YouSaid · the spoken record

William Hockey

lines on the record: 77
first: 2026-03-17
most recent: 2026-03-17
sittings or episodes: 1
sources: podcast

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“Is a complete product of my parents, and I think that's a huge gift. And I feel super lucky for them every day. A beautiful place to close. Thank you for your time. Thank you.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“And I've lost teeth. It was honestly crazy. It's like embarrassing. But I'm like, you know, I was pretty good at getting punched in the face. And you can only teach that as a little kid. You can only have that childhood that makes that comfortable in a very specific environment. I have a six-month old. And as I look at my peers and look at everybody else, we are quite obsessed with creating this perfect environment for our children. We send them to the best schools. They have the nicest people in their lives. And that is valuable. But maybe creating children that can do linear algebra at seven. And I guess it's like going to be great AI researchers, but is that what we're going to need in 20 years from now? Or do we want kids that are going to be pretty good at taking risks, that are going to be pretty good at being punched in the face? And I think my parents did a really good job at that. I feel very lucky for that. If I copy off my peers, I don't know if that's the path we're going to go down. And I think the fact that I am pretty damn resilient.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Plaid in a liquid column. I think you know my traditional closing question what is the kindest thing that anyone's ever done for you? I've had a lot of kind people in my life, but I think it's challenging to not look back and be like, oh, like your mom and dad were like the kindest people. My mom and dad do not have the most like straightforward life and not the easiest. And Mike Shaw could have been a lot more difficult than it was because I think they insulated me from a lot of things that were going on. I have a lovely childhood and I feel super lucky for that. And I think we talked about a little bit as a founder you have to be willing to take on risk. And if you grew up in an environment of fear, if you grew up in an environment where like you were constantly de-risking when you're a little kid, it's very challenging to feel comfortable going up the risk spectrum as you go to an adult. And I feel very lucky my mom and dad did that. They also taught us like, it's okay to fall. It's like, okay, we punch in the face. Like, see these? They're all fake. The night time I got punched in the face.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“We're all the smartest people. That's maybe like a cool space. That's probably like the most crowded with the smartest people. And so your ability to compete, your competition is pretty intense. YC puts out this request for startups. My recommendation is like that should be a list of startups you should not start because by the time like it's so consensus that this is a good area or super interesting the amount of capital and the amount of smart people is like moth delight I would almost go the opposite way heyc i love you guys please continue to fund our customers you guys are amazing but as a founder i would maybe be a little bit skeptical that your perspective is so unique and interesting i always love talking to you i always find it very inspirational on the dimensions of just really going your own way but also just the willingness to fall in love with some part of the world and get devoted to it and just outlearn everybody and stick with it i love your diversification strategy of illiquid”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“That stuff, and that can happen instantly, we can actually take that tail away and it actually is massively beneficial for everybody else. Do you think it's a good time to be a new entrepreneur? Anybody who tells you that it's a bad time to be an entrepreneur, that probably means it's a good time to be an entrepreneur. If you look at there's all these stats on Twitter, I'm sure people have seen where the best companies are created in the worst environment. And I think that's generally true. It is cheaper than ever to be an entrepreneur. It's the least risky time to be an entrepreneur. It's also pretty crowded, but by looking at like the last YC batch, I'm sure like my 90 plus percent of them were like AI related. So yeah, I think it's actually probably a pretty good time to be a founder in a non-AI related place right now because there's less competition, less smart people. If you want to be successful, you can go look at every single industry and you can say, okay, who is the dumbest people? And what makes the most money? And if you go attack that area, probably pretty good space. The problem is sometimes Silicon Valley or founders, you look and say like, hey,”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Finch sometimes start with is they start with hey, we're going to make it like super easy to like super free to move money all over the place. It actually starts to slow down. The reason it slows down is because fraud is like super expensive. And if you make it really easy if your grandma to send money to somebody in Nigeria, yes, that's great for mittences, but that's like really bad for romance gams. That's really bad for fraud. But I do think with AI, we can actually build those detection models a lot better. And so it's probably less likely your grandma is going to fall prey to elder abuse. And if the banks don't have to optimize so much for that, and it comes a little bit for free, we can actually make the UX better for everybody else because we have the technology right now to make financial services almost entirely instant and like entirely friction free. All the friction is actually built to protect the five to ten percent of consumers that can get hurt. And people forget that. But I think if we can build models that are just as good at humans.