Description

Henri Stern (X, LinkedIn) is the co-founder and CEO of Privy. Privy builds wallet infrastructure for developers, enabling them to let their users hold and use crypto, including stablecoins. Privy was acquired by Stripe in 2025, and remain an independent organization within the company. They work with large fintechs like Ramp and Klarna while also supporting some of the most notable crypto-native platforms like Hyperliquid. Henri also supports a number of other crypto efforts within Stripe.

Henri is thoughtful, measured, and principled. Yet he is also pragmatic. He doesn’t like to play philosopher and yet he is one of my favorite people ask big questions about our future and our digital lives. Our conversation is anchored in the phrase at the bottom of Privy's website: *"technical decisions are moral decisions." *

He and Asta Li started Privy to focus on user data privacy, and we talk about what digital privacy means and why it still matters. After realizing they were trying to serve the market something it didn’t want, Privy found an inflection point initially by enabling developers to embed crypto wallets in their apps. We talk about the painful decision to pivot, and later, to commit to both ends of the crypto market: hardcore, trading-oriented products and stablecoins as they flooded into traditional fintech infrastructure. We also talk about joining Stripe, what Crypto’s future looks like, and his level-headed mindset for our tumultuous future.

**Dialectic is presented by **Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. Check out Brian’s X/Twitter sync worker. You can learn more at notion.com/dialectic.

Timestamps

0:00 - Opening Highlights
1:40 - Intro to Henri
3:10 - Thanks to Notion
4:51 - Start: Technical Decisions are Moral Decisions
15:41 - Ambition, Startups, and Crypto
23:39 - Why Digital Privacy Matters: Self-Determination, Security, and Identity
41:52 - Embedded Wallets, the Pivot, and Privy's Core Bet
55:18 - Reinventing Around Stablecoins Without Abandoning Crypto-Natives
1:06:42 - Joining Stripe, Privy Today, and What Stripe Is Becoming
1:22:54 - Crypto's Future, Power Laws, Optimism and Pessimism
1:38:14 - Closing: Asta, Stripe's Leaders, Being French, and Never Compromising
1:52:48 - Thanks Again to Notion

Transcript

(0:00) Opening Highlights

(1:40) Intro to Henri

(3:10) Thanks to Notion

(4:51) Start: Technical Decisions are Moral Decisions

Jackson: (4:51) Henri, thank you for having me here at the Privy office.

Henri: (4:56) With pleasure. Thank you for being here.

Jackson: (4:58) We've got all the secrets on the whiteboard.

Henri: (4:59) Let's see. As you can see, this is hard-hitting work we're doing here.

Jackson: (5:03) Yes, well, if we have to explain anything we have the whiteboard available to us. I want to start with—first of all, thank you for doing this. This is an honor. I've known you for a long time and I've been rooting for you for a long time, and you keep winning.

Henri: (5:20) Yeah, it takes a village, as you know, but we have a long way to go.

Jackson: (5:25) Indeed. At the Privy website, at the very bottom right, you have a phrase. It says, "Technical decisions are moral decisions." Why is that important to you?

Henri: (5:42) I'm thinking. I mean, the reality basically is as software eats the world, the question of what part of moral valence software builders are accountable for just grows. I think when we set out with Asta to build Privy, we were building something that had to do with ownership and with privacy and with how the web works. I want to start with the premise that we are fallible and we will make mistakes, and the best thing we can promise is we care so deeply, and when we make mistakes we will react accordingly. That's what it stood for. I was like, we should actually just have this on the site and have it be something that we remember. Whenever we start larping as though we know truth and if you don't agree with us then you're a heathen—or conversely, some nihilistic converse where they kind of meet of "it's all about pragmatic distribution" and "stop overthinking it." I think that the truth is more nuanced. So I think starting with a premise of "this is going to be complicated, but we're in it and we're thinking about it and we're accountable to our work" was kind of the bottom line that we want to set in starting.

Jackson: (6:57) The company you mentioned is close to the metal in some sense. The story of computers is abstraction—getting farther and farther away from the metal. Obviously, there are elements of crypto that involve technical rigor, proximity, ideology, all these things. But what we've seen is that people prefer convenience over whatever ideological or technical or "trust the metal" thing ad infinitum. So how do you think about that, maybe under the lens of that statement?

Henri: (7:38) Crypto is a very interesting foil. I have many views, but it's an interesting foil because it is the best and the worst of a lot of creative endeavor. You have a lot of extremely ideological people who are fighting for what they see as a future path for the internet—that's the best version. At the same time, that often veers into such an extreme level of non-pragmaticism and a belief that everyone will adopt these experiences that, if you take a step back, are so obviously broken. There's no world in which it happens. We had a few experiences where we would go to talk to a user and say, "This is how we've built it." We would get absolutely destroyed: "But you guys are building this on AWS. How can you trust a centralized cloud?" We'd say everything is encrypted end-to-end and the keys are managed by the user. They're like, "Yeah, but the data won't be available if AWS decides to censor you." That's a really good point. There are solutions we can come up with when that becomes the threat model, but for now, the threat model is more about privacy than censorship. You would talk yourself hoarse. Nothing would happen. This person would say you were demeaning the space, and then you'd go back to this person three months later and they were taking PII and dumping it in a Postgres database on their side. You're like, "What happened?" and they're like, "Well, gone for gone. In for a penny, in for a pound. Insofar as I'm going to do this, I might as well just do it easily and I will take on the risk." I was like, there's no intellectual consistency here. I think a lot of the lesson here was, one, let's move away from trying to please everybody. Let's try and figure out what's right for us as users. You're right that a lot of tech is about intermediation, but we want to know that if we scratch, we can figure out how things work. That stood out as the right line for us to have as a company. If you go to our security website, we have a security FAQ. It makes me deeply uncomfortable because it's very transparent. It's how Andrew McPherson, who runs our security team, ended up joining the org. He was like, "This is a very unusual security FAQ, but it's very honest in a way that I haven't seen and makes me want to work with you guys." But I think that was the line. Intermediation is a fact of life. Privacy is not something people will go out and buy in and of its own right. But that doesn't mean that we can't try and build better tooling just the same. This is why I'm in many ways—and it's obviously a very complex issue—a big Apple fanboy. Sometimes things are just nice because they can be. Catering to human qualities is not a good product-building thesis; catering to the seven deadly sins is a much better product thesis. In our case, we tried to appeal to privacy, and we actually found that appealing to convenience and greed were easier, but baking privacy and sovereignty in was the way that we could do it.

Jackson: (10:42) What do you think? Maybe back to that first statement—sorry.

Henri: (10:45) I'm painting greed with a wide brush by saying basically the ability to monetize your products better. Capitalism is greed under that definition, which I don't find it to be.

Jackson: (10:53) Yeah. And you're abstracted probably even a further level in that, ultimately, you serve developers.

Henri: (10:57) Yeah, for sure.

Jackson: (11:01) I talked to a philosopher late last year ad nauseam about a bunch of elements of how things have started to fall apart. One of the big parts of it is that, at least in his view, Silicon Valley or the technology industry writ large has this view that technology is morally neutral. You should just build technology, and it's about what people decide to do with it. I'm curious about your reaction to that idea in general, and then how that sits next to this: "Technical decisions are moral decisions." If that's not in complete disagreement with that idea, it's certainly not in total alignment.

Henri: (11:45) I think it's just a narrow field of view in a sense. Again, software has eaten the world in many ways. Technology is everywhere. If you take a wider lens at it, maybe the technology itself is neutral, but the way in which you market it and the people you cater to—you're ultimately trying to spike the ball to tell people how to use it. That's certainly not neutral. So I broadly agree with the idea that the same technology can be used for great things or bad things. Nothing is inherently one way or the other. But I think by the time a human is involved, it's like Schrödinger's cat. The technology, the moment you've looked at it, it has moral valence to it. Again, I'm less interested in defining what is moral and what is immoral. I'm far more interested in people not being hypocritical and owning up to what they're trying to do. That's my main piece: you should own the outcomes that you're trying to drive the world towards. As someone building tech, you have a responsibility towards that. I interned at Palantir for a hot minute and absolutely drank the Kool-Aid. During that internship, there was a Privacy and Civil Liberties Board that they would put the interns in contact with to show them how we make morally complex decisions. At least at the time, the viewpoint was that as an engineer on the team, you need not work on anything you don't want to work on. However, the company may choose to work on things that you personally disagree with. Please voice it. We will take it into consideration and make a company decision, including this Privacy and Civil Liberties Board, as to whether or not we want to continue doing this. Ultimately, the bottom line is there will be someone to do these things. Given a choice, we would rather sit at the table and be a part of building it, rather than let someone else who cares less do it.

Jackson: (13:40) Or do the Google thing where you're just like, "We're not going to bother. We're not going to work with the government at all."

Henri: (13:44) Exactly. So I think that's my point: you lean in and you own up. The tech itself, as a cold instrument, I agree, is probably just an instrument, but as soon as a human touches it, that's gone.

Jackson: (13:59) Right? And part of the, I think, intrinsic to this idea—at least his criticism was—if you believe technology is morally neutral, you sort of take this view that more technology is always good. Maybe to put it a different way: you are morally motivated, is my sense.

Henri: (14:18) I come out of it thinking action is good and creation is worthwhile in its own, and having to lie to yourself as to why you do it or what it means for you to do it is the thing that cheapens the whole affair. And so I think, broadly, the thing that impresses me so much with the US—I was having this conversation with my wife yesterday—is the sheer arrogance of Silicon Valley in thinking that you can just do things. To the French mind, it is so absolutely incredible. And this is why Silicon Valley is what it is. There's so much to be excited about—that we think we can reshape the world. And we can, in fact, because we believe we can. But I think a lot of very mission-aligned companies espouse giant worldviews and then the actions just don't match up to the words. That rubs me a lot more poorly than, say, "I want to build the world's best toaster oven because I really like toast." As long as people speak it the way it is and acknowledge the complexities, I'm good with it. I generally find that more technology is probably better and, if nothing else, more technology is inevitable. We are on an accelerationist world path. And so, again, I'd rather sit at the table than move to the woods somewhere and try to not participate.

(15:41) Ambition, Startups, and Crypto

Jackson: (15:41) You aren't building a toaster. You are also a French mind. I think one of the reasons you're such an interesting person is you are deeply pragmatic and you've been successful. This isn't just this purely looking-ahead, idealistic thing. You're super principled and you do care about certain ideological things. And so I guess I'm curious about, maybe twofold: one, what caused you—maybe from previous parts of your life or academia—to want to just do things? And two, why this part of the world? Why is this important to you and why does this matter in a way that—maybe no offense to toaster makers—is a little bit more of substance?

