-
Patrick O'Shaughnessy 37:16 Give me some of that illiquid equity. [laughs]
Finding Leverage
William Hockey 37:18 Yeah. But I think that's what makes it special and I think that's what, that's what drives me every day, which is if you don't have something you are driving towards, so- such as for me, like, you know, like solvency, that is... It, it's really hard to be motivated [laughs] every day.
Patrick O'Shaughnessy 37:30 The other thing, though, too is that, um, very often the thing you own and control and are building might be your best investment, and, and getting money out of something is costly from a tax standpoint-
William Hockey 37:39 Totally
Patrick O'Shaughnessy 37:39 ... and other things. So you're, in, in some ways you're just, like, continue to be all in on what you're building.
William Hockey 37:44 I mean, I, like, you know, it's like bet on yourself. I'm sure, like, every like, you know, fancy executive has probably told you that, but I, I think it is, it is somewhat true. Compounding on yourself is probably the best investment to make. Like, I, like, I'm not a generalist. Like, I'm a specialist. I'm, like, probably the best in the world at, like, a couple small boring stuff. Like, I, I'm, like, really good at creating really confusing boring-sounding companies that's really hard to explain on podcasts.
Patrick O'Shaughnessy 38:11 [laughs]
William Hockey 38:11 And I think that's, like, that's, like, my expertise. That's, like, [laughs] my niche. I feel pretty confident in my business because I do not think in my business you wanna compete with me. I'm, like, I'm mean, I'm hungry, and I know my little niche space better than anybody in the entire world. And if I'm, like, investing or doing something else, I'm like, there's, like, a me on the other side of that trade. Like, like, I don't wanna do that. I'm a builder. And I think sometimes there's a trap where builders think they're investors and investors think they're builders, and there are rare cases when you can do both. Um, but in a world where it's increasingly competitive, um, I do think the world for builders is going to... I- is, is the world of specialists. Um, and you have to go extremely, extremely deep into your area, and that's where you fi- that's where you find value. And, like, I, I probably have read more about just, like, the history of my space, the history of financial services. Like, like, like, I studied, you know, I studied banks in Japan in, like, the 1800s. I, you know, read, like, a very boring 2,000-page book on the history of, like, banking in China in the 19th century, and there's stuff I got out of that.
Patrick O'Shaughnessy 39:21 What's something... Not necessarily that book, but, like, what's something you get out of that degree of extreme study?
William Hockey 39:25 The hard part about this is you probably get, like, one small thing in a 2,000-page book.
Patrick O'Shaughnessy 39:29 Yeah.
William Hockey 39:29 And so it's probably, like, not efficient unless you own a thing that happens to be in that space-
Patrick O'Shaughnessy 39:33 Has crazy leverage on that
William Hockey 39:34 ... and that, like, one little thing can create, like, millions of dollars of value. Two of these and it creates, like, hundreds of millions of dollars of value. And so without kinda going too much into detail on it, like, like, that is, like, that's where you find, that's where you find your leverage. Um, and I'm, I'm pretty good at that.
Patrick O'Shaughnessy 39:50 This notion of being the best in the world at the thing you do is re- really interesting to me. It, it, it seems the environment today makes that harder than ever 'cause there's so much distraction.
William Hockey 40:00 Totally.
Patrick O'Shaughnessy 40:01 And there's such a high rate, uh, and ease of comparison-
William Hockey 40:04 Yeah
Patrick O'Shaughnessy 40:04 ... um, which is certainly the thief of joy. [laughs]
William Hockey 40:07 Yeah.
Patrick O'Shaughnessy 40:07 Um, but, but it's really hard to ignore people doing other stuff.
William Hockey 40:11 Totally.
Patrick O'Shaughnessy 40:12 Spending a third of your day reading about Anthropic or, or whatever. It's exciting.
William Hockey 40:15 Totally.
Patrick O'Shaughnessy 40:16 So what have you learned about how to become... Apart from reading, you know, obscure-
William Hockey 40:21 Yeah
Patrick O'Shaughnessy 40:21 ... 19th century Chinese banking books-
William Hockey 40:23 Yeah
Patrick O'Shaughnessy 40:23 ... like, what else have you learned about how to become the best in the world at what you do, assuming that there's less people interested in that, like, that mission or that idea?
