Lenny's Podcast: Product | Career | Growth - How to see like a designer: The hidden power of typography and logos | Jessica Hische (Lettering Artist, Author)

Starting point is 00:00:00 Most people are better at understanding the feelings and sensations that typography and logos give us than they give themselves credit for. Because what we are as people are endless absorbers of patterns and information and all this kind of stuff as we move throughout the world. We don't take time to sit and digest it, but it's still coming in and getting logged. And so even as like a non-designer, I think you can look at examples of, of logos where something's not quite right and be like something's not right here,

Starting point is 00:00:33 I just don't know how to name it. But I think a good exercise is just sort of like looking at fonts that are available in the world and asking yourself, what feeling does this give me? Today my guest is Jessica Hish. Jessica is a design legend and it was such an honor to both have her on this podcast and also to work with her on a refresh

Starting point is 00:00:56 of my newsletter and podcast logo and brand, which is launching around the same time as this episode comes out, Jessica is a lettering artist specializing in tapographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, the United States Postal Service, Apple, Nike, Tiffany and Company, The Gap, and Penguin Books, and her work has been featured in design and illustration annals, both in the U.S. and internationally. She's helped create logos for Phil's Coffee, Eventbright, and Mailchimp, is a best-selling children's book author, and if you live around the Bay Area, you've seen her work all over the city without knowing.

Starting point is 00:01:31 In our conversation, Jessica shares the process that she went through to update my logo and brand from my needs learned podcast, what specific elements of a logo and brand impact how you feel about that brand, why a good enough logo is just fine for a long time for most startups, and when it makes sense to refresh your look, also some really clever productivity tips, design advice, and a bunch of really fun stories. Jessica is a master at what she does, and I am excited to spread the Jessica-Hish gospel. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously.

Starting point is 00:02:10 With that, I bring you Jessica Hish. Jessica, thank you so much for being here. Welcome to the podcast. Happy to be here. I thought it'd be good to start with asking you just to describe what it is you do, because you're very atypical of the kinds of guests I have in this podcast, and you also have a very unique skill set. Yes, well, I will describe what I am most prominently known for because I'm a person who just does a lot of things, but the thing that I do the most professionally is custom typography, like bespoke lettering pieces. And so that translates to working for all kinds of things. Sometimes it's for film and television. I've done it. I've done like movie titles and things like that and television credits and stuff. Sometimes it's book covers, actually a lot of times it's book covers.

Starting point is 00:03:01 and then a big part of my business is doing logos and logo refreshes and things like that. So basically being like the person who knows all the things so you don't have to have that person on staff when it comes to typography. This episode is brought to you by the Enterprise Ready Conference, a one-day event in San Francisco, bringing together product and engineering leaders shaping the future of Enterprise SaaS. The event features a curated list of speakers with direct experience building for the enterprise. including leaders from OpenAI, Vanta, Checker, Dropbox, and Canva. Topics include advanced identity management, compliance, encryption, and logging, essentially at complex features that most enterprise customers require.

Starting point is 00:03:46 If you're a founder, exec, product manager, or engineer tasked with the enterprise roadmap, this conference is for you. You'll get detailed insights from industry leaders that have years of experience navigating the same challenges that you face today. And best of all, it's completely free since it's hosted, by WorkOS. Spots are filling up quickly. Make sure to request an invite at enterprise ready.com. That's enterprise ready.com. I'm excited to chat with Christina Gilbert, the founder of OneSchema, one of our longtime podcast sponsors. Hi, Christina. Yes, thank you for having me on, Lenny. What is the latest with one schema? I know you now work with some of my favorite companies

Starting point is 00:04:28 like Ramp, Vanta, Scale, and Watershed. I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs? Yes, so we just launched one scheme of file feeds, which allows you to build an integration with any system in 15 minutes as long as you can export a CSV to an SFTP folder. We see our customers all the time getting stuck with hacks and workarounds, and the product teams that we work with don't have to turn down prospects because their systems are too hard to integrate with.

Starting point is 00:04:56 We allow our customers to offer thousands of integrations without involving their engineering team at all. I can tell you that if my team had to build integrations like this, How nice would it be to be able to take the soft of my roadmap and instead use something like one schema, and not just to build it, but also to maintain it forever? Absolutely, Lenny. We've heard so many horror stories of multi-day outages from even just a handful of bad records. We are laser-focused on integration reliability to help teams end all of those distractions that come up with integrations.

Starting point is 00:05:24 We have a built-in validation layer that stops any bad data from entering your system, and one schema will notify your team immediately of any data that looks incorrect. I know that importing incorrect data can cause all kinds of pain for your customers and quickly lose their trust. Christina, thank you for joining us. And if you want to learn more, head on over to one schema.co. That's one schema.com. Part of the reason I was excited to have you on this podcast is that I was lucky enough to get to work with you on a refresh of my logo and brand for my newsletter and my podcast, which I'm very, very excited about. It's actually going to be launching right around the time of this episode going live.

Starting point is 00:06:00 So this is in part of celebration of the new look and logo and brand. And I thought it'd be an awesome excuse to bring you on the podcast and kind of given inside glimpse into the process of updating a logo and a brand. Partly because I think it'll just be people are like, what the hell? How do this change? Where do this come from? Why this versus that? And also just for people that are thinking about this for their own product or business to understand the process and understand when it might be right for them, when it might be not right for them. So broadly, how does that sound?

Starting point is 00:06:31 Sure, yeah, of course. So one of the things, like, everybody that starts a company knows that they need a logo, right? That that is like a big thing. Some people start a company and think the logo is going to drive the culture of the company, which I don't think that that is true. I think that, you know, like the product itself and the team you build and the people you put together are the thing that should be driving things forward. But I do think the logo and the brand assets can generate a lot of both, like,

Starting point is 00:06:58 internal and external excitement and just kind of like tell people what to expect from the thing that they're about to engage with. You know, in that way like when I, you know, some people say like don't judge a book by its cover. I'm like the opposite where any book should like the cover of the book should be giving you incredible insight into what is on the interior of the book and setting the tone and setting the vibe so that when you open the book and read the book, you under like you, it's a symbiotic thing where you're like, oh, I understand. what I was getting into. This got me excited about starting it and whatever. It kind of like keeps that ball rolling. But with the refresh work that I do, a lot of people start companies and

Starting point is 00:07:39 they have a certain amount of money. If they're bootstrapping it, they have less. If they get venture money, they have a little bit more. But what they don't want to do is spend venture money on like a massive brand exploration when you're still in the hiring process. You're still trying to get early stage engineers and all that kind of stuff. And so I am sort of like a weird contrarian in this way in the brand world where brand people are like, brand is everything and you need to like take a significant investment in brand because that guides the vision of the product or like whatever. But I think being a bit more of an insider within the sort of tech world, I understand

Starting point is 00:08:19 that sometimes people start companies and have an intention to do something. and while they're doing that, they're building the team, they're doing cool stuff, but then the company has to pivot for one reason or another, whether like a competitor immediately comes out with a thing that you're doing or the technology that you're doing gets postponed, like whatever's going to feed into it. And so if you invest super heavily on like the whole brand vision from the jump, sometimes it's like throwing away money if you have to pivot. And so what I love about the work that I do is that I understand that a lot of

Starting point is 00:08:53 of people have to like just have something to put on decks, you know, and have something to put on a holding page or whatever. And internal teams are totally capable of doing that early work. But then if it does become successful, you don't want to get locked into whatever it is that you had to throw together like before an investor meeting or something. And so I come in then to take the existing, the existing vibe and smooth it out, address any of the concerns that came up. A lot of times it's really utilitarian stuff like this doesn't scale well or this thing falls apart in this context or we never had a good avatar version of it or whatever. And so sometimes it's really specific utilitarian fixes.

Starting point is 00:09:37 And sometimes it's just about sort of growing it up and sophisticated it without losing like what was there in the first place that people got excited about. to give people maybe a couple more tactical piece of advice here. What's a sign that it's maybe time to do something with your logo and brand from like you took a first pass. It's good enough. Your wife made one. Your husband made your logo. It's like, oh, this is great.

