Mercurial Artifacts with Nicholas Jitkoff

[SOLEIO ]: First of Kind Season 1 would not be possible without the support of our sponsors. Thank you to Perplexity, Cursor, Framer, Granola, and Linear. Maybe we should go through each of the interviews. Yeah, yeah, yeah.

And talk about why they fit that mold of first of a kind.

[SOLEIO ]: Nicholas Dykhoff. He is first of a kind in so many ways. His work first appeared on my radar as a Mac app that you installed and it gave you a lightning-fast way to search across your entire computer. And it was like an entry point into not just like opening apps, but just accessing anything that you can type in 3 or 4 keystrokes. He ended up selling this business to Google and was lost there, but in practice was the person spearheading things like Material Design and orchestrating acts of corporate jiu-jitsu that I feel like are first of a kind. Nobody really had to kind of wrangle a company of Google's scale in the manner that he was able to kind of coalesce disparate design elements into a single unified design vision. You know, Material Design launches, byline Nicholas Zhikhov. It's like spotting like Bigfoot in the forest. It's like, there he is, he's out there, he's real. And I feel so fortunate to have been able to get to become friends and colleagues and to see him work at the same companies that I did, albeit several years removed, but to get to circle back and back and back again on this idea of like, how do you bring new life to familiar form factors and how do you converge emerging technologies into consumer experiences that are simple and straightforward and that give you the same sense of raw power that his first application, Quicksilver, gave to me, you know, decades ago. I feel like with this new business, they're going to get to go back to basics and really kind of reimagine what an operating system might look like, what it might look like to have agents working at your disposal and what that point of integration looks like for a given consumer. And I think it looks radically different potentially from, you know, the email and text messaging and docs that we're so familiar with. So I'm really excited to see what they end up bringing to market there. I want to start with where we left off last, which is design hiring for a new company in the year 25, mostly because I think that it's easy to just kind of work through some of the things that are squirrely in your mind, but really just to be able to come back to the same topic towards the end. All right, once we've had a chance to kind of talk through some of our shared experiences and what kind of keeps you coming back to software as the realm for plying your trade.

With the caveats of this is my first time doing design hiring for a new company without the structures of a larger one. Lots of interesting aspects I think come from larger companies and the way that you build out teams or work on new efforts in them. But this is partly what I would get value out of talking to you about is just how do you think about bootstrapping the design discipline within a completely new context.

[SOLEIO ]: Yeah, the analogy I often use to folks who are familiar with Calvin Hobbes is the cardboard rocks or the transmogrifier, right? You set it to cloning and you start with the founders. You sort of start with the assumption that somebody on the founding team is involved with designing the product. And there's a shape to how they participate in that process, whether it's directly manipulating the user interface, setting product direction, being, you know, editor-in-chief, or being some combination of all the above. When we identify that person, we clone them. I often start with the question of like, well, what's still missing? Even if you had two of you in this team, where do you feel like there's like immediate gaps that come to mind from like a practical staffing standpoint, but also from like a complementary skill set way?

It's also looking at not just that one person, like in the case of the folks I'm working with, there's actually a lot of overlap between our skill sets. Like where 3 of us are actually working on engineering as well as whatever else we're doing.

[SOLEIO ]: Right.

And like 2 of us are working on product thinking, maybe 3 of us. So like it's, there's a lot of the gaps aren't just with like a single person, but more like what helps fill out that group of people. Starting from the, like the concept of cloning, You immediately make me think of like, what are the gaps in my own abilities, which tend to be more around deep visual design, like those kinds of things where I can recognize what's good, but like it, I lean on other people who like have the skills to like imagine those things and put them together and to bounce ideas off of them. So maybe it is kind of like an awkward forcing function to look at like, what are you not good at?

[SOLEIO ]: Right.

And what is your immediate need as you expand a team to like to bolster that? I've been drawn both to visual design and branding, but also like writing, research, like, right? Those are things that I appreciate, but don't have as much skill to drive them forward on my own. And given a very limited number of opportunities to hire, like would look towards those kind of like hybrids, people who can actually combine some set of those skills. Usually because it involves a lot more both empathy for users and how you would construct a product and gets you out of this very urgent, just make a thing, take the next step, iterate in a very healthy way.

[SOLEIO ]: Yeah. I also think that founders set a certain degree of moral authority within a company and that moral authority often aligned with what they value, what they really care about, how they project their best selves. Onto the team strategy and approach to problem solving and virtually approach to anything. And a good way to kind of like suss that out is often like, what are the kinds of former collaborators you found in very different contexts where you're like, you know, when that person did XYZ, that really resonated with me. That sort of like reflected what I kind of take pride in myself. Making a decision as to whether or not that value set is appropriate in this context, in this new company. At its current stage. Because sometimes there is also this issue of like, well, is this a great hire for right now or for next year? Because of how ambiguous things might be in our current state, maybe they won't be set up for the same degree of success as they would be if we're a little bit further along on our vision.

Depends quite a lot on like what the product and things people are building. In our case, we've leaned much more towards engineering is like a very valuable thing to have now. And ideally engineers who can think through design problems and can experiment in the right way, which stands in for design for a small period of time, but it's very helpful. And you also end up with good partners to work with in the long run.

[SOLEIO ]: For folks that are hearing about this new company for the first time, what's sort of the current summary, the elevator pitch that you share?

Exploring the opportunities that AI and LLMs are going to afford and how you can help improve people's lives, like bringing together the information that they need or performing actions on their behalf, that kind of thing, which is a very open space that there have been lots of people working in for now decades, but new technology that can be applied to it.

[SOLEIO ]: And at your heart, are you viewing yourselves as a consumer company, as a company that's ultimately serving a very horizontal, broad set of people?

I think so. Our initial leaning was towards consumers, but acknowledging that they have professional lives that are very closely attached to their personal lives so that it's not— I've seen just working in large companies so much division between like, this is the work-life stuff and this is the personal life stuff. And it's always been a point of friction. And so trying to design for something that can comfortably span them and acknowledge that people have these not split lives, but conjoined lives, I think there's an opportunity in doing that well.

[SOLEIO ]: Interesting. Okay. Has this evolved meaningfully from what you first discussed as a team, or is it more of just like a more thoroughly expressed version of that initial vision?

I think it's continued to be refined and heatedly debated. And like, a lot of it is anchored in stuff that we have collectively cared about for a long time. Like, many of us met working together on voice interfaces, like mobile. Apple will work and Oculus as well. So it's just like, it gets into building operating systems and operating systems at their base are actually trying to help people accomplish things. So just finding a new way of doing that in a new medium or evolving existing mediums, it's just an easy draw for all of us.

[SOLEIO ]: Right. How much have you had to personally adapt your approach to design across all these different cultures that you've joined kind of mid-stride, where there's a preexisting team, a preexisting product, people with design in their title doing design work. You've had storied stints at Google, at Dropbox, at Facebook Meta, more recently at Figma. You know, when you sort of look across those different scenarios, is there Do you sort of feel a responsibility to kind of be Nicholas Jakoff in each, or to, to use your word, pathfind inside of each of these cultures to identify the way in which to practice design or apply oneself in that given context?

