Alex Cornell - How to present your designs and get buy-in for your ideas (Dive Club Ep. 58)

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It's all communication, but there's so many hidden knobs that you can tweak, and most people either don't know they're there or they don't really care or they don't think they're that useful. I think that's sort of, to me, how I view work as successful these days is I'll spend all my time thinking about the idea and then eventually a lot more time how it gets to you. And ideally, people will only recognize the power of the idea and they don't Notice the stuff in between. If people knew the crazy things that I was doing before I sent that video, they would think that I was either totally insane or wasting time.

Welcome to Dive Club. My name is Rydd, and this is where designers never stop learning. When you think about storytelling in design, Alex Cornell is often the first name that comes to mind, and that's a really big reason why he was one of the most requested guests on this show. So this episode is a masterclass in the finer details of communication. We get into the backstory of his startup Cocoon, and he even shares some lessons learned while designing the Substack and Linear mobile apps. But first, let's hear more about Alex's background in video, because it plays a major role in who he is as a designer today.

You know, you get your first video camera and take it on vacation and see what you can make with it. It's Pretty exciting. So my first job in college was working at the media lab that we had, and this is like 2003. So media lab back then is like a Mac and Final Cut, and nobody knows how to use it. And they're like, if you can figure out how to use this thing, maybe you can tell other people how to use this thing. And since like nobody knew how to use any of the technology in this room, nobody would ever visit the media lab. So it would just be me there all day. with these very powerful computers that were there theoretically for students to come in and use, but it was just basically me in there the whole time, which was amazing. And I think like that laid the technical groundwork for understanding how to use video at all, which translated to YouTube when it became popular. I think it was like 2006 or '07. And I was really into music as well. So combining those 2 things, making videos and making music, I spent a lot of time doing that for maybe till like 2010 or so. And again, just sort of honed the technical side of it. And then I think that eventually translated into a more storytelling aspect when I started doing interface design and like kind of just bringing video along for the ride everywhere. Like it was the, it was sort of my original skill and I've figured out how to use it in every context, even if it's maybe not obviously relevant.

You have this really fun chunk of time on your LinkedIn where you're making videos for startups specifically. Can you talk about that a bit?

My first company was called UberConference, which is now called Dialpad. And when we started, we were kind of trying a few different apps. And as a result, I was making videos for those, like to just to promote them because at that time, it's hard to remember, but back then videos were sort of like the way that you could get your startup noticed. And it wasn't just like a nice to have, it was like, gosh, if you had a video and it was kind of good, it could really blow out your initial audience in ways that aren't possible anymore. So it was worth— we felt like it was worth investing some time in making those videos. And I did that. I did it so often that I got— I think I fell in love with it almost more than what I was doing, which was building the company and designing, you know, like doing traditional interface design. And so I thought, you know, I could probably make this a business because I was friends with Adam of Sandwich Video and he had a business, probably like the ultimate business for this still to this day. They do incredible work. And I kind of thought if I could just do a 15th of what he's doing, that would be really fun and really lucrative because people were paying hundreds of thousands of dollars for these things because nobody knew how to do it. You know, so it's like, if we're going to get one, we have to pay somebody to do it. And so I think like that, all of that led into me eventually deciding to leave the design side of the startup world and attempt to kind of create a commercial business, like a making commercials for other companies, which was very fun from on the video side. You know, think working with companies and trying to think of how to express their ideas, actually executing the video. I think probably my favorite professional environment is a movie set. It's very efficient. Everybody knows their role. There's a ton of people, but somehow everybody works in harmony. And it's very unique. Construction sites, movie sets, kitchens. Like there's a few examples of these places where you have like, You know, a hornet's nest worth of people that somehow all like collaborate in a way that is really efficient, which is pretty unusual. So I love that about it. But the thing that I guess I should have known, 'cause I'd done client work before, video work is sort of the ultimate client work. And that aspect of it, you know, you go on a day shoot and you come back and you send the client, you know, what you, what you have. And they're like, oh, we like it, but like maybe not that location. And then you think, okay, well, we can change that. It's just gonna require like another, Like the machine's gonna have to start up again completely. I'm gonna have to go all the way back to the beginning. And that part of it, I think, started eventually to become pretty tiresome, which is, you know, client work of all kinds sort of has that, but video had it to a higher degree because it was just so much more logistically complex and expensive. And that part I didn't enjoy, but it was really fun. I think like, again, you know, the, that time period, which I think was maybe like 2 years, specifically honed. There was one missing piece maybe to that part of what I was doing, which was the writing side of all of it. And when you're writing scripts for companies and sort of trying to take on their vocabulary and their tone, it forces you to learn to write in a very different way than you maybe would have before. And so while I was enjoying the video side, I think I learned to express myself verbally in that period of time way more than I had before. And that skill I think is sort of like the ultimate foundation to pretty much everything I have done after that, you know. And a lot of times people point to video because it's sort of like the shiny object that you see. But when I see the work and when I see it resonate with people, to me what's resonating is usually the 3 days that I spent moving words around and not the 2 hours I spent recording and editing it, you know.

You know, you're one of the most requested guests By far. And the common thread is always that people want to hear you talk about storytelling, right? Like they've seen your videos and this is something that you've almost been, almost become synonymous with in some ways. So maybe we could use this as an opportunity to go a little bit deeper into this connection between your movie background and what you're doing in more of a day-to-day as an interface designer. You talked a little bit about the writing, but like, what are the ways that this background in video and scriptwriting has impacted the way that you approach storytelling as a designer?