Henri: (16:32) It's a lot of questions. I'll go to the last one. I think there's so much path dependency, basically. I went to grad school, so why this and why this field? The honest take is I have a lot that I'm very excited about in terms of building. I think that when I was in college—it's very embarrassing, but it's a very good snapshot of a version of a millennial—I watched The Social Network. The thing that struck me was not actually the whole story about Facebook and so on, which is great, by the way. Good movie. But the thing that struck me is there's a moment in which Jesse Eisenberg, playing Mark Zuckerberg, has to relabel files and writes a Perl script for it. I was like, "Fuck, what am I doing manually relabeling my files every day? I need to do computer science." I'm the only person with that takeaway from The Social Network, but beautiful.

Jackson: (17:29) Beautiful.

Henri: (17:31) And so I came into it thinking, "I need to learn to talk to computers because I cannot be a functional human if I don't do that." Then I got to really love the people who were in the computer science department at Columbia at the time when I started doing it. Then I think through that, when I went to grad school, I thought I was going to do coursework in AI because I was like, "This is where the future is headed." This was in 2016, '17. Then I took one class by a professor called Dan Boneh, who is a cryptography professor, and I was like, "Oh man, I just need to take all of his classes. He's amazing." And that's how I ended up basically doing the crypto curriculum, more or less, and ended up in this field. I really find that there are so many areas of deep meaning in human endeavor, and I just happened to, via pure path dependency, gravitate towards this one. I think the future of ownership and money and what it means to be a stateful actor on the web as pertains to these things is something that I find very interesting. But I don't think I was born thinking, "I want to work on crypto."

Jackson: (18:36) When did it flip for you—maybe to go back to the French part—to go from academic to entrepreneurial? How did that gradient happen?

Henri: (18:48) I think it took a bit. I finished my undergrad, went to work with a friend of mine, and we both had "real jobs" lined up, quote-unquote.

Jackson: (18:58) This is the first company with...

Henri: (18:59) The first company I started, exactly, with Zach, who started Ro now, which is a really successful direct-to-consumer healthcare company. I think we really both just wanted to work together and we went through YC. At the time, I think what was most shocking to me was just how people took us seriously. We were just making shit up as we went along, and people just saw that we were going to grind and were willing to give us a shot. I felt that was very infectious.

Jackson: (19:32) Well, I guess this was pre-grad school, actually. This was almost...

Henri: (19:36) This was pre-grad school. I went into it and I felt like I had unfinished business with CS. I got into CS too late and I was like, "I really should try and get a PhD or something at some point, but let me do this." Basically, when Shout, the company we started, failed, I went back to grad school. A core part of my endeavor there was, "Do I get a PhD or not?" At that point, it stood to me that I wanted to build products. What was a good place to do research and build products? That's how I got into crypto post-fact. Actually, this is the job I should take out of grad school—in crypto, where I can do research but it leads to products being shipped.

Jackson: (20:10) Remind me, when did you move to the US? College or earlier?

Henri: (20:13) Earlier, in middle school.

Jackson: (20:15) And so, was it because of that? What created this sort of more American bug in you around some mix of ambition and agency?

Henri: (20:27) Arrogance? Yeah, the arrogance. I became arrogant when... No, I mean, I think the honest take is I lived in New York a very long time, from when I was 10 or 11 to college. I think probably a lot of it... I was in a French school, and a lot of it, I think, came through college and the people I hung out with. I started my undergrad at Stanford and I was around folks who were just very unusual in the best of ways. One of the projects I was very lucky to get involved in through one of my RAs, Alan, was we built a tree. We went in a backyard of one of the row houses—this was the wide-eyed freshman joining along because it sounded fun. Basically, these were folks who were really into theater tech who had decided to try and build a physical sculpture. One year they built Egypt in a dorm room where they'd put down a tarp, stolen sand from the volleyball courts, and then tried to rebuild that. This year was a tree. They were trying to build the Tree of Life from Norse mythology, and they wanted to host dinners in the tree. It was a metal structure that had been welded together with some chicken wire and monster mud. We had shaped this theatrical tree that ended up having a table for 12 people and hosting dinners. I was just like, "This is really fun and cool." Finding myself in that environment felt very intoxicating. So I think honestly, the take is a lot of it is just I was the pure product of that, plus going through YC in 2014. It's a very specific part of the world at a very specific point in time that ended up making a big impression on me.

Jackson: (22:13) When you went back to grad school, did you think you would do another startup?

Henri: (22:16) Yeah, no doubt.

Jackson: (22:17) Okay, so it was always a matter of time.

Henri: (22:20) And in fact, the first startup we ended up shutting down. I specifically remember at the time thinking, "I do not want to be a founder for founding's sake." There's nothing inherently valuable to the act. And so unless I have an idea that I believe is worth having in the world, why should I do this? Obviously my mindset changed a lot because I came out of grad school being like, "I want to build something." As long as I start with that premise, there are too many interesting things that are broken in the world for me not to find an idea that's going to be interesting.

Jackson: (22:54) Speaking of that, I think it'd be cool to trace a few of the arcs of Privy.

Henri: (23:00) Sure.

Jackson: (23:02) I think it was on Cheeky Pint you said to John or to Zach, every year we look at the company and it's unrecognizable from the prior year, even the last few years. You're also dealing with a market—crypto is a market that probably has experienced not moving as fast as people would want and it moving maybe in directions that they might not want. I think you probably have experienced both of those, and I think that has made it a really interesting substrate for your deftness in balancing ideology and pragmatism.

(23:39) Why Digital Privacy Matters: Self-Determination, Security, and Identity

Jackson: (23:39) So maybe to start, you mentioned it earlier—you have all these old Medium posts about how we actually have a world where we can smuggle in privacy or whatever it might be. Let me see if I have it. Well, one of the titles of this post is great: "There's too little to be gained from treating your users' data with respect," which is probably broadly still true or still felt, and really an example of "nobody actually cares about this." Why does digital privacy actually matter?

Henri: (24:12) I think for me, the reality is the majority of our lives are now spent in the digital medium, and you have this data exhaust that you're putting out every day. I actually just went through a digital audit by a firm where they went off of my name and they tried to pull everything. And it's really impressive. I'm very aware of what's out there and what is intentionally out there versus not, and there were a few things that surprised me, but broadly it's pretty wild. They went through my entire family tree, all of the things, both in crypto terms and not. It was a very interesting experience. Basically, I'm just deeply aware of how much digital exhaust we all drag with us. I think there is this disconnect in terms of risk and danger, the fact that our sense of fight or flight has been developed in the physical realm. If you go like this, I feel that viscerally. But the amount of risk I'm taking on in a digital surface is very real, and yet my brain is not at all wired to perceive it in the same way.

Jackson: (25:16) And so unless it slaps you in the face.

Henri: (25:18) Yeah.

Jackson: (25:18) AKA somebody finds a Snapchat of you doing cocaine or whatever and people lose their minds—or the iCloud photo leak.

Henri: (25:25) But even then, the feedback cycle is so different than it is in the real world that I think we're not exercising the same judgment in digital spaces as we are in physical spaces. And so at least I grew up very aware of those risks and dangers and thinking, "How do we build back into that?"

Jackson: (25:45) Why did you grow up so aware of them?

Henri: (25:46) From a technical and personal standpoint, I think what I really valued, maybe as an immigrant coming to the US and so on—the most privileged version of random white French dude coming to the US—was being able to control how I present myself to people. It is extremely important. The idea for a long time of people being able to Google someone made me very uncomfortable. It was always the case that you could show up and you decide what you brought with you into the room. And now actually there is this hidden baggage that you're dragging with you everywhere. And that felt very real to me. So I think to that end, digital privacy ended up being something I really care about and was very interested in, and still am. I think the thing that's so interesting in the moment today in tech is just that the arms race has changed completely. The launch of Sora makes it that you can spend a lifetime trying to be careful about your digital exhaust, but now all you need is two angles of your face and three sentences spoken aloud, and that's it. You have been ingested by the machine, who can now output you at infinity saying anything that it wants.

Jackson: (27:06) We won't even need to do this podcast.

Henri: (27:07) That's the point. One of the things that came up in this audit was "there's too much of you on YouTube" and the deepfake potential is infinite now. And that is just a cost of living at this point in time. It's true. So I think that's very interesting, which is we're in a shifting threat landscape. And maybe this is the place where I reject the French ethos the most. This is going to be a very Euro-poor themed podcast, unfortunately. I love France, I feel very French. But the French response to global warming is "turn off lights when you leave a room." It's so clearly not a useful mindset as opposed to thinking about how do we change how nuclear waste is recycled. And so I think the acceleration has been to see the world as it is, be truth-seeking, understand the way things actually function. Given that fact, how do you then counter-position to lead to the best outcomes as opposed to trying to rewrite the world? I'm coming back to the prior question, but I think crypto's biggest sin is trying to reinvent the Internet and financial systems from scratch. It's a very useful intellectual exercise, but that is not how change happens. Change happens based on where we are today to then moving the machine in the direction that we want. Very seldom, in my opinion, is there such a disruption that completely negates past innovation. We don't just get the Neanderthal to compete with the Homo sapiens; it ends up being some inner binding of the two. We're seeing it play out in AI today. But I think the question of how do you protect your digital privacy on the web when AI just makes it that the level of input that you need to destroy privacy is infinitely small is actually quite interesting. I'm actually not here lamenting AI and saying it’s the end of everything, just saying the stakes are super high and the tools at our disposal are very interesting. To the earlier point still of the moral valence of tooling, the creation of napalm led to the creation of the best burn creams we've ever had. And so the solution is in the problem if we know how to look for it, is, I guess, my hopeful take.

Jackson: (29:09) You use the words "destroy your privacy." In one of those old Medium posts, you have this interesting distinction between privacy and security that I’d like to go a little deeper on. You say you can define privacy as the state of being free from unwanted public attention or observation. This is different from security, whereby a product or service works as its creator intended and does not unwittingly expose or leak information. The relationship is one way. Bad security means bad privacy, but good security does not necessarily mean good privacy. Secure products can degrade their users' privacy. In that sense, security is about creator intent, while privacy is about user intent. Outside of making sure you are secure or safe, what are the ways that privacy actually matters?