It shifts depending so much on the company and also the context of joining a company. Like Google was very different for me because I essentially grew up there and like it was evolving from an engineer to design work and establishing hundreds of connections to people while there.

[SOLEIO ]: Right.

Versus at Meta coming into essentially a company of the same size, but having no connections, it relied a lot on like the design leaders or the executives within that space to create a room to do pathfinding or other kind of work. And that acts as a replacement for having to form relationships quickly to accomplish stuff.

[SOLEIO ]: Right.

The role of design has shifted so much over the course of those like 20 years that I've been working that like, one, it's nice that design has more of a seat at the table and doesn't need to argue for that piece of it anymore.

[SOLEIO ]: Right.

If anything, you have almost overwhelming enthusiasm from people of like, design needs to figure this all out.

[SOLEIO ]: Right.

What are the resources we need to do that? And it's, it's a great opportunity, but it also puts a lot more like, yeah, almost like product weight and directional strategy work.

[SOLEIO ]: Do you feel like it's an overcorrection in some respects?

No, no, it's fine.

[SOLEIO ]: Okay.

It is, I think it's—

[SOLEIO ]: But it's better than stapling it.

It's everything the design has always wanted. They just got it and then I think are surprised by how much work it is.

[SOLEIO ]: And how much responsibility it is too, right? Yeah. Yeah.

Pathfinding is somewhat unique and I appreciate it just because it is somewhat off the critical path, but ideally close enough that it can have a near-term impact. I think Meta is interesting because it had a range of the team making the operating systems for VR, the research teams thinking like 10 years out to build crazy new displays and other technology, and then sitting somewhere between them of like, what are things that are coming from that that feel near-term actionable? It's some of the most exciting parts of design that I really enjoy because there's a little bit of urgency but also freedom to explore things that doesn't always exist.

[SOLEIO ]: And what form does pathfinding take in your case. When you use that term, that conjures up a set of images pretty rapidly. For folks who are outside of the field of software design, or maybe really early in their journey in software design, like what does that mean in practice?

It really is about storytelling and vision setting, just thinking through what are the things that we could create that paint a picture of the things that can be built, and in my case, more towards the near term, things that feel feasible but also inspiring. Pathfinding doesn't always strictly exist as a team. Very often it's an activity that's taken on by any design team, like where you're both helping with the bugs in the current product and like near-term feature releases, but then also trying to figure out what the next step is. Often it takes a company that's ready to make a change. Like Google prior to Material wasn't really open to doing anything until Larry was just like, no, we must make a change. You all have 9 months to do this. And where there was an impetus to do it, and willingness to commit resources. And in some cases, design acts as a catalyst to do that, where they have to explain why this is going to be of value. Sometimes it's just a decision that is made. In either form, like, you just need to be able to jump on it and, like, run with it. That combination of being empowered to do pathfinding with the ability to execute on that vision later happens cyclically within companies in a really nice way, but it's like being able to take advantage of it and be okay with how somewhat chaotic but also generative and exciting it is.

[SOLEIO ]: Yeah, yeah, is important. Your work first came into my sphere long ago in the early days of Mac OS X. Quicksilver was Spotlight before Spotlight even existed, if I recall correctly. And the thing that's probably most visceral to me is the The Chrome cue, the speed of the product, and it's very opinionated. Like, I'm going to have this visual element that it will be synonymous with this tool, with the feature. I think— I don't know what order events took place, either Quicksilver was acquired by Google or macOS shipped Spotlight. Effectively, they Sherlock'd you. Right? But I remember it being a step function change in how I worked with a computer because it sort of sat right at the very core of what you do next, which is often spin open an application or spin open an existing document. And it sort of satisfied both fast. It's great. When you look on that work, like kind of like the thought process for bringing that to market, and you look at the work that you've done across all these very storied companies, what are the types of work that you're doing today that most resemble the past?

The key aspects of Quicksilver was one stakeholder, which was myself. And I had the ability to iterate quickly with a group of people who were like trying it and getting feedback from them constantly.

[SOLEIO ]: Right.

And even if the base product had very natural value to people of quickly launching things. By having it available to you, it was possible then to tack on other stuff. My favorite feature of Quicksilver was the ability to send stuff to others. And this is a problem that I feel has never been solved, which is like, if I could type the name of a document that I know the name of it, and I could type the name of the person I wanted to go to, and I could hit return and it just happened, it bypasses a lot of the extra nonsense that is part of what it is today, is deciding on a medium, actually locating the object. And it was very nice to be able to place that next to app launching, which is happening hundreds of times a day, so that it could be adjacent so people might even try it. So it was a very good platform to test out little features in a way that was very extensible. My experience working in this new venture is very similar of getting into like, okay, what are the things we could do to learn from people rapidly? Like what are the simple tasks that happen frequently throughout the day that you could be adjacent to that makes it possible to try other more advanced or interesting things? One of the best ways I think to be able to build products if you have the space to do it, which is to like have an experiment, experimentation platform, be able to react quickly and be able to respond to both even internal users, like dogfooding engagements with it or external folks. But building that into the way that you make the product. A lot of companies have gotten quite good at that as an approach. I think it's very easy for the first or second version of a product, but that kind of falls by the wayside for later ones when they calcify into something specific.

[SOLEIO ]: Right. Or they're kind of married to a specific customer segment or particular approach or to their own work, to their own kind of methodology. Yeah.

And Chrome sort of got into that point where it's like Chrome was very malleable early on and ChromeOS as well. But over time they sort of drifted into like, no, this is more of a traditional browser. A couple gestures were made to be like tabs moved up to the top or like there was a single search box rather than two. A lot of it becomes more refinement.

[SOLEIO ]: Right.

Because there's expectations from people around what the product is at a certain point.

[SOLEIO ]: Right. And there's also the tension around like, well, you can argue on the one hand, it's a designer's mandate to go and tear down the walls and make the hard choices of refactoring the experience. But on the other hand, if you have hundreds of millions of people that use the product every day, they're not going to be delighted with the fact that there's now a gaping hole where they were expecting a key bit of functionality to be, and they're bumping up against all their muscle memory that had become invisible by virtue of using a browser day in and day out. And now you're really fighting against like almost like the design of a car, right?

And it's interesting to see stuff like Arc come along where they're able to take a step back and make a very different approach to this, to a similar problem, right? Because they start with a smaller user base and have all the learnings of the prior ones, right? Build on that.

[SOLEIO ]: Speaking of prior learnings, you again are coming from a pretty rich set of doctrines or ways of making software. And there's all the conventional wisdom that comes with like starting a new venture in the year 2025. All the YC videos, all the all the essays and how-tos, everything at your disposal. And there's also your personal philosophy and lived experience in making software. Are you finding that any of it's holding water? Are you finding it to be the case that maybe you're second-guessing any of the conventional wisdom or even your own approach to software? That now that you are in the pilot seat of a new rocket ship as it's being assembled in real time, that you're like, oh, actually, wait, I used to have some high conviction around this, but now I'm not so sure.