Starting point is 00:10:01 Let's just go with this. What's like a sign that maybe it's time to, okay, we should actually at least uplevel this, not necessarily higher studio, but take something to make it better. Well, one of the things is if suddenly you're starting to deal with the greater role. rollout of the look and feel of the brand. So like if you at first just basically had like a really beta website and like small version of the app, but you're about to do a new one that kind of updates and expands it,

Starting point is 00:10:32 that could be a really good time to roll it out. So one of the things that a lot of people do when they're starting a company is that they'll make a logo with a font that is really popular or widely available or free. and if you are about to, let's say, like, print a bunch of swag for new hires or you're hosting a conference or, you know, whatever is that event where suddenly you're going to physically invest money in making stuff with your brand on it, that might be a good time to do it. One of the reasons why I like tell people why having a custom logo or custom typography can really matter is that if you're using something that's available to everyone,

Starting point is 00:11:14 the chances of someone else coming in and copying you are very easy and high. You might be one of these lucky companies that just out the gate is like outrageously successful, but with success comes people climbing up behind you trying to copy your success. And if that success is very easily copyable, and people will try to like sort of trick your customers into coming their way by repeating the things that you're doing, including the branding, One way to avoid that is by doing something that's more customized when it comes to the logo and brand. So let's actually talk about the work that you put into updating my logo and brand.

Starting point is 00:11:52 And from that, we can spin off into lessons and insights that you have along these lines. Overall, just high level, what's the process you go through to go through a logo refresh? Sure, of course. So super high level, it's figuring out what the goals are. Some people have a goal where they want their customers to not notice it at all. You know, like they're like, oh, everybody loves this, but I, the person with a design eye, can see all the problems with it. And I need to roll something out that fixes the problems that I see, but that no one else

Starting point is 00:12:22 really notices. So if that's like one approach to it, right, which is like a very close in refresh, where we're just like trying out little things to make it feel custom or fixing things that have come up when stress tested, like whether it looks crazy when you scale it and looks like, horsey and sort of heavy-handed when you scale it too big, or when you scale it too small, you lose a lot of legibility and stuff like that. So that's what would be like a really close in exploration. And then for other people, they might have bigger goals where they're about to pivot the company to like try to attract a different audience or things like that. So they might have,

Starting point is 00:13:02 they might have this really cool and successful like group of people that are like their super users, but they're trying to expand it. So then it's about like, what can we do to like shift the vibe to make it include these new people without excluding our core folks? And so my first round is sort of figuring out what that scope is. Like how experimental, how broad are we going to go for that first round? Because then everything else cascades from there. So if we go really broad for the first round, then we're in this process of narrowing down the scope as we go down, whereas if we go really close in for the first round, we're already just talking about really technical stuff. And then this is another thing that is a little bit unique to me that not

Starting point is 00:13:47 everybody else does, but I will like hand off files to clients to try in situ like really early on if what we're trying to do is solve utilitarian issues. And most other people are like, no, you don't get the files until we do the final because I don't want you to like run away with this or whatever. So there has to be some trust with it. So yeah, figure out what we're trying to accomplish and always keep those goals in mind and then scope out the process based on what those goals are. And so for each round, we're addressing different things. Like first round might be about like just capturing the overall look and trying things as broad as we can. And then the next round is, okay well now we have like generally a look that we want but is it the right weight is it the right

Starting point is 00:14:36 um you know letter height do we have enough details that kind of thing and then we kind of get narrower and nerdier as we go along in the process awesome and then in the experience of my podcast logo we uh i was an ass and at the end of it i'm like no this isn't right uh because we narrow narrow narrowed And then I was like, no, this isn't, I'm not feeling it. And then we unnarrowed it and went back. That is not an uncommon experience, though. This is why, you know, like, there's a few things that I'm not opposed to that I know people that are very opposed to.

Starting point is 00:15:09 I'm not opposed to Frankensteining options together. To me, it's like I'm giving you a menu of all the things that we can do. And if you're, and, but I'm like a chef that puts a menu together where you can kind of combine different appetizers and different mains. and they all still make sense. Some people will give you a menu, and if you try to do that, it's insane and it tastes terrible, right?

Starting point is 00:15:30 But for me, like, everything that we're doing, I feel like mixes and matches fairly well, and I will let you know if it doesn't. And then it's not unreasonable for clients to go down one path and then use that as validation or confirmation that something that we did much earlier was actually the right way. And in that way, like, you know,

Starting point is 00:15:49 if a client ever asks me to do something, they're like, let's see it in purple or whatever. Like there's designers that will really fight you tooth and nail because they're like, that is wrong, that is wrong. But I know that some people just have to see it before they can let it go. You know, like sometimes you have to walk down a path before you're able to understand what the right thing to do was all along, you know? That's exactly how I felt for me.

Starting point is 00:16:12 Going back to the goals, the different goals people have when they're exploring this, you mentioned there's like, there's just like little problems with the logo, it doesn't scale, doesn't print well, that kind of thing. Another goal is people are pivoting and they want to change the vibe. and the feel of the brand. What other goals might appear that you've come across of, like, why people want to do this? Well, sometimes there's like a legibility issue that is, like, really glaring once you see it. And then people are, like, too close in to notice it.

Starting point is 00:16:39 So this is why it's like you have to show it to a lot of people that aren't familiar with, like, looking at those letter forms and stuff. The one that came to mind immediately when you asked was when I did a refresh for Jenny's ice cream, which is a really, like, amazing ice cream brand based out of Columbus, Ohio. they had a few utilitarian things in mind. Like they had this long J that created this pocket of white space underneath it that made it really hard to design with. But then the biggest glaring one was that they decided to make the apostrophe of the Jenny's over the eye as like a cool thing. And it made the word look like it said penis because of the way that J was drawn. Like it had a little loop at the top of the J. And so that was like the most specific fix that I've ever had to do.

Starting point is 00:17:24 is like make the logo not say penis anymore. But yeah, I feel like a lot of it is like misreads. You know, when you think about logos and things like that, you want it to be something that at a super fast glance, people can read it right away. You know, that doesn't mean that everything has to be simple, but it just means that everything has to be incredibly legible, especially when you're starting a new company or you have a less recognizable brand because eventually you become a household name and then people can look at just the color and recognize that it's you or like whatever. But it takes a long time building equity before you get that. And until that, it's really important that the legibility is just super tight. Let's talk about actually thinking through my new logo and

Starting point is 00:18:08 brand. Can you just talk about what you had in mind as you started to explore directions and we started narrowing? What was kind of like the mindset and the approach and the vibe? I think with the Lenny's brand. You are what I would call a person that has a beloved fan base that we don't want to exclude or offend by shifting gears super crazily. And so when I was looking at redoing your brand, it was about like what's here that we can look at that we should keep or at least explore keeping in order to make sure that it still feels the same on the other side. You know, like we didn't want to do anything super drastic. So some of the things to think about in that way are you have this sort of like handwritten approach to a lot of the parts of your brand.

Starting point is 00:18:56 And I was like, how do we do something that feels handwritten that feels like it could jive with the handwriting scripts and stuff that you were using, but might feel like a little bit more refined moving forward. And in a way that could blend with illustration so that the illustration and the letter forms all feel like they were created in the same, by the same hand. You know, like a lot of times for me when it comes to doing an exploration like that, it's about like, how do we make sure everything feels like it was created at the same time and not that we just tacked on new things and figuring out how to blend everything together is important. Color was also a big one. I feel like people's color stories are something that like is an immediate like read where if you blur your eyes and look at a brand, you can tell, you can recognize it by its color.

Starting point is 00:19:44 And so I think keeping your color similar was a big one too. But then I really wanted to try different approaches with the typography, you know, doing stuff that was a little bit more clean, doing stuff that still had a bit of like a funky edge to it because your original Lenny's podcast type had this sort of like cut papery, you know, a little bit off kilter vibe to it. And so trying to capture that but with new cleaner typography and that was really fun. So we had, like I was using a typeface degular as part of it, which has like a nice kind of wonkiness to it. It was drawn by a friend of mine, James Edmondson, who I love all of his stuff. So that was one of the things that we approached because I felt like it could kind of capture the look of the original cut paper-esque type.