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Beneficiaries because banks don't have a lot of physical assets. Places have massive CapEx and physical assets. It's hard to tell a good AI story there. How's AI going to make roads more efficient if 99% of your money is spent on fuel, track maintenance, and people like the human cost in rail raids is like de minimis? You take conductors down from $1,000 to $500. It doesn't like change the equation at all. But if you think about a traditional bank, it's pretty headcount focused and it's pretty technology focused. That's where majority of the money goes to. The actual physical branch infrastructure is such a minority of your balance sheet. I do think they will be either the most disrupted or probably actually like the largest beneficiaries. It's like the banks that are like most effectively run have the largest distribution of largest cost structure are going to be the largest beneficiaries. I think the UX of financial services will exchange a lot because people would think, oh my gosh, my bank is hard to use. My bank is hard to move money. It's like slow to move money. That's actually a feature not a bug. I think what”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Financial services, especially large banks, they suffer from the fat of the business model is too good. Banks are pretty profitable. Financial services, it's like you're like, I'm a bank and you aren't profitable. That's a problem. You've clearly done something wrong. The business model fundamentally is what I get that's made them laggards in a lot of ways. But that also, I think, makes their massive opportunity where I think financial services and legacy banks tend to be larger than efficiencies out there. They also are very hard to take over. There's not a lot of private equity activity in financial services because it's highly regulated. And so I think”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Accrue to the people like building the mobile phones, but the value actually accrue to the people that could harness that the best. The value in railroads accrue to the oil companies. That's a little bit hard to fundamentally understand. The standard oil is the biggest beneficiary, biggest boom for railroads by an order of magnitude. What is the equivalent area for AI? And I sometimes don't think we're focused on that enough. Hot take here, I think like the biggest, fattest, most inefficient brands are even the best beneficiary of AI because brands have a massive moat and man, there's a lot of cossack out there. A”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“One of the things that I think about AI is here. We're going to get much closer to ASI than people think. And it's going to be on the tidal wave for the economy. You have to think about what's the implications of your business. And I think in my perspective, if you're not a researcher, if you're not a lab, how do you play? I actually don't think quote unquote AI companies are very set up for success. That's actually probably not where value is going to accrue. If I was going to accrue like in two areas, most important area, I think, do you have massive distribution? Because if you have massive distribution, if you have massive costs, AI is going to be a massive boom for you. And so I think I think a lot about is how do you think about not just from a software perspective, but from a distribution perspective and a brand perspective that you would best capture to utilize AI? Because I think people talk a lot about the railroads. Yes, the value accrue to the railroads. Yes, the value accrue to the ISPs. Yes, the value.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Can't send money 24 7 isn't because the technology doesn't exist at the Fed. It's because there are constraints in those business models that make it very challenging to 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 been to a rural community. The community bank with 50 people, you can't get people to work on the weekends. 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 people conflate, we don't have something. We don't have access to something with, we don't have the fundamentally ability to do that. But actually, the reason is implementation, not the analytic infrastructure.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“With the Federal Reserve and all these places, there's no cobalt in a lot of these places. It's actually pretty good. Go on the record talking about this. The Fed is a pretty good tech team. Their systems are actually pretty good. If you think about the US right now through the Fed has the capability to move money into clear money throughout all these institutions 24-7, faster than stablecoins, faster than crypto. Right now as we speak, we've had that for decades. Systems are very good, extremely reliant. They're fantastic. I think it's very challenging for Silicon Valley to build something better. The problem isn't in the fundamental infrastructure. It's in our implementation of it. The reason why community banks”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“It ended up just accumulating in the prolete. And say what you will about the US. And there's probably way too much power concentration in certain industries. Financial service is actually quite fragmented. JP Morgan's the largest financial services country in the US, but like it's not that dominant. It's still pretty diversified. Take Canada. 95% of Canadians have four banks. Take Australia to be more concentrated. Go to most countries that have been more concentrated than that. We do have a little bit of financial service today, a relatively decentralized financial services system. Is you still keep fragmenting, right? We should still disperse the financial power throughout multiple US corporations, multiple US people. We need to do a better job there. But we're actually starting from a pretty good baseline. The other thing I tell people is there's this narrative of like, oh, financial services is fundamentally broken. Our institutions are actually pretty damn good. There's this narrative sometimes people talk about like, oh, U.S. financial services. It's like built on like cobalts and stuff like this. It's just not. It's like a fun talking point. I rack Myron.