Probably more due to the current state of new technology, like LLMs and AI emerging. Like they themselves almost demand a different approach to doing stuff where a lot of design in the past was sort of iterative copying and expanding on things that were there before. And what the form that takes for this is like everything is a chatbot. And it's an easy thing to do, but you'll sort of pigeonhole yourself into like that solution.

[SOLEIO ]: Right.

And it's hard because it's reinforced by like, this is a conversational piece of technology that like wants to be that. Like you want to chat with it, you want to call it. And like, those are the main things. Yeah. In this case, it's kind of hard to shed those. And it's a little bit harder to innovate just by like doing it, layering a new aesthetic on top of it. And in some cases you actually want to stick with what is familiar rather than trying to innovate there. So I guess it just raises interesting questions of where do you devote attention and innovation to? Some of it may not live within design. It might be like within engineering or like, as I was saying about writers and researchers, like it might be within their realm to define like a different even way of describing or like contemplating how to like move through the system. That traditional product design has more work to do to get off of the way they approach things normally.

[SOLEIO ]: Right. What about the actual modalities for inputting into the system? I think you touched on it briefly. Now in a household with kids that are becoming teenagers, and what's remarkable to me is their penchant for using voice as input, which seems obvious in retrospect because you and I grew up learning how to use keyboards on physical keyboards. And so our path to proficiency felt very different than the clumsy touch interfaces as a starting point for learning QWERTY, right?

Touch was already slow for us. Voice is even more so.

[SOLEIO ]: And so I don't think it's— it makes me take for granted just the simple ability to type without thinking, right? The muscle memory there. And for them, it's like, well, just use voice. That's clearly the faster, more efficient way to talk to the computer. And so I wonder, To what degree are you factoring in modalities, emerging modalities, given the focus on consumer and given these big generational divides that I think are starting to really show themselves in the market?

I think it's almost problematic to call them modalities, because they're not even new. Voice stuff we've had, it's never been particularly satisfying. It is error-prone. It feels slower, even if it might be as a as equivalent to typing on a phone, certainly.

[SOLEIO ]: Right.

But it still feels like an inadequate way to convey what's in your head into a system. And experts who are using a desktop interface actually have the ability, they're still forced to go through a keyboard or through a mouse, but they have a slightly more high-bandwidth way of doing it. But I think the reason I said it's weird to think of them as modalities is that it doesn't mean that, it means that you don't try to get them to complement each other. I think good examples of people playing games in a group, where you are using voice to communicate with other people while simultaneously also doing things on your own, like that combination where you are coordinating multiple people or entities becomes really powerful. And so like, I don't know that just talking to a system is really as valuable as like you are working and doing something, but you ask something to help you and you may use voice to do that. But you have a way of switching modes, which can kind of layer on top. Like it's the same way that you can both drive a car and talk at the same time. Like you can combine those different things where the combination of them has like the best expressiveness about what you're trying to accomplish. And doing whatever is appropriate for a person at any moment in time where you're not locked into like, no, this is the only interface that you have to type. So like park your car so you can go over and like type something out and then get back on the road.

[SOLEIO ]: Right.

You let the user decide What's the right medium? A combination of them, right?

[SOLEIO ]: Yeah. Why do you— and I'm guessing maybe that's at the crux of it. It's like the reason why we were comfortable toggling between mouse and keyboard, mouse and keyboard, and not mouse, voice, and keyboard, mouse, voice, and keyboard, is because voice input was laggy, indeterministic, socially problematic in some places. Socially problematic in some places. Do you feel like right now we're across the threshold where like that now we can kind of go back to that as a way of, I'm just going to talk to the phone and it should like be able to respond and turn or at least like toggle over to the right input mode.

I think it's voice still feels very much like a fallback. It's like, I can't type right now. I can't use my preferred method. So this is my fallback method.

[SOLEIO ]: I see.

Even though it actually is a preferred method for humans to like communicate with each other, partly because it feels so interruptive. I think it's very hard for, your example, if you have kids and you who are in a space, when they're using voice, it still requires almost turn-taking where you have to silence those around you to be able to get a clear command through. Versus a voice interface that was actually intended to handle 3 people who were all yelling at it and understand what to do with that. Imagine the most chaotic.

[SOLEIO ]: Driving a car.

Well, like a chaotic food order or a demand for certain kinds of music where multiple people could be participating in that. Simultaneously. If anything, I think a computer could handle demultiplexing the set of voices into something coherent. And humans are better at actually even being able to separate that than machines are currently, but are naturally limited to listen to one thing at a time. But I think an exciting place to take voice would be making it possible to be present in an environment with multiple people who are all in a conversation together with whatever the agent or entity that's listening to them is.

[SOLEIO ]: One of the things that I struggle with empathizing with today's designers that have to grapple with a combination of new ergonomics and new concepts. And I don't think that those things are one-to-one in the way that I felt like they were when we were building stuff for desktop web. In desktop web land, those two things were basically the same. They were kind of fused together. The representation of this concept of this object of a newsfeed of a post of a person, they were synonymous with its representation in the interface. Yeah. Now that we're working across these different modalities, different devices, different products, the work of introducing conceptual architecture, mental models seems really fucking hard. How do you think about that work in your current context? And how relevant is it to the first design hire, the second design hire? As a way of working effectively at a team of this size?

I think it affects like the desire to hire people who will ask me questions like that. Like it is easy to fall back on these are the existing modalities or ways of presenting the product. It's harder to think across them. I think that like the introduction, the mobile UI did a very lovely thing of unsettling desktop UI, creating an alternate, I think watches and VR and voice have also added more of those where there, people started to think about how do you design across all of these so that somebody can accomplish something in a familiar way using whatever they have at hand and understanding the limitations of it, but not so much that they feel like they shouldn't even try. I think a lot of those conceptual things tend to be constrained by the form that people expect them to take. And maybe that even affects the way that designers think. I myself get locked into mobile-first thinking and then expanding from there because it's the only way I can actually start to tackle a problem. So in some ways, I think it is a tool because it's a constraint. But it is a constraint that if you don't allow it to be relaxed later, can overly focus towards pigeonholed towards one solution that design now needs to have, needs to think across things in a more free way. But it's hard when you're limited in the number of people you have. So when I'm thinking about how to build a team and I'm looking for design partners to work with, the ability to think broadly but not be so distracted by that, it's both Understanding the breadth and what the choices will cause, but being able to focus on one or two to refine them to be really compelling.

[SOLEIO ]: Yeah, because otherwise you can end up in this cosmic space where you're sort of like pinwheeling around all the possibilities and never actually grappling onto anything tangible that you're kind of anchoring a bet on or a viewpoint on. Your work at Meta was largely centered around VR. Yeah. And I want to believe that there was like a an approach to the design pre-VR for you personally, and then a, a different way to think about software post-VR once you've spent enough time behind a headset. Is there a delta there? Do you sort of feel like that part of your career is feeding back into what I call the more traditional, you know, bounded two-dimensional design spheres that we've worked in for, for some, for so many years?