Starting point is 00:20:33 But yeah, it was really fun to try a lot of different things and work within the iconography that you had used on a few stuff with the microphones and also marshmallows. and campfires and all kinds of things and just trying to make like a more unified system. Are there things that didn't work as you tried to explore this process that you recall? That might be worth sharing of just like, oh, that was a cool concept, but it didn't quite work the way you thought. With working on this refresh, like so much of it was thinking about

Starting point is 00:21:02 what are the immediate uses of the logo. And so like your logo, you have these very specific uses that you need it for. like the avatar for the podcast being like a top one. You know, like some people, they'll design a logo and then have these sort of like illustrative versions of the logo that get rolled out for other things. But I feel like those layouts were actually kind of more important than even just having

Starting point is 00:21:27 like a basic letterhead-esque logo. And that's an interesting way to approach it because usually it's like let's start simple and expand and make it crazier. And I felt like we had to always keep those things in play. So it was like designing brand assets while also designing the logo. And I feel like it's usually like sometimes you'll see examples of that in early explorations just because like it makes it feel real to the client. That's why like there's always like the tote bag.

Starting point is 00:21:55 Like you got to put the logo on the tote bag and then it feels real or whatever. But in our case, we had really specific uses that needed to get explored very early on. And that made it, you know, a slightly different process for me. In terms of things that didn't work, though, I think, you know, just trying to work on the level of detail within the illustration and type so that it could shrink down because we knew like one of the primo examples of the logo being used was on that podcast avatar. And some of the versions felt like a little bit too detailed to shrink down that much and trying to kind of get the balance of that having the illustrations feel illustrative and whole, but not when they scaled up to feel like, too simple, like a, you know, like we just pulled it from an icon library. Like, I think that was like an interesting challenge. Yeah, one of the impetus is for changing my logo for motivating me is my wife's a designer, as you know, and she's got strong opinions about my logo. And she always

Starting point is 00:22:55 was making fun of my logo saying it was a, it looked like a clip art fireplace that anyone just could just plug and play. And she was like, oh, that's so bad, you got to change it. So that was one of the motivators. I think I might have shared that when we started working together. Yeah, and also too, I think that really talks to what I was saying earlier about making sure that everything feels like it was created together rather than it feeling like these disparate elements. Because I think you can have an icon or logo that is quite simple as long as the rest of the brand matches that simplicity. So I think for you, like the biggest thing was making the illustration and the typography just feel like it came from the same universe instead of feeling like these separate elements. when I first moved to San Francisco, I moved to San Francisco from New York. And as a New Yorker, I had an apartment with a full kitchen that never got used.

Starting point is 00:23:45 I just ate at restaurants and did takeout, like for the seven years or whatever that I lived in New York. And learning to cook, at first when you learn how to cook, it's like you're making a pot full of ingredients and none of the ingredients are actually working together. But then the more you do it and the more you understand how these things are meant to blend and cook at different temperatures at different times, you start having this cohesive dish rather than like hot ham water. You know what I mean? And so I feel like a lot of clients come to me and they have hot ham water when it comes to their brand. And it's just about turning that into a soup, like something that feels real. I want to take a quick tangent. So most people listening to this podcast are not designers. They're product managers, founders, engineers and folks building product. And I think

Starting point is 00:24:36 there's always this, like I've always wanted to see the world through the eyes of a designer because there's so much I don't see and there's so much that affects how I think about something that I don't understand when I look at a logo. And so I thought it might be helpful just to spend a little time helping people see like a designer a little bit. So let me just ask you this question. When people look at a logo or a brand, what are just elements that make it what it is, that make you feel the thing you want to feel that we may not recognize? I think most people are better at understanding the feelings and sensations that typography and logos give us than they give themselves credit for, right? Because what we are as people are endless absorbers of patterns and information and all this kind of stuff as we move throughout the world.

Starting point is 00:25:28 We don't take time to sit and digest it, but it's still coming in and getting logged, right? that's why like if you see something funky in the world, you're like, that's weird. I don't like that. I don't know why I don't like it, but I know I don't like it. And I think like even as a non-designer, you can see that in typography, you know, because we like the whole being able to recognize patterns thing. And I talked about this a bit at config. It's like it's a safety thing, you know, like looking into the world, your eyes can spot

Starting point is 00:26:02 that thing that's a little bit off. and that thing that's off feels not safe to you. And it's like thinking about when we look at a meal and there's a thing on the plate that looks like it's moldy or something like that. You understand like, that doesn't look right to me. This doesn't smell right to me. And your body knows it before your brain knows it. And so even as like a non-designer,

Starting point is 00:26:24 I think you can look at examples of logos where something's not quite right and be like something's not right here. I just don't know how to name it. But I think a good. good exercise is just sort of like looking at fonts that are available in the world and asking yourself, what feeling does this give me? And just write them down. And it doesn't matter. Just give yourself permission to say whatever is happening in your mind, like the first thing. It's like, don't overanalyze it. Just look at it and be like, that feels calm to me.

Starting point is 00:26:55 That feels exciting to me. That feels whatever to me. And then the more you do that, the more you can start seeing similarities in the ones that feel exciting, in the ones that feel calm, in the ones that feel whatever, and then get into analyze mode of like, oh, these 10 things that I said feel calm are a lighter weight, have more generous spacing, have rounded edges, have, you know, like have rounder bowls to the letter forms. You know, you just start seeing commonalities between the things. And it's just about sort of like seeing them all together to understand like why, what those similarities are. So I think anybody can do that. I mean, you're not going to have the language of like the leg of the R and the tittle of the eye. Like whatever. Don't worry about

Starting point is 00:27:44 that. Like you don't have to know like typography language to like think about it. But anybody's capable of doing that. And it can be really fun to sort of just like stop and ask yourself and notice, you know. This is great. I want to go actually a little deeper. So what I'm hearing is look at something, tap into the feeling you feel when you look at it, like actually pay attention to it because there's wisdom in that. And then the specific things that you pointed out that impact that feeling are you mentioned spacing between the letters, the edges. I imagine there's just the color of it. What other kind of specific elements impact the way someone feels when they look at a logo? There's the width of the letter. So if it's like really narrow versus really wide, you know, so I always think about the width, the weights, the way spacing, sort of detailed treatment of things, whether things are very like hard and jagged or soft and how soft it is. Like sometimes we just add a tiny bit of softness so that it just feels like printed. So you can take like a typeface

Starting point is 00:28:51 like Helvetica, right? Like just the one everybody. knows, right? But if you take Helvetica and just ever so slightly round the edges, just a little bit, all of a sudden you have this typeface that feels more vintage or softer or whatever, because we're perceiving it like we would perceive it if it were printed on paper, versus perceiving it as this like hard geometric piece of technology that we're viewing. You know what I mean? And I know that it's because when you look at stuff printed on a page, it bleeds into the paper a little bit, which means that that softness reminds us in our bodies of a thing that we've seen that was printed, you know. And so it's cool to sort of walk back your feelings also.