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Still hope it's very US bound. And I think we sometimes want to believe this world where there's a lot of people in Silicon Valley that I fundamentally disagree with, that want to put the power of financial services outside of the US. And the US has a lot of problems that we can spend hours talking about. I still think we're the greatest country in the world. And we have changed the power every four years. We change our mind on stuff. Yes, there's some problems, but we're still the best place to be. And I think we are the ones that we should still have the nuclear weapons. We should still have the nuclear weapons of financial services, which is we control the world's trade. And I hope that continues to exist. And I think if we don't, I think if it just hands in the power of other people, I think that's a scary place. And I don't think people have really thought through the ramifications of that. If you look at most countries, financial services is still power, but it ends up just accumulating to government officials.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“That is real. So I think China has definitely this increasing might, but the strength of the dollar that is so fundamental for national security. And in many ways, we don't talk about it because it's a little bit uncomfortable truth. A global bank doesn't want to sit up and say, we're part of the national security strategy because the government tells us to, we're going to collapse the economy. That's not like a fun narrative that people want, but I think there's a way to tell that narrative that says we are a weapon that can be used like when our citizens come to harm, when we need to do something that is like super important for the U.S. interest. And we are part of that strategy just in the same way that Palancia is part of that strategy. Lockheed Martin's part of that strategy, Boeing's part of that strategy. And financial services is the key pillar. You can argue that financial services is like the first end to war to our country. We start with sanctions. We start cutting them off from the US trade. We start with that before we put boots on the ground.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Destroyed the economy before how? Sanctions. We had completely collapsed their ability to export oil. We completely collapsed their ability to actually trade with other people. That friction is real. And so when we went in there, Venezuelan people were probably like, yeah, okay, we good. We're maybe not going to trouble shoot these helicopters from the sky. We're pretty happy here. That is fundamentally so amazing. If France wants to shut down another country in order to go enforce their will, they have an option. Well, they have two options, which is don't drink our wine and hear some missiles. Okay. The missiles can enforce their will. They have a strong military, the strong special forces. They can go do that. But their lives, the special forces on the ground, they're going to have a much harder time because they haven't, 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. One of the things that China can do is they can start to enforce their will by shutting down a country of Mexico.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Is part That almost like Part of the The importance of the dollar 100, one of the best shifts, I think Silicon Valley has done is we now are like Silicon Valley, like we take an active role in the national security of the country. We didn't six, seven years ago, even though like American society, American GDP growth is even more than ever completely indexed on the success of Silicon Valley. Probably too much and it's way too levered in that regard. Now Silicon Valley, whether it be social media, whether it be defense or whether it be soft or whatever, we're starting to recognize our world in the world. And financial services is probably the most important component of the vet's any general I have. They want to 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're showing Venezuela, you kind of need both. The reason we were able to go to Venezuela is because we had fundamentally”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Still is in the dollar. That's crazy. And we don't recognize that. The soft power the American has, or even the hard power the American has with that, is so fundamental to our life and the fact that like we have such a strong economy.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Qatar and let's take Switzerland. Okay, you're shipping gas from Qatar to Switzerland. I would argue right now by neither one of these countries love America like a ton. That trade is nominated in dollars. The money that's moving from the Switzerland to Qatar, Glencore to Qatar, the Qatari Gas Company crosses through US financial institutions. It's crazy to think about. Let's think about boom maybe our two like quote unquote enemies like China, Russia. Okay. China is a big importer of Russian gas and oil. It's kind of crazy to think about. That trade is still denominated for a vast majority in the US dollar. That's mind-boggling. That's a luxury and that's such an insane national security strategy that nobody else has. Russia doesn't want Chinese currency. China definitely doesn't want the ruble. The ability to have access to it. They almost hate each other as much as they hate us. And the fact that they then choose a dollar is still so critical. Then you could argue that like maybe the dollars eroding over time and stuff like that, but still in the vast majority, it's like 75% of global trades.