VR is a very, very useful provocation. I think it's where I like where you see fallback to 2D UI, which for good reason, like in many cases, 3D interfaces can be hard for a lot of people to understand. And in practice, what you do is you give somebody something that's familiar. It is like a flat plane that you can interact with or maybe curved, but it doesn't tend to have a lot of like depth cues and things that you have to navigate around. What was really nice about VR that made it different was that it was very malleable. Like it could span that spectrum from like watch form factors up to like massive displays. Displays and didn't have to get locked into any one of them. Like, it could shift as needed to those others. And it makes you think about, with no constraints, how would you surface this experience, these controls within somebody's life, especially when you get into like AR forms of VR. Because you have the ability to place things contextually relative to the things around them, tailor them to that specific use case, the design itself needs to be very opinionated because that optionality is like option space is so huge that there's not an obvious answer to it. Or maybe there's an obvious answer where it's like the thing that you had before of like, take the mobile app, put it here, float it in front of you. It's like the introduction of like multi-touch, like where you have now some new expressive input method that hasn't really been considered. And generally most of those innovations happened early on. All of the pinch-to-zoom stuff, like the things that—

[SOLEIO ]: Hold to refresh.

It's really only 2-ish touch that really mattered, except for on iPads and larger devices. VR started to pick up some of those same things. The issue is it doesn't have as broad distribution. Like phones became ubiquitous, and so everyone sort of learned how multitouch worked.

[SOLEIO ]: So VR's not sort of feeding back into the mobile paradigm the way—

It kind of quickly, impact the broader set of patterns because people don't really experience it. And it's so much development that happened on VR platforms is locked into very basic— they'd assumed controllers that you could sort of point and click with. And then those became hand controls, which were more expressive, but mostly you were like pointing and clicking with them. So they went more of a path where they were evolving pointing and clicking rather than getting into like, oh, I have 5 fingers that I can do completely different things with. With the exception of some games, which were good at that.

[SOLEIO ]: Yeah. One of the topics that I've noticed is kind of almost organically kept recurring, at least in my sphere, is designers who want to found and the question of choosing who to found with.

Yeah.

[SOLEIO ]: Founder dating, as it were, because it's probably the most structural decision to make around a new business. Tell me a little bit about what that process was like for you and in general, like what you think is good hygiene or good counsel for designers specifically thinking about, well, I want to start a new company, I have some specific ideas I want to pursue, and I have collaborators, people I've worked with in the past, we've done amazing work together, and we're sort of doing the, hey, you want to go to— do YC? Go to South Park Commons?

Well, in my case, I ended up working with people who I've known for probably 15 years now. And it was folks that I worked with all in different contexts, but some of them, like when I was moonlighting within Google on a different project, like I went to London to work on the iOS, the first voice search app that we had. And it was this like 20% project working with people in a lower, like a lower risk project at the time. It was nice to be able to work with people in almost like a hobbyist capacity. And even since then, I had sort of stayed in touch with them. And then there was some element of testing that out. We took some, we did a few meetups where we would talk through the kind of things that we could build. My decision-making was almost entirely influenced by people though. The main focus was I want to work with these people. We can figure out what to build. And it was, as I said, to people who were more ambitious around like they want to build platforms. Like they don't want to just go build something small. They want to think through like what is the developer experience? What is the customer experience of it too? And I think then also just looking for, like we got back to hiring first designer, it's like what is the complementary set of skills and how do they fit together? And I was doing this for the first time. So like I don't have a very, I didn't have a good sense of like what is the right approach to do it? It was more just I was looking for people that I would enjoy working with, with skills that I felt would complement mine, and collectively an interest of doing everything from the company formation and organization to the product definition, design, building of it. And then that has then turned into like, how do we start to hire people that continue to extend that? Like the culture is pieced together person by person. And there are some things like the choices you make in hiring end up, each of them taking a small step towards that.

[SOLEIO ]: Say a little bit more about the side project dynamic. One, because I know that for every side project I'm familiar with of yours, there's probably 5 more lurking in your hard drive or in your closet or like roaming around your house. But because it's also in my mind, part of your reputation, the books that you've worked on. It's like when things are getting hard and there's a lot of stuff on a critical path, Nicholas Zhukov was springing another side project. And they're awesome.

Yes, as a stress release.

[SOLEIO ]: When does this guy sleep? Is it stress release? Is it a particular dynamic? Is it— the reason why I bring it up is that your energy shifted when describing this project out in London. It had a low-stakes side projecty kind of feel. Yeah. But I often think about Facebook as one of the quintessential side projects, right? It had that same kind of energy. When these guys were fundraising at some point in 2004, they were more excited about Wirehog than they were about Facebook. Yeah. Because I think they really genuinely thought of these as like a collection of side projects, not realizing that that was the thing. Yeah. And I've always found that like that playful dynamic in some ways kind of inverts the relationship to the problem space. It turns it from like a knot to be untied to something to be spun.

Yeah.

[SOLEIO ]: If that makes sense.

What's underneath it is that people are passionate, like do something because they're passionate about it. Like it is not driven by anything else. Like, especially when people have sort of day jobs and other stuff. I tended to have more side projects when I was at Dropbox because my day work was so focused on organization and like helping grow, retain, hire that it left less space for like me doing design work on my own, so it just became an outlet on Caltrain.

[SOLEIO ]: Right.

Versus when I've been engaged in more like, or the pathfinding work, which is more like Meta and Figma, like I would do, I would do projects within there that had that same sort of feel. Yeah. But what I, what I find particularly compelling about side projects is they are indicative of people's passion about something. And like even when I was hiring folks at Dropbox, like I would tend to look for people who had something that they were doing on the side that they really excited about because it was a better indicator than their past work of like the things that they would do well. And so similarly, like looking at, okay, what are the side projects of potential co-founders was a reasonable litmus test for that.

[SOLEIO ]: Right.

There is an interesting like follow-on to that though, which is there's a point at which the products that you were building shift from being like a side project thing to like, you know, this is what we're actually building. I think it's fairly gradual. Like there's, especially in a startup environment, there's a lot more energy and time being put into things. Like people working extended hours on things because they're like, oh, I just want to, I want to see how this thing works. I want to like try this out. What I've experienced of like initial startup energy has been driven by that same, like, this is like the project that we are working on. It's like exciting. And I'm interested to see how it shifts into like execution mode. Like any of those other sort of like larger projects, like where they get more defined, but hopefully don't get less exciting as a result of that. Or they leave space for like things that extend from it. And building a platform, I think is maybe a bit of a cheat because you build a platform that you can build other stuff on top of.

[SOLEIO ]: Right.

So it leaves space for like exploring something.

[SOLEIO ]: Right. How do you ensure that you don't sort of stay stuck in explore mode? Because I sort of feel like at some point every startup has to exploit the opportunity that they found in that prior explorer mode. They have to sort of claw themselves into existence, right? And then grapple from there.

Some of it is like, I think self-enforced deadlines, like even if they're arbitrary, some of it's external forces, like competitors are a pretty good motivator for some of that.

[SOLEIO ]: Yeah.

