Jessica Hische: Why a logo is a feeling before it is a shape

1. 0:00 – 1:32

   Jessica’s background

   1. JHJessica Hische0:00

      (instrumental music) 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 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 exercise is just sort of, like, looking at fonts that are available in the world and asking yourself, "What feeling does this give me?"

   2. LRLenny Rachitsky0:45

      (instrumental music) Today my guest is Jessica Hische. 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 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 typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, the United States Postal Service, Apple, Nike, Tiffany & Co., The Gap, and Penguin Books. And her work has been featured in design and illustration annals both in the US and internationally. She's helped create logos for Philz Coffee, Eventbrite, 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 it.

2. 1:32 – 9:45

   The logo refresh process

   1. LRLenny Rachitsky1:32

      In our conversation, Jessica shares the process that she went through to update my logo and brand for my newsletter and 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 Hische 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. With that, I bring you Jessica Hische.

   2. JHJessica Hische2:12

      (instrumental music)

   3. LRLenny Rachitsky2:16

      Jessica, thank you so much for being here, and welcome to the podcast.

   4. JHJessica Hische2:19

      Happy to be here.

   5. LRLenny Rachitsky2:21

      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 on this podcast-

   6. JHJessica Hische2:30

      (laughs)

   7. LRLenny Rachitsky2:30

      ... and you also have very unique skill set.

   8. JHJessica Hische2:32

      Yes. Well, I will describe, uh, what I am most prominently known for, 'cause I'm a person who just does a lot of things. But the thing that I do the most professionally is custom typography, uh, like bespoke lettering pieces. And so that translates to working for all kinds of things. Sometimes it's for film and television. Um, I've done, uh, I've done, like, movie titles and things like that and, and television credits and stuff. Sometimes it's book covers. Actually, a lot of times it's book covers. 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.

   9. LRLenny Rachitsky3:17

      (instrumental music) 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, Checkr, Dropbox, and Canva. Topics include advanced identity management, compliance, encryption, and logging, essential yet complex features that most enterprise customers require. 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 enterpriseready.com. That's enterpriseready.com. I'm excited to chat with Christina Gilbert, the founder of OneSchema, one of our longtime podcast sponsors. Hi, Christina.

   10. C(Christina (OneSchema)4:21

       Yes. Thank you for having me on, Lenny.

   11. LRLenny Rachitsky4:23

       What is the latest with OneSchema? I know you now work with some of my favorite companies like Ramp, Vanta, Skail, and Watershed. I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs.

   12. C(Christina (OneSchema)4:39

       Yes. So we just launched OneSchema 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. We allow our customers to offer thousands of integrations without involving their engineering team at all.

   13. LRLenny Rachitsky5:01

       I can tell you that if my team had to build integrations like this, how nice would it be to be able to take this off my roadmap and instead use something like OneSchema, and not just to build it but also to maintain it forever?

   14. C(Christina (OneSchema)5:12

       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. We have a built-in validation layer that stops any bad data from entering your system, and OneSchema will notify your team immediately of any data that looks incorrect.

   15. LRLenny Rachitsky5:32

       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 oneschema.co. That's oneschema.co. 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. And it's actually gonna be launching right around the time of this episode going live. So this is in part a 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 give an inside glimpse into the process of updating a logo and a brand.... partly 'cause I think it'll just be purely like, "What the hell? W- how did this change? Where did this come from? Why is, 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?

   16. JHJessica Hische6:32

       Sure. Yeah, of course. So one of the thing... 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. (laughs) 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, 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 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," (laughs) like, "take a significant investment in brand, 'cause 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 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 we- wh- whatever's gonna 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 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 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, uh, w- in this context," or, "We never had a good avatar version of it," or whatever. And so sometimes it's really specific utilitarian fixes, and sometimes it's just about sort of growing it up and sophisticating it without losing, like, what was there in the first place that people

3. 9:45 – 11:45

   When to refresh your logo

   1. JHJessica Hische9:45

      got excited about.

   2. LRLenny Rachitsky9:46

      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, you know, your wife made one, your husband made you a logo. It's like, "Well, this is great. 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 hire a studio, but take something to make it better"?

   3. JHJessica Hische10:10

      Well, one of the things is if suddenly you're starting to deal with the, the greater 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 ge- m- expands it, 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 gonna 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 custom, a custom logo or custom typography can really matter is that if you're using something that's available to everyone, the chances of someone else coming in and copying you are very easy and high. Like, you might be one of these lucky companies that just out the gate is, like, outrageously successful, but with success (laughs) comes people climbing up behind you, trying to copy your success. And if that success is very easily copyable, like, the... 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, um, one way to avoid that is by doing something that's more customized when it comes

4. 11:45 – 18:04

   High-level overview

   1. JHJessica Hische11:45

      to the logo and brand.

   2. LRLenny Rachitsky11:47

      So let's actually talk about, uh, the work that you put into updating my logo and brand, 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?

   3. JHJessica Hische12:01

      Sure. Of course. So super high level, it's figuring out what the goals are. Um, 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 really notices." So if that's like one, 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, and, uh, 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 m- 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, how experimental, how broad are we gonna 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 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 (laughs) until we do the final 'cause 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, uh, we have like generally a look that we want, but is it the right weight? Is it the right, 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.