The fundamental that's the same is you're trying to get an idea from your head to somebody else's, pretty much. That's like the— if you're designing a logo or a menu or you're making a movie, at the core of it, you kind of just like, I've got an idea. I also want you to have that idea. So here's a vessel for it to be transferred between us. And the common thread often, I think, is the language that you use to do that. And I think that's why I've become so obsessive over it. And I think something that people usually are somewhat astounded by, and I think a little bit weirded out by, is what— 'cause I often will meet with people to discuss this, and I'll tell them how I work there. It's a level of precision and obsession over language that I think would seem like totally over the top. But I think that's why it can be so effective. And as an example, it would be if I would sit down to write something, like let's say I was gonna say that, make an argument for why using a guitar pick is better than fingerpicking. And I'll put that in a video. The very first word that I say in that video, I will spend a crazy amount of time thinking about, you know, like, I wouldn't say using a guitar pick is better. I wouldn't say to learn to play the guitar, you should use a guitar pick, because all those, all those sentences are starting with words that are really neutral and sort of like vanilla, like using or to. It's like, ideally, it would start with guitar or like some, some other word that's like much more immediately interesting. And then once I have that sentence, I'll spend probably, I don't know, an hour Figuring out all the different ways I could read it, you know. So let's say the sentence is like, learning to play the guitar is the most effective. So you could say it like that, or you could say, learning to play the guitar is the most effective. Or you could say, if you want it to feel like it's going to go to another sentence, you could say like, learning to play the guitar is the most effective. Now it feels like I'm going to say something else. Or you could like, and there's like 1,000 different ways you can say each word and intonate your voice like All over the place. And when I'm saying the sentence, I can feel all the little knobs that I'm turning to like make it kind of ride one way or another. And when I used to do music, something that's very common is when you're doing vocal work, you'll, you'll do a verse, you'll do like a take, and ideally you get it in one take. You sing, you sing the verse, it sounds great, on to the next. Very rarely happens. Usually what will happen is you'll hit the verse, the first couple phrases will sound great, And then you'll go out of key, but you're like, man, I really love the way I came in on that. So you'll use that, you'll freeze that, and then you'll punch in, as they say, to get the next, the next part. And so it's not that uncommon for like a vocal take to be sort of a composite of, of all these different takes. It's very common in music. It's also common in voiceover, but it's not super common in like, I'm just going to make a video for my team today and send it to them this afternoon. Just like, here's some ideas I'm thinking about. If people knew the crazy things that I was doing before I sent that video, they would think that I was either totally insane or wasting time. But like, I'll do— I will composite voiceover takes to send. I didn't send you a video, but I might. If I had, I might have done that just because I know it will have a subtle impact on how things translate when it gets to your mind. You know that? Is sort of what became my obsession with all of this was just like, it's all communication, but there's so many hidden knobs that you can tweak. And most people either don't know they're there or they don't really care or they don't think they're that useful. I think at the end of it, I look at these things and love them for their efficiency and their clarity. And then also enjoy that most people don't even care about that stuff. And to them, maybe— Ideally, all they care about is the quality of the idea that is conveyed. And I think that's sort of, to me, how I view work as successful these days, is I'll spend all my time thinking about the idea, and then eventually a lot more time how it gets to you. And ideally, people will only recognize the power of the idea, and they don't notice the stuff in between.

I just have a big old smile on my face. Like, it's so fascinating to hear the level of, like, depth and precision that you're thinking about this. I've never heard that answer. Like, I asked related questions, and a lot of the times it comes back to like, well, you know, set the context effectively, you need to outline the problem, make them feel the pain that the user's feeling. And you're like, actually, like, voice inflection. I love it.

I love it. Yeah, there is a, there is sort of an underlying assumption that the idea is of like a good, of good quality. And that you've picked a framing that will be effective as well. And so I think like, I don't, I definitely consider these things as somewhat different modes that you'll go into. So if the beginning's very messy, exploring the space, figuring out what you want to say and how you're going to say it and all that kind of thing, I don't really shift into execution mode until that's taken care of. And I much prefer, maybe it's just because I spent so much time in a technical setting, I love when an idea forms solid enough that now the challenge is how are you gonna communicate this thing? That's my favorite part. When I'm stuck in the idea phase and I'm like, oh shoot, this still doesn't really make any sense, that's frustrating because I don't have as many frameworks in that zone as I do in the other to really like work through those problems. It's a lot more loose exploration. And so, yeah, and I think maybe the reason I care about it so much is I've just observed in my time that you can— it's hard to say it without making it sound manipulative, but it is a little bit. Like, manipulative has negative connotations, but like, if we just take the literal definition of the word manipulate, like, you— I do think you can kind of manipulate people into seeing a thing a different way via the delivery of the idea, you know? So they— even if the— not to say if the idea is bad, they'll think it's good. That would, that would still be a failure state. It's more like they'll see things about it that they might not have and help them feel like it's a good idea.

Even just the energy transfer that would happen in something as small as like a Loom video. Like if people can feel that you're excited about it, I do think that it has an effect and you're kind of even taking that to a whole other level.