This is something that I'm currently wrestling with, with the co-founders. How do you actually create momentum towards something but also don't sacrifice the exploratory aspect, balancing it with very limited resources? And I think leaving time for anybody, design, engineering, product, the rest, to be able to do a mixture of them.

[SOLEIO ]: Let's go back to the clone thought exercise.

Okay.

[SOLEIO ]: How would you divide and conquer? How would you divvy up the work to be done? Would you want to have one person in full explore mode?

Having been on a couple pathfinding teams, like, it's never great to have the, like, such a division between, like, these are the people doing, like, the day-to-day stuff and these are the people, like, exploring what the future should be.

[SOLEIO ]: Right.

Partly because it's nice because it liberates the future people to, like, think about stuff, but they also can, like, get detached from reality so far that, like, it's not useful.

[SOLEIO ]: I find I get allergic to that. Every time I've seen instances of that, I'm like, oh my gosh, ivory tower has emerged. Why do they always show up?

Yeah, but it's very hard to make space for people who are on demand or in demand, like filing, dealing with bugs and working on the product to make space to think. So I think the important thing is to have them in proximity to each other where they feel like, where people feel like they can participate in either one of the roles and maybe they do spend most of their time doing more execution work or they spend more of their time doing more exploratory work, but they feel like they can impact what each other does. Or they feel like it's like the exploratory work has meaning because it can become something that's actually shipped because that detachment is almost as bad, if not worse, than exclusively doing execution work and not feeling like you've made a change. It's just all forced labor.

[SOLEIO ]: Where are we going? Yeah. Where are we going? Yeah. What is the strategy here? Yeah. Yeah.

And that's a huge part of the design of design teams. How do you set them up? Individual smaller teams to do that mixture.

[SOLEIO ]: I find that it doesn't hurt to sometimes ask if people thrive in setting strategy versus executing product. It often is as simple of an exercise as joining a soccer team and you're like, what position you want to play? Yeah. There's a different psychology to offense and defense. It doesn't mean that offense refuses to play any sort of defense whatsoever or vice versa. You don't sort of exploit an opportunity to come out of the back.

Yeah.

[SOLEIO ]: But there's a clear stance on the field as to what your job is principally. And I think that everybody has a mutual respect of like, yeah, our defense gives up goals. It doesn't matter how many we put in the other net, we're going to lose this game. And vice versa. If we don't put up points, that's that. It's all that works for not.

Well, and there are probably various tools that sprints, I think, are a very good one where they're like a vacation where they invite— you invite people to engage in a different way. You take them out of their day-to-day operation and can elicit really good insight about like what the future direction should be from somebody who may not be focused on that most of the time.

[SOLEIO ]: Right. Yeah.

And also extend that beyond design too, like people who are adjacent to get their thoughts and capture ideas from PM and Eng about what the design should be, even though they don't realize that's what they're talking about.

[SOLEIO ]: I think one of the things that I've constantly been enamored by with this field is how diverse our backgrounds are. Yeah. It's not like being a lawyer, right? People come from like so many different walks of life and despite it becoming more and more industrialized, it still has this facet of play and access that I feel a responsibility to kind of project forward. Yeah. In large part because I think people who classically, maybe one clock back 15 years ago, would not see themselves as software designers, maybe came across a stray bit of content, or a friend of a friend who made them realize, oh, actually, the way I think and work and approach problems is kind of very design adjacent.

Yeah.

[SOLEIO ]: And what that guy's doing in Figma doesn't seem that hard. Maybe I should try my hand at it, right?

Yeah.

[SOLEIO ]: I've got some tasteful stuff. I'm good at photography. I'm good with visual communicating. Maybe I should try my hand at it. I'm curious to hear your thoughts on like, Why software? There's probably like, you know, winding the clock back, the question of why software versus every other medium that's out there, I think is still true today. And I love that different people just have different articulations of the same answer.

I feel it's in the name, like it is the most malleable medium that you could choose. Designers come from a wide variety of backgrounds. But I, our adjacency to artists and sometimes like overlap with artists is very interesting. Like, and it almost gives license to be more exploratory of stuff. Software design kind of comes from graphic design. Like so many of those principles were carried through into it because of the structure, because of the constraints of the systems.

[SOLEIO ]: And the presentation. Yeah.

But also like designers who come from further afield backgrounds, like either who were trained in architecture or in like performance and other like photography. Those are all, it gives sort of different ways of trying to solve those same problems. And I think it's led to software having such a wider variety. Like there are structured systems and there are designers who go deep on design systems and building those out. But there are others who like create sort of wilder experience, getting into like game design and those kinds of interactive experiences. But they all benefit from that. Like it could actually go anywhere along that spectrum. Like there's a wide variety of solutions that it could come up with and like the ability to imbue it with aesthetic or like really thoughtful writing. Like it is a creative medium that I think shifts more than most other roles do. Engineering has a huge amount of like ability to be creative and do those kind of things. That's why like sort of prototyping and like design, like that intersection of the two of them, like you could also see a lot of creativity in the way people solve things. I think people are drawn to design because it is inherently very like open to like lots of ways of trying to solve a problem. Like it, so much of it is about storytelling and you can tell a story in like a dozen different ways and it could be a prototype, it could be art, like artboards, a video or just talking. Yeah, like it's It's all you're really trying to convey is a possible future. And it can be overly compelling. Like it doesn't have to actually, it's not necessarily backed by real usage and data, but it is a powerful tool that people enjoy working with.

[SOLEIO ]: My son a couple of years ago, he was being really charming. He was asked to fill out for his yearbook. What he wanted to grow up to become. Yeah. And he wrote software designer. And I was like, that's really charming. But I've reflected on that choice for quite some time, because with every incremental year, I thought it would be clear how to enter the fields. And over the last 3, any advice I could dole out gets murkier and murkier. Help clarify those waters for me. If I had Elon call you up and and say, "Hello, Mr. Zitkoff, my dad says I should talk to you about what I should spend my time doing to do what you do 10 years from now." What would you say to him?

I think software is standing in for other words. Like, it is, experience designer might be the most accurate, although it's kind of a mouthful. Like, what you're talking about is people's engagement, not just with software, but also like the hardware that it's on, the environment that it's in, And the most interesting problems are ones that span all of those. Because if you were just exclusively thinking about software, it's very limiting and not interesting. And I, everything from the marketing and onboarding and the way people first experience something and then how they get into using the product and the context in which you're using the product, like it is such a broad set of things that design and programming covers part of it, but being able to think about how it fits into that system is what's really interesting. And that almost always involves you need to deal with other people and like work with them and like understand their strengths of like, this is the marketing team, these are ways that they think about stuff and how they could best position this product in the space. It's a wonderful role to look at, but mostly because it sits within this like constellation of other people who are all trying to like guide how people would experience something. Like there's so many different ways to get into it where you can tackle it from the like, software side or tackle it from the hardware side and, or just do more pure design or like aesthetic experiences. But they're all contributing to that whole.

[SOLEIO ]: With the work you're doing, are you still giving yourself space for side projects?