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Just shows how trade and how money and how lots of like really connects these cultures and connects these societies. And I find that super fascinating. We can talk about how that's impactful in a lot of ways. But that is something that we don't really get in the US because the US has this very unique luxury of we can almost somewhat sustain ourselves. Like you can sustain businesses only building for yourself. US market is just so fantastic. I am so long in 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 it makes America so unique. I don't think we get like how much of a luxury that is. But outside of the world, it is not. And that comes down to trade. That comes to like financial connectivity. That is so impactful and it's so important. I think you also forget how reliant the world is on the US financial system. Let's take two insanely developed countries. Let's take”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“In the entire world, probably without all history, but that's not every single business, and you have to look really intensely at yourself in order to do that. Given your unique perch, what have you learned about how the world works through the lens of this dollar focused, this demand for dollars being the opportunicating system for the global dollar system, through the lens of the dollar? What are your takes on the ways the world works or interest you that might surprise people? What the dollar does, it connects countries in very interesting ways that I think in the US, when you can pretty much just build incredible company by the US alone, you lose that perspective. If you look at the official stats, most economies spend less than 10% of their GDP trading with their neighbors. And that's been a big focus point of the OECD over the while. But when you actually dig into it, the unofficial trade that's going on over government rails, it's actually closer to 90%.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Than going to zero and 100 million in three years. However, the venture model only works if you can grow above 30% off of a billion, two billion dollar base. And you have to like really look inside yourself and be like, does my model make sense for that? And can I do that in a way that I can ingest hundreds of millions, if not billions of dollars of capital on the way and put really good use to that? Because I think sometimes businesses grow at the rate of the market or businesses grow differently than just dollar and dollar out. And the venture model is built off of 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 there's so many amazing tech companies that works for. And that's why that venture is really good asset class in Silicon Valley is probably like the best place to keep capital of any.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Picket investors is important. I don't think there's a lot of transparency in the environment on like when investors are seven year timelines, which ones are 10-year timelines, and which ones are actually truly super long-term oriented. So I think figuring that out. But I think the most important thing you should do is say, okay, realistically, what is my margin profile look like? What is my revenue growth over time? How should I find a capital structure that matches that? And am I actually going to grow at a consistent enough period? Do I want liquidity in 10 years that the venture model makes sense for me? Because the thing that people forget is, yes, growing 100% on a $10 million base or a $20 million base or $30 million base is not like that hard. Everybody likes these graphs not LinkedIn. Like, who are the fastest company to get to $100 million of all time? That's awesome. But you know what's like much harder? Greatly above 30% a year off of a billion dollar revenue base. That is 99 times hard.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“And you need to be able to weather through those down here. And there's so many incredible companies that couldn't survive like a couple bad periods. And you really want to make sure you're not one of those. If you were in a classroom setting and it was a bunch of founders or would-be founders and it was a Chatham House rules off the record session teaching them about working with investors and what investors care about, how they behave, things to look out for. What would you tell them? I actually feel pretty lucky where at Platt in the early days, I should have pretty hard time fundraising. The first one I think we probably chatted with like 80 or 90 investors and we got rejected. Sometimes I think I have a reputation of being, oh, like WAMS like someone anti-DC. It's actually like not for this from the truth. Plaid would not exist without VCs straight up. I just don't necessarily think the VC model is perfect for every single type of company. Or maybe VC owns like 10% of your company or 20% of your company. And maybe the employees yourself on like 8%. There are different cuts of this you can make. But I think for me.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“NBD, we good. Let's keep moving. Down to the extent of now, we're like, hey, if something goes wrong for 10 years, how are we like, we're good. There's a lot of societal change going on. There's a lot of crazy stuff going on in the environment. I can totally paint you a picture where like the markets get insane for the next 10 years. How do we make sure I can survive that even with a lot of our companies go up or the economies are no changes? That goes back to that ore chest because markets go like this. Sometimes like, yes, the line through it goes like this. You forget it when you're one of the good ones. Yes, exactly. And we look at slope, but a lot of times like we have down years.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Patchwork of software vendors on top of legacy bank or something like that. And so I have to show that I am more sustainable than you. And I think that earnings is a critical part of that. And I think people like, oh, like your margin is my opportunity type thing. And my argument would be like, you run this business at a lot lower margins. You're going to be dependent on somebody else that you probably don't want to be dependent on. You also have to be introspective about your business. Is my business the type of business that if I raise a bunch of money or I have a ton of earnings, I can throw all of that back on growth. And I think a lot of times enterprise software companies, they cannot ingest like a huge amount of capital. Like if you give me like a billion dollars right now, I don't know if I grow it a thousand times faster than I am right now. And I don't necessarily think I should. And so what we do is we say, okay, of this earnings, what goes are employees? What's going to go to growth? And what's going to go to capital, which is pretty much in case something goes wrong, or we have a bad couple of years.