So I used to do this at Facebook when I worked there in 2015. I would do this a lot internally to communicate ideas out to the org or to my team or whatever. But back then that was not necessary because we were all on site all the time. Like the entire, I could see the entire video team at any given time, which is kind of wild to think about now. So making a video was purely additive to our comms channels. But then during the pandemic, that became the only way to communicate because your team's distributed, so now you're async. You still have a lot you need to say and a lot you need to show. So tools like that became absolutely required to communicate certain ideas. And I was really happy about that because I was like, wow, this is the thing I was doing already. And now it's a thing that we kind of have to do. But I think that the trick is all the same rules still apply. So for example, if you made a video that was over, I don't know, 2 minutes long, it's like, you can look at your Loom stats. Most people drop off. And like, it would be hilarious. I'd be having arguments with people and we'd be talking about the ideas in the Loom and I could go look and see, it's like, well, you didn't watch the whole thing. So, you know, it's just so funny. Like, I don't think people know that about that product. But the point is, is that all the same rules around like posting to YouTube and making it engaging engaging and like thinking about how you're going to hold people's attention apply in corporate communications as well. And I think there's like a mistaken assumption that people will read everything you write and watch everything you post, and that's absolutely not the case. So you have to kind of work against it.

You mentioned the videos for Facebook. I recently shared the 3-dot chevron newscast that you made in the newsletter and people loved it. And so maybe you could talk a little bit about why do you think that that video stood out? But then also, how often are you doing this kind of thing? Are there other related examples that you can share?

Yeah, very often, I would say. And the reason I think that that one resonated was it's sort of the way I think about almost everything, which is that if you have a thought, which in that case, the thought's pretty simple. It's like, I think The indicator, the icon for more actions should be different. I don't think it should be a chevron. I think it should be a 3-dot. There's 1,000 ways you could attempt to make that change at a company. You could write something, you could say something. There's all kinds of ways. And maybe you could say, well, one way would be to make a video and you just make a video and you talk about it, whatever. In my mind, I'm always thinking about how would I take it not like 1 or 2 turns, Further, but like 7 turns further. Because at a certain point, once you take it that much further and like maybe weirder or more intricate or whatever, the fact that you did that almost becomes itself an object that people react to. So even if we're not looking at the ideas in the video, the fact that it's me debating 2 of myself live. So that's another turn, like doing it live makes it way more complicated because now you've got— 3 cameras, 2 of which are mirroring their perspective. So I can turn to my left and then cut to that other camera and it looks like that guy's turning to his right. So it's all done live. So it's like the diagram for that video was so crazy because I remember thinking about it on the bus. I'm like, how would— if I turn to my left though and there's 3 cameras, it's gonna look like this guy, I'm turning to my left and the other guy's turning to his left. It's like, that's not gonna work. So they have to be mirrored. It was like drawing it around and like just the fact that that happened is enough for people to be like, What the hell's going on? Like, why would anybody do that?

You know?

So that becomes its own little thing. And I think sometimes that's the key that sort of lets people in and they're like, well, this is weird as hell. I'll maybe I'll listen to it for a second, you know? And then of course it's important that the ideas that are being communicated once you've got people are good. And I spent a lot of time writing that. So I think again, it was live, but I wrote everything and I'll, I'll do it very, this very frequently. I'm not doing it now, but it wouldn't be unusual for me in a situation like this to actually have written everything I'm gonna say. And I've gotten very good at delivering things in a way where I'm reading something, but you can't tell that I'm reading it. So I think that's why it resonated. There are plenty others that there, and I think one, one that I can share because it specifically didn't have any real details in it on purpose was I created like a fake feature.

Hypothetical feature.

And sort of filmed a thing which sort of presumed it had been shipped. And as a result of it being shipped, there were— there was some controversy that people, different people felt differently about it. And that was sort of the video, was people arguing about whether or not it should stay that way. And the nice thing about it was it sort of allowed me to say everything that I wanted to without incriminating anybody or making anybody feel bad, because I'm just talking about this thing I made up, doesn't even exist. You know, my favorite part of it was to make it look like it was real. I filmed an actual presentation in a conference room, so I had the audience and I had the speaker, and then isolated the audience, then filmed myself in the same room speaking it to the— like, in the same perspective and everything, isolated myself, and then cut a keynote, isolated that, replaced it on the video. So then composited all that together. It looks like I'm talking to the audience with this deck on the screen. So then now I can intercut between me, the keynote. So I can often would just cut to the keynote because then it's just, just I have full control over that. My audience loop, which was usually, I think it was like 15 seconds long, so I couldn't stay on that shot for very long. And then I had like a closeup of myself as well. So it looked like if you just looked at that in newsfeed and you're looking and you're just going about your day, it looks like I'm presenting to an all-hands audience, this, this concept. And that was, I think, enough for people to be like, what the hell's going on? And again, the weirdness of that, like that 5 or 6, 7 turns beyond how you might otherwise have communicated that idea, became an object itself that people could react to, the secret way, the Trojan horse, I guess, into their mind. I actually did one while I was there that was like a fake promo video for a thing I thought we should do in live. And I just posted it to my profile and I got a message from legal like almost immediately and it was like, we haven't seen this. You like, you can't ship, like you can't ship things like publicly without going through all these processes. And like, like I was basically getting like reprimanded for, for this thing. And I had to write back and I was like, oh no, no, no, nothing about this exists. Like this doesn't, they're, they're like literally not even the, the app icon, not a thing about this is real, you know?

I sourced some questions from Twitter on this topic, and one that I really liked was from Kyle Barber. He said, what does your process look like when you have a product or like a demo or something that you're getting ready to tell a story about? How do you identify the things worth focusing on after you've spent a while like in the weeds designing it?