Yes, I, this definitely does take more of my time and like attention. I think I have a few things that I'm actively working on, but they're just like, I'm trying to learn how to design a font and like working on a set of widgets that use that font and like just things that I've wanted. It's easier to keep those scoped small and where I'm again, the like the only stakeholder for now.

[SOLEIO ]: Can you guess which is my favorite side project of yours? I probably said it to you already. Which one?

Itty Bitty?

[SOLEIO ]: Itty Bitty for sure. Yeah. So Itty Bitty to the folks at home is a way in which to encode a small web page with small web page-like functionality into a URL. It's like a little portable self-blooming universe, the way I kind of think of it. And it's less the clever implementation of itty bitty, which I still think is quite clever and wonderful, but it is like, in my mind, like a facet of like the kind of design work that you do. That appeals to me not merely because of its cleverness and its tidiness, but there's something like big and metaphysical about this idea of like a self-blooming universe. Yeah. And now I'm like fixated on the idea of minimum viable universes, flash fiction, like the things that can, like what is the smallest amount of information you can kind of put into a system that would allow it to grow? Yeah. And, you know, how much fidelity you need to have a fable become a full-blown world, right? And what inputs would it require? The reason I'm bringing it up is I'm curious to know whether or not there are facets of your side projects that feed into an idea for a new platform, where there are new actors, new constituents that haven't existed before, but are emerging today, agents. Machines that can set policy and then act on policy and revise their policy and review their own work and sort of act independently of human participants.

All of them are connected. Quicksilver was designed as a platform for experimentation with UI paradigms and other stuff. And it was well suited to that. I think Itty Bitty was mostly a way to build little things. I have unreleased products around recipe sharing and coding environments that are also built on top of that.

[SOLEIO ]: Yes.

I don't know. I like platforms just because I think it's like, what can you enable people to make is the most interesting question. Because those are things that are surprising that you didn't expect. It's the emergent utility behaviors, like all come from something being made to be flexible and then seeing what was compelling about it. So yeah, that definitely feeds into stuff that I'm interested in now. And that's why I would want to approach it from a platform standpoint.

[SOLEIO ]: Do you think it's difficult at this point to grapple with the agent as a constituent? Or is that a pretty concrete idea in your mind? Because for me, that's probably the part of the whole equation. Like if we were in a pre-GPT world, that feels a little bit easier to kind of grok. It's easier to sort of project the desires of a human being.

Yeah.

[SOLEIO ]: The desires of a small or large or robust agent that works while we sleep or while we're having this conversation, it's a bit foreign to me. It's probably foreign to everyone.

I don't think it actually is foreign to you though. It's like what most of these systems are trying to approximate is like another person and a person that you trust. And hopefully as few as possible. Like I think that imagining worlds where you have like hundreds of entities that you are like worried, then you have to worry about coordinating them. Or like what they're all doing, what their motivations are.

[SOLEIO ]: Yeah.

Big companies have made assistants over the years and they have been varying degrees of capable or competent. I think that in the end, what you're after is like someone that you can work with that understands you well enough to actually like complement the things that you're doing. And it would be lovely if that was another person. It's interesting if it can be done as, and people look at ChatGPT and all of these things as like a stand-in for that. And I think that it will gradually get there more and more. It's interesting to think about how do you frame it in such a way that the expectations are right, that you're not inevitably disappointed like you may have been with many phone assistants of like, they just didn't do the thing that I want. They're not capable of this. And you write it off. Limited opportunities to present to people like, here is a new entity that you can collaborate with before they make a judgment about how capable that is. And a whole set of questions around like how much you trust them, like what information they actually need to do this that you may ask the same question that's in dealing with any new person that you meet. A very fruitful area to explore because there's just so much unknown.

[SOLEIO ]: Do you think the abstraction will be like an entity in the way that, you know, Starbucks is an entity or an entity in the way that like Siri is an entity? When it had a personality and a name.

I don't think entity doesn't go away. Like, I can't imagine a world in which there are not brands that you are interacting with. Starbucks in some form as a brand is most online services anthropomorphic or not, like another primary entity that you are dealing with has a lot of promise and people associate things with Siri, Alexa, Google, as well as the choice of do you choose a human name? Do you choose a sort of more unusual name or do you use your company name? And each of those choices has a different impact on like what you expect it to do. Right. Google's shift from Google to Gemini is interesting because it kind of resets those expectations, but also loses some of that access to this knowledge aspect.

[SOLEIO ]: Right. It almost like sandboxes in some ways your expectations and the brand to a certain degree, right? Yeah.

And then you have just the ability for people to create entities as they need, like Character AI and all those, which people define or share personalities that they want to interact with that for specific purposes, that's very valuable. And for the feeling of like familiarity with them, I think is really important.

[SOLEIO ]: Do you think that level of customization of experience will be rampant? Or do you think we might be overstating it because we tend to over-index on what's possible rather than what people want?

I think that the identity has such a weird intertwined relationship with trust of the thing. And maybe if people are taking part in defining the identity, they may trust it more. I went through a very weird experiment where I actually used my own voice as an assistant voice, and it had this very, like, having this doppelganger was weird, but it also implied like it has the access to the same knowledge that I do.

[SOLEIO ]: And like, it implied that to other people?

To me. No one else was using this, but I was just sort of speaking and having it speak back to me in my own voice was unsettling, but—

[SOLEIO ]: Have you tried other people who, where there would be at least the, you would answer the question of like, does it feel like it's somebody I know because it sounds like somebody I know and therefore I'm projecting a theory of mind.

I think you will project the expectation that they, it is that person and will then judge their responses or like evaluate how do they feel about me in interesting ways. Yourself is is particularly odd because you're not as likely to infer meaning in the things that it's doing. I don't know, I was more raising it of like, it was just this weird experiment of like, if I could pick any identity and I chose my own, what would it be like? Some people have actually created mirrors of themselves online that you can communicate with, and they're in text form, it's not as obvious, but when you have voice, it has a heavier implication that it is them.

[SOLEIO ]: I selfishly want to orchestrate a trip to Pittsburgh Pittsburgh and call like all the possible favors of Andrew Bosworth at Meta to capture an avatar of my children at their current age before they get too much older. Because I feel, I intuit that it's reached a level of fidelity now that we can always refine it further down the road. We can enhance it. We can kind of upscale it. But I wonder as an object, it might be useful to them down the road to be able to just talk to themselves.

Yeah, that would be interesting.

[SOLEIO ]: I sort of have that as a resource because I often wonder that we underestimate how much self-talk seeps into our subconscious and seeps into our self-perception and seeps into every interaction we have with the world and with other people. And that if we had a way in which to dialogue with ourselves, we might have a bit more compassion. We can just sort of increase the compassion, maybe increase the Narcissism too, but I wonder if sometimes we have an easier time discussing certain things with ourselves. We just have to find a new form factor for it.

Either the evolution of technology or someone's own like mental disposition helps paper over the gaps that might exist in technology. Like, I think if you were to scan yourself for your children to be able to talk to in 40 years, even if the technology improved, the time since you had been around potentially would be the most effective way of like not worrying about like the holes in that. Things like grief will make it possible for people to like not care. Like seeing photographs of a grandparent that have been animated into videos.