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Switching costs are really high, and they are putting a lot of their customer trust in Roskinio. So I am playing a longevity and a risk game just as much for me as my customers. I take that extraordinarily seriously. And I think earnings and being profitable and sustainable and not relying on somebody else's decision making framework is extremely critical for our customers. And that's extremely important to me as well. I tell people the risk falls on me. I can't pass my risk to some other venture fund or like their LPs or something like that. I want you to be successful. I want you to be successful if we're not like I'm the one who takes the pain here. That's quite unique in Silicon Valley because at some point your critical vendor could get like acquired or maybe the founder could get like a 20 million dollar offer from anthropic. It's the rational decision for them to do that in many ways we aren't competing with other Silicon Valley companies. We're competing against maybe them doing themselves or maybe competing with them trying to like build.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Can't build it themselves, and they're going to pay a lot of their hard earned money to you. That's the goal. And that person doesn't give a flying fuck about what your mission is. They just care about, does this product create value for me and am I willing to pay for it? That's it. And if you start to like drink even Kool-Aid too much, you kind of forget that. It makes me smile to think about your earnings and cash flows. It's such a novelty that a company like yours would have a bunch of this so young in its life and at this scale. How do you pick your margins? How do you think about how profitable to be and why you mentioned earlier that's like having a funding round every year does that imply that you're actually spending it so you're not paying taxes so that you can spend it on growth? How do you think about earnings in a high growth technology business? Our customers pay us for safety and our companies pay us for longevities. It's a unique thing around financial services where I'm going to look at you as a customer like I'm going to be your best partner of like a 10 to 15 year period.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“You need to say, like, hey, we are building something bigger. And I think we absolutely are. But I think mission can actually be a little bit distracting. I think a lot of times people focus a ton on, hey, what are like the values of my company? What good are we doing? And I think that's like an important part of the equation, but I think it's on a list of five things most important. I think it's probably on the bottom end of that five list. And I think a lot of times we can be kind of distracted by that. That's because when you're pitching investors, investors want to feel like they are part of something. They want to feel that, man, I'm not just recycling pension fund money into other capitalists. And that's what we do. Like we want to feel like it's bigger than that. And so I think we've taught people that, man, you need to focus on the millennia journey. You need to focus on the impact that we're doing. And like, yes, numbers go up, but like numbers go up is only one part of the equation. And I think that's important for employees, but I think it's sometimes not the best. Like in the end, what do you want to do? You want to convince somebody to buy your product and like you deliver them enough of an experience that they”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“the third category of employees which are generally what I think are probably like the best which is like the combination of everything but really what they care about is they care about yeah we want a ton of upside but we also want stability we also want people that hey i like to be friends with my coworkers i like to be in an environment that is like warm and welcoming but also gives me like the near term and long-term financial value and i'm willing to like work really hard to get there everybody has personality types everybody has different styles and you have to figure out what is right for your business But I think it's very challenging to tell that on LinkedIn. everybody's like, okay, cool. You went to the right New York prep school. Thus you went to like the right ivory school that happens at like this good engineering program. And then you have these couple of LinkedIn things that are like good for me. Boom, done. That can be super successful, but that is also not the right for everything. And so just getting that hone for talent is super important. How much do you care about mission? This is an interesting part of the equation. You need a mission. Otherwise, people just go work at hedgephones.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Mercenary framework. You have to look into employment, which is, okay, super smart, probably super pedigreed. And really what they were doing is they are using your company as a launchpad for something else. They're using their company to collect a bunch of two-year invested options from the top five companies and hoping one of them goes up. That can be a valuable employee, but you have to have a very specific type of company that is used to debt churn and burn in order to take advantage of them. Then you have the missionaries, which is this person is very mission focused, inspiration is super important to them. And if you get that right, they will go to like the ends of the earth for you regardless of like their short-term benefits. People also have some downsides as well, which is the moment maybe you want to be a little bit more commercially oriented. The moment you have to maybe make trade-offs on your mission or something like that, that can cause a lot of societal unrest inside of your company.