William Hockey 40:31 So 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? Like, who doesn't find, like, AI interesting? Like, yes, geopolitics, fantastically interesting. There's all these, like, general topics that are quite broad that is very, like, mass market interesting, and that's what makes Twitter so fascinating and that's why podcasts are fascinating, is because people like to feel that they are, they are, like, really smart across a broad swath of categories. Um, but that, that doesn't really align to company building. Um, so many people right now are thinking about and/or 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, like, be the next, like, CRM. These are, like, generalist topics that I can probably find 1,000 people that have, like, pretty, like, 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 be, like, can generate billions of dollars in revenue over time." But the problem is, is those places are really boring. Like, the fun ones, like food and, like, surfing in Thailand or whatever, like those are solved categories. Like, yes, I would also love to be an expert on, like, hospitality in, like, Thailand and Southeast Asia. Like, that's a fun problem. I could imagine one going niche on that for, like, a multi-decade period, but that's solved problems. But I think finding the extremely boring thing that requires you to read hundreds of thousands of pages that you cannot, like, Gemini deep research your way through, that's where value is, but it's fucking boring for a lot of people. Like, you have to, like, you have to suffer in silence for a huge amount of time, and if you can find that, you know, if you can find that, like, super fascinating, you can, like, love to learn that, then I think you'll be successful. But I think it's a, it's a mi- it's a minority of people.
Patrick O'Shaughnessy 42:33 Mm.
William Hockey 42:33 Like, like, like, my partner kinda gives me shit all the time, but, like- How on earth do you find that book interesting? Like, what is wrong with you? Um, I was like, "Well, like, if I don't, like, you and I are gonna be super poor."
Patrick O'Shaughnessy 42:43 You, you said earlier that building a company for the second time is a lot easier than the first time.
William Hockey 42:47 Yeah.
Patrick O'Shaughnessy 42:47 What are the most, uh, extreme ways that that's true? Like, what, what are the things that you've done the most differently this time than the first time?
William Hockey 42:54 Yeah. E- e- experience is valuable. Like, I started, uh, I started Plaid right out of college, and I think, um, Zach, who was my absolutely incredible, incredible co-founder, we both kinda said like, "Man, if we would've just, like, worked at a company for like nine months-
Patrick O'Shaughnessy 43:07 We would've learned a lot. [laughs]
William Hockey 43:08 ... like, we probably would've saved like three years." Because the amazing thing [laughs] about working at a company, especially an early-stage company, is you just, like, you just get to, like, fail forward all the time, and that's, like, incredible. That's an incredible lesson. But, like, when you fail forward as a founder, that's a lot of dilution. [laughs] 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 'cause, like, everybody's YouTube videos on like, you know, YC Startup School, and there's, like, a playbook, and there's like some PDF for everything, and you can probably, like, Gemini your way through, like, the early [laughs] stage part of a company, but experiences matter a lot.
Patrick O'Shaughnessy 43:41 What about picking talent? Like how, how... What things do you optimize for now that, uh, have been honed because of your prior experience?
William Hockey 43:50 I mean, people always think about employees and this, like, like kind of missionary-mercenary framework, right? Which is like, like you have to look into employ and like what, like what do you wanna do? There's, like, the mercenary type, which is, okay, super smart, probably super pedigreed, and like, and really what they're doing is they are using your company as a launchpad for something else. They are using, they're using their company to, like, collect a bunch of, like, two-year vested options from, like, the top five companies and, like, hoping one of them goes up. That can be a valuable employee, but you have to have a very, like, specific type of company that is used to, like, that churn and burn in order to take advantage of them. Then you have, like, the missionaries, right? Which is, um, hey, like, y- this person is very mission-focused. They're very, like, 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. These people also have some downsides as well, which is, you know, the moment maybe you wanna be a little bit more commercially oriented or the moment you have to maybe make trade-offs on your mission or something like that, that can cause a lot of, like, societal unrest inside of your company, right? And then there's, like, the third category of employees, which are, um, you know, generally what I think are probably, like, the best, which is, like, there's a kind of a combination of everything, but really what they care about is they care about, yeah, we want a ton of upside, but we also want, like, we want some stability. We also want people that, hey, like, I get... 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 willing to,
Longevity and Profitability in Banking
William Hockey 45:20 like, work really hard to get there. Everybody has personality types. Everybody has different styles, and you kind of have to figure out what is right for your business. But I think it's very challenging to tell that on LinkedIn. Like, everybody's like, "Okay, cool," like, "You went to the right New York prep school, thus you went to, like, the right, like, Ivy League school that happens at, like, this good engineering program." And then you have, like, you know, these, these couple, like, LinkedIn things that are, like, good for me, and, like, boom, done. That can be super successful, but that is also, that is also not the right for everything. And so just, I think getting that kind of hone for talent is, is super important.