Jackson: (29:55) I think to me it's the most hokey sentence ever, so bear with me. I think it just comes down to how much right to self-determinism do we have? And that's the distinction between privacy and security. Security is systems work as intended. Privacy is, to me, people can have the expectation that the things they think are happening are, in fact, happening. And so it's much more in the eyes of the beholder. And again, privacy—there's just no single definition for it. Some people love being extremely public on Instagram and they have a very different sense of privacy that matters to them, but their definition of privacy is very different. I think in a world in which, basically, you were just a composite of all the things you've ever said, written, and done—this maybe has some weird tie-ins into cancel culture as well—but in a world in which you are just those things and that is what exists of you, then there's just very little ability to make willful decisions to change things in life. You are the sum product of everything you've ever said or thought, and saying, "Actually, I've changed my mind on this," doesn't really matter anymore. And so I find that there's something deeply problematic with not being able to have—maybe humans, we're so far down a rabbit hole, so please take us out—but humans, I guess, intrinsically have some version of a decay function where the things I thought a year ago are not that interesting to me anymore, the things I thought six months ago a little bit more, and so on. There's probably actually some weird curve where the things I thought when I was seven years old remain extremely important to me. But I think the way we're able to filter out opinions, hold opinions, and then over time filter them out to get to where we are today is really important. And I think in a world in which everything is recorded and stored and can be brought back, it just completely changes our ability to determine what we want to do moving forward.

Henri: (31:45) Lightness is a virtue. Lightness can be—you don't want to... accountability matters. And being able to move through the world without the weight of everything is freeing in a way that I think is... This might seem so strange, but I was listening to Kevin Kelly talk about how having a belief in the future is really important for being able to move forward in the world. And this almost feels like the inversion of that. It's like not having to know that your past is chasing you. Again, it can be easily taken out of context and applied; it's not an argument against accountability.

Jackson: (32:24) Maybe this just points to my deep cowardice, which is: one way to do it is to try and be extremely vocal about the ways you change your mind and have original viewpoints felt strongly that you embrace. You have a handful of figures on the web who have very strong ideas, very polarizing ideas, and they change very quickly. And again, as long as I can see some version of an intellectual through line for how they got from A to B, I love that and I find it to be so inspiring. But I think the alternative—that's the point, it's not very private. The alternative is don't engage in that way. Don't let people see these things. These are conversations that we get to have, in this case on a podcast, but typically one-on-one. I've also, in this, been very careful to not espouse any opinion here. I'm spewing about what it means to have opinions, but I've not said anything of any valence on any topic. But that's the other point is, basically, given that I don't know how this plays out, being more private is the way in which I get to keep my thoughts to myself, have those thoughts, and move about in the world unencumbered by having to relate my present set of actions to my past set of thoughts, in a sense.

Henri: (33:37) And maybe to tie it back to identity, there's some level in which maybe part of what this informs is an ability to move lightly through the world with multiple identities, too—that don't need to be the classic thing, like who you are with your mom versus your wife versus with your best friends from college. Those being different doesn't mean you are in conflict as a person. And yet our digital lives make it harder for those things to be harmonious.

Jackson: (34:03) There's this rumor going around crypto circles and Stripe that I am, in fact, the heir to the Patek Philippe family. And that's because there's a Henri Stern.

Henri: (34:13) I saw this. I saw this in my research and—

Jackson: (34:16) It's obviously very untrue, but I've had people come up to me and say, "Man, your watch, it's so cool. What a fuck-you to your family." I'm like, "I have no idea what you're talking about." But then I found out that's what they meant. I find it really fun when, basically, that version of the substrate of information that we have in the world ends up being completely wrong. And so actually, that's a fun idea that I like to toy with, which is: can you have misinformation canaries about yourself on the web where you just put out every here and there a completely false fact, just to kind of trace how data makes it through in identity? So, various musings.

Henri: (34:54) It's fascinating how we evolved to have this gossip and these local contexts of information you might have heard about a person. And now over the last 25 years, but sort of over the last 80 years, now there's a possibility that someone can know a tremendous amount about you, or have a tremendous sense that they know a lot about you, and bring that in.

Jackson: (35:23) But I think the other interesting question—and for what it's worth, no one cares about me, which is so lucky at the end of the day.

Henri: (35:24) We're trying to change that here.

Jackson: (35:26) Claro. Thank you. There's a Victor Hugo quote: "To live happy, live hidden." And the point is, anonymity in itself is such a blessing. I think it's a very complex thing because I only have a Twitter because of work, personally. But also, I'm a deep lurker. I enjoy reading other people's stuff. But I don't enjoy putting out my opinions because it feels so valent in a sense. I think the point is this: we basically went from phase one, which was we exist in the moment and the activation energy to capturing something for the future is wild. Actually, maybe phase one happened with the printing press. So there's the pre-Gutenberg days where it was oral history for the most part, and you had to get a scribe to do anything. Then post-Gutenberg, capturing information for posterity becomes that much easier, to probably the advent of the internet and microblogging, where now putting out information to be captured for posterity becomes that much easier. We went from the activation energy in putting out basically long-lived information going way down. But we were always saved by the fact that no one cares. And the amount of work it would take to do a really deep psychological draw-up of someone on the internet is probably not worth it economically. And that has changed. It is now really easy to send out three agents to collect these things. And I'm curious how your research for the podcast has changed and so on. But my guess is just that, basically, you can get a deeply harmful psychological profile of anyone for really cheap in a way that used to be reserved for blackballing someone in a deep way. The question for me is what happens next? And the reality is society will be too schizophrenic if it becomes too easy. I mean, this is what we're seeing in many ways with what has happened from 2018 to now in terms of what was the moralization. Now, tech itself is an interesting foil for how society is evolving. I find it's a good Rorschach test for cancel culture to now very abrasive masculinity to some version of what will come back. And we're just swinging back and forth here. I guess my question is: in a world where everybody has that power, I actually suspect it becomes a lot less powerful.

Jackson: (37:57) Yes, the Overton window has to—I always used to joke, back to my crude Snapchat analogy, at some point we'll get to where everybody's got dick pics.

Henri: (38:04) Is your dick that interesting? And I think that's—how do we keep carrying on meaning in a world in which everyone's dicks are out there is the question that I have. That's our sound bite.

Jackson: (38:20) Two things that come to mind—and we'll finally move on, although I could talk to you about this all day. I think his name is Nathan Jurgensen. This guy used to write for Snapchat. It's possible I have the name wrong, but basically this philosopher-in-residence thinking about the impermanence of digital identity, or the permanence of it. I feel like you would find it interesting. I don't know what he's doing now, but it's an interesting sort of dumpster dive on somebody who was thinking about this actually quite early. The other thing that brings to mind, actually hilariously, is I don't know if you've heard Tyler Cowen talking about how he's writing for the LLMs. And his whole thing is he wants the LLMs to know as much as possible about what he thought. So I think part of it is like, once he's gone—but also, he's reading some interview and he's talking about Iceland. He's like, "Now the LLMs know what I think about Iceland."

Henri: (39:05) And if people want to know what I think about it, they can ask them.

Jackson: (39:09) They can ask.

Henri: (39:10) And for what? It's sort of—this is maybe my call to action, which is ultimately what we're going through right now is the quintessential intellectual masturbation exercise on so many levels. I think again Silicon Valley sometimes talks itself up in histrionics around all of the ways in which these are all very deep. But I think then taking a step back and seeing what action was taken, how has it actually impacted the world? And is this good or bad? It ends up being quite simple. So I think being able to move in and out of this context to just: "Is this company producing something valuable? Does it make me happy as a consumer?" It isn't that much more complicated than that. I find it very important to get back to. Maybe this is why working in tech in New York—this is a call to arms for tech in New York—which happens to be much more easily grounded in reality than probably if you're operating in Silicon Valley.

Jackson: (40:03) In what ways does Privy still work on privacy?

Henri: (40:07) It's really tough. To a large extent, we pivoted; the core product failed. And I think a lot of the infrastructure and architecture that we built remains—like data encryption, key splitting, running secure environments in which we can provably show that no one knows the information. It used to be about knowing information, now it's about securing keys. But the core concept is very much the same. Just the substrate of data has moved from intelligible information to now key information. So I think the reality is basically it works on it because I do believe that encryption is key to privacy, and having everyone have keys is key to enabling encryption to exist throughout the web. And so I'm probably holding out hope that the self-sovereignty project of Web3 will come back as we distribute stablecoins across the world and as we make it that digital currencies work. I think the project itself is a risk in a sense that there have never been darker days for Web3, and yet I've never been more optimistic about crypto. I think finally the space is having real deep impact on people who otherwise don't care about the technology, which is maybe the definition of impact. It's the only space that has ever so deeply pandered to itself for so long. So I'm as optimistic as I can be about this space and about the ability to do meaningful, impactful, positive work in this space. But also I think this idea of "we're going to build an alternative internet that is user-owned" has never been in more dire straits. And I think my hope is that Privy is still working on privacy because we are laying the groundwork for how to enable people to have keys to signify intent and encrypt data.

(41:52) Embedded Wallets, the Pivot, and Privy's Core Bet

Jackson: (41:52) To jump forward a little bit—I think around the time I met you, you were starting to think about embedded wallets, which sort of became this massive, amazing wedge in. The crypto wallet at the time, and certainly for most of the early history, was this idealistic idea that you were going to bring your self-custodial wallet wherever you went. And it wasn't just your money; it was all of the things you were—your identity, whatever. Do you think that there's still merit to the idea of the wallet in that form factor at all?

Henri: (42:30) Yes, and I think in a sense this was the interesting take we had. The biggest issue of identity writ large—how do you define identity on the web? Typically people will say this is about basically portable identity. I record something once, I get to have it everywhere, it is controlled by me, not by a platform. That's at least a very common way I would think about it. And basically any work on identity ends up being a question of how do we incentivize platforms to play along in a game that cuts out their edge and that disintermediates them from their users, which is to say their lifeblood. And so I think that's the core reason why identity projects end up going astray. If you are pure enough about following the identity path, you end up building a protocol that you can never get anyone to adopt, because all of the people who have the greatest impact in adopting it are the most disincentivized from adopting it. And yet I think what we'll end up with is maybe federated versions of identity localized. I think there's basically a gap between you only existing within the platform ecosystem or you existing at a government-mandated level. I think basically being able to federate different parts of identity between platforms is still a very viable dream. And I believe that having digital currency that can flow between platforms is actually a very easy testbed for figuring out what a wider wallet can do. If I have a wallet that allows me to take currency in a digital form from platform to platform—and then saying currency is just one type of data, but I can take other data, I can take KYC information, I can take my driver's license—it's just a spring from there. So I think there's still merit to the wallet, but in itself, I would recommend that no one work on that wallet in itself because it doesn't solve a lived problem for any user in a very direct way.