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Things that you've done the most differently this time than the first time? Experience is valuable. I started plaid right at a college. And I think because Aku was my absolutely incredible co-founder, we both said like, man, if we would have just worked at a company for like nine months, we would have learned a lot. We've already saved like three years because the amazing thing about working at a company, especially an early stage company, is you just fail forward all the time. And that's incredible, that's an incredible lesson. But like when you fail forward as a founder, that's a lot of dilution. That's a lot of time. That's a lot of like wasted resources. And if you could do that on somebody else's dime, amazing. Now I think it's like a little bit easier because everybody's YouTube videos on IC startup school and there's some PDF for everything and you can probably like Gemini your way through the early stage part of a company. But experiences matter a lot. What about picking talent? What things do you optimize for now that have been honed because of your prior experience? I mean, people always think about employees and it's like I'm a missionary.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Fun ones like food and like surfing in Thailand or whatever. Like, those are solved categories. Yes, I would also love to be an expert on hospitality in Thailand and Southeast Asia. Like that's a fun problem. I could imagine one going niche on that for him with a 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 Gemini deep research your way through, that's where value is. It's fucking boring for a lot of people. You have to suffer in silence for a huge amount of time. And if you can find that super fascinating, you can like love to learn that, then I think you'll be successful. But I think it's a minority of people. My partner gives me shit all the time, but like, how on earth do you find that book interesting? What is wrong with you? And I was like, wow, like if I don't, you and I are going to be super poor. You said earlier that building a company for the second time is a lot easier than the first time. Yeah. What are the most extreme ways that that's true?”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“AI interesting. Yes, geopolitics, fantastically interesting. There's all these like general topics that are quite broad that is very mass market interesting. And that's what makes Twitter so fascinating. That's why podcasts so fascinating is because people like to feel that they are really smart across a broad swath of categories. But that doesn't really align to company building. So many people right now are thinking about and have a lot of knowledge around how AI is going to disrupt software, how AI is going to disrupt vertical software, how AI is going to be the next like CRM. These are like generalist topics that I can probably find a thousand people that have interesting, compelling ideas and can go pretty deep on that. But you can't create value there. You can create value if you're like, I'm the number one person in the entire world at this little niche thing. And I think this niche thing can generate billions of dollars from ever over time. But the problem is.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Where you find your leverage, and I'm pretty good at that notion of being the best in the world at the thing you do is really interesting to me. It seems the environment today makes that harder than ever because there's so much distraction and there's such a high rate and ease of comparison, which is certainly the thief of joy. But it's really hard to ignore people doing other stuff, spending a 30-year day reading about anthropic or whatever. It's exciting. What have you learned about how to become, apart from reading obscure 19th century Chinese banking books, what else have you learned about how to become the best in the world at what you do, assuming that there's lots of people interested in that mission or that idea? I think one of the best determiners for success of founders is can they find the most boring thing humanly possible interesting? And can they find that interesting over a multi-decade period? Who doesn't find it?”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“The hard part about this is you probably get like one small dang in a 2,000 page book. And so it's probably not efficient unless you own a thing that happens to be leverage on that like one little thing can create millions of dollars of value to these creates like hundreds of millions of dollars of value. And so without kind of going too much into detail on it.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“mean I'm hungry and I know my little new space better than anybody in the entire world and if I'm investing or doing something else there's a be on the other side of that trade I don't want to do that I'm a builder I think sometimes there's a trap where builders think they're investors and investors think they're builders there were cases when you can do both but in a world where it's increasingly competitive I do think the world for builders is the world of specialists And you have to go extremely, extremely deep into your area. And that's where you find value. I probably have read more about the history of my space, the history of financial services. I studied banks in Japan in like 1800s and read like a very buoyant 2,000 page book on the history of banking in China in the 19th century. And there's stuff that got out of that. What's something done so that book, what's something you get out of that degree of extreme study?”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Confusing, boring sounding companies that's really hard to explain on podcasts. And I think that's like my expertise. That's my leash. I feel pretty confident in my business because I do not think in my business you want to compete with me.