Patrick O'Shaughnessy 45:51 How much do you care about mission? It's like such an-
William Hockey 45:53 [laughs]
Patrick O'Shaughnessy 45:53 ... interesting part of the equation.
William Hockey 45:55 You need a mission, right? Otherwise, people are just gonna work at hedge funds. Like, you need to say like, "Hey, we are building something bigger," and I think we absolutely are. Um, but I think mission can actually be a little bit distracting. I think a lot of times people focus a ton on like, "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, like, 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. And I think that's because when you're pitching investors, like, investors wanna feel like they are, like they are part of something. They wanna feel that like, "Man, like I'm not just, like, recycling pension fund money into, like, other capitalists." Like, even if that's what we do, like, we want to feel like it's, it's bigger than that. And so I think we've taught people that like, "Man, you need to focus on, like, the millennia journey. You need to focus on, like, the impact that we're doing." And like, yes, like, you know, the numbers go up, but, like, numbers go up is, like, only, like, one part of the equation. Um, and I think that's, like, important for employees, but I think it's, like, sometimes not the best. Like, in the end, like what do you wanna do? You wanna convince somebody to buy your product and, like, you deliver them enough of an experience that they can't build it themselves, and they're gonna pay a lot of their hard-earned money to you. Like, 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 [laughs] for me, and am I willing to pay for it?" That's it. And if you, if you start to, like, you know, drink your own Kool-Aid too much, you kinda forget that.
Patrick O'Shaughnessy 47:18 [laughs] It makes me smile to think about your earnings and cash flows. It's, like, such a novelty that a company like yours would have a bunch of this-
William Hockey 47:25 Yeah
Patrick O'Shaughnessy 47:25 ... uh, at this sta- you know, so young in its life and s- at this scale. How do you pick your margins? Like, how do you think about, um, how profitable to be and why? Y- you mentioned earlier that it's like having a funding round-
William Hockey 47:37 Yeah
Patrick O'Shaughnessy 47:37 ... every year. Does that imply that you're, you're actually spending it so you're not paying taxes-
William Hockey 47:41 Yeah, yeah
Patrick O'Shaughnessy 47:41 ... so then you can spend it on growth? Like, how do you think about [laughs] earnings-
William Hockey 47:45 Yeah, yeah
Patrick O'Shaughnessy 47:46 ... in, in a high-growth technology business?
William Hockey 47:48 Our customers pay us for safety, and our companies pay us for longevity. It's a unique thing around financial services where I'm gonna look at you as a customer like, "I'm gonna be your best partner over, like, a 10 to 15-year period." Switching costs are really high, and they are putting a lot of, like, your customer trust and risk in you. And, and so I am playing, like, 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, and not relying on somebody else's decision-making framework is extremely critical for our customers and, and that's extremely important to me as well. Like, I, I, I tell people, I'm like, like, "The risk falls on me." Like, I can't pass my risk to some other venture fund or, like, their LPs or something like that. Like, I, I wanna be... Like, 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, like, quite, that's, like, quite unique in Silicon Valley because, you know, at some point, like, this company could get, like... Your critical vendor
Matching Your Capital Structure to Your Business
William Hockey 48:46 could get, like, acquired, or maybe the, the founder could get, like, a $20 million offer from Anthropic. And, like, it's the rational decision for them to do that. In many ways, like, we aren't competing with other Silicon Valley companies. We're, we're competing against maybe them doing it themselves, or maybe competing with them trying to, like, build a patchwork of software vendors on top of, like, 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, you know, people are like, "Oh, like, you know, like, your margin's my opportunity," type thing. And my argument would be, like, you run this business at, like, a lot lower margins, you're gonna be dependent on somebody else that you probably don't wanna be dependent on. You also have to be introspective about your business. Is, 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, 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'd grow it, like, you know, a thousand times faster than I am right now, and I don't necessarily think I, I, I should. And so what we do is we say, "Okay, like, of this earnings, what goes to employees, what's gonna go, what's gonna go to growth, and what's gonna go to, like, capital?" Which is pretty much like, in case something goes wrong or, like, we have a couple bad couple years, like, 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"? Like, there's a lot of societal change going on. There's a lot of, like, 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.