Starting point is 00:29:36 So you'll look at something and go, that feels like this. And then ask yourself, why does it feel like that? And it might be because you saw it on like a flyer for a band when you were 22 and it brought out that feeling in you of what it felt like to be 22 at that thing. And that's a very spree. specific feeling to you, but it can inform your decisions about design. Because you can be like, oh, I'm not that much of a special snowflake. Other people might have that same reaction, but have different experiences that are adjacent to that reaction. So it's cool because you are sort of reverse justifying decisions. And I think that's like a really fun exercise to do is like to sort of song explode or your intuition. You know, so you make a decision intuitively or

Starting point is 00:30:24 or look at something and like into it what you feel from it and then really try to dive in. Why do I feel that way? What could this have reminded me of that made me feel that way? And you have to be just so forgiving and loose with yourself as you do it because then you'll get into like some really weird stuff. And it's really, and that's like really great inspiration juice for like picking other things, you know. I love the exercise that you gave. So, so the one you gave earlier is look at a bunch of fonts like look at your font folder is that like a place to go just like open up your font folder or go to my fonts or like a place where there's like a ton of fonts and like just search for something like search for sans serif or whatever like search for a really

Starting point is 00:31:09 basic category of fonts serif sans serif script like whatever like the top level uh edge of stuff and then just page through page through page through screenshot stuff that you like and make a folder of screenshots and then you can kind of take those screenshots and start categorizing them. This one feels feminine. This one feels masculine. This one feels aggressive. This one feels whatever. And just kind of take some notes on it. And then then you ask yourself like, well, why did I feel that way? And you're like, oh, well, this feels feminine because it reminds me of wedding invitations. And wedding invitations feel inherently brides versus groomy, you know. And then all of a sudden you're like, okay, well, now I know that if I'm going to do,

Starting point is 00:31:50 use a script for something, this zone of script feels very wetting. So maybe I avoid that for this brand that's actually like a cutting edge food packaging company or whatever, you know, because it feels too aligned with that industry. And those things happen. Like stereotypes are real and trends are real. And what can sometimes happen is like some industry kind of usurps an entire style for a period of time. So then if you use anything within that style, it's like you're aligning yourself to that industry. And so that's why it's sort of important to sort, I mean, everybody that does branding, one of the things that they do is they analyze the competitors of the company, right? And so you just like look at a landscape of like, what are all the competitors

Starting point is 00:32:36 doing? What is their visual vibe? And do I lean into that or do I avoid that? Like if I lean into it, then I'm immediately getting this like everyone that looks at it understands. I'm a fintech company because I look like a fintech company. If my whole thing is I'm trying to be divergent from that, I'm trying to show how different I am from the status quo, then you use it as like a reactionary thing of I want to do nothing like that and do something really different. So people understand this isn't just another fintech company. Yeah. I'm thinking green. The color green has to be a part of the logo if you want to be a fintech company. Yeah, exactly. And if you're trying to be weird, then you're like teal, you know.

Starting point is 00:33:19 On this topic of seeing like a designer, is there any other tip just before we move on to a different topic of just like how someone could learn to see like a designer a little bit more? Yeah, another thing to notice because I'm assuming you're like product people, I feel like a lot of product people end up having some engineering background, whether or not they're engineers themselves, right? They have to interface with the engineers and they build stuff. and so they come at it from like a data standpoint.

Starting point is 00:33:47 And so I can always tell when there's an engineer that has suddenly taken an interest in type design and is now a type designer. Because everything is very, very regular, right? So like you can draw a grid on top of everything and the lines all line up perfectly. You can, and you see lots of reverse justification of that, like when people are making logos

Starting point is 00:34:08 and they have like sort of a more engineering background. The thing to notice that is interesting within type is that yes, you're absolutely following rules, but you're breaking those rules quite often to correct for optical tricks. And so if you look at a geometric sans-sauph, for instance, that's like a category of sandserofs, and they're meant to have a lot of really strong geometry,

Starting point is 00:34:32 be very regular. You know, like most of the sandserfs that you think of, that you're like, I'm in love with this of the last 10 years, like geometric sanzas. But when you really start to examine them, you notice that there's all these little things that people are doing to make them look perfectly geometric, even though they are not mathematically perfectly geometric. So that's another thing that you can do, whether you're doing it in Figma or doing it somewhere else,

Starting point is 00:34:56 is just like type out a couple of lowercase letters. Lowercase specifically are really good for analyzing this because there's more, because they're smaller than the uppercase letters, you usually have to accommodate for the weight a little bit differently. And so you'll notice that when strokes combine, so say I have an A and I'm combining the lower bowl of the A, I'm going to get a little thinner as I come into that. Or if I have, say I have a two story A. So two story A is like the one that's like this and then a bowl, right? You might notice that this vertical of the A there, the bowl actually eats into that stroke a little bit to erase a little bit of that added weight that would have been perceived optically, you know, had you kept everything perfectly regular. And so it's weird because you end up, like, creating something that's perfect and then

Starting point is 00:35:54 have to make it not perfect in order to make it be perceived as perfect. So that's like another just like fun thing to start noticing. And you notice it a lot more on typefaces and typography that is heavier in weight, because when things are heavier weight, you're constantly managing. these like really inky moments where things join together and you have to subtract a bunch of weight from that so that it doesn't get perceived as this dark mark where the letter is happening. So I think about like lowercase R's and lowercase ends. So the where the shoulder of the N or the R comes out, sometimes like the top of the R is actually narrower at the top than it is on the bottom. And that's to try to subtract some of that weight in there where that join happens.

Starting point is 00:36:40 So anyway, that's just like a fun thing to notice that you have to do that. And then once you start seeing it, you start seeing where it happens more often. And the answer of like why it happens is because you're like correcting for this optical weight issue. And then you're like, oh man, now I have x-ray vision and I can see all these weird things I've never seen before. It's very fun. But anyway, a lot of people when they first start out doing typography, whether you're an engineer or whether you're a designer, they don't account. for that. And so I can always just look at something and see whether someone is truly an expert at typography or whether this is like a fun hobby for them and they're pretty fresh at it.

Starting point is 00:37:21 And so the exercise here is like open up Figma, start typing and make it really big so you can basically see the font really zoomed in. Like a single letter, like make a single letter like the whole page. And then just draw some vertical lines or do the thing where you draw like a little circle or whatever and see if that circle is the same size at the point where two strokes joined together or the point where the stroke is just vertical and on its own. And you'll notice that there's differences even in typography that's meant to look extremely rigid and geometric. I want to come back to my logo and just a closed loop there. Talk about just like the final result that we landed on and why you think that was the final answer and kind of the way what you think people might get

Starting point is 00:38:05 from it, whatever comes to mind. Yeah, totally. I think like the final answer or the final logo, we took it down a lot of different paths trying to see where it was going to land, but ultimately ended up keeping it like pretty close to home and really focusing on that asset of the fire. You know, like we tried so many different versions of like, it's microphones with the fire and it's, it's, you know, marshmallows with the fire, et cetera. And it was just about like, you know, sometimes the simplest solution is the correct solution. And I don't know. I just feel like in terms of what we were doing for blowing it out and making it really cohesive, we went a lot of directions where there might have been like multiple versions of the logo depending on the scale and ultimately ended up

Starting point is 00:38:49 in a place where it's like much more, you know, in line and consistent across the bar. Yeah, maybe what I'll do is we'll share, I don't know if you're comfortable with that. We'll just share all the iterations somewhere that we went through. Oh yeah. I love sharing iterations. Okay, cool. Yeah. Like the biggest issue we had with the podcast logo specifically is originally, I was thinking the mic made sense to differentiate it from the newsletter. And then at the end of it is just like, why do we have this frigging mic in there? It just feels strange.

Starting point is 00:39:16 So that's where we kind of revisited the whole idea and killed the mic and went back to a different version of the fireplace, but with marshmallows. Yeah, I love the marshmallows. Awesome. I love it. That was my wife's, my wife loves the marshmallows also. And it's so versatile. We can use it in so many different ways. Indeed.

Starting point is 00:39:33 And then I guess maybe one last thread there is we explored handwritten kind of topography that you created yours from scratch. And then there's like the block letters, maybe just thoughts on those two options and benefits and why go one direction versus another. The handwritten one I really liked because I felt like we could bring the line quality of the illustration into the handwriting. But then the only problem with the handwriting is that if you want to blow that out, if you want to include other handwriting throughout the rest of the brand,

Starting point is 00:40:05 finding something that matches that perfectly without creating a custom typeface is a whole thing. And so I really like being able to kind of combine the two where we have this like broader visual vocabulary that we can pull from because you're going to have headlines, you're going to have subheads, you're going to have all these other uses for typography moving forward. And if you just have one thing to pull from, it's a lot harder to work with. You know, it's just nicer when you have like a few elements to play with. It's like having a wardrobe, right? Like if you have only one shirt and one pair of pants,

Starting point is 00:40:36 like there's only so many things that you can do. But if you have all these things that kind of work together and can recombine, then you can blow out a brand system like much more easily. Yeah, that's one of my favorite things about working with you is you create all these different variations of ways to use it and it doesn't always have to be the handwritten one. It could be the blocky, outlining one. And it's not like, this is it.