Jackson: (44:20) And yet in some inverted way, as I understand it—feel free to correct me—the embedded wallet was really the unlock to really make things start to work for you guys, at least in terms of the core goal of serving developers. Do you disagree?

Henri: (44:41) No, I completely agree. But I think what we did in doing this was also—there's a reason the embedded wallet doesn't have a first-class feature right now around Social Security number encryption or things like that. We moved from being this horizontal platform that can capture any data to being a very verticalized one that can capture one type of data, which is what assets do you hold and how do you make them easy to spend. And then what we did was say: this moves from being something the user has to willfully, intentionally bring with them, to this being something that a developer can build into their platform. So they are now building a global store of value or fintech, whether or not they sought it. But now value can be captured at the app level, controlled by the developer in the UX that they want. And so I think the unlock was saying developers can build with crypto without needing their users to be crypto people.

Jackson: (45:35) I see. And is that what made the company work wildly?

Henri: (45:43) Yeah.

Jackson: (45:44) When did it go from you working on allowing customers to basically manage their users' data in a way that was responsible—it wasn't really working—to being acquired by Stripe last year and being quite successful in some dimension? If we put the crudest analysis on it: there are millions of people who have Privy wallets by way of your developers. What was the inflection point?

Henri: (46:14) I think there were a few chapters. Basically, through the first version, it was purely vision-built. It was: "This is what we think ought to exist in the world. Can we get people to agree?" We launched a product in December of 2021. By April, Asta was like, "This is not working."

Jackson: (46:36) You weren't?

Henri: (46:36) She was. She was like, "This is too hard. We're pulling teeth." And I was like, "Yeah, but this is about grit and so on." By July, I was like, "All right, yeah, you're right. This is too hard. It should not be this hard to get people to care." We were trying to reshape nature, as opposed to—the market always wins and we were trying to change human behavior. That is not the right path.

Jackson: (46:57) In what way were you most trying to change human behavior? You really were just trying to sell developers something they didn't care about.

Henri: (47:03) Something they didn't care about and something their users weren't asking for.

Jackson: (47:06) I see.

Henri: (47:07) And we were trying to convince them, "You should care about this." By the time you're doing that, you've already lost the game, you've lost the plot. We're not an advocacy group; we're a company building products. So I think by July, I came to agree with her. We had a few paths. We were like, "Okay, what have we learned?"

Jackson: (47:29) You had already raised from Sequoia.

Henri: (47:30) We'd already raised from Sequoia. I think this is where there's real truth to the idea that the "idea maze" really matters. In so many ways we pivoted, but it's so related to what we were doing before. Part of the question we had over that summer was: do we just reset, start something entirely different, go to AI or whatever? The take was like, "No, we still really believe that there's something here in the idea maze. We just went in through the wrong gate." So let's get out of the maze. What did we learn about the path we charted? Let's go back in. We were pretty methodical about it, and we came to a few ideas.

Jackson: (48:03) How sacred was selling to developers?

Henri: (48:05) Very. Because I'd worked on consumer products before and I know how hard it is. So that was not questioned.

Jackson: (48:13) But it was always developers, specifically developer infrastructure.

Henri: (48:16) I think the sense here was it's what we know. We're both developers, we care about the craft. And frankly, again, if you want to be selling the means of creating the future, that is a very good way of having impact. Developer tooling is the way in which we get to start. That wasn't questioned. Interestingly enough, we got to this idea of: we need to change onboarding. It started with onboarding, and we knew that embedded wallets were a part of it. Actually, the first launch was not embedded wallets. It was enabling people to auth into crypto apps and link their existing crypto wallets to an auth system more easily. We'd seen the data, and the data was people want to have key management be easier, so we'll have to build that next. But we're trying to cut very thin MVPs. Basically, by January of '23—so a year later, after the initial launch—we relaunched with this new product, and we had very "one foot in front of the other" goals. Our first quarter, we were like, "We need to have five customers in prod." Our second quarter, "Can we make it 12?" Our third quarter, "Can we make it 25?" We got very lucky because there's an application called Friend.tech that used us—and we were very clear that they used us—that blew up, and then everybody started copying them. So we went from our goal being 25 in Q3 to having about 150 developer teams building with us at the end of Q3. At that point, we had enough data and enough customer contact that oblivion or irrelevance was no longer the threat model for why this wouldn't work. It was just us messing the product up or not being able to scale.

Jackson: (49:54) Was there any fear of...? Because interestingly, we knew each other back then. I remember well before Friend.tech, you had envisioned this correctly, which is: "I need to get enough developers that one of them rips." Basically, after that one, I guess—one: do you think that was a real, reliable strategy that can actually work? And then two: was there any fear that there wouldn't be another Friend.tech?

Henri: (50:20) I think the fear was: can crypto exist beyond the cult following it has? We were basically very comfortable—or at least appropriately uncomfortable—making a core bet which was: we have to have one. We can't stack bets. I think that was a very important mindset: the startup can't be a series of bank shots in pool where you have to hit three sides before you get the ball in. There needs to be one core bet that we're making. Then if that macro core bet works out or doesn't work out, we can succeed or fail. Our core bet was crypto—be it in the Web3 version, the digital assets version, or something else—is such a fundamentally interesting idea. Having a state that is not owned by any party, but that every party in the world can connect to across the internet, is so clearly valuable. The first application of it is magic internet money—which is the old name for stablecoins, I guess, now.

Jackson: (51:18) I was going to say, back then it almost felt like Web3 didn't work.

Henri: (51:24) Yeah.

Jackson: (51:24) And so in some sense, at the very least, it didn't seem that obvious then that there was still this very long-run bet that stablecoins and the quote-unquote boring stuff was still...

Henri: (51:38) I think that for us, the point was Friend.tech gave us relevance and enabled us to test things. The guiding star was: can we work with tasteful developers? If we find customers who have taste, what they're working on is far less important than the fact that they understand what they're working on.

Jackson: (52:00) What does taste mean?

Henri: (52:01) It means—the negative signal is someone who is mimicking a trend as opposed to doing something because they believe in it for first-principle reasons, whether the first principles are correct or not. And it means somebody who understands their audience and their customers deeply and is making decisions based on that understanding, rather than just based on proxies for what an audience might be. We've been able to just spend a lot of time with our customers and identify who has real vision for what they're trying to do, and then let's just be better for them. We basically spent this first chapter—Chapter One was pre-pivot; Chapter Two is this period of getting to a place where we had enough of a customer base to start iterating; Chapter Three is how does this stretch the product and what are the places in which we can just build better tooling for these people? Leading to Chapter Four, which is seeing the emergence of stablecoins and a new class of user coming into crypto and making sure we were well-built to support that use case. We wrote a strategy paper early on which basically said there are three markets. There's the extremely die-hard crypto natives for whom storing a mnemonic is a non-negotiable fact of self-sovereignty, and we will never be able to convince them that actually these are really viable, self-custodial systems that they should use. There are crypto developers who want to build for a mainstream audience, and then there are mainstream developers who want to use crypto. Basically, we said we will never win one, and three doesn't exist. So we have to go for two. We have to build for crypto devs who want to cater to a wider population. That will teach us the things that we need so that when three comes about, we'll be ready. And we just got massively lucky with timing that three is coming now. Three is here.

Jackson: (53:54) I mean, I don't know if you got massively lucky. It was over the course of four years.

Henri: (53:58) Yeah, we were patient and lucky. You hung around, we hung around. But we're now in a place where most of our biggest customers aren't here because they care about crypto; they're here because they care about the impact that this technology can have on their users. They're here to build better financial systems. They're here to enable people to hold US dollars globally if they don't have access to local currency or a stable currency. They are here to build better products for orgs that already exist and are massively scaled. And we're really well set up to work with these people because we have two markets. We have the folks who are really pushing the technology — these are the deep experts, the crypto natives who are forcing us to be faster to scale globally. The reality is DeFi is just doing so much more transaction volume today than stablecoins. So, we know that we can scale to hold any stablecoin thing because we've scaled to support Hyperliquid, Uniswap, and Jupiter. On the other side, the fintechs and marketplaces will actually distribute this technology more widely. It's very much a two-pronged approach to product development, being very clear around what our customer's optimization function is here so we can make sure that the product is right for them, but then making sure that we're able to work with startups and enterprises in a way where they feed each other in terms of product quality.

(55:18) Reinventing Around Stablecoins Without Abandoning Crypto-Natives

Jackson: (55:18) You referenced on an earlier podcast having written this document — I think probably in 2024, but maybe it was 2025 — about the two paths between trading and stablecoins and not choosing. Maybe that's a similar cut on what you were just talking about. Somewhere else you talked about how part of the role is to be a hoodie among the suits and a suit among the hoodies.

Henri: (55:43) Yeah.

Jackson: (55:44) How has that been? Maybe it was especially relevant pre-Stripe, but it's certainly still relevant today. I know that you've talked about this: making sure that you don't just go after the stablecoin rise.

Henri: (55:58) I think that was probably the second hardest moment. The pivot was probably the hardest moment in the company's life. We were in a room on 600 California Avenue in San Francisco — it was a WeWork. We were doing an off-site and the atmosphere just sucked. It was six or seven of us, the entire team. And at some point, I said, "Clearly things aren't working, right?" And you felt the body language change and people relax, being like, "Finally, at least someone said it." At least we have eyes. Of course it's not working; we all see it, but now it's part of the conversation and we can do something about it. That was the start of a very painful period. I mean, it was already quite painful to be working on something no one cared about, but it was the start of just figuring out what we were doing. It was done very publicly. We have one teammate, Ankush, whose first job out of college this was. I think he was probably a few weeks into the job, and I'm just so thankful that he hung on because that was not a fun time to be around the company.

Jackson: (57:02) He's still here?

Henri: (57:02) He's still here. And he's amazing. His job has changed 18 times in the course of the org, but he runs a lot of what we do in product generally. That first summer, we'd set it up so we would do random research to try and figure out what we would do. The second hardest moment was basically much more of a private moment between me and Asta, seeing the market changing. This was October 2024. I wrote this doc that I sent to one investor, saying, "I think we're headed towards a wall." Hyperliquid was already a customer.