Patrick O'Shaughnessy 50:18 Mm.
William Hockey 50:18 How do I make sure I can survive that even with a lot of our companies go up or, you know, the economy's under changes? That kinda goes back to that, like, that, that war chest. Markets go like this. Like, sometimes, like, yes, like, the line through it [laughs] goes like this.
Patrick O'Shaughnessy 50:31 You forget it when you hit one of the good ones. [laughs]
William Hockey 50:33 Yes, exactly. A- a- you know, and, and we, you know, and, and, and we look at slope, but a lot of times, like, we have down years.
Patrick O'Shaughnessy 50:39 Yeah.
William Hockey 50:39 And you need to be able to weather through those down years, and there's so many incredible companies that just, like, couldn't survive, like, a couple bad periods, and you really wanna make sure you're not one of those.
Patrick O'Shaughnessy 50:49 As your business scales up, everything gets more complex, especially your compliance and security needs. With so many tools offering band-aids and patches, it's unfortunately far too easy for something to slip through the cracks. Fortunately, Vanta is a powerful tool designed to simplify and automate your security work and deliver a single source of truth for compliance and risk. There's a reason that Ramp, Cursor, and Snowflake all use Vanta. It frees them to focus on building amazing differentiated products, knowing that compliance and security are under control. Learn more at vanta.com/invest. I know firsthand how complex the tech stack is for asset management firms, and seemingly every new tool and data source makes the problem even worse, adding more complexity, more headcount, and more risk. Ridgeline offers a better way forward, one unified platform that automates away the complexity across portfolio accounting, reconciliation, reporting, trading, compliance, and more, all at scale. Ridgeline is revolutionizing investment management, helping ambitious
The Unseen Power of the US Dollar
Patrick O'Shaughnessy 51:44 firms scale faster, operate smarter, and stay ahead of the curve. See what Ridgeline can unlock for your firm. Schedule a demo at ridgeline.ai. If you were in a, a classroom setting and it was a bunch of founders or would-be founders-
William Hockey 51:57 Yeah
Patrick O'Shaughnessy 51:57 ... and it was a Chatham House Rules off the record-
William Hockey 52:01 Yeah
Patrick O'Shaughnessy 52:01 ... uh, session, teaching them about working with investors and what investors care about, how they behave-
William Hockey 52:07 Yeah
Patrick O'Shaughnessy 52:07 ... uh, things to look out for, what, what would be... What would you, what would you tell them?
William Hockey 52:11 I actually feel pretty lucky where, you know... At, at Plaid in the early days, we, we actually had a pretty hard time fundraising. At first, I think we probably chatted with, like, 80 or 90 investors and we got rejected. And so I, uh, like, sometimes I think I have a reputation of being like, oh, like, William's, like, somewhat anti-VC. It's actually, like, not furthest from the truth. I... Like, Plaid would not exist without VCs, straight up. I just don't necessarily think, like, the VC model is perfect for every single type of company. Um, or, like, maybe, like, a VC owns, like, you know, 10% of your company or 20% of your company, um, and maybe the employees own something like 80%. Like, like, there are different cuts of this you can make. But I think for me, I think picking investors is important. I don't think there's a lot of transparency in the environment on, like, which investors are seven-year timelines, which ones are 10-year timelines, and which ones are, like, 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, like, how am I... Like, realistically, what does my margin profile look like? What is my revenue growth over time? And what... 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, the venture model makes sense for me?" Because the thing that people forget is, yes, growing 100% on a $10 million base or a $20 million base or a $30 million base, you know, it's not like, it's not, like, that hard. Everybody likes shows these graphs now on LinkedIn, like, "We're the fastest company to get to $100 million, like, of all time." And, like, that's awesome, but you know what's, like, much harder? Growing, like, above 30% a year off of a billion dollar revenue base. That is, like, 99 times harder than going from zero to $100 million in three years. However, the venture model only, only works is 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 in, dollar out, and the venture model is built off the fact of you can make a company like an ATM, which is you put in a dollar, you get $1.30 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, and there's, like, so many amazing tech companies that works for, and that's why that venture is, like, a, like, 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.