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“I do need to probably diversify. And so that is a goal for me at some point as a 36 year old. You should probably not be this concentrated. But it's also, that's what makes building companies unique. There's probably a lot of people that look at me and they're like, oh man, billionaire amazing. I think that's what makes it special. I think that's what drives me every day, which is if you don't have something you are driving towards, such as for me, like solvency, it's really hard to be motivated every day. The other thing, though, too, is that very often the thing you own and control in our building might be your best investment and getting money out of something is costly from a tax standpoint and other things. So in some ways, you're just continue to be all in on what you're building. Bet on yourself, I'm sure every fancy executive has probably told you that, but I think it is somewhat true compounding on yourself is probably the best investment to make. I'm not a generalist. I'm a specialist. I'm probably the best in the world, a couple small, boring stuff. I'm really good at creating really...”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Companies to be just super safe companies. Like, hey, we're going to pivot to AI, wrap open AI, wrap anthropic, whatever. Like, that's not bold. That's not ambitious. And it's because we're attracting founders that actually maybe want to be employees. They don't actually think about the long term. They actually don't think, say, hey, if I don't pull this off, I'm going to become bankrupt. My life is over. And I think that's pretty healthy. That's when you bring out the rawness of humanity. And I don't see that very much anymore. How have you felt that in yourself? So how has your behavior changed or your perspective changed or like just the ways that you show up that are different now than prior to this pretty extreme three-year period? I am not the most diversified person on the planet. I own two things. I own Column and Plaid. That's it. I don't even own a majority of my house. That is truly it. Those are the only two things. And that's motivating to me. At some point in my life, I have a six-month-old son.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Maybe in five, six years, I'm going to make like millions of dollars that I couldn't make at Google and Meta. That's actually a lot of risk. Say, I'm going to live with my friends instead of living by myself. Like I'm making massive, massive changes to my life. But as a founder, you're not. It's a much higher likelihood at the next round, regardless of your company, you'll be able to sell some secondary. You know that Yvit shuts down. You can go be employed a great company. You have a C on your resume. That first employee, they have first employed like a failing company. That's actually not a great resume light item. And so we've de-risked the founder, but we haven't de-risked the early stage employee. And I don't think we should actually de-risk the early stage employee for what it's worth. I just think we need to increase the risk for founders. I think we need to make failure much more expensive. I think we need to say, hey, you're a second time founder of liquidity. Put all of your money into that. If you're going to be asking this if employees are just asking for yourself, and I don't think we're having that conversation enough. And I think starting companies to just do fucking safe. I think it's caused a lot of”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Let's talk to an example here. So I'm a 24 year old. I'm making TTC perspective 400K, 500K at Google and Meta or something like that. Okay. And I'm going to go to an early stage company and I'm going to go get 1% of this company and I'm going to make $90,000. Well, I've now changed the trajectory of my life. I can no longer buy a house. I can no longer go on the vacations I want. So I'm making like a four to five year trade off where I'm saying I'm going to make pretty much no money over the next four or five years.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“A lot of great founders and a lot of great companies because there is no risk in And I think that creates just so much intensity and creativity and fear that is such a critical part of the founder journey. And I don't know why we don't talk about it more. We don't create environments where a founder has to bet themselves. And I think if we did that, I think we'd actually be in a slightly different place. I always am somewhat perplexed by I'm a second time founder, but I'm not alone. Like there's a lot of great founders I shall not name that have made a bunch of money. And you go dig into like, oh, here's my second company, the third company. And you dig into that of the hundred million dollars they've made. They're putting like a million dollars of the capital risk and they've raised $500 million. And I was like, why if you believe in this so much, if you're going to dedicate your life to it, why the fuck aren't you going all in? And if I'm an employee, I look at them. I'm like, you asking me to go all in, but you can't go on. Because the weird thing is an early stage employee takes way more risk than an early stage founder. Explain that.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Literally only one door in front of you. You don't have a choice. You have to go in. And that fear and that innate desire creates another part of your creates creativity. It creates inspiration. It's extremely valuable part of the founder journey. In many ways, I think in Silicon Valley, we've actually removed that. Do you think about most founders these days? I talk all the time like, hey, you talk to a 23-year. I'm like, you know what? I'm thinking about going to be like the 12th employee at this company or starting a company for myself. And I don't know. I'm kind of like mixed. And we've created this incredible environment in Silicon Valley that it's really safe to start a company. And there's like a playbook and you go through YC and assuming you're moderately competent and went to the right high school and college, you're going to get like a $3 million seed round. And worst case scenario, you can go work at a great company as an engineer. You'll have a found on your resume. Life is good. And that has created a lot of value. But I'm not quite sure it's created.