Jackson: (57:45) The trading stuff is working.

Henri: (57:47) The trading stuff is working. But I think our stance was always: we want to be big fish in a small pond and then grow the pond. We will not focus on monetization; we have built a SaaS business. In many ways, this was the actual crux of the doc: we're seeing the boat depart from the dock. We are on the dock. We have to either jump on the boat or stay on the dock.

Jackson: (58:12) The boat is stablecoins.

Henri: (58:13) The boat is a new vertical coming into the space — stablecoins, tokenized assets, and generally the fintechs entering the space that will clearly be massive. It requires a set of changes to our product and the org that we need to make to stay relevant. If we stay on the dock, we cannot be a SaaS product. We have to figure out how to be a very different type of product because there are great businesses to be built in trading, but we had not built such a business.

Jackson: (58:41) You never intended to combine SaaS and trading.

Henri: (58:43) Exactly. It doesn't make sense. And conversely, if we want to jump on the boat, that's great, but we're giving up what was hard-earned — but also what was a very meaningful set of customers who have great ideas, who are really insightful, and who we want to keep working with. So, this needed to be a very intentional, deliberate decision that we made for how we want to be in the world. The point was: we have to do both. We can't control the timing of stablecoin adoption, and not using the platform we have would be such a mistake because it's a valuable platform. I actually think it feeds product quality in a deep way. We have now made the transition. Most of our customers are moving stablecoin volumes. They're fintechs again — folks like Ramp, Klarna, or Deel. These are very modern companies who are here for the user impact. At the time, it was: we actually have a platform, we just need to rethink our customer base a little bit in order to make that movement. The conversation that had a real impact on me was when I went to see Roelof from Sequoia right after we had raised our Series A. I asked him what it would have taken for Sequoia to be excited to do the A. We talked for a little while and he said, "You're talking to me about how far you've come, and I don't give a shit. The only thing I care about is: am I excited looking forward?" That was such a wake-up moment. The obvious searing pain of trying to create something from nothing is so wild in your mind that you end up saying, "Oh, but we've done so well," and no one gives a...

Jackson: (1:00:27) "We're not dead."

Henri: (1:00:28) Exactly. So, that's been a very useful lesson to carry forward: the only thing that matters is looking forward. Let's restart the clock today. What do we have to do? This is why I find the entirety of SpaceX as a company and the way folks are operating in AI so interesting. You have a fantastic business and you're now going to — I'm speaking a little bit provocatively — but you're going to risk the entire business to go after the next biggest thing. That ability to only look forward is what makes them so good at that.

Jackson: (1:01:01) Yeah, Elon’s good at that.

Henri: (1:01:03) So that's very important.

Jackson: (1:01:06) So easy to say from the outside looking in. But I guess you could say, obviously you should have done both. What did you have to compromise on, and what did you not compromise on to actually make that happen? And why was it so hard to do both?

Henri: (1:01:19) Yeah. And to our credit, maybe the thing I like is we did not ape into the space. This is at a time—I really do credit Zach and Bridge for inventing a lot of how people think about stablecoins today and making "fetch" happen. Sorry, Mean Girls reference.

Jackson: (1:01:40) I thought you were talking about some tactical fetch.

Henri: (1:01:41) Yeah, "fetch"—it's a technical term. I think we were early enough that it felt very risky to make this bet at the time, which now every company that is still operating in crypto has pivoted to stablecoins. So it seems very obvious post-fact, but I think we were lucky to see it a bit earlier. I think there were probably three core trade-offs. One: marketing and product positioning. We rebranded. We did a number of things to actually self-actualize for the market we wanted to build toward. Two: actual decisions in the stack. Privy, while key reconstitution was all happening on device at the time, and key management wallets were very tied into auth because most of our customers did not have authentication systems. We're like, "Well, there's no world in which a bank is going to rework their auth system to integrate wallets." We’ve completely fucked up the stack here by tying these things together. So we need to rethink core abstractions. We need to rethink the relationship between wallets and authentication. We need to rethink key management because it can't keep happening on device. This is what led us to TEEs and secure environments in the cloud where we could provably have keys that no one could touch but the rightful owner. But also, it did not need to run locally in order for that to be true. So it was a deep set of—it took us the better part of eight or nine months.

Jackson: (1:03:01) Just like a resource—it was focused?

Henri: (1:03:03) Focus and resources. And then it was clarity internally. The question of who are we building for then comes up a ton. I think basically building a resilient culture in startups is getting everyone very comfortable with ambiguity and with saying, "We don't know, but we know that we don’t know so we can figure it out." My core theory of startups—great start to a sentence—is you basically have three audiences: your users, your team, and your investors, in that order of importance. Whenever you start to talk to one of these audiences in a way that is too unlike the way you talk to the others, you're setting yourself up for failure or reckoning. So I think trying to keep the right tension on the rubber band so that we know the ambiguity, we're transparent internally. We know we haven't figured it out, but we have to figure it out. That's the most costly thing—just feeling on a day-to-day basis, "Man, this could be wildly wrong and we're wasting precious brainpower trying to figure out this made-up thing," when in fact we're doing pretty well on the crypto-native side of the house. So why should we threaten to destroy the entire enterprise in order to make this leap when, in fact, post-fact, not doing that would have been disastrous? And again, this is so easy mode, right? I had this other conversation—I'm going to keep name-dropping Sequoia partners—I had this other conversation with, I think, Alfred Lin who was talking about a company that was at a $100 million run rate and had to decide whether they were going to destroy their business to start a new business. We were doing this as a teensy, 20-person org seeing something that was, in hindsight, very obvious. But there are companies that are having to reinvent themselves at such massive scales, and that's real courage in many ways.

Jackson: (1:04:49) I think you benefited, certainly post-pivot, from being very customer-obsessed through this period despite a customer base that was a little all over the place and a moving target. Where do you think vision has remained really important?

Henri: (1:05:07) Yeah, it's a really good take. And I would argue that this is one of the things I'm not very good at as a founder, which is to say customer obsession in many ways is the vision itself.

Jackson: (1:05:16) By the way, lots of amazing companies have been built basically on that alone.

Henri: (1:05:20) We’re working in an interesting place that is complex and hard technically, that is morally valent and important. I believe in the future of how the web gets built. And as long as we pick the right customers and we kill ourselves to serve them really well, things will kind of work out—maybe serving all the way. I think that's been a lot of it. I think from there, the parts of vision are: imagine a world in which every Uber driver can get paid out globally in a currency of their choice, can save in the app directly, and can refinance their next vehicle to build a bigger business off of that. That world exists today, and that world is no longer just one that only Uber can build. Any three-person team actually has the means of doing that. It's extremely powerful. We're rebuilding the financial stack from the ground up in an internet-native way. I really do believe that, but I think I'm a very skeptical person. So when I hear founders talk about vision, I'm like, "Oh, this person's trying to sell me bullshit." It makes it less exciting to me than actually talking about the craft.

Jackson: (1:06:28) And that last example, or frankly a lot of the stablecoin examples, are kind of boring to Americans who have a pretty good financial system. So the vision part of it is like lowercase "v."

Henri: (1:06:40) That’s fair.

(1:06:42) Joining Stripe, Privy Today, and What Stripe Is Becoming

Jackson: (1:06:42) When was the acquisition? Mid-2025?

Henri: (1:06:46) Yeah, it closed in—we now say—June of last year.

Jackson: (1:06:50) Right. You run Privy as a somewhat separate org inside of Stripe, and then you also work on, I think, some Stripe things. What is Privy today? What is the right way to model what it is and what it will continue to be versus being just folded into Stripe's sort of massive crypto effort?

Henri: (1:07:16) It's a great question. I mean, I think a lot of what was exciting about joining Stripe was just the quality of leadership at Stripe. Here you have me brown-nosing up to my bosses, but the reality is it was genuinely just impressive to see the scale of ambition, the commitment to craft, and the humility—with all three being true together—with which they were approaching the space. That made me feel like if there were to be a home, this is the right home. And I think the point was, when we entered, I think we had sort of three principles: we need to continue to operate as a startup. If we stop, we die because this market does not exist and we are in a market formation phase. Same is true for AI, in my opinion, by the way, which is the market is annealing and we need to heat the product and the market to the same temperature to shape where the market goes. But product-market fit is not a good framework for working in a market like this today.

Jackson: (1:08:05) What do you mean?

Henri: (1:08:06) The market moves too quickly. If we start settling down and just trying to scale the shit out of something, it'll move out from under us. We need to be much more dynamically questioning everything all the time and making decisions that don't scale accordingly. So I think that was the first thing. The second is we can't just be a stablecoin shop. I think stablecoins are the lion's share of where value is being built, and I think they are such an exciting development. But I think there's a lot of interplay between different parts of the space that needs to be fed over time as well. We should continue to work on both. In appropriate measure, but we should continue to work on both. Then I think the third is we have to be able to work with Stripe Bridge competitors. I'd include Tempo in that now, but basically a lot of this stack is being built as an open platform. If we try to overly verticalize the product, the experience needs to be seamless in the parts where we are working together. A developer should not have to see where one product begins and the other ends. It should just feel like a cohesive whole. But for those developers who want to shape their own stack, the pieces should work modularly as well. So those were three very clear things that I felt strongly about coming into the conversations.

Jackson: (1:09:11) Is Tempo already a part of the—

Henri: (1:09:12) —conversation? Or at least not for me. And so a lot of that was an explicit part of the conversations that we were having. Then I think it came down to some version of: do I believe the powers that be, that they mean this and that we get to do really excellent work together? And that in places where we disagree, we will come out better for the disagreement with something that is actually something I can be prouder of building? This is the core substrate within which I operate. And then I think the point is Privy is two things. Privy is a developer tool that people can use to embed wallets and access and ownership of digital assets into their platform. Privy in many ways is like Stripe's wallet stack. Within Stripe products—Treasury, Link—we are working to power basically the inner piece. We're spending a lot of our time with Stripe teams to help shape this. Then we're spending a lot of time with our other customers that are extremely important. Again, the two feed each other. The work that we're doing for Stripe benefits everyone because it is extremely demanding, it scales, and it has all of these requirements. Likewise, a lot of our customers are running so far ahead of the market that we get to build a future-proof tool. So I think that is the core definition of Privy. Increasingly, we're trying to figure out where we make it that one plus one equals three. I'm helping run the on-ramp team at Stripe, and Privy basically just really needs on-ramps to work better in order to enable people to load up their wallets with assets. After that, it becomes much more interesting to have a wallet. So the question is how do we work both with on-ramp vendors across the board—because no product is perfect for everyone—but how do we also make sure that the integration surface between these products is really good? How do we make sure the integration surface across the entire crypto ecosystem—which is to say Tempo, Bridge, Privy, Stripe—is really good? That's what I would say. My three hats today are focusing on Stripe products wholesale that touch stablecoins and crypto. There's many of those and I just manage a few of them, like merchants getting paid with stablecoins and on-ramps. Then it's Privy. And then it's how do we build an ecosystem that can run at speed on point solutions and yet build a greater whole as we do?