Patrick O'Shaughnessy 54:50 Given your unique perch, what have you learned about how the world works through the lens of this, like, dollar, this dollar focus, this demand for dollars being the operating system for the, you know, global dollar system? Like, through the lens of the dollar-
William Hockey 55:03 Yeah, yeah
Patrick O'Shaughnessy 55:04 ... what, what are your takes on, like, the ways the world works or, or interest you that might surprise people?
William Hockey 55:10 What the dollar does and, like, it, it, it connects countries in, like, very interesting ways that I think in the US where you can pretty much just build a incredible company by, like, the, by the US alone, you, you kind of lose that perspective. If you look at the official stats, um, like, like, uh, like most economies spend less than 10% of their GDP, um, trading with their neighbors.
Patrick O'Shaughnessy 55:33 Mm.
William Hockey 55:34 Um, and that's, like, been a big focus point of, um, of the OECD over, over the, o- o- over the while. But when you actually dig into it, like the unofficial trade that's going, like, not over, like, l- l- uh, government rails, it's actually closer to 90%. And it just shows, like, how trade and how money and how that stuff, like, really connects these cultures and connects these societies, and I find that, like, super fascinating. But it's, it... And, and you can talk about, like, 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, like, very unique luxury of, like, we can almost somewhat sustain ourselves and, like, you can do the same businesses only building for yourself. The US market is just so fantastic. Like, 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 fucking unique. I don't think we get, like, how much of a luxury that is. But outside of the world, like, 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. Like, let's take, let's take two, like, 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, like, you know, probably neither one of these countries, like, love America, like, a ton. That trade is denominated in dollars. That... The, the, the money that's moving from Switzerland to Qatar, from, like, Glencore to Qatar, the Qatari Gas Company crosses the US financial institutions. It's crazy to think about. Let's think about, you know, who are maybe our two, like, quote-unquote enemies, like China, Russia, okay? Um, China's a big importer of Russian gas and oil. It's kinda 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, like, nobody else has. Russia doesn't want Chinese currency. Chi- China definitely doesn't want the ruble. They barely have access to it. They almost, like, 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, like, maybe the dollar's eroding over time, stuff like that, but, like, still in the vast majority of, like, like 75% of global trade still is in the dollar. That's, that's, that's crazy, and we don't recognize that. Like, the soft power the American has or even the hard power that the American has with that is so, is so fundamental to our life and the fact that, like, we have such a strong economy.
Patrick O'Shaughnessy 58:18 Do you talk to your team as though this is part of the mission? That, that, like, n- almost like national security is part of the mission because of the importance of the dollar?
William Hockey 58:26 100%. One of the best kind of shifts I think Silicon Valley has done is we now are like, "Hey," like Silicon Valley, like we take an active role in the national security of the country. I... We, we didn't six, seven years ago, even though, like, like America, like American society, American GDP growth is even more than ever completely indexed on the success of Silicon Valley. Like, probably too much, and it's, like, way too levered in that, in that regard. But now Silicon Valley, whether it be, whether it be social media, whether it be defense, or whether it be software, whatever, we're starting to recognize, like, our role in the world and financial services is probably the most important component of that. You can ask, like, you can ask any general and, like, I have. It's like, like they wanna use a sanction before they use a missile. The great thing about a sanction, the great thing about the dollar is you can enforce American dominance without putting boots on the ground, without putting anybody at risk. And sometimes you show in Venezuela, it's like, hey, like you kinda need both. But like, like the reason we were able to go to Venezuela is because we had fundamentally destroyed the economy before.
Patrick O'Shaughnessy 59:29 How?