Starting point is 00:40:55 Don't change anything about this. This is the only way to use it. Well, part of that is because like some, Some brands, like if you have a massive company, like, you know, hundreds of employees generating hundreds of things, sometimes having too many assets can be, can overcomplicate stuff because unless you have a really, really well-written brand book outlining how to do everything that people are adhering to very closely, you can get like the assets kind of running rampant throughout all of the stuff and being used incorrectly. But because you're not a massive company and you have creative

Starting point is 00:41:29 control over the things that are happening and can help direct that, we can be much more playful with the assets and give you the ability to sort of use things in different ways. So it kind of depends on how much you trust all the people that are handling your assets. If you need, like, I am of the mind that you shouldn't need like a 500 page brand book in order to direct the, the, how the brand is used moving forward. And that if you do, the brand might be quite complicated, you know, or there might be even just parts of the logo that make it difficult to work with. My goal always, when designing a logo is to design a logo that's so easy to use that you don't have to be an extremely skilled designer to design well with it. That's my number one goal because I know not everybody is going to be

Starting point is 00:42:17 at a stage where they have like an internal brand team or like a designer that's like a rock star designer that can work with really complicated assets and make them look good. So I just want the assets to sort to teach you themselves by just how they exist, how to use it. You know, like you as a person that has any taste whatsoever, and hopefully people that you're hiring for any job at your company have some degree of taste. You know, if you hire an engineer, they have to have taste about how that happens. If you hire a marketing person, they have to have taste about how that happens. They should be able to look at that and intuit most of the way that you should be able to use it without being explicitly told, do not do this.

Starting point is 00:43:00 This episode is brought to you by Merge. Product leaders, yes, like you, cringe when they hear the word integration. They're not fun for you to scope, build, launch, or maintain, and integrations probably aren't what led you to product work in the first place. Lucky for you, the folks at Merge are obsessed with integrations. Their single API helps SaaS companies launch over 200 product integrations in weeks, not quarters. Think of Merge like Plaid.

Starting point is 00:43:28 everything B2B SaaS. Organizations like RAMP, DRADA, and Electric use Merge to access their customer's accounting data to reconcile bill payments, file storage data to create searchable databases in their product, or HRIS data to auto provision and deprovision access for their customers' employees. And yes, if you need AI-ready data for your SaaS product, then Merge is the fastest way to get it. So, want to solve your organization's integration dilemma once and for all? Book and attend a meeting at merge.dev slash Lenny and receive a $50 Amazon gift card. That's merge.d.dev slash Lenny. This is a good circle back to something you touched on earlier that I wanted to

Starting point is 00:44:11 come back to, which is a lot of companies, in your opinion, put too much weight on the power of brand and rebranding and how much a brand can fix their problems. Can you just again share your perspective on just how this might be an issue for people where they almost over-emphasize the power of brand? Yeah, I think, well, there's different companies, right? There's companies where brand is literally everything, where they're doing something that's not crazy innovative in the first place, and the brand is the thing that is the whole company.

Starting point is 00:44:45 And that's fine. That's a completely valid way to do stuff. It's sort of like people that can take in information and re-communicate it in a way to another audience or whatever, that they hit that audience in a way that the original information couldn't do. Think about all of the people who write books on psychology and medicine and all kinds of stuff that write it for a broader popular audience. They're the ones reading the medical papers.

Starting point is 00:45:13 They're the ones digesting all of this really huge, complicated data and turning it into something that normal people can read, right? And I think that there are companies that are doing that. They're taking a thing that is not innovative or isn't like they're not the only ones doing it, but they're repackaging it in a way that takes that and makes it so accessible to so many people. In that case, brand can matter immensely, right? Where the brand really is the thing that shows people that the thing that you're doing has value. But for a lot of people, the brand should be somewhat invisible so that the thing itself becomes the star. You know, like if we think about

Starting point is 00:45:54 the experiences that we have using products, right? Sometimes there's products where there's a ton of like fun and delight built into how you use it and that can happen through brand through like, you know, design choices and things like that. And sometimes the delight is the fact that nothing is getting in your way as you're using that product. And so you just kind of figure out what is your, like, what's your ethos of your company? Is your, is the whole thing about like doing a thing well, doing it simply, and making sure that everything gets out of the way of that experience, or is it like we're trying to generate this delightful thing or we're trying to open it up to a new audience or whatever. And depending on whatever that goal is, brand can have a different

Starting point is 00:46:39 place in that equation. I think some of this unique perspective on the power brand and the need for it in tech companies comes from, you're not like a tech person and you work with tech people. tech companies. Do you feel like that has an impact on the way you think and the value that you bring to companies to give them this kind of very outside perspective? I mean, most of the folks that I know that work in brand or, you know, kind of traditional graphic design, print design, they don't necessarily have a lot of insight into how building companies works. You know, like they're not friends with a ton of startup founders and things like that. And I've just had been in this very fun position being like everyone's token creative person in the bay for a while.

Starting point is 00:47:28 And this has been for a long time, right? So I remember speaking at like a Silicon Valley event that was like women in Silicon Valley in like 2009 or 2010, something like that. And it's interesting to be a person that has never actually themselves worked at a tech company, but felt so involved and understanding about how all of that works. You know, my partner, the reason why we're in the Bay is because he got hired by Facebook back in 2011. And we were kind of like olds at the time and take that with a grain of salt. Don't judge me. Because we were like 28, 29, like coming over to work at Facebook and everybody there was like 23, 24.

Starting point is 00:48:08 And so all the people that we ended up meeting in the Bay were more people our age that were like moving on to start companies and things like that. And so we just got to see that perspective so clearly of like, what it is to branch out on your own, to fundraise, to do all this stuff, to pivot, to do little experimental apps and see where that goes, to get acquired as a team versus getting acquired as a, you know, technology or whatever. And I've been able to see that in a way that I feel like a lot of people that do my job don't get to see. And that makes me very sympathetic and towards what it is to want to build a brand as a founder. You know, like, I understand that you have limited resources and those resources aren't necessarily going to get devoted

Starting point is 00:48:56 to doing a $200,000 brand exploration because when you have, you know, $500,000 like of money at all to like, for a year to like try to get things going, you certainly should not spend half of that money on branding. And that's, and that's my opinion. But that's not to say that brand can't be important and can't come in at some level or can't be thought of as a partnership between you and someone else where, you know, there's this whole idea of like fractional leadership now, which I feel like hasn't really infiltrated my world as much, but I don't know why it hasn't because most people don't have internal comms teams, internal brand teams until the company is very mature. And the idea that you could bring someone in

Starting point is 00:49:44 who is a real expert in whatever it is they do just as you need them, you know, and they just get kind of like consultant equity kind of thing. Like that should be more present because people don't necessarily need to have internal brand teams for like the first six months to a year of when they're doing stuff unless they grow really significantly. So along these lines, you have a pretty unique way of pricing your work. So for people that may want to explore this with you, share whatever you can about just how you think about pricing and ideally even like an order of magnitude of pricing.