Jackson: (1:11:42) So is a wallet just like a way for a developer's app to let users have crypto?

Henri: (1:11:50) Yes, in my definition of it, yes. You have consumer wallets, which is a way for a consumer to hold and trade crypto. You have developer wallets, or embedded wallets, which is a way for developers to build these assets into their app. Then digital asset accounts, as you were saying, is this higher-level abstraction that brings together the many integrations. It brings together card issuing, orchestration, and wallets so that a developer doesn't have to think about putting the stack together themselves. They can just build with one thing and it just works. A bank account in a box, so to speak.

Jackson: (1:12:22) What does it mean for Privy to—you talked about customers—what does it mean for Privy to be a startup within Stripe? Versus you working on other things, like on-ramps at Stripe, which is another team? Is Privy just a team at Stripe? What is that?

Henri: (1:12:36) It's an interesting question and one where my answer is probably very different the more I do work within Stripe and the more I understand Stripe. The short answer is yes and no. I think one of the great things that startups have going for them is continuity of vision and continuity of culture. In a sense, Privy is another team within Stripe, but it's another team that's had very consistent staffing and direction for four years. We have a lot of internal memes that exist through pain and good times that can carry forward. And that's extremely powerful, which accounts for some difference in how we operate.

Jackson: (1:13:17) It's a little like, "I'm an American and I'm a New Yorker."

Henri: (1:13:19) Exactly. That's exactly right. And I think the reality is the Privy and the Stripe culture are very well matched for each other, and that's not a mistake. We literally looked at Stripe in terms of how we want to build this company. We tried to fashion ourselves after the bizarro version of, or after the marketing version of Stripe. We're very lucky in that the marketing version of Stripe and the reality are very close together. So that worked out pretty well. Culturally we share a lot of things, and I think there are cultural quirks, ways in which we work, and some operational tendencies that are a little bit disjoint. Just because we want to keep running at scale for our customers, and trying to fall in line has no intrinsic value. What does is being able to do good work together quickly.

Jackson: (1:14:06) What do you say, maybe to go back to some of our ideology and pragmatism? I'm not the best person to ask this, and you may not be the best person to answer this, so we don't need to spend a ton of time on it. But there is concern amongst people in crypto that you're building the monolith. Great, after all of this, you're going to build a really amazing performant database thing that basically the mostly good guys at Stripe—it's a pretty benevolent God. I'm conflating many things. If you were pitching a Henri from 2020...

Henri: (1:14:51) Yeah.

Jackson: (1:14:52) Who is unconvinced on this, what would you say to him?

Henri: (1:14:56) I have three things. The most blunt one to the Henri from 2020—and this is not a good sales pitch for the folks who are very worried about this—but it is: what do you prefer? A space that is irrelevant, that has no adoption, or a space that is making pragmatic decisions to drive things forward?

Jackson: (1:15:10) I think they would say that on some level that's a cop-out.

Henri: (1:15:13) Yeah, I really don't think it is. First, I think that reports of crypto's death have been greatly exaggerated, to quote Winston Churchill. I think we should be as optimistic as we've ever been. Now is a great time to build a business. Is it crypto? Is it stablecoins? The word itself carries too much. But I think it's a great time to be thinking about what ownership on the web means and what it means to have global financial rails. So that would be the first version. I don't think it's a cop-out because I genuinely think some people would—

Jackson: (1:15:44) Rather nothing at all than this.

Henri: (1:15:50) So that's the first part. I think the second part is there is a real commitment—and this is such a lived reality—to an open stack. We work with Lightspark and Plasma and Solana and Base, and these are all very close partners, some of whose infrastructure we power. The reality is we have made commitments and hopefully lived up to them. I live to get called out, basically, because that's the point, but we're actually building in an open ecosystem and an open stack. Now I'm saying Stripe is an ambitious company that, wherever it runs into issues, will try to solve them by building software, which is what we know how to do, especially when we feel like we have good instincts for what the software should be. This is how I think Tempo was born. It was born out of issues with chains that needed managing. I think choosing not to do something that we think we can do a good job of because it looks bad is such a bad way of trying to have impact on the world. I would say I think it's a very valid concern. I think the commitment to an open stack is absolute, and so the pieces work well together and you don't need to do the whole thing if you don't want to. But also, I wish there were a lot more people in this space trying to build end-to-end solutions that could transform developers' and consumers' lives. I genuinely think it's a really good thing when some people do. So that's kind of my take. Again, whenever people dunk on us on Twitter, it's usually, "Ah, of course this is the Stripe acquisition. Privy's gone downhill since," or some version. It doesn't happen that often, thankfully, and we work our asses off. But let me say, our incompetence is very much our own. In the many places where Privy falls short, it's because we are incapable in those instances; it is not because there's something else. I actually think working in service to the user is a deeply ingrained cultural value that both orgs share. That's kind of true north.

Jackson: (1:17:56) Something I was thinking about recently is there's a difference between—in the AI context, people are talking a lot about values—and I'm more interested in incentives than I am in values. I don't think Facebook necessarily has bad values. Maybe they do, but I think they've had some bad incentives. Even something as simple as a commitment to being open source. What are the structural things that actually allow this to happen and have it still be aligned with Stripe's business goals?

Henri: (1:18:26) My honest take is Stripe being a private company and having very strong-willed founders is a lot of that. Which is to say, Tami and Stripe Press existing, Stripe Climate being a thing, Atlas being a thing.

Jackson: (1:18:40) Yeah.

Henri: (1:18:40) There are just so many examples of things that make a priori no business sense but happen to be intellectually interesting and meaningful. I think Stripe's core belief—this is the core incentive—is that startups will always have a place in moving the world forward and that serving individuals and small teams who are trying to build things is intrinsically valuable.

Jackson: (1:19:09) Yeah.

Henri: (1:19:11) It is a belief in the future. In a sense, it's a very optimistic place in that regard. And so the point is closer to—

Jackson: (1:19:17) A value, but it's a value that they really are showing that they believe.

Henri: (1:19:20) Exactly. And so I think it's a very long—again, these are all conversations that I had before joining, and I kind of had my bullshit meter on to try and make sure we knew what we were getting into. At least for me, it feels like a very real hill that they'll die on, not out of a principle, but out of sheer economic interest, which is that the future will be very exciting and the only way to stay relevant is to embrace it. That means to embrace new things being built, including competition. I think frankly a lot of the decisions that have driven Stripe products being built in the crypto space have been born out of frustration as users that we can't build on this substrate. We need something better and, oh, in fact, we have this idea. I think in many ways the short-term economic interest would be much easier to not do these things. So I think, again, it's up to us to stick the landing and make sure that the developer experience building on these rails is absolutely excellent.

Jackson: (1:20:23) What do you think Stripe is becoming?

Henri: (1:20:27) I've heard a sentence, and I don't know that this is canon, so don't quote me on it—

Jackson: (1:20:30) I'm not asking for the company view.

Henri: (1:20:31) But I think first, great developer tooling that can be used for anyone to build meaningful businesses on the web is probably the lowest-level true thing. You see it because Atlas is a way to build a company and Stripe Payments is a way to monetize it. Now we have these financial rails for money movement and all that. So that's the first thing: the platform that developers come to to power the financial infrastructure for businesses they want to build online and in the real world. I think the second one is much more of a tooling-first perspective, which is kind of AWS for money in a sense. If you move into a world where money is data, then what are the core tools and infrastructure pieces that have to be assembled to build with that construct, money? I think a lot of the things happening in the agentic world speak to that. We are moving into a place where sub-cent transactions were never a very big concern, I'm guessing, because no one was making sub-cent purchases. But in a world in which agents can stream payments for content and you're buying by the megabyte—terrible idea—the physics of money change. I think that role as "how do we build the tools to power it" and "how do we become guardians for the sanctity of the consumer and business interest in being able to rely on these rails to grow" is a core part of what Stripe is becoming. Then I think the third—and here I'm just reading through the same lines everyone else is by looking at what Stripe is putting out in the world—is hopefully an agent for acceleration of tasteful things in the world. The commitment to beauty and craft. I've spent more time than I care to think about talking to Patrick about the floral arrangements at Stripe offices and the smell of Stripe offices—not actually a joke. There is a real point that craft is in itself something that is worth pursuing. If we can help people hone their craft by focusing on the right things and we ourselves can put out things that are beautiful, that is intrinsically valuable and something that moves the world forward. You can see I've drunk the Kool-Aid, but I believe it.

(1:22:54) Crypto's Future, Power Laws, Optimism and Pessimism

Jackson: (1:22:54) A couple questions on crypto, broadly. You have a line somewhere where you say the difference in crypto between the theoretically possible and the actually true, which obviously runs through a lot of our conversation. I guess at a super high level—I mean, I did a tour of duty in crypto. That’s how I know you. There was this grand vision. There were different words for it. I never really loved the Web3 name. Maybe the thing that felt most important about it was ownership. And that could be digital ownership of different types of assets, some of which may be worth more or less than they were in the past. But even something as simple as users should own the networks they use, the tools they use. Do you think that that dream is dead?

Henri: (1:23:44) I don’t think so. I think things are cyclical. This is going to be a very cop-out answer, but I think things are cyclical. And I think, frankly, again, the tension between hype and reality in any space is such a dangerous thing. You can only go so far in stretching the band towards hype before reality and impact has to catch up with it, or the band breaks and bubbles burst. And I think right now, us focusing on delivering value to the world through concrete economic tools that are empowering to people in the Western and non-Western worlds alike is so fucking important to actually building the means of bringing that back. So I’m feeling very optimistic because I’ve basically never seen crypto deliver so much value to the world in a way that wasn’t necessarily what we tried. But I think this will come back. And this doesn’t necessarily mean the crypto bros of old will come back. I think many of them have washed out forever because it’s such a hard space to work in in many ways. But I think if you give it 10 years and impact can wash some of the stink off of crypto, then it just stands to reason that people thinking about, "What does ownership mean on the web?"—the web is becoming more and more important. AI in general, digital cognition is not going anywhere. These questions are becoming more important than ever. And we are building out, again, just a very important rail for reasoning with what does it mean to own things on this platform. So I actually feel very good because this is an essential question for the future. Now, whether it ends up looking like what we thought Web3 was going to look like or not, I’ve learned to be less fussed about trying to shape the market to my will rather than hopefully make forward progress in a positive way.