William Hockey 59:30 Sanctions, right? Like we had completely collapsed, like, their ability to export oil. We completely collapsed their ability to actually trade with other people. That, those, that, those, that friction is real. And so when we went in there, Venezuelan people were probably like, "Yeah, okay." Like, "We're good." Like, "We're maybe not gonna try to, like, shoot these helicopters from the sky." Like, "We're pretty happy here." That is fundamentally so amazing. If France wants to, like, shut down another country in order to go, like enforce their will, like they have, like, an option. Well, they have, like, two options, which is like, I don't know, like, "Don't drink our wine," and, like, "Here's, like some, here's some missiles," okay? Like, the missiles can enforce their will. Like, they have a strong military, they have strong special forces, they can go do that. But their lives, the special forces on the ground, like they're gonna have a much harder time because they haven't kind of in many ways controlled that economy before, and that is so, so unique to the US. And I think China's obviously developing this with trade and exports. Like, one of the things that China can do is they can start to enforce their will by shutting down a country from exports, right? And so that, that is real. And so I think China has definitely this, like, increasing might, but the strength of the dollar and the strength of that is so fundamental for national security. And in many ways, like we, we don't talk about it because it's a little bit uncomfortable truth. Right? Like, I don't think anybody wants to sit up there and say like, like a, like a global bank doesn't wanna sit up and say like, like, "We're part of the national security strategy because, like, if the government tells us to, like, we're gonna collapse this economy," right? Like, that's not a, that's not like a fun narrative that people want. But I think there is a, there's a way to tell that narrative that says like, "Hey, like, 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 US interest, and we are a 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 like, is a key pillar. Like, you can argue that financial services is like the first end to war to our country, right? Like, we start with sanctions. We start on cutting them off from the US, from the US trade. We start with that before we put boots on the ground.
Patrick O'Shaughnessy 1:01:28 What do you then hope is the future of global financial services? Like, obviously you're bui- y- you're actively building the technology backbone for it, but if you think big picture-
William Hockey 1:01:37 Yeah
Patrick O'Shaughnessy 1:01:37 ... how do you hope the system changes? What would be best for it?
William Hockey 1:01:40 I still hope it's very US-bound, and I think we sometimes wanna believe this world where, um, 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 hours talking about. I still think we're the greatest country in the world and, um, we have a change of power every four years. Like, we change our mind on stuff. Yes, there's like, there's like some problems, but we are still, 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, the world's trade. Um, 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
How AI Will Transform Legacy Banks
William Hockey 1:02:30 think people have really, like, thought through the ramifications of that. Um, 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 in the public, 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. Um, like JPMorgan's the largest financial services country in the US, but like it's not that dominant. It's like, it's, like, it's still pretty diversified. Take, take Canada. 95% of Canadians have four banks. Take Australia, it's even more concentrated. You go to most countries, it's even more concentrated than that. Like, we do have a little bit in financial services today, a relatively def- decentralized financial services system. It should 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. And I think the other thing I tell people as well is like there's this narrative like, "Oh, financial services is fundamentally broken." Like, our institutions are actually pretty damn good. There's this narrative sometimes people talk about. It's like, "Oh, like US financial services, it's like built on like cobalt and stuff like this." It's just not. It's just, like, not true. It's like a fun talking point, but like, like I like, I rack my own hard with the Federal Reserve and all these, like, places. Like, there's no cobalt in a lot of these places. Like, it's actually pretty good. Like, like go on the record talking about this. The Fed has a pretty good tech team. Like, their systems are actually pretty good. If you think about it, like, the US right now, through the Fed, has the capability to move money and to clear money through all these institutions 24/7, faster than stable coins, 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.
Patrick O'Shaughnessy 1:04:19 Mm.
William Hockey 1:04:19 The problem isn't in the fundamental infrastructure. It's in our implementation of it. The reason why community banks can't send money 24/7 isn't because, like, the technology doesn't exist at the Fed. It's because there are constraints in those business models that make it very challenging for them to do. Give you 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, like, been to a rural community with a community bank with 50 people. You can't get people to work on the weekends. Who's gonna go there? Sure, if you're JPMorgan, if you're Stripe, yeah, you can manage 24/7 liquidity. But if you're a small community bank, you can't have that. And so I think, I think people conflate we don't have something, we don't have access to something with we don't have the fundamental ability to do that.
Patrick O'Shaughnessy 1:05:14 Mm.
William Hockey 1:05:15 But actually the reason is implementation, not the underlying infrastructure.