   4. LRLenny Rachitsky14:45

      Awesome. And then, uh, 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, 'cause we narrowed, narrowed, narrowed, and then I was like, "No, this isn't... I'm not feeling it." And then we un-narrowed it and went back.

   5. JHJessica Hische15:00

      (laughs)

   6. LRLenny Rachitsky15:01

      So I apologize.

   7. JHJessica Hische15:01

      That is not an uncommon experience though.

   8. LRLenny Rachitsky15:03

      Okay. (laughs)

   9. JHJessica Hische15:03

      This is why, you know, like there's a few things that I'm not opposed to that e- that I know people that are very opposed to. 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 an... but I'm like a, 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? 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, 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 'cause 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?

   10. LRLenny Rachitsky16:02

       Mm-hmm.

   11. JHJessica Hische16:02

       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?

   12. LRLenny Rachitsky16:10

       Mm-hmm. That's exactly how it felt for me. Going back to the goals, the, 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, it doesn't print well, that kind of thing. Another goal is people are pivoting and they wanna change the vibe and, um, the feel of the brand. What other goals might appear that you've come across of like why people want to do this?

   13. JHJessica Hische16:31

       Well, sometimes there's like a, a legibility issue that is like really glaring once you see it, and then people are like too close in to notice it. 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. Um, the one that came to mind immediately when you asked was when I did a refresh for Jeni's Ice Cream, which is a really, like, amazing ice cream brand based out of Columbus, Ohio. And 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 Jeni's over the I 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 (laughs) to do is like-

   14. LRLenny Rachitsky17:24

       Mm-hmm.

   15. JHJessica Hische17:24

       ... 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. Um, 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

5. 18:04 – 24:25

   Approaching Lenny’s brand refresh

   1. JHJessica Hische18:04

      tight.

   2. LRLenny Rachitsky18:04

      Let's talk about the, uh, actually thinking through my new logo and 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.

   3. JHJessica Hische18:18

      I think with the Lenny's brand, um, 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, um, 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, and I was like, "How do we do something that feels handwritten, that feels like it could jive with the, the handwriting scripts and stuff that you were using, but might feel like a little bit more refined, uh, moving forward, and in a way that could blend with illustrations 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, it, you can tell, you can recognize it by its color. 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. Um, 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, uh, 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 'cause I felt like it could kind of capture the look of the original, uh, cut paper-esque type. But yeah. It was really fun to try a lot of different things and work within the iconography that you had used on a, 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.

   4. LRLenny Rachitsky20:47

      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, uh, concept, but it didn't quite work the way you thought?

   5. JHJessica Hische20:57

      With working on this refresh, like, so much of it was thinking about 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, 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. You know? 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. 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 t- 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.

   6. LRLenny Rachitsky22:46

      Yeah. One of the impetuses for changing my logo, for motivating me, is, uh, my wife's a designer, as you know, and she's got strong opinions about my logo. And, and she always 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's always 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.

   7. JHJessica Hische23:08

      Yeah, and also, too, I think that really talks to what I was saying earlier about getting, making sure that everything feels like it was created together rather than it feeling like these disparate elements. 'Cause 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. I just (laughs) like, 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, a, something that feels real.

   8. LRLenny Rachitsky24:24

      I

6. 24:25 – 37:53

   How to see like a designer

   1. LRLenny Rachitsky24:25

      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 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, what are those elements that make it what it is, that make you feel the thing you want to feel that we may not recognize?

   2. JHJessica Hische25:06

      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. 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." You know? And I think, like, even as a non-designer, you can see that in typography. You know? Because we... I, like the whole being able to recognize patterns thing, and I talked about this a bit at Config. It's like, um, it's a safety thing, you know? Like, looking into the world, your, your eyes can spot that thing that's a little bit off, and that thing that's off feels not safe to you, because... And that, it's like thinking about when we look at a meal, and the, there's a thing on the plate that looks like it's moldy or something like that. You, 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, 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 exercise is just sort of like looking at fonts that are available in the world and asking yourself, "What feeling does this give me?" You know? And just write them down. You know, you just... And it doesn't matter. Just give yourself permission to say whatever is happening in your mind, like the first thing. It doe- like, don't overanalyze it. Just look at it and be like, "That feels calm to me. That feels exciting to me. That feels whatever to me." And then the more you do that, you, the more you can start seeing similarities in the ones that feel exciting and the ones that feel calm and 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 gonna have the language of, like, the leg of the R and the tittle of the I. Like, whatever, don't worry about that. Like, (laughs) you don't have to know, like, typography language to, like, think about it. Um, but ev- 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?

   3. LRLenny Rachitsky27:58

      This is great. I, I want to go actually a little deeper. So, 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, 'cause there's, 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. Uh, 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, a logo?

   4. JHJessica Hische28:26

      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 weight, the 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 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 verse 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. 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, 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 specific feeling to you, but it can inform your decisions about design 'cause you can be like, "Oh, I'm not a, that much of a special snowflake." Other people might have that same reaction but have different experiences that are adjacent to that reaction, you know? It's, so it's, it's cool 'cause you are sort of reverse justifying decisions, and I, I think that's, like, a really fun exercise to do, is, like, to sort of...... song exploder your intuition, you know? So you make a decision intuitively or, or look at something and, like, intuit 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 real-... And that's, like, really great inspiration, uh-

   5. LRLenny Rachitsky30:48

      Mm-hmm.

   6. JHJessica