Jackson: (1:25:32) Yeah, I guess my feeling is it sort of feels that crypto has barbelled, which is that there’s the boring part which is stablecoins, which basically can’t have speculation—I shouldn’t say can’t, but it’s very hard. And then wherever there can be any speculation, there’s max speculation, which basically means trading.

Henri: (1:25:49) But this is the interesting part. There’s a good Vitalik tweet which was some version of, "What we thought was going to happen: crypto will become sane and start resembling normal markets. What actually happened? Normal markets look like crypto." And so I think crypto has been a forerunner and distillation of a lot of what’s happening in the world. But I think you see it in so many other places, and maybe in that sense, there is such a thing as crypto-native culture, and I think it is like a hyper-concentration. It is the moonshine of the internet in many ways where it just front-ran what happens when you over-financialize things to a large extent and when internet memetics take on an intrinsic importance. And I guess my point is I think the barbell is real. I think in both cases each side of the barbell is seeping out of crypto. I think prediction markets in many ways, where a lot of the speculative liquidity from crypto... it's a bigger market because there are a lot of people who are using those in very different ways that have no relation to crypto. But a lot of the folks who were dabbling in meme coins or prior to that in other spaces have recycled capital to move towards those markets. You're seeing two worlds meet there, and on the other side, on the stablecoin side, you're seeing two worlds meet of folks like me working with financial institutions and traditional global marketplaces to deliver real value to the users in that way. And so I think both sides are very interesting. And basically, I think the question of—very soon we're moving into the age where saying I'm a VC investing in internet companies so obviously makes no sense. We had that version, then we had cloud, makes no sense anymore either. And we're moving to an age where saying I focus on AI makes less and less sense. And I basically just think crypto is slower. But there will come a point where saying my products touch digital value will be part of the fabric. And so I don't know, basically, what won't happen, I believe, is crypto-native culture will be everyone's culture and we will move to a cypherpunk world in which everyone's carrying a Ledger in their pocket. I love Ledger, but I just think it is going to become part of the fabric of the internet in a much deeper way and it will not resemble what we thought it might. So yes, Web3 is dead.

Jackson: (1:28:08) I agree with all of that. And neither of those things is these more idealistic ideas of users being able to own a network.

Henri: (1:28:19) Oh, sorry, yeah, bringing that back. I am—

Jackson: (1:28:21) Or even something as, whatever, digital assets that aren't rampantly speculative.

Henri: (1:28:27) When I got into crypto, what excited me was visions of Limewire and Kazaa. And this was basically, we've taken the very cool distributed systems research from the early 2000s and we have now bolted incentives into them in a very deep way. And that will be the resurgence of federated and decentralized networks as the core substrate for building information. And you see it even right now with the AI labs, the fact that we're in a—depending on how you look at it—version of an oligopoly for intelligence. There are so many fundamentally centralizing forces in the world. I'm just unconvinced that user-owned networks... I think it is a beautiful idea and I worry that market realities and human nature make it that actually... like, kibbutzim and communes.

Jackson: (1:29:22) Isn't this part of the dream of markets? Aren't markets supposed to be how we—

Henri: (1:29:24) Well, so far capitalism is winning. So the kibbutz and the commune: great ideas, works at a small scale de facto.

Jackson: (1:29:31) Oh, I don't mean that. I more mean like, let a thousand flowers bloom. Why don't we have... the fact that there are two AI labs or three AI labs and it seems that the power law is going to keep hitting harder and harder and harder, which is the—if you were going to create a bear case against capitalism and markets, it would be that they actually enable the extreme end of the power law. I realize that's a—

Henri: (1:29:50) No, I understand, but I guess I worked on Filecoin for a number of years, which is trying to decentralize access to storage. And basically there are two things at play: there's market forces and then there's technological advancement. The reality is Moore's Law is continuing to run and so the relative value of decentralizing storage is much less important because storage is in itself getting cheaper. And so the market need will be reduced. And we were already up against centralizing forces in the market. And so I believe that we're seeing the same thing play out with AI. The incentives determine outcomes. There is clear demand for intelligence and GPU production and general ability to do matrix multiplication is growing like a weed where we are now energy constrained as the core bottleneck rather than chip constrained. I believe that there's too much path dependency for such a system to come out because people have thought it was a better alternative. To me, it's the same futility as asking AI labs to pause research while we figure it out.

Jackson: (1:30:51) Yeah, okay. Fair. There are two threads I want to pull out that I'm going to conflate into one question, which may deliberately be difficult—which is there's this Power Law thing. It seems like technology is making the world more Power Law and more concentrated, not less.

Henri: (1:31:08) Well, yes and no. Because at the same time, I remember an era circa 2014 or 2018 where it was like we are kind of at the end of history in terms of what big tech can mean. You've got the FAANG at the time, and no other big platform can compete—like AWS has got this and Facebook has got that. And that's just clearly so not true anymore. Disruption has come from left field. But basically, I think what is so cool and exciting about working in this space is we are just expanding what is possible for humanity to do. You've got SpaceX and multi-planetary systems existing in a very real way, and you had Loon versus Starlink. So I'm just saying, I actually think old systems ossify and the Power Law is relentless, but innovation and creative destruction is an unstoppable force.

Jackson: (1:32:04) The Power Law keeps getting bigger and bigger, and yet we have new disruption.

Henri: (1:32:07) Exactly right.

Jackson: (1:32:08) I guess that it was a question about optimism. My other question about optimism, which is—

Henri: (1:32:11) —is a very optimistic take for what it is that I have. Yes.

Jackson: (1:32:15) What I was going to conflate is, are you really that optimistic about the future? That was one piece of it. The other piece, though—you brought up the Vitalik tweet I had written down. You had retweeted Andrew Reed on the same note, and you had likened it to Vitalik. He says everything is crypto now: the launch videos, the fake AR, the fake users, the affiliate kickbacks, the coordinated pumps, the group chats, the random FUD from competitors—wild financialization of the world.

Henri: (1:32:41) You are.

Jackson: (1:32:42) I always joke with people. Crypto is hilarious because you have the worst people ever and then just the most thoughtful, brilliant nerds ever. And they're combined into one thing. That's less true than it was three years ago. What do you think? And again, you're not working—although you guys pumped out fun uses for Privy.

Henri: (1:33:01) We're very proud of our work with, again, these very tasteful developers.

Jackson: (1:33:04) What do you think's going to happen? Are we just headed to a world where we all have UBI and people gamble their lives away? That's overly nihilistic.

Henri: (1:33:16) But first, who the fuck am I to espouse any views with regards to this thing? So I'll just say I'm wildly outclassed. I can share my personal opinions.

Jackson: (1:33:23) I'm more curious if you're more optimistic or pessimistic and how you think about it.

Henri: (1:33:29) My take is twofold. I think the "permanent underclass" meme is very powerful. For those who don't know, the meme is basically, if you move to a world in which intelligence is on tap and you have a slot machine for intelligence, then basically, being the richest and being the smartest are the same thing. And there is no upward mobility anymore, because how much capital you have by the time the singularity comes around is the direct determinant of how successful you will be in the future. The escape from the permanent underclass is—we have two years, by the way.

Jackson: (1:34:04) A lot of the world, including probably a bunch of Europe, has believed this a lot longer than AI.

Henri: (1:34:08) For sure. This Marxist theory, I don't know. But my point is, I worry a lot about AI safety, but I also think humans are extremely resilient, and we're talking about something that is unknowable. That is the definition of the singularity. But I'll take that out of the equation for a second, because that's another topic. I think my main response is I actually really believe in market forces and creative disruption and destruction and the fact that there are always ways of building newer, better things. Broadly, the thing I'm most worried about is social upheaval as a response to these things. I think we are probably due a very big tech backlash. France was never so innovative than in the post-war years. It's very hard to think that it did not take World War II and the Shoah and all these things to actually get us to a place where we could do this. So I think I'm basically macro very optimistic about the future. Micro, I think the path to getting there and to continuing is going to be a little rough. I'm very worried about how polarized things are and how much stock people are putting in things that I think are—everything has become a litmus test. That's the definition of polarization. I worry that the path to getting there is going to be a little bloody.

Jackson: (1:35:40) Is there anything we can do about it?

Henri: (1:35:42) The point is to say, I think being intellectually consistent and nuanced across both sides—because nothing is ever as bad or as good as it seems—is the only way I can find to deal with it. So if you're utterly convinced about something and you can't be spoken out of it, I would treat that with extreme caution because it probably means you're wrong.

Jackson: (1:36:01) Thanks for bearing with me on the existential question.

Henri: (1:36:05) Sorry, I'll just come back. I'm trying to think about this for my kids. I have very young kids and I think the main thing I'm trying to do is make sure they are agentic. Make sure that they feel like they have the power to change things around them. Again, I've grown up with so much privilege that it's easy for me to think so. But the point is that remembering that the folks who are making the rules are no smarter than you are is such a powerful reminder that you should try and be an actor rather than a victim of events.

Jackson: (1:36:36) How do you teach that?

Henri: (1:36:37) I think through small things. My son is super into the Eiffel Tower and we made a bet that I lost. And so we're going to go to the summit of the Eiffel Tower. I honestly forgot what the exact bet was. But the point is showing him that I take him seriously as a kid and that basically I'm putting stuff on the line in the relationship. In this case, we get to go to the Eiffel Tower together. It's not a terrible loss. I think the way to prove it is to have him question things and have him be an agent. So if he wants to ask someone something on the street, he has to go and ask someone something on the street.

Jackson: (1:37:17) There is a low-hanging fruit joke about how you're teaching your kid to be a wild gambler.

Henri: (1:37:21) True, true. In fact, I bet him yesterday a watch that he would not come wake me up in the middle of the night. After two failed attempts, it is now worth—it's a bribe. So he had to earn it. That's funny-ish.

Jackson: (1:37:39) But.