Patrick O'Shaughnessy 1:05:19 I feel like because of your unique setup as a business and your unique focus on the boring problem, as you describe-
William Hockey 1:05:26 Yeah
Patrick O'Shaughnessy 1:05:26 ... um, 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, um, that you think is interesting that we've missed?
William Hockey 1:05:38 One of the things that I think about is like, okay, like AI is here. We're probably like cl- much closer to ASI than people think, and it's gonna be on a tidal wave through the economy. You have to think about like, okay, like what's the implications for your business? And, and I think in my perspective is like if you're not a researcher, if you're not a lab, how do you play? And I think one of the things I think a lot about is, okay, like I actually don't think like quote unquote AI companies are very set up for success. That's actually probably not where value's gonna accrue. The value's gonna accrue like in two areas. In the most important area, I think, do you have massive distribution? 'Cause if you have massive distribution, if you have massive costs, AI's gonna be a massive boon for you. And so the thing I think a lot about is, okay, like 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 like, you know, the railroads. Like, like the value didn't... Like 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, like, harness that the best. Like, the value in railroads accrued to the oil companies. That's like not like ... That's like a little bit like hard to fundamentally understand. The Standard Oil's the biggest beneficiary, biggest boon for railroads by, by, by an order of magnitude. Um, what is like the equivalent area for AI? And I sometimes don't think we're focused on that enough. Like, uh, like hot take here, I think like the biggest, fattest, most inefficient brands are gonna be the best beneficiary of AI because brands have a massive moat, and man, there's a lot of cost to cut there.
Patrick O'Shaughnessy 1:07:18 How do you think AI will most affect financial services specifically, maybe even just like your own products and services?
William Hockey 1:07:24 Financial services, especially like take like large banks, um, they suffer from the fact that the business model's too good. Um, like banking's pretty profitable. Financial services, it's like, it's like if you're like, "I'm a bank and like you aren't profitable," like that's, like that's [laughs] a problem. Like you've clearly done something wrong. Like the business model fundamentally is really good. And so that's, that's, that's made them laggards in a lot of ways. Um, but that also, I think makes their massive opportunity where I think financial services and like legacy banks tend to be like the largest inefficiencies out there. They also are very hard to take over. Like there's not a lot of private equity activity in financial services because it's highly regulated. And so I think the, the large banks that can actually effectively harness that are gonna be some of the largest beneficiaries because banks don't have a lot of like, like physical assets. Like places have like massive CapEx and physical assets, it's like hard to like tell a good AI story there. Like how's AI gonna make railroads more efficient if 99% of your money is spent on like, like fuel, track maintenance and people? Like the human cost in rail rates is like de minimis. Like cool, you take, you take conductors down from like 1,000 to 500, it doesn't, doesn't like change the equation at all. But if you think about a traditional bank, it's pretty, it's pretty headcount focused and it's pretty technology focused. That's where majority of the money goes to. Like the actual like physical branch infrastructure is like such a minority of your balance sheet. And so, so I do think they will be either be the most disrupted or probably actually like the largest beneficiaries. And so the banks that are like the most effectively run, have the largest distribution, have the largest cost structure are going to be, uh, the largest beneficiaries. I think also the ... I think the UX of financial services will change a lot because like people think like, "Oh my gosh, like my bank is hard to use. My bank is hard to move money. It's like slow to move money." That's, that's actually a feature, not a bug. I think what Fintech sometimes start with is they start with like, "Hey, we're gonna make it like super easy to and 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.
The Kindest Thing
William Hockey 1:09:24 And if you make it like really easy for your grandma to send money to somebody in Nigeria, like yes, that's like great for remittances, but that's like really bad for romance scams. It's really bad for fraud. And so but I do think with AI we can actually, we can actually like build those detection models like a lot better, and so it's probably less likely your grandma is gonna fall, fall prey to elder abuse. And if the banks don't have to optimize so much for that and it's a ... 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, to make financial services like 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, and people kinda forget that. But I think if we can build like 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 beneficiary for everybody else.
Patrick O'Shaughnessy 1:10:19 Hm. Do you think it's a good time to be an entrepreneur, a new entrepreneur in financial services?