Starting point is 00:50:16 So they're like, oh, okay, we should actually do this. So again, and to go back to the process, how it's always about like figuring out what people are trying to accomplish. So a lot of my process scales depending on how broad of an exploration that we're doing. So the way that I treat it is I treat my branding work not dissimilarly to how I treat commercial lettering, which is atypical. You know, like brand people, what they typically do is because the client has to own the assets outright at the end, no matter what, what they tend to do is bill everything that they're client owns everything as you are moving along. So it's all sort of like work for hire, but the idea being that it's a buyout of everything that is being made. And so what that means is that when a branding agency is pricing stuff for you, they're taking the buyout rights

Starting point is 00:51:05 and baking it into every round of work so that every round gets more expensive because you are owning all of the work. Right. And so what I do is I treat it much more like a commercial lettering project where I say you have to own the rights to this eventually, but hey, let's break that out and let's keep the creative process lighter and less expensive. So then we have more room to explore. So then if some stakeholder comes in last minute and is like blows everything else up and we need to start over, you haven't already paid to own everything that we've created. You just pay to own the thing that we create in the end that gets chosen. And so I really like the idea of keeping the creation process, more flexible and to try to scale to what people need versus having a really rigid way

Starting point is 00:51:52 of approaching everything. And so sometimes people will bring me on really early in the process where if they have an internal team or if they're working with an external agency or something, they want me there from the get out. And then some people are like, we have no money and we are going to try to do this as much as we can inside of our business, but then can we hire you at the end to make it look good, you know, if we can get everybody bought in and get it like 80% of the way there. So depending on what people's budgets are, I kind of have different ways of working or just depending on their needs are because my whole thing too is I don't want to step on anybody's toes because sometimes companies have these really amazing designers that are working in house.

Starting point is 00:52:32 And it sucks as a designer who started at a company and thinks that you might be able to get a chance to work on what is considered the most important asset in terms of the brand. and they just farm it out to someone else instead of letting you touch it. So to me, like, that's a recipe for anything that I create to be immediately killed because someone inside is going to be like, it's time to shine. And then they're just going to kill all my work. So I'm always like, how do we collaborate? How do I make it so that I'm an asset to you?

Starting point is 00:53:02 Not that I'm trying to step on your toes. Not that I'm trying to like take over what's the cool, juicy work from the people who inside that are really excited to do it. So I just want them to feel as bought in as I can be. But yeah, it becomes interesting. So it means that like sometimes, and I feel like I get told by branding people that I'm like too inexpensive because they're like, oh, for what you do, it should be like $60 or $70,000 at a minimum to do all this kind of stuff.

Starting point is 00:53:25 And I'm like, I feel like the majority of the projects that I do end up being between like 25 and 35. But, you know, depending on how you bring me in, it can be less if it's just kind of like as a consultant. And so it's not like out of the realm of podcast. possibilities to hire like a proper crazy expert at stuff, you know, it's not like you're thinking about sinking half a million dollars into the brand, you know, that's a very different experience. Awesome. Thank you for sharing that. Before we get into other stuff that you do, because like you said

Starting point is 00:53:55 at the top, there are many other things you do outside of this specific time of work. Is there anything else you think might be helpful or important for people to know about working with you on a logo refresh or just thinking about logos and this whole space we talked about. The best thing is just sort of like seeing what's there and really being able to like understand what's not working about it and what your goals are. And so like I said with that sort of like reverse justification of, you know, intuition, I think if you know that the logo is not quite where you want it to be, just spend a couple days like asking yourself why.

Starting point is 00:54:34 Like what is the thing about this that bothers me? and don't get specific. Don't be like the way the R is or whatever. Like maybe that's the thing that we talk about down the line. But always think big picture before you think minutiaa. Because sometimes people think that like they'll throw a bunch of minutia stuff at me. But it's because they haven't really stopped to think about what is the overall thing that's bothering them. And you just never get there if you're always trying address detail before you address the big picture stuff.

Starting point is 00:55:03 So you have to just like always start super top level and really ask yourself like very broad questions about why you think it's not working. And then kind of go tighter and tighter and tighter and be like it really could be like this C has always bothered me. You know, like, and then you then we can get real specific about that when I'm doing the refresh. But I think I also need to understand like sort of the overall reason why we're doing this, not just the like little bugaboo that bothers you specifically. not bother anybody else. Yeah. When I was thinking about this, I was like, it feels like my whole feeling was this could be better. That's kind of all it was. For me initially, it's just like, I feel like it could be a lot better. I imagine that's enough for some people. Just like, I think this could be better. And then like, here's things. That's definitely enough for some people.

Starting point is 00:55:52 Because I think like sometimes, like I think you specifically had a very clear vibe going on with all of your brand stuff. You know, like some people, it's totally like a mishmash grab bag of random trends. And there's no real voice that's coming through. But I feel like you've been doing this for a while. And like when you see everything together, there's definitely like a very clear sort of vision and vibe that you get from everything. Like I always tell people that like having terrible vision can be like your your best asset when it comes to like logo and brand because it allows you just like take your glasses off if you have terrible vision and look at it and get the feeling when you can't see the detail. You have to be looking at it with blurred eyes. Like what is the,

Starting point is 00:56:42 what is the overall look of this thing and just trying to get as broad and noodily as you can with it instead of it being about those really specific one by one stuff. You know, and I think like when you blur your eyes on your brand, there was a really clear cohesiveness to it already. And it was just about massaging it into a more consistent professional looking place. Well, I can't look at the old logo anymore now that I've gotten this thing coming together. So I'm really excited for this to come out. Just a couple of closing questions. One is you have a lot of other stuff going on that is not just topography and logo refreshes.

Starting point is 00:57:23 You have children's books. You do lettering for classics. You have a store in Oakland. talk about all these other things you got going on in case might interest people. Sure, yeah, of course. So I'm based here in the Bay, as we've talked about. And I have a studio in downtown Oakland, and my studio is kind of like Barbie's Creative Dreamhouse,

Starting point is 00:57:41 where the top floor is my office. That's where I am right now. And then the bottom floor on one side is a workshop, so I do a lot of printmaking. I've just always, I went to college at a school that was very focused on, like, interdisciplinary work. And I feel like I bring a lot of, like, manual analog processes. into my work a lot. And I find it really important to like make physical things as a part of my

Starting point is 00:58:03 creative process. So I do a lot of printmaking. And then on the other side, downstairs is a brick and mortar store. And so I've always wanted to have a brick and mortar store because as an artist, I think having people have a physical connection to your work can be really important. I think one of the reasons why a lot like people hire me to do things for them is because one of the gifts of working with someone that is like a real nerd professional about whatever it is that they do is that they bring you along the journey and give you the language to talk about the thing through their eyes and through their experience. And so like to me like my the funnest thing for me is actually telling clients and teaching them about all the things that we are doing

Starting point is 00:58:50 along the way. So then they go out into the world as like a newly minted type nerd and can communicate all of these things to other people. And that connection is just really important. The connection to the work, the story behind it, I feel like that's what, that's one of the ways that we create lasting work is understanding that the work exists because there's a story behind it. And things, if they're just created because of like the aesthetics or they're just created, you know, quickly or whatever, it's really easy to discard them because there's not a story behind it. But if you think about all the objects in your life that have followed you throughout your life, right? Like, what's the thing that you've had since you were in fifth grade or whatever that is still magically in your possession in your house?

Starting point is 00:59:32 You have that because the story of that thing is so important to you. And I think that the work that we create, the design that we create can have that. It can be like imbued with so much story and meaning that when we think about moving on from it, we're like, oh, but this. And I think that's one of the ways to build a last. brand is to just make sure that the story of creating it feels so real and visceral and important. And so the store is like a way for people to have a physical connection to other work that I create, like the prints and things like that. And then with the kids, the kids book stuff, that's also sort of about creating like lasting stuff. Like I like creating physical things in

Starting point is 01:00:13 the world. I like repackaging like things that I've learned in therapy in a way that kids will appreciate and enjoy. You know, like I'm just always thinking about like, what's a way that I can say a thing that has been said before, but hasn't been said in this way. And if I can turn that into a physical object that people can have and appreciate, like, all the better. But yeah, I don't know. I just feel like I can't, while professionally what I do is considered very niche, I feel like all the things that I do are quite diverse because they tickle different parts of my brain, you know, and I have to use my hands in different ways and my mind in different ways. And it's how I've and able to not, to generally avoid feeling burnt out as a creative is just being able to move on

Starting point is 01:01:00 between different kinds of work and just feel excited about different things at different times. For folks that want to maybe check out the store, how do they find it? It's called Jessica and Friends. Is that right? Yes, it's called Jessica Hish and Friends. You can just Google Yeah. So I put J.H.N.F. on as a part of the Google Maps name, so I don't just spell my name to strangers, because I have like a weird German spelling last name. And I also have a second store called Drawling, which is like drawing with an L thrown in there. And that one is like an all ages art supply store. That's sort of a kids art supply store. So that one is kind of grew out of J.H. and F as well. So those two stores exist. And then with my books, if you just look at my last name on any of your. favorite booksellers, you'll find me. Last question, I'm just going to throw this out there in case something interesting comes up. We have a segment on this podcast called AI Corner, where I like to see how people have found ways to use AI in their work and their life to be more productive, do cool things.