[SOLEIO ]: Yeah.

Like, or like really old photos, people just find like so quickly emotionally like affect.

[SOLEIO ]: Yeah. Yeah.

And that's only going to get better. Or these like creating proxies of people who have existed, not for like actors in movies, but more for like just personal relationships that you have. If used well, I think is really like a kind and interesting thing to have, but there'll be a lot of fud about it, I'm sure, for quite some time.

[SOLEIO ]: I always say though, like if it's not sufficiently dystopian, it's probably not going to be progress. Yeah, you're not, you're not, you're not surging towards the future. You have to sort of shift people's expectations. What's the non-obvious set of design challenges that somebody joining the team right now would get to tackle? Because I feel like there's a lot of stuff you can infer from across the street. People working on it, the mission statement, the really cool websites, sort of all the promise. And in practice, I feel like every startup owes it to their future hires? Like what are the things that are not obvious? What are the things that are actually kind of unique to this company in this time?

I think it's malleability. Like that's also part of the reason to look at startups generally is like the product could be so many different things that certainly within large companies it's harder to have that or that moment exists very rarely. And any product is even a year or two further on has started to figure out all aspects of its direction.

[SOLEIO ]: So I—

this is what draws me to it. It's just, it is a moment in time thinking about things with a platform lens and then thinking through all the things that you could build within that offers so much, like, area to explore and need to, like, focus. That's what gut design is good at, is, like, distilling down all these options into, like, a thing that is compelling.

[SOLEIO ]: I feel like we've had this sort of staggered career path where we've worked with various identical companies at different phases in their journeys and also in different phases of our respective journeys. One thing that I don't think I've often heard you talk about is people who've provided you mentorship or have kind of helped you at certain phases that you're grateful for looking back upon it. I'm eager to hear like, you know, What were some of the people that were kind of like, were pivotal for you, maybe without even realizing that they were that?

Other than you? Like, other than you not so subtly nudging me into like different companies where you're just like, I'm gonna go make a presentation about this person to like encourage you to hire them and then like facilitate that happen. I'll appreciate it.

[SOLEIO ]: That presentation has gotta be so That presentation's traveled pretty far and it's actually proven to be a pretty more useful resource than I realized.

So I will go into others, but there was an aspect, you have been a good advisor for either nudging me towards stuff. I probably would have stayed within Google indefinitely without some nudges and because I like to operate within large companies and other stuff. And so I am grateful that You have consulted on each of the different shifts that I have made. No, it's often the like kind of patron of the arts within larger organizations that I really appreciated. Like the VP who was in charge of Chrome was like just so good about, as I shifted from wanting to work on Chrome to be like, Chrome is kind of like, it's reached a point where it's going to just evolve. Like what else do we need to do to make Google better? And then—

[SOLEIO ]: What does patron of the arts mean?

It sounds like— Well, that makes it sound a little more charitable, but more just like there's people who empower design because they believe it is like the best way to improve a product or a company.

[SOLEIO ]: Got it.

Okay. And are willing to put resources behind it. Like Linus, who led Chrome, helped build a team that I worked with that that didn't actually work on Chrome. They exclusively worked on making our web apps better. And it lived within Chrome and had complete autonomy to decide what we worked on, but it allowed us to do a lot of the pre-work that Material would need. And it was ostensibly, yes, to make the web better, to improve the quality of Google's web products.

[SOLEIO ]: But you're almost coming in through the side window in some ways, right? Yeah.

And it essentially was establishing a pathfinding team, but we just wouldn't have called it at that moment. In general, like any other companies that I've been to that are willing to establish pathfinding teams kind of did so with a similar mindset of like, design is important, but it's important in an ambiguous future-looking way that you have to kind of take a risk to staff people working on it that way.

[SOLEIO ]: Yeah.

Especially like as companies focus down and like do have smaller teams.

[SOLEIO ]: If you had to kind of encapsulate the current form of your design philosophy? I feel like Julie Zhuo did an interesting job of sort of arriving at like, I'm starting to arrive at like a higher level design way of just approaching the world. It's like a mental framework, a mental engine, endlessly reusable. It's like a simple motor. Do you have an approach or a way of talking about design that you feel like is true to you more so than true to any one company that you work at?

Two answers to that. One of which is like, what is the impact on the product versus what is the way that The design is done. Maybe they're the same. I've always had an affinity for the Tao Te Ching concept of act without doing stuff. Just the notion of people being able to have impact often sort of effortlessly through the others that are around them and supporting them in doing it, setting things up so that the right things just tend to happen. This is something I hope that I see because I work on expanding a design team Now it's just like building a team that feels empowered and like has the autonomy it needs and is self-driven and enthusiastic about things where like work feels effortless for them. And that it is just like a delightful group to work in. And like it feels worth doing even independent of what the thing being made is.

[SOLEIO ]: Right. So why didn't more of your like side projects become commercial entities out there in the world, companies, buildings a block away from South Park?

Because that would no longer have been a side project.

[SOLEIO ]: I— where does this stop energy like emerge from? Like, at what point does the side project sort of like cease there, sort of, um, stop growing or stop sort of taking on a life force of its own?

I think it comes down to what you spend your time doing.

[SOLEIO ]: Right.

Like there's something around side projects where it's like you work on the side project.

[SOLEIO ]: Yeah.

And like this new venture, I'm comfortable with the shift because I'm also surrounded by people who are like very talented and understand all the aspects that are needed to build a business around a thing. And that makes it more interesting to do as this needs to be built, but it also needs to be built as part of like an organization that will eventually exist.

[SOLEIO ]: Right. But let's go back to that transmogifier. I hit go, go, go, go, go, go, go. Now I've got like 7 Jickoffs running around. That sounds like a disaster. Are there any side projects that you feel like, oh man, that one's just sort of sitting in the back garage there waiting to be turned back on again? That's where I'd throw some, a Nicholas Jickoff or two at.

That is the side project that makes side projects. You get it from Transmogrifier, yeah, I get that. No, that was like, that is the intent behind Artifact. Like, I would like to think about how do you actually cultivate people's ability to create side projects, or like, But without the burden of like, does this need to have meaning or like purpose? Like, how can you encourage people to build stuff just to discover? And if it is a valuable thing, find a way for them to like hand it off. I was very lucky to be able to hand Quicksilver off to like a talented group of people who would maintain it for now 20 years. I was just like, great, thank you for doing that. I'm super grateful.

[SOLEIO ]: I love that.

I don't know, sad part of side projects often is just like, 5 years later being like, this thing can't work anymore. Like, it's just the world has, like, technology has evolved so these things aren't captured. And I, I do, I do think there's something to be said around like, how do you make sure these very ephemeral things are not lost?

[SOLEIO ]: Yeah.

And part of that even gets into the discipline of like designers to document the things that they have done. And some people are great at this. I'm terrible at it. Kind of like celebrating things, especially as you move beyond them and be able to like keep them and remember them, and in some cases have them continue to be used and useful for you.