The 2 analogies I would make maybe are to a math proof. And also to just an upside-down triangle. So like, I think whenever you're shifting from, okay, you have, let's say you made an app and it's like, how am I going to explain this thing? I think that it's really important to start with fairly broad message that's like relatively not that controversial that people agree with. And that's the math proof element of it, which is basically like, if I want to convince you that, you know, C equals D, I would start with something like, well, do we agree that A equals A? You'd be like, yeah, obviously. And then say, okay, great, A equals A. So 2 A's equals 2 A's? You're like, okay, yeah, sure. And you just sort of like, you just layer like one new thing at a time to eventually like to where when you finally do have to force somebody to cross a chasm that they may have not crossed before, You've built up all this momentum with them where they're like kind of nodding along and they're like, yeah, yeah, this makes sense, this makes sense. That when that moment comes where you sort of have to take the leap together, it's not that crazy because they're already kind of with you. The alternative approach, which sometimes can work, is to just start with that and just be like, here's a surprising idea, you've never thought of this before. And then some— and that can send people one way or the other. They could be like, whoa, wow, that's really crazy. I love this idea. or they could immediately be like, wait, what? C doesn't equal D. Literally, they aren't the same. Why would I— doesn't make sense. So I think a lot about what style is going to work depending what it is. I think the hardest I ever felt this was when we worked on Cocoon, which was the company my friend Sachin and I started after working at Facebook the first time. That was probably an app that had the closest overlap or the tightest overlap to my skillset being in design and what we're talking about. And then also a problem that I like personally really wanted solved. 'Cause I'd worked on lots of things, you know, live video, I liked going live, but it's not, that wasn't like core to my life, you know? But what we were working on at Cocoon was core to my life. Like it was like a problem that I really, really enjoyed our solution for and like really wanted other people to experience. And so then when it came time to communicate that to people via video or whatever, that was by far the hardest I ever felt it was because maybe it was so close to me or I cared so much about it that every idea that I had of how to communicate it, I would shoot down for one reason or another. And that was an interesting experience because I never had really been stumped in that way or like quite so for so long as I was. with that. And funnily enough, the thing that broke me out of it was TikTok at the time. I know it's thou shalt not be named anymore, but at the time, this was when TikTok had just on the cusp of people realizing that it was actually a really good native ad channel almost. Where like, you would, like it was before, I forget what the app, maybe it was Anchor or something. Some app blew up because of a TikTok. And after that, it was like the floodgates were open. But before that, One of our friends, one of our early employees had told us, he's like, guys, I'm messing around with TikTok and it's crazy. And so we were like, all right, we'll give it a go. And I made maybe like 6 or 7 TikToks about Cocoon that opened up a whole new world for me of how to communicate the ideas I wanted to. And it was amazing. I never had, I hadn't had that experience in a really long time. And I don't know what it was about the media. Maybe it was just that it was sillier I think that was probably what it was. It was just like less pressure. But it was pretty weird because it was definitely not my normal style. And I'll sometimes post them 'cause they make me laugh still. But what I actually really enjoyed about them was that I think back to them as being like the thing that finally allowed me to try to communicate what I was trying to communicate, which had been pretty hard up to that point. If you watch the first Cocoon launch video, I don't even know if it's online, but if it is, it's very—

It's funny.

stiff for me. It's very like, here's what this app does. Would you like to use it? And that I think was not the right delivery.

Can you give a little bit of background as to what Cocoon was for people who are not familiar? And also, it's clear hearing you talk that you cared deeply about it. So maybe you could even touch on why was this such a big deal for you? And ultimately, how'd you get to the point where you were like, yeah, I'm going to leave Facebook to start working on this?

We actually left without an idea. Sachin and I had become friends working together at Facebook, which is an experience I hope for anyone in the field, I guess, to find a working partner that inspires them. And, you know, I think when we started working together, it felt very different than like almost anybody I'd worked with before. So we left kind of just feeling that, like we enjoyed working together and we thought we could start something. We didn't have any idea of what we wanted to do. We actually applied to Y Combinator in that state with no idea. We were like, here's kind of what we're thinking about, but we don't have an idea. But then before they looked at the application, we thought of the idea. And I remember we reapplied almost like before they looked at it, which was pretty— it was a good forcing function. In that process, we would spend a lot of time talking, like all day, like 6 hours of talking just about everything that we— all of our experiences and like what we we care about. And I think we came to a similar place, which was that we felt kind of distant from our family in particular, friends also, but mostly our family, despite all these advances in communications and Zoom and iMessage and everything. And I think that insight was sort of what eventually led to Cocoon, was it's like, why is it that our most important relationships are somewhat relegated to the same comms channels as everything else? That was one of the things that I used to enjoy saying was it was not unusual to get a text from DoorDash saying like, your burrito's here, and then get one from your mom. And it's like, this is weird that the same style of message is delivered in the same zone. And on the one hand, it's like, wow, cool, what a versatile tool. It can handle all these things and nobody wants multiple apps. It's like we want everything in one place. Totally get it. But also there's a lot of very specific things about, you know, talking to your family that are different.