Starting point is 01:02:03 Is there some way that you've found a way to use AI in the work that you do that makes you be more interesting stuff? A little bit. I am sort of in this really interesting position in terms of AI where, my partner works at Meta on Gen A.I. stuff. So he's like a director on the Gen A.I. team at meta and is very bought into AI as a whole thing. And I am a little like about its impact on a lot of the things that we do. I think overall it will become a tool and be very useful, especially in a lot of different fields. But I think this sort of time frame in which it's more novelty is going to have

Starting point is 01:02:41 kind of a not the best impact on things like illustration, but eventually we'll all come out of it and it will be fine. In terms of how I've been able to integrate it into my process, I did some work for Salesforce last year where the theme for Dreamforce was going to be very AI driven. And I felt like I needed to explore AI as a part of the generative process for creating that art. So I did have fun creating custom lettering and then trying to run it through stable diffusion to get stable diffusion to generate instances of my lettering in different styles. We were making these like clouds. We ultimately didn't end up using it, but it was still really neat to see. And I could see the validity of that in the creative iterative process. I think the biggest thing for me is that

Starting point is 01:03:32 I find that the sort of sloggy, slow dregs of work is very fulfilling. to me that like a lot of the evangelists of AI are like, oh, imagine if you could spend all of your time high level thinking and coming up with the concepts and guiding the vision and whatever and then just get AI to do everything else that you don't care about. And for me, that just sounds like not the most holistic approach to how I work. Like, because I can't, the reason why I do all the things that I do and why my process is the way that it is is because while I I love thinking and I love coming up with conceptual stuff. I find it to be very like cerebrally taxing.

Starting point is 01:04:16 And then I need a break from that by doing the more like low key production end of stuff. And that's kind of my favorite part of the process is like we know what we're doing. And now it's just about like going in and like, you know, when it comes to judging logos, for instance, like the days that I spend knowing exactly what I'm going to do, and all it is is me just moving little Bezier handles around and getting it feeling right and whatever, those are like pure therapeutic Zen for me. And so I think like I will always have that as a part of my work and will probably not have AI be outputting that part. But I have been able to have it be helpful in the iterative process a little bit, both through generating sketches with that project.

Starting point is 01:05:05 and then also through like a lot of stuff with, you know, writing with my kids' books and things like that is like coming up with lists of words and concepts that are adjacent to each other or whatever. And I have found that sort of like Claude and ChatGBTGBT are very good for things like that. Like I'm working on another kid's book now and I'm trying to think of the directions that it can take. And one of them is sort of like illustrating different feelings and things like that. And like I could sit there and like brainstorm what are the different emotions. or whatever, or I can just ask Claude, like, list 50 emotions, and then I can cherry pick the ones that come up that feel right.

Starting point is 01:05:43 You know, so I do find it's really good for that early brainstorming stuff, and that's been really nice. Is there anything else that you want to share or leave listeners with before we get to our very exciting lightning round? Yes, well, I do have a new kids book coming out in October. And so, aside from all the logo stuff, like, please do check. out my kids' books. It's called my first book of fancy letters. And it is like a new spin on an alphabet book. But instead of it being like an alphabet book for brand new babies, which you could

Starting point is 01:06:16 totally buy it for brand new babies because it is very simple and fun and they'll like the bright pictures, it's kind of for the age where kids can recognize letters but can't necessarily read and write yet because they get so into seeing letters drawn in these different styles and like imagining what other letters could be drawn in. So each of the letters is drawn to represent the word that it sounds like. So letters can be athletic, bubbly, or creepy. And then it's like, well, what does a creepy see look like? And then when kids are starting to understand letter sounds and recognizing letters,

Starting point is 01:06:53 they can start thinking about like what other words start with that letter sound. And then they start listing stuff out and become immediate like over the shoulder art directors. And so it's been really fun, like showing it to other preschoolers and, like, TK and kindergarten kids because they're immediately like, well, our should be a river. It should be a river. And I'm like, well, how do you draw a river? And then so it becomes this fun imagination exercise, too. So definitely check that out. It's up for pre-order now and comes out October 22nd. That is so delightful. I know you have multiple kids. Do you start to see the idea with one age of kid and then by the time the next kid reaches that age, it's like ready and published. Does that work timing once? Yeah, the only thing is both of my old, well, my oldest child is a real super reader. She's always like ahead of the game. So the second that she could read, she was like, oh, picture books are for babies. And so now she's reading like, she goes into Pegasus books and it's just like,

Starting point is 01:07:47 where are your books for teenagers? And they're like, you're nine. We're not going to show you that, but here are the middle grade books or whatever. And so there is a little bit of that. There's also, I mean, you are a parent, but you are a parent of a very young person. Kids don't want to buy anything you're selling as a parent. There's a little bit of that where I feel like I get so many wonderful letters from

Starting point is 01:08:12 other families about how it's like their favorite book and they read it every night and it's so important. And then my kids are like, yeah, yeah, it's just mom's book, whatever. You know, like, so. That's bittersweet. Well, with that, Jessica, we've reached our very exciting lightning round. Are you ready? I'm ready.

Starting point is 01:08:30 Speaking of books, first question, what are two or three books that you've recommended most to other people? Rick Rubin's creativity book is so good. Definitely recommend that. I feel like it was a real, I haven't listened to it on audiobook. I read the physical book, but I also heard the audiobook is very zen. And I feel like it's just a very good palette cleanser in terms of being an artist and creating because it feels both high level but also very actionable. So really recommend that in terms of, of learning about and understanding typography, there's this book called Inside Paragraphs by Cyrus Highsmith. It's very small and very digestible. You can like read it in one bathroom visit, you know, and it's illustrated really well. It has cool illustration. So if you want to learn about some basics of type and typography, it's a really great book and incredibly accessible and not like reading like Bringhurst or something like that. So big ups to that. But book. And then, oh, what's another book? I don't know. I feel like I'm just going to end up

Starting point is 01:09:34 recommending all the books that I'm currently reading. This month, I read both Patty Smith's Just Kids, which I loved also and was also, I feel like I'm reading a lot of books about sort of being an artist more so than being a designer. And that book I found really interesting, just sort of like hearing her story of moving to New York and having nothing and just sort of like trying to be an artist and make art and having that be the thing that drove everything that she and Robert Maplethorpe did. And I don't know. I just feel like I'm looking for ways to kind of get out of my very business driven sensibilities around art making and get into a space that's more loose and free and driven by passions and feelings more so than necessarily like career-based milestones

Starting point is 01:10:26 and things like that. And then this is. is a wild card one too. I just finished the emperor of all maladies. And I'm just like a big fan of reading things about human biology and things like that and found it totally fascinating. So do read that one too. I can't help but ask. How do you have time to read, raise children work on so many projects,

Starting point is 01:10:46 have a run a store? What is your secret? Well, you get pretty ruthless about your schedule when you're a parent where like when you're at the office, like you are just heads in like working. and so I think like just trying to stay as focused as possible in that way I do this thing where I bounce back and forth between projects a lot as I'm losing steam and so having multiple things to work on actually keeps me motivated to keep working I think it's kind of an ADHD thing where I will start my day one way and then as soon as I start losing steam I switch to a different

Starting point is 01:11:23 thing, lose steam, switch to a different thing, lose steam, switch to a different thing. So rather than taking like breaks, I just take a break by working on something that feels fresh. That can be super helpful. That's an awesome tip. Yeah, I mean, it's like, it's incredible. I also would tell people when I had first started out, I had a full-time job and then was doing freelance in the evenings and people were like, how do you not get burnt out, whatever? And it's because my day job was so different from my night job that it felt like I was doing two separate eight-hour shifts instead of one continual 16-hour shift. And so I think that's something to sort of think about is that there's always going to be

Starting point is 01:11:59 things that need to get done as a part of your work or things that you're interested in and passionate about. And just having enough diversity and what that means is going to allow you to, like, maintain enthusiasm for doing all those different things for much longer. And actually, like, the more homogenous your life and career and job is, the faster you're to burn out. So just making sure that you have enough variety and all the things that you do. That was an awesome tip. I'm glad I went there. Okay, back on track to our lightning round. Is there a recent favorite movie or TV show? You've really enjoyed?