William Hockey 1:10:24 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, um, like there's all these like s- stats on Twitter that I'm sure people have seen where like the best companies are created in the worst environments. Um, and I think that's generally true. It is cheaper than ever to be an entrepreneur, and so it is, as we talked about, it's probably, it's like probably the least risky time to be an entrepreneur. It's also pretty crowded. Um, but here like, like I don't know, you probably look at like the last YC batch, I'm sure like may- 90-plus% 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 like, like probably less competition, less smart people. I, I think i- if you wanna be successful, you can go look at every single industry and you can say, "Okay, who has the dumbest people and what makes them most money?" And if you go and like attack that area, it's probably a pretty good space. The problem is sometimes Silicon Valley or founders, you look and say like, "Hey, we're all like the smartest people." Okay. That's like, yeah, it's like maybe like a cool space, but it's probably like the most crowded with the smartest people and so your ability to compete is like, like your competition's pretty intense. You know, YC puts out this, um, you know, quest for startups. My recommendation is like that should be a list of startups you should not start because by the time [laughs] like it's so consensus that this is a good area or super interesting, the amount of capital and the amount of smart people, it's like, it's like, you know, like moth to light. I would almost go the opposite way. Like, "Hey, YC, I love you guys. Please stop ... Like continue to fund like, you know, our customers. You guys are amazing." Um, but as a founder I would maybe be a little bit skeptical.
Patrick O'Shaughnessy 1:12:14 I think your perspective is so unique and interesting. I always love talking to you. I always find it very inspirational, uh, 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, and just outlearn everybody and stick with it. Uh, I love your, 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 ever done for you?
William Hockey 1:12:40 I've had a lot of kind people in my life, but I think it's challenging to, to not look back and be like, "Oh, like your mom and dad were like the kindest people." Um, my mom and dad did not have a, um, have the most like straightforward life and not the easiest, and, and my childhood could have been a lot more difficult than it was because I think they They insulated me from a lot of, a lot of things that were going on. Um, and, you know, I had a, I had a lovely childhood, and I feel super lucky for that. And I think we've talked about it a little bit, like, as a founder, you have to be willing to take on risk. And, 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 go into adult. And my... And, and, and I feel very lucky my mom and dad did that, you know. And they also kinda 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've got punched in the face and I've, like, lost teeth is honestly kind of crazy. It's, like, kind of embarrassing. Um, but I'm, like, you know, I was pretty good at getting punched in the face. And, and, like, you can only teach that as a little kid. You can only, like, like, have that childhood that makes that comfortable in a very, in a very specific environment. And I think, you know, I have a, I have a six-month-old, and as I look at my peers and look at everybody else, we are, like, quite obsessed with creating this, like, perfect environment for our children. We send them to, like, the best schools. They have the nicest people in their lives. And, and that is, that is valuable, but we're maybe creating children that can do linear algebra at seven. And that, I guess, is, like, gonna be great. They're gonna be, like, great AI researchers. But is that what we're gonna need in 20 years from now? Um, or do we want kids that are gonna be, like, pretty good at taking risks, that are gonna be pretty good at being punched in the face? And, 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, like, the-
Patrick O'Shaughnessy 1:14:41 Sure
William Hockey 1:14:41 ... that's, like, the path we're gonna go down. And I think the fact that I am, like, pretty damn resilient, um, is a complete product of my parents, and I think that's a huge gift, and I, I feel super lucky for them every day.
Patrick O'Shaughnessy 1:14:53 A beautiful place to close. Thank you for your time.
William Hockey 1:14:55 Thank you.
Patrick O'Shaughnessy 1:15:00 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. As your business grows, Vanta scales with you, automating compliance and giving you a single source of truth for security and risk. Learn more at vanta.com/invest. Ridgeline is redefining asset management technology as a true partner, not just a software vendor. They've helped firms 5X in scale, enabling faster growth, smarter operations, and a competitive edge. Visit ridgelineapps.com to see what they can unlock for your firm. OpenAI, Cursor, Anthropic, Perplexity, and Vercel all have something in common. They all use WorkOS, 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 WorkOS comes in. Instead of spending months building these mission critical capabilities yourself, you can just use WorkOS 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. WorkOS is the fastest way to become enterprise ready and stay focused on what matters most, your product. Visit workos.com to get started. 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.
Episode duration: 1:17:12
In the uListen app, the transcript lights up word by word as you listen. Get uListen
Transcript of episode hFIvttHf0oo