Yeah.

than talking to your DoorDash or whatever it is. So we started from a place where like, okay, let's build an app for you and your family. And I think the core insight there was okay, but what we pivoted very quickly to allow you to have more than just one group, because we, we started in a somewhat crazy place. If you think about it, you can only have one group and there were no notifications. So it's like, if you want to like set your app up to not grow, that is a great way to do it. And it was actually a really good learning because we felt, and I think a lot of people get sucked into this belief that like people hate their phones or people hate notifications. And we kind of were like, yeah, we'll not have notifications. I think we kind of bought into that narrative at the time, which is that like notifications are bad. And it was interesting because all of our early users were like, hey, if there's anything I want a notification about, it's when this group messages me. It's like, I don't want all the other crappy notifications, but I want these, you know? And that was like very obvious in retrospect, but it was kind of, So it was a good reminder not to get too caught up in the nonsense noise out there, 'cause I think there's always nuance. So we eventually opened it up to be more than one group, and it worked a bit more like a traditional messaging app. And I think that's where we had like a little lull where we almost had like started to replicate a lot of the features that existed in other apps, and it was less clear why you'd use ours than another. And I feel like where we ended right before we got acquired was the product I wish we'd launched with, 'cause I felt like we had gotten to a place where it was like, This is the right solution to this problem. But you only really get one chance at like the big bang coming out. And it's pretty rare for apps to iterate after people's initial conception of what they are has formed. It's then it's a little bit harder. I mean, you see this, I mean, in the market today, we could probably list tons of examples, but yeah, anyway, it was, it was, it was a really fun product to work on. I really, I really did enjoy it. I actually worked with the same iOS engineer on that app. As I did at Substack, 'cause we got acquired. And then also we ended up at Linear together too. So we worked on 3 apps together in 5 years or something like that. It's hard to give advice 'cause sometimes it's like, my advice would be to find that person in your career, but it's, you can't really manufacture that. But man, if, when you have that kind of relationship, especially as a designer, finding an engineer who you trust that can execute your designs in the spirit and maintain like the intent to where there's really like almost no lossiness. It's like everybody would agree that's kind of the holy grail, you know?

Hey guys, real quick. If you know me, then you know I love products. So I want to take just 30 seconds to tell you about 3 of my favorites. Now, anytime that I'm designing and building a website, you better believe that I'm going to use Framer. I made the switch recently and I'm never going back. Now, once it's time to animate my designs and showcase my work, that's when I'm going to use Jitter. It's like Figma only for motion design. And every step of the way, I'm going to be using Raycast constantly. It's the cornerstone of how I use my computer and the way that I stay in flow while I work. Now, I hand-selected Framer, Raycast, and Jitter to partner with me so that I could do these interviews full-time. So if you want to show them some love, it would mean a lot. Okay, now on to the rest of the episode. Let's move forward in the story a little bit. So Substack acquires Cocoon. You're now tasked with taking something that's working on web and going kind of zero to one on their new mobile apps. And one of the things that I heard you say about the experience is that it gave you the opportunity to nerd out on typography for the first time in a while.

So.

Yeah. Can you share a little bit more about what it was like designing the new Substack mobile app?

That was a unique experience for me from the get-go to take a product that has fit in the market on desktop email and translate it to a mobile context. Because before that, I'd almost always been trying to find product-market fit. So with Cocoon, it's like we are iterating to get to that state. We're not translating a use case to a different form factor. And so I really enjoyed the specific nature of the Substack app is that it's a reading app. So you're focused quite a lot on people's experience reading on the phone. And that had not really been something I'd thought about a ton before that. And in Cocoon, we did use a custom typeface, but the reason we were doing that was mostly for character. So we had started with the system fonts. We switched to something that had a tiny bit of A little bit more softness because we wanted it to just feel that much friendlier. But it was very much like a brand thing. It wasn't really like a legibility thing. We accepted it because it felt just as legible. But in Substack, it was the first time in a long time, and I went to graphic design school, that I hadn't really thought about typography. How many characters are on this line? What's the line height? What's the x-height? Are we worried at all about these serifs being a little bit less legible when the contrast is high? Like, what we're all— like, all that stuff brought a lot of my early career back flooding up to the forefront, which I love because it's actually really depressing, I guess, to me where we are as an industry now, where we pretty much mostly use system fonts. And when I say we, I mean like most of the apps I use, you know, like I know there are apps that don't do it, but like most do. And on the one hand, that's amazing because I love San Francisco. And I love all its little variants. I love Apple Symbols. I love using San Francisco. It's, it's a great font, but also it's weird that that's not a decision anymore. You know, like I don't even think about it anymore. I'm just like, I, like I said, I hate 15 and 17 point type. So I always did like 16, 14, sometimes 12 or 11, maybe if it's all caps. But like, you know, like I don't, I don't think about it. Like 16, great. 22 or 24 line height and I'm off and running and I know all my colors. I have all my hex codes memorized. I don't. decide anymore on these things. And the weird thing is, when you start out as a designer, especially in traditional graphic design, you probably spend, I don't know, 60% of a project worried about the specifics of the typography. What's the typeface? Can we get it licensed? You know, okay, we bought one variant. We have this one variant we're going to use. And it's like you're dialing in things, especially in like static graphic design, to such a level of precision. That, you know, I think mobile designers would, would kind of balk at now. And I, I do miss that. And I miss when, when it, when it came up in Substack that we could maybe do a little bit more on the typeface selection. I got really excited just because I hadn't really thought about it for a while. And I think one thing that I, I found when I was selecting the typefaces was depending who you talk to, there's a lot of feelings around how objectively good or bad certain typefaces are for reading. And that's true. Like there are things that affect Legibility. And there's lots of little dials that can be turned to push that in either direction. But I do feel like at a certain point, especially with modern typefaces, the decision is really a feeling decision. There's a set of typefaces that have all achieved all the certain objective things that maybe need to be achieved. And now you're just sort of picking what feels good. And I love how hard that is to articulate. Why do I like, let's say, my favorite mono Uh, space typefaces, JetBrains. Why do I like it? I don't know. I like its weird little zero, although I've recently switched it to the slash zero because I prefer that sometimes too. But the, the little feet that it has and like the, all that's a little weird, the weirdness about it, I just prefer in a way that the only analogy I can draw is maybe if you're trying to argue why something tastes better or not, it's like there's a baseline of this food is edible. and it's healthy. And, but now what? It's like, okay, all this food on the table is edible and vaguely healthy. If we're gonna argue about why you like certain things better, you're not really gonna win an argument. Like, I love bell peppers. My wife hates them. I will never convince her that they're good. It's just the way it is, you know? And I probably would be that way with somebody suggesting that Tiampos is the best serif typeface. You know, other people might be like, you're absolutely wrong. I like New York, which nobody would say that, but like maybe somebody would.