Starting point is 01:12:34 Severance was like my favorite TV show. I think I've ever watched. There's a second season's coming out. I know. So that came to mind because I knew the second season was coming out. So I'm just really excited about it. But yeah, I think that's, that was probably tops for me. Is their favorite product you've recently discovered that you really love? Oh, yeah. Well, there's a few things. Well, there was one that's just like a super random one that was just pure delight. So there's a Japanese brand Penco and they make a lot of wonderful stuff. I carry a lot of their stuff in my store. And one of the things I bought recently from them is this like a pen a pen cup, like a pencil cup and it's ceramic, but it looks like a paper bag, like kind of a lightly crumpled paper bag. And then it just has like printed on it like Penco, whatever. And I just really like it when objects, like when you take an existing object and give it a new. form and I find that to be like very delightful. And so that was I think one of the things that I really left recently that I bought for the store. Awesome pick. Two more questions. Do you have a favorite life motto that you often think about, come back to share with folks, find useful in

Starting point is 01:13:37 work you're in life? You know, it's funny being a lettering artist because I'm not much of a quote scale, like all things considered, I should be because I could like make a million dollars by just making live-left love pillows or whatever. But I'm not like usually continually collecting quotes, but I was just at a conference up in Portland called XOXO, and one of the presenters showed a quote on the screen that resonated with me like more than most things that I've seen in recent memory. And I feel like this is my new, it was one of those quotes that,

Starting point is 01:14:08 like I was like, maybe I should get a tattoo of that. You know, like, when it gets to that level where you're like considering a tattoo, you're like, okay, that's official. And it was that it was hope is a. discipline. And I just really loved that. And it's by Mariamme Caba or Mariam Kabah. The idea that we have to choose to create positivity, that it's like a choice and that like in order to dream of these things, like you can actually create structure and discipline around it. And that it's not just something that is just inherent and comes. Like you

Starting point is 01:14:44 have to actually have like a practice around being hopeful and positive. Like I just really liked that as a concept because I kind of feel that I feel that way just about like navigating through life that, you know, everything that we do is a choice and that we can choose to frame things one way or frame things another way. And like understanding that you have power in that, I think is really important. And so I just like really loved that. Like hope is a discipline. I really love. I really love that. I love any quote that inspires you to not feel like a victim and gives you agency and reminds you the agency of her. Exactly. And that's, I think, was the biggest thing for me is just because I feel like I feel very well resourced in being able to deal with hardship because

Starting point is 01:15:34 I'm always able to sort of like recontextualize and reframe. And I think part of that is doing so much like intuition justification, which is what we talked about, is like sort of walking through things, being like, why is this? Why does that happen? La, la, la. And so when something bad happens, it's like understanding why it happened and then understanding the paths that it can take forward and the different attitudes that you can bring to it that can help you come out of it. That's beautiful. Okay. Final question. I know that you recently remodeled your home. It's quite stunning. You share photos of it online. You worked with as a amazing architect to help make it as amazing as it is. As a designer, here's the question,

Starting point is 01:16:16 how do you find the balance between trusting someone that is their own perspective and design approach versus pushing into a direction you think that it should go? How do you find the balance as a designer? Well, I actually feel like it's quite easy for me to trust people to do their own thing because as long as I go to them as being like, I appreciate you and your vision, and that's why I'm paying you, then the last thing that I want to do is micromanage them. Because the reason why I'm paying them is because I don't have the bandwidth to do that myself. Because honestly, I'm one of those people that, like, if I had nothing going on, like,

Starting point is 01:16:55 if my job totally blew up or whatever, I would probably be one of those people that just specialized in a different thing, like, every six months and would be like, I'm going to build a house now from the ground up. I'm going to do this from now, whatever. And I just feel very capable of doing anything that I want to do because I understand that I can like find the resources for it. So when I hire people to help me do a thing, it's because there is this implicit trust in what they do and that that's why I want to work with them. So with the house, like I definitely had opinions about stuff. But in general, I'm just like, hey, this is your thing. You're the ex. expert, like, what do you think? Like, let me give you the parameters and the things that we have to think about. And then, because you know more about wood resources and you know more about, like, the cabinet spacing and like, whatever, you tell me what you think is going to work best based on all these things that I, like, laid out for you. You know, so I found it to be quite easy. I only got really, like, wigged out about very, like, a couple of different fine tunies stuff. I imagine architects and designers are like, oh, no, it's going to be. This is a lot.

Starting point is 01:18:03 I'm working with. They're going to have a lot of opinions. I'm glad it wasn't that bad. I feel like my strength with the work that I do in general is just being incredibly decisive and understanding that there's 10 good answers to everyone question. Some people are real maximalists about decision making and need to look at like every gray sofa that exists before they can choose the one gray sofa. Whereas I feel like I can look at 10 gray sofas and go, it feels like there's two or three categories of sofa here. And then within those categories, there's a couple of good options. Here's a brand that I recognize is known for being of high quality. That one's good enough. And I can get to it really quickly. And I feel like not everybody

Starting point is 01:18:45 can do that. And I think that that permeates through like everything that I do in my life. It definitely is a huge part of the logo work because you really can do anything when it comes to typography. Like it can go in 50 million directions. And it's just about having someone and tell you, like, yes, we could take this anywhere, but these are the valid paths. If we go down this path, this is the most intuitive and most correct way to do it. That is closest and most accessible to us. And we can noodle on it until kingdom come, but do we have to? Like, you know, like, this is good, you know? So I don't know. I feel like it's like understanding. I feel like there's some weird knowledge around understanding that nothing is ever 100%.

Starting point is 01:19:31 perfect and the most you can expire and like you know get to is like 99.8 or whatever and that last like 0.2% you could spend your whole life trying to do that or you could move on and do other things and understand that it's like nearly perfect. That is really good advice and a freeing piece of advice. Jessica, it's been an honor to work with you on this logo. I am really excited for people to see it for it to be the new look of everything I'm doing. Two final questions. We can folks find you online if they want to learn more and potentially work with you and how can listeners be useful to you? Oh yeah, of course. So I have a website that I occasionally update. It is jessica hish.is slash awesome. I have, you'll notice I have a bunch of weird URLs on my website.

Starting point is 01:20:21 So that's a place to find me. Otherwise, I am on Instagram and threads a lot. And so I was formerly a very active Twitter person and now I'm not really there so much and I kind of bop around with the other the Twitter clones but I'm on threads quite a bit. So Instagram and threads are good for social and then email I'm easy hello at jesska hish.com and then what your readers could do for me. I think it's you know the the work that I do in terms of the logo refresh stuff. I feel like this audience is just totally my perfect audience for it because you guys are all a bunch of smart, awesome founders that want beautiful logos, but understand that like sometimes you just got to get that first, you know, viable option out the door. And then once you're

Starting point is 01:21:09 ready, you come to me and I help you. And it's great. A match made in heaven. Jessica, thank you so much for being here. Happy to be here. Great convo. So good. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lenniespodcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - How to see like a designer: The hidden power of typography and logos | Jessica Hische (Lettering Artist, Author)

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