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Usually the exact time when you do not want to hold that private jock. I have immense appreciation for the people that did it for me. I'm not quite sure they got like a great deal out of it. And I'm not quite sure I would definitely be in that business. The reason I feel this story is important to tell is that it's these things where so much of the value gets created, the extreme entrepreneurial risks, the act itself, but also the psychology behind it. And I'd love you to just riff one bit more what the psychology was like and how your mind is different after that three-year experience than it was before, even though I know you'd already been through the entrepreneurial ringer with Plaid. What changed about your mind, your perspective on the world? How did that experience affect you? I think that the good founders bet on themselves and take an extreme amount of risk to do that. And I think the extreme amount of risk part is something that we no longer have. But when there's”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“But I think the idea of like, oh, like, you know, billionaire buys thing and stuff funds it's probably a little further from the truth than people die. What's it like getting margin called? What is the literal thing happening? How do you manage through that? Surface to say you owe a bank a million dollars AOU, you owe bank a billion dollars like you own them. Like I think that's a little bit. I mean, there's a reason that like margin lending in private companies is not a great business because when you want to take collateral of that stock.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Because I had a fundamental thesis that we could pull this off and we could build a business at 100% of employees and myself out. But to do that in a world where you need to invest and not make money for multiple years is very, very challenging. And if the regulatory climate at the time and the building company, it was intense and I have this loan I have to pay off. It was probably the most intense period of my life. And as a founder, you have to shelter that from everybody. You need to be transparent. You need to bring people in, but you also need to like not bring people all the ways in. I had pretty extreme conviction myself and I thought I knew 100% over a multi-decade period I can pull this off. But there's that quasi quote of markets can stay irrational longer than you can stay solvent and it's true. And I look at that quote and I'm like, which side of the equation am I on in my day? And we ended up making it through and I got an amazing place now. We have a big company that I own.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“It didn't go through it. We got blocked by the DOJ. And I did not sell my company. Thus, I did not have any money. And so my liquidity versus paper wealth was pretty extreme. And so I think I got a lot of credibility from people like, oh, this guy's like for this guy to say, yeah, he's a yeah, but I did not have any money. Is that going to go into too much details of it? Like I pretty much funded the entire company with debt, dwind to a bunch of banks and I said, here's a bunch of plaid shares. Please give me money. And the best I got was like a sofa plus 10% loan at 5% LTV. And so I pledged over a billion dollars of stock to get 70 million dollars. Wow. And I bought the bank for $70 million. I haven't had a lot of money in my bank account for a long period of time. And yes, and I ended up business profitable. I got to pay off that loan period of time. But in the process, I probably got margin called three times and almost went bankrupt multiple times. Talk about that stress. Let us in a room. I mean, the first three years were definitely the most stress of my life.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“But it doesn't resonate with everybody. And so building a company, building a culture that actually optimized it 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. How much of this was just possible because you were already rich at the start and had money to fund something like this? Is this portable advice? Could someone else that hadn't had the experience you had with PLAD do something like this without taking outside money? I think it's hard. I think it was definitely successful at first. But what I would say is, I'll kind of go too much details. Yes, I started a very large company. I think I was probably less liquid and less rich than probably everybody thought at the time. When I started this, Plaza, funny story, we attempted to sell it to Visa for $5 billion. And that's the point when I left to go start something.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source
“Times is like founders of VCs. We think that people join companies because they want to become billionaires. Maybe that's true up to a point, but a majority of people join companies because they hit into like the late 20s or the early 30s. And like, what are they optimizing for? I don't send my kids a good school and private school. I want to not live with roommates and like a one-bedroom apartment up until like I'm 35. Housing and education, that's super important. You can't feed that on a liquid stock. So how do you think about optimizing for that? Basic things like team, cultural, that stuff. Like people want to work for somebody who feels like they are taken care of, not just a 20-year period or like, here's your path to being like a deck a millionaire. Do they understand my short-term needs? Can you take care of me in the short, medium, and long term? And I think sometimes we are maybe too long term oriented. Sometimes they, hey, yes, of course, come with me. We'll work on this for 20 years and you're going to be a decade million after that. That resonates with the servant type person.”
2026-03-17 · Invest Like the Best · William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] · IDENTIFIED FROM THE TRANSCRIPT · source