Henri: (1:37:39) Yeah, but so I think in that sense, the thing that maybe pisses me off most with tech is Gell-Mann amnesia. Gell-Mann amnesia is you read a newspaper column, you think, "Oh, I know about this field and this is all bullshit," and then you read another column that you don't know about and you take it as gospel. I think tech tends to forget this. And I think the way in which extraordinary tech leaders then think they know everything about everything is a little odd. So I think just remaining nuanced and humble, but also knowing that you can shape things is the way at least I'm trying to behave.

(1:38:14) Closing: Asta, Stripe's Leaders, Being French, and Never Compromising

Jackson: (1:38:14) You wrote a founder variation of the Proust questionnaire back on Medium. What makes Asta wonderful and great in her own right, and what makes her such a good complement to you?

Henri: (1:38:33) It's a great question. I think in her own right, she is—the meme I really like is Paul Graham's "formidable founders." I think she's formidable, and I think it comes in two different ways: she is extraordinarily self-confident and extraordinarily good at what she does. She is the epitome of competence. She's just very good and very self-confident, and so she doesn't waste time. But she's also very low ego. Accordingly, she doesn't waste time thinking about the meta of it all or anything beyond what is the most effective path and who is the best person to do it. That makes her just such an amazing person to work with and leader at the company, because she has very strong opinions or she has very weak opinions, and she knows exactly which is which. She's very clear in how she states both. I think Asta is probably the toughest manager that I've ever seen operate. But that's because she has—I don't know how good this is—but she has the slight "tiz" of being very no-holds-barred and straight with people, but in a way that really pushes them. So I think she's, in that sense, really, really formidable. I think she's a very good fit to me because—and hopefully me to her—we're very different in the areas where we spike, and we have been able to build implicit trust so that we know where to lean on the other. I think basically there's probably some sanctity to our relationship at this point that goes beyond any given question or outcome. It's interesting because, again, I started working with Z as a really close friend from college, and we spent so much time assuming that our personal relationship was all you needed to be business partners. With Asta, I didn't know her at all before starting Privy. So we came in, and for me, it was: "Am I finding the right business partner?" It is costless if the answer is no, because then I don't have to see this person again that I have spent these last 20-whatever years not seeing. So we went in very intentionally, and there was for the first year a question that we kept asking each other, which is: "When is the honeymoon over? When will the shoe drop and we'll find out all the ways in which we suck?" There's enough mutual respect and admiration, basically, that the honeymoon hasn't ended. I can say all the ways in which she's not good at what she does, and she can do the same for me. But we have found a way to build that trust and buttress each other in really good ways. There just isn't that much ego when we work together. It is about the work. I think any relationship where, when you work with someone, it is about you or it is about them, is a telltale sign that the fit isn't there.

Jackson: (1:41:29) When you say different spikes, is that domain expertise? Is that way of working with people? Is that...

Henri: (1:41:35) I think it's domain expertise. I think it's things we value and respecting it. For example, I'm a pretty atrocious manager; she's a very good manager, in my opinion, and we know that about each other. I think I'm a very intuitive decision-maker and she's a very rational decision-maker, and we know this about each other. So I think it's in the ways that we operate, and then obviously spikes. I understand parts of the crypto market exceedingly well, but I can't hold a candle to how she operates technically and the way she's been able to scale the system in a huge way. The way Privy has scaled on a relative basis—kept four-nines uptime throughout our existence, basically through periods like Friendtech where we had week-on-week, like, 40x the traffic for multiple weeks on end—is so impressive. So it's stuff like that.

Jackson: (1:42:26) You have this three-headed dragon of very impressive people at Stripe: Patrick and John, and then Will Gaybrick, who's maybe a little less known. What have you learned from those guys?

Henri: (1:42:38) So I'm really impressed and I really enjoy working with them—the three of them. Honestly, a lot of it is operating as a triumvirate, and the way in which they operate together is pretty wild and impressive to see. The force multiplication that you have is really great. I think I've probably learned a few things. One is everything at Privy feels really personal to me in a way where any person leaving, anything happening that's bad, feels like such an indictment on my work. They've been at it for decades, and so there is a sense of steadiness from them. They've been able to basically fuel ambition and get more and more ambitious over time, but also be steady in their vision and their execution and be resourceful in that way. That's one thing that I think I'm learning in real time by just observing them. I'm very grateful because I get to basically scale Privy, even though we're part of Stripe, in that way. Two is, I think, balancing short-term kinetics with long-term structure and building it right from the start. I actually think Privy is quite good at that generally, but that's another area where there's a lot to be shared. And then maybe the third is giving room for whims.

Jackson: (1:44:15) Whims?

Henri: (1:44:16) Yeah. Again, I look at Stripe Press, I look at Climate—I look at these things that need not exist, and yet I think both Stripe and the world are better off for them existing. My sense was always you kind of have to earn that. It's easy to do once you've got a very successful business that is pumping out cash.

Jackson: (1:44:35) But it's Google hiding its own...

Henri: (1:44:36) Exactly, exactly. But I think finding stage-appropriate ways of having that exist is really, really important. Then maybe the third thing—and this is the thing I have most to learn on—is leverage. They're running a massive org, and yet when I talk to Will, I feel like he is so deep in the weeds. Basically, the breadth and depth means he has learned to scale himself endlessly, whereby he is able to be very high-context and precise. But he also knows when to delegate and how. So I think there's something to leverage and cultivation of talent that they are doing that I really want to learn from.

Jackson: (1:45:20) What have you learned from Chloe?

Henri: (1:45:22) Oh, many things. I think Chloe's interesting because she's endlessly pragmatic. She's both very intellectual and drawn to all the things that we've talked about, but she has very low patience for conversations that spin and don't lead to outcomes. I think basically some versions of proper impatience with, "All right, should I get off the pot? Where are we driving here? And what is the thing that we want to get to?" Then I think she is also just much more civically minded and thoughtful about bigger societal ramifications. She reads economics books for fun. In that sense, she is much more Collison-like than I am. But I think thinking about what are the repercussions of what we're building and, broadly, the interplay between private and public is something that she's taught me a lot of—beyond the infinity of many things that we've learned in 20 years of shared life.

Jackson: (1:46:27) Just a few final things. You worked on the declassification engine at Columbia?

Henri: (1:46:33) Yes.

Jackson: (1:46:33) Can you tell us a little bit about what was interesting about that?

Henri: (1:46:36) It was very interesting. I worked on two things that were AI-related and that are now so quaint, which is so interesting. One was a system for training machine learning models—at this time it was Markov chains, so this dates where we were at in NLP terms. It was training on Yelp data to try and work with the—I forget what it's called—New York Department of Health and Mental Hygiene, basically food health. The point was to look at Yelp reviews to try and figure out what restaurant kitchens should get inspected because they're making people sick.

Jackson: (1:47:12) Wow.

Henri: (1:47:13) And the interesting problems were that "sick" can mean very different things depending on intonation and sentence. So we had to train the models in interesting ways. Again, 20 minutes of vibe-coded agent tech work today was like a research project then, so the space moves. The declassification project was a similar thing: can you actually take redacted government papers and try to declassify them based on basically interpolation from other papers that have been declassified? Can you basically correlate data across different FOIA requests to try and understand what's going on behind the scenes and take a best guess—this is how I remember it, in any event—as to what's happening under the hood? It was both a data structuring problem—the classified data is a mess—and how you actually look through the full archives to reconcile things that maybe have already been declassified here but not there. It's an inference problem. You know, "Cuba's Fidel"—there's probably one word that's going to come after that, and it's pretty easy to tell what it is. So how do you actually infer the likely piece behind it? It begs an interesting question, which is that things are overly classified in many ways, so how do you get to a better standard? Again, I actually think this is back to how systems evolve. You could spend some time coming up with a better classification system, or you basically introduce a new process of declassification. This is where bureaucracies kind of go wrong, both in private and public sector: you create a solution to fix a problem when you should have just fixed the problem, in a sense.

Jackson: (1:48:56) In what way are you most French?

Henri: (1:49:01) I don't know. I think probably some amount of innate skepticism around vision and things like that. There's a very Jesuitic mindset to not getting overly sold on these things. I think probably whilst I'm extremely capitalistic at heart and believe in the importance of private enterprise in moving the world forward, I know what great government services look like and the extent to which I've missed them in many a place in the US. And then probably there's a lot of stuff around food. Bread sucks here. There's the sanctity of having a great meal, probably some version of it as well. Stuff like that.

Jackson: (1:49:52) What's the best French film, or at least your favorite?

Henri: (1:49:59) Such a hard question, an impossible question. I'll give three that are different parts of the spectrum. The very wonky cult classic, the equivalent of Scary Movie but with French humor, is called The City of Fear—La Cité de la peur—which is an old one. I don't think it would be funny to anybody not French, and I don't know if it would be funny to anybody Gen Z. But that is an open question, and that is a very quintessentially French movie. There's an old movie called The Rules of the Game. That is a great French classic. And then probably the third would be more recent. There's a movie called Heartbreaker with Romain Duris and Vanessa Paradis, which is a very good French rom-com about a guy who gets hired to woo a woman. It's the exact right type of French rom-com that kind of works. I'm assuming it has either already been adapted or will be adapted in the US.

Jackson: (1:51:09) Can you tell us about your watch?

Henri: (1:51:11) So I'm the descendant of a very famous—no. This is a watch I find really cool. Sean McGuire is the last Sequoia name-drop of the session, but he's the investor that we worked very closely with. Josephine Chen at Sequoia is a really good friend and had this watch that was awesome and quirky. I lose shit all the time, and this is the watch that I've actually not lost in a long time. That is just something I like.

Jackson: (1:51:46) My last question: You are very principled, despite all the pragmatism. What do you hope to never compromise on?

Henri: (1:52:00) I think any place where I'm not saying what I think hurts me a little bit. That isn't to say I say everything—I'm quite private, and I think being silent is a very good default mode of operation. How do we save the world? People shut up a little bit more. That might be a really good place to start. This is why part of this exercise, obviously, is ironic because I'm just spewing my thoughts on things, but I'm okay with not saying things. I think being asked to say something I don't believe is very, very hard for me. You probably see me get physically uncomfortable in those places. Espousing a worldview for convenience that isn't my own feels very hard, and I hope not to change in that regard.

Jackson: (1:52:50) Well, thank you for thinking out loud with me today nonetheless. That's all I got. Thanks again.

Henri: (1:52:54) Thank you.

48. Henri Stern - Principled Enough to Be Pragmatic