Yeah.

But why? So New York is a great example. There's something about that typeface when you see it in body copy that doesn't feel right. And I don't know what it is. It's almost like a— there's something like circular about it or like it flows in a weird way. I don't know what it is. I've never been able to figure out what it is. When we would do it, because New York is in the Substack app, but so is Tiempo's. And when my app would sometimes flip back, they're close enough that you wouldn't maybe notice right away. But after like reading 2 sentences, I would be like, what is going on?

You know?

And I cannot describe it. I, if forced to, I could, like with the, all the technical reasons, but those aren't the reasons why I don't like it, you know? So yeah, anyway, I love that experience. I like putting in the little type selector and making that a big part of the app and, and putting a lot of care into that. I also really like doing it the proper way, licensing everything. I like, you know, TypeFoundries and the, the whole thing. That's one of my favorite areas of the field to support just because it's crazy. I just can't imagine doing that, executing a typeface and commercializing it. It's like, seems so crazy. And so for the people that do it, especially foundries like Klim is probably my favorite. I would go a long way to like try to support, you know, those, those efforts.

I want to return to something you said, which is that this was kind of your first time working from a place of established product market fit and then translating it to a new medium? Because it's kind of interesting, like, you went from doing that for the first time to then doing it immediately afterward with Linear. So are there common threads between those 2 experiences that would maybe shine a light on how you approach your practice as a designer?

Yeah, but I'd have to dig for them because they're such different products and they're such different teams that the experience felt dramatically different. The thing that was the same I think is every— there's a really weird instinct that designers, I think in particular, have, which is to look at a problem space that's been explored already. So, and that would fit the category in both of these where solutions have been established. And I don't know what it is inherent in many designers, myself included. There's that feeling to just, what if everything was completely different? That's like an instinct that people have. And you hear it in critiques all the time and it drives me crazy. When people are like, why are we even doing it? Should we step back and like figure out why are, why are we doing this? What's this? And it's like, okay, okay, we're going to go down, we're going to go down that path. It's like, I, it's, it's very tempting and I understand that, you know, but I, but I felt, yeah, yeah, yeah, yeah. I felt it too. I think in both times where I would look at the architecture that I'm moving over to mobile and like in Linear's case, for example, cause I, there was like 100 million iterations of it. Which I hope to one day be able to share. I was just caught up in like, what if it worked a different way? What if it was organized a slightly different way? And it was funny because like for somebody who finds that, or who's so allergic to that instinct, when I experience it directed at me, it was kind of weird to do it myself because I would imagine it was probably kind of annoying. But it was, what I loved about working there was Kari, And the team was really open-minded to that kind of thing. They were very into the idea of like, yeah, let's go look over here, see if that makes sense. Let's go look over here and see if that makes sense. And I think it was probably one of my favorite experiences in being allowed to explore. It's actually what every designer asks for. It's like, what if I could work somewhere where the CEO and leadership cares deeply about design? They let me do whatever I want. They let me work with The people who I want to work with, and the product is cool and interesting, and in their case, profitable and like an incredible product. It's like you could not draw up a more perfect situation, you know, which is like, was really interesting for me because similar to as I was describing before with Cocoon, it was hard for me in that perfect scenario to figure out how to articulate some of the ideas that usually would come so naturally. It was similarly difficult. I think at Linear to decide on the final form of what that app could be because there was like so I could do anything, like everything was available. And I really like where, where it ended up just before I left. I think it was in a really good place and I'm really excited for it to come out. But it was a very interesting experience, like having everything be, all the circumstances be totally ideal. And then find, it's not so much that my skillset wasn't there because I felt like it was, it was more like I almost had too many ideas and it was hard to like pick one, you know?

Can you talk a little bit about how you're bringing people along for the journey while you're navigating that idea maze? Like at some point you do kind of have to check off some alignment boxes to ensure that you're moving forward towards shipping something. So like what did the process look like outside of just having this freedom to explore like crazy?

Yeah, so Linear is fully remote, so it was a lot of asynchronous video communication. And video in that case, not because I'm trying to— not of the sort that we've been talking about. This is much more just like, hey, I gotta show you something, so I'm gonna make it a video. I'm just gonna talk to you like you're with me now, but like there's nothing about it. In those cases, I'm not tweaking the delivery or anything. It's just like, this needs to be a video 'cause you need to see my screen. That's it, you know? So I did a lot of that. And I think that one thing that I would try to do there that I think is useful anywhere is not just display the prototype and the idea and show 1,000 iterations. 'Cause I think sometimes that can overwhelm people where you're like, it could work like this, it could work like this, it could work like this, it could work like this. So there's like 100 options and people don't know when you came up with those options, they don't know what you had in your mind, what you were trading off, what framework was sort of guiding you as you put those different things together. And the differences are just gonna be visual at first. The way they, when they see the different things, they're gonna be like, okay, well that one, the menu's on the top. That one sits in the bottom. That one, there is no menu. So I think it's very important to establish and make very clear the framework that was guiding you when you did the thing so that it can sort of create an architecture around the ideas that you show that is very clear to people so that it's not like just getting a whole bunch of mocks thrown at you. You actually help them understand. What is distinct about this idea? Why is it even being included in this combination? And where does it sit on this little map that I'm gonna draw for you? So now you know all the things that I was trying to balance as well. And so I think that can be very helpful. I just did it yesterday, actually, communicating something where I guess I get frustrated how often I feel like I'm describing option 1 versus option 2 versus option 3. Like, I'm always like, This or that, this or that, this or that. But sometimes it can be useful to kind of whittle something down to like, here's a decision that's scoped that I can fully describe to you all of the sort of background. And as a result of all that background that now you have, you could kind of either go this way or that way. And here's the reasons why you might go one way or the other. And here's what they look like. Here's a prototype of each of them. And here's why I think option 2 is the best one. And then it gives people a vocabulary that they can use in their asynchronous message back to say, well, option 2 is good, but it doesn't, whatever. And then they can— you're now referring to these things as named entities. And maybe sometimes it's even worth giving them a name. This is the no menu option. This is the gestural option or whatever. And that I found to be pretty helpful because I think especially in that environment when you're remote, if you're just sharing a whole bunch of work, What do you guys think of this? And you don't really make it clear what you were really toiling over, you're gonna get feedback all over the place, you know.

I like the idea of thinking of it almost less as like options and more of directions where it's like, yeah, if you put things on a spectrum, you're not just picking option A, you're picking this chunk of the spectrum and this is the axes. It reminds me of something that Kevin Wong said to me, who's the, he's the Head of product design at Webflow. And he talked about like basically having a flashlight and design is almost like exploring a cave where you kind of run ahead and you're just like, this is generally what is down this tunnel versus this is generally what's down this tunnel where it's like, this isn't an option A. There's a million options that all kind of orbit around option A. We're just kind of picking this general tunnel rather than saying, yes, like this is the concept.

Yeah, yeah, yeah. And, you know, once you sort of have that loose cave and flashlight's good 'cause the map is blurry, you know, it's not super defined, the edges of where you could go. You at least understand that if we go this way, we're not going that way. And there's certain things down that way that we liked, but we are leaving them behind. And that's, I think, a good place to be when people understand those trade-offs.

You said, You could not draw up a more perfect situation when working at Linear, which obviously tees me up for the question, why'd you leave? Why'd you decide to return back to, well, Facebook, but now Meta?

Yeah, I get that question a fair amount. There's lots of factors, I should say. Probably the main one, so now would be my version of like, I want to start with the upside-down triangle. I don't want to tell you that there's a couple specific reasons why I came back. But they're so small that it's like, I don't want to start with that. It's like, what's really like the biggest reason? And then we'll work our way down. I think the biggest reason was I'd had enough experiences that I could reflect and think like, what actually is my favorite professional environment? I think that Facebook or Meta, well, I shouldn't say I think, it is that for me. Like, I can say that with confidence that when I look back at 2016, 2017, like that was my favorite. And a large part of that was the people. that worked there and what we were working on. And so I think one thing that changed, 'cause like I left, so why would I come back? One thing that changed was a lot of people started to come back. A lot of specific people who are my really close friends either came back or were still there. And so, and not to mention that, it started to be that they were all on the same project as well. And I think in particular what I liked about working at Facebook last time was I was working on Live, Which at the time was a new thing for the— not really for the world, but it was a new product space. And so that was exciting. The company was treating it with very high priority, which adds a little bit of chaos and urgency that I like in an environment like that. And so you combine the people with a new space like that, which in this case is AI. And then I think I'd spent 6 years in the startup world. And I do think of being in the startup world, especially early stage, is like kind of being off of your home planet. Like, it's less oxygen, it's more dangerous, and potentially it's way more exciting and interesting and valuable. But at the end of the day, if you're gone for 6 years from the home planet, it's like you start to kind of run out of food. You know, it's like, it's, you miss your family. It's like kind of intense to be out there that long. Yeah. And so I think there was something interesting too about returning to home base in a way. And I think ironically, I don't want to— the misconception would be that I'm describing that it would be somehow easier or less intense coming back to the home planet. I can say with confidence that having returned, working at Meta is way more intense than working at a startup. That I can say for sure. So that's not it. It's not like you're coming back to rest or anything. But I do like the kind of cadence of being on the home planet, leaving the home planet, going back to the home planet, and then maybe, who knows, maybe one day leaving the home planet again and starting something else. But I've been very pleased that in returning, I did find what I remembered about working there before, which was that it's a great company to work for and the people there are amazing. And I don't know. I think that that was kind of what I hoped would be the case when I left and why I would even have considered leaving. Because people were pretty surprised. Like, I remember when I was talking to Kari, we're like, whoa, what? This is kind of a crazy thing to do. Like, why would I even want to do this? But he was very understanding. And I think especially when people are involved, when you're like, look, all my buddies are back there. And I really like this space. It's kind of hard to argue with that at a certain point. And also, so now we're down at the bottom of the triangle. I think also I like working with people in person. Like I said, when I worked at Facebook before, I could see my entire team. If somebody wasn't there, everybody knew, 'cause it'd be like, oh, where's Josh today? It's like, he's not at his desk. That means he's not working today, which was crazy. And I'm happy to just sort of agree to disagree on this one with like the general world. I feel pretty strongly that remote is, less effective. That doesn't mean it's bad, but like, if you're gonna start a company, if I'm gonna start a company, it will absolutely be a hybrid at least.

When you reflect on the last 6 years, what's a way that you think that you grew as a designer while you were on the alien planets?

Well, I could say there's lots of very just technical ways you grow when you are building an app from zero, which I did 3 times there. So you get a lot of experience doing stuff that you don't get at a big company often, which is like, How is settings gonna work? You know, how is login gonna work? What are the trade-offs to auth? Are we gonna do phone? Are we gonna do, I don't know, God forbid password, you know, like that kind of thing. You get a lot of experience with the sort of the fringes of app design, even the app icon, for example. You know, it's like that's the kind of thing that you, you don't really touch as much when you're in at a big company or even just a bigger startup. So that was good because there's certain things I do now, whether it's like, okay, time to design comments. It's like, which one of the 12 that I designed over the last 6 years should I choose? Now it's time to design a composer. Which one of the 30 would I like to choose from my repertoire of design composers? And so it's like that kind of thing became pretty helpful because a lot of these problems we solve these days, they can be new. I actually hate that expression, there's no new ideas, because there absolutely are new ideas. I could think of a ton of new ideas today, probably, if you really want. It's like there's lots of new ideas, but the ingredients are all the same. So like I said, I've designed 1,000 composers, 1,000 setting screens. When I go to make a new dish, I will take my ingredients. So like, I like this composer, I like this auth flow, I like this size of avatar, and I will mix them all together. And then I will take my new ingredient, which I discovered in the garden, and I'll sprinkle that on this thing that otherwise resembled everything else you've seen before. But now it's different because we had this one new thing, you know, and That I think was nice because when you just, the reps of doing that, you know, 'cause you're not just doing it 3 times, you're probably doing it 300 times 'cause each app lives 1,000 lives, you know? If you consider every version of each of those apps that existed at any given moment, Cocoon, Substack, or Linear, like they've all been fully formed and killed many times. And so I think it just reps at a certain point. That was the most valuable thing probably.

Are there things that you're doing outside of Reps to invest in your ability to understand the different types of ingredients, how they fit together, and ultimately like shape your taste palette as a designer?

You know, I do a lot of music, and I think it's the same with design. It's like being sort of a rabid consumer of the thing you practice is pretty important because of how it will inform you even subconsciously as to like what moves you can make in a given moment, you know. So if you're writing a song, you know, even if you didn't realize that the last song you listened to was making heavy use of the Lydian mode, maybe now like that sound kind of feels good to you and that's the kind of the way you go, you know. If you only interact with system apps and don't really mess with your phone too much, it's like you're kind of only really going to be exposed to those moves, you know. Whereas if you take an app like Amy, the calendar app. I don't use it because I'm happy with Google Calendar, but like, this is a weird app, you know, like they've got like a little panel, the little pane that slides around. There's a really cool interaction when you tap on any of the things in between the panes. And it's like just being exposed to that idea that somebody had now makes you think like, oh yeah, what if, what if apps did have like multi-plane, you know? And I saw it actually, there was somebody on Twitter the other day, they posted an idea. And it was a little panel back and forth like this. And I was like, I know where that came from.

It's taken off. I've seen it too. I've seen that idea multiple times. I actually had Dennis on, I don't know, like 6 or 7 episodes ago to interview. And he, the way that he talked about like the underlying why for why they created it that way was so interesting. 'Cause he was basically like, he almost went as far to say that it was like a failure of design to have things split up into isolated pages where it's like, no, no, an app should be more of like this fluid experience where things connect and everything is like that. It all like is just different sheets that expand and collapse. And it's really interesting. And I do think that it is having an impact on different UI explorations that I'm seeing on Twitter.

It is, yeah. And I think that's the value. And even if you don't use it, being exposed to it and understanding and ideally doing what you described, which is talking to or listening to the person who thought of the thing, would be the best way to, to kind of get inspired because then not only have you seen it, but now you sort of understand that, like, the things that were going through their mind. So yeah, that's probably something that I do, which is pretty common, I guess, but it's very important.

Well, Alex, I feel quite confident that we could have this conversation for a full other hour. I have a limited calendar invite though. This has been amazing. Thank you so much for coming on and just Sharing a little bit more about your journey and telling some of the stories and things that you've done along the way. I think it's been really inspiring. And I'm hoping a lot of people can get even just excited to kind of put themselves out there and do their own thing from listening to you talk.

Awesome. Well, thank you for having me. Fan of the show, as they say. And yeah, honored to be here. So thanks. Thanks again.

Hey, it's Ryd. Don't forget, if you want to go even deeper, each week I send an email out to over 10,000 1,000 designers with bonus resources and key takeaways from these conversations. So head to dive.club/email to sign up. Okay, I'll see you next week.