[SOLEIO ]: Yeah, I'm always astonished at how I had this visceral reaction to things that were deeply familiar but went away as recently as like 10 years ago. You know, old iPhones that get rebooted and you're like, oh, it's amazing.

Like, old phones are like the best time capsule ever. Yeah, as long as they don't like explode in your drawer, right?

[SOLEIO ]: Right. You have to kind of have everything turn all the Wi-Fi off, all the cellular off, and make sure that the phone can actually like power up.

Yeah. I was playing with Path on a phone recently. I was like, ah, this was nice. But I think that's part of like kind of an irony about software. It's like it actually is surprisingly ephemeral.

[SOLEIO ]: Yeah.

Even though a lot of digital stuff is ostensibly more easy to preserve, it's like the quantity of it and the constant change means that it's actually very hard to have the context in which to run this thing or to experience it anymore.

[SOLEIO ]: Right.

You can capture videos of them, but it's very hard to capture the feel of them, especially used in the context of like, I'm walking around and I'm using Foursquare. It's just like, it's not a thing anymore.

[SOLEIO ]: Right. Even like old versions of browsers just has a completely different feel, right?

Yeah.

[SOLEIO ]: It feels like driving an old car from decades ago.

Yeah.

[SOLEIO ]: It's like completely the same vehicle, but nothing like it. Hello, dogs. I'd like to thank you for taking the time to chat with me. Of course.

It was wonderful to talk to you again.

[SOLEIO ]: Yeah. It's always fun. Do you have any questions for me?

My questions for you, having far more experience over like having seen companies come into being and design teams being spun up usually in earlier stages than ever I've engaged with them, it's just what advice do you have around like how to balancing enthusiasm for hiring and like what kind of ways to complement skill sets that scale the team well?

[SOLEIO ]: Yeah, I think for me there is a bit of the soul-searching, self-knowledge of what are the parts of me that shine bright in all these different contexts that people sort of look to me for and how do they align with our business strategy? How do I sort of like amplify that Yeah. With the people that I work with, not in the form of necessarily like documents, but just in action. And then how you recognize behavior of others. But I think the other piece is like being selective about like a collaborative fit. I think collaborative fit is a big part of it. So many skills are teachable and they're like, the thing that I'm honestly just blown away with is folks 10, 15, 20 years our junior, are like on a much steeper slope of learning than like I sometimes feel like we give them credit for.

And are somewhat rushed into it, 'cause like the tools themselves encourage like working fast and learning things.

[SOLEIO ]: But there's like something that like is really precious about the naivete that like I think is impossible for me to manufacture anymore. It's like we just know too much to be clumsy and willful and ambitious in these like kind of unspoiled ways that sometimes lead to these genuine leaps of like thinking where you're like, I never even second-guessed this like core assumption. And like, now that you've shown it to me, I cannot unsee it. And it has that quality of like spacetime where you're like, it has vast explanatory power. And I think that that's that's often unique to folks early in their career. And so I think if you can just isolate what are the qualities that tell you in a short amount of time this person is going to be great to spend a lot of time with, like that gives you a font of energy and that they're open to learning in this environment and being the person that has license to take these crazy evolutionary leaps. All the skill stuff, all the prior work stuff, I think is highly teachable and in some respects isn't all that relevant. I sometimes really laugh at like my portfolio of work pre-Facebook. Yeah. Because it's like, I'm really, I don't know if they even looked at it. It doesn't seem remotely relevant to the work that I did there. But maybe the qualities that resonated were that like, maybe I was amongst the first to show up and say like, I'm good with web browsers. I can make stuff.

Yeah.

[SOLEIO ]: I can make internet better than most people in this room.

I think it's just identifying who you are as a person and your work is an echo of that, but it's like not exact that. So as long as you're able to get the signal for that, it's more than enough.

[SOLEIO ]: Yeah. And I remember like replying back to them, they had given like not a homework assignment, but sort of like, what are you thinking on XYZ? And I remember just circling back really fast with an answer. And I think that sometimes that alone was both like true to me, but what they were looking for. It's like, oh yeah, that's what we want. Yeah, like speed. Come on, let's go. There are periods in my career where I second-guess speed, and I've really come back to that now. I've really come to appreciate that, like, well, speed is energy.

Like, it is energy. People value that.

[SOLEIO ]: And, and, uh, you know, I think every person sort of has a book-sized theory in their heads. And for me, it's like there's a, there's an explanation of luck that I think is far different than what I think most people receive as wisdom or what luck is. And I think there's a notion of like, luck is something we can shape. It's malleable, like software. And it does favor motion. It favors depth. And that favors optimism, right? Expecting the best of people.

How do you feel operating, not necessarily outside of design, but where you are, you spend time now sort of thinking about, well, design as an overall discipline, but also how people are moving between companies and like design is being invested in wholesale. I'm just curious, like you have changed your role from working within companies as a designer to now designing the design of design and the people who are doing it. Like, how has that shift been for you and what do you enjoy about it?

[SOLEIO ]: The difficult part has been that you cannot take any credit for the work that's done in the background or in the foreground. It often has a feeling of being like a ringer/cheerleader, but not being a part of the team. And that's fine. Sort of, I come to accept that. I think that's an appropriate kind of boundary. Experience more imposter syndrome now than like ever before. Yeah. Because it's like, yeah, I'm just so far removed from the metal. Like, what have you been designing lately? I'm like, I've got some great spreadsheets you can check out. I mean, I'm kind of proud of these spreadsheets. These are really nice. That's where I apply my trade. I think what I've enjoyed in particular is two things. Founders sometimes are like telescopes peering into a hazy future. And more often than not, their timing is wrong or the thing that you're seeing is not actually what is being seen, something else. Sometimes it is a prediction of like what's coming around, and it sort of formulates a larger view of like where things are headed that I think no one company can necessarily direct you towards. Some companies can direct more of the picture than others for sure, or what they see has much graver implications than others. But I think there's also an element of designers who are now reaching this point in their careers where they're like, I I don't want to be the next VP of Design somewhere. I want to start something new. And I want somebody I trust to be straight with me about what I'm doing. And I'm surprised at how lacking that is still in venture. That is the thing that I admire the most about the VCs that I feel like earn every ounce of, you know, prestige or wealth or success that they get in that role. Are the ones who are like stewards of not just like great careers, but like great organizations that spawn great careers.

Yeah.

[SOLEIO ]: And so like, yeah, corporations are beautiful platforms unto themselves. And I think it does often start with having people that you can call up with the difficult stuff because they know the problem space, but they also know you and what you're uniquely attuned to and how to kind of talk through the things that are murky. And that goes back to where I feel like I shed my imposter syndrome. Like machete design scenarios where it's like, okay, I'm very comfortable with ambiguity and being wrong and generating 9 bad ideas so that the 10th idea, which is yours, is actually the right idea. Because sometimes it helps to just have that person in the room. And yeah, that's if I can do a small bit of that with the enough friends, I feel like that, that, that is the making of a perfectly great career. Nice. Yeah.

Thank you.

[SOLEIO ]: Thank you. We done? Done. Wrap it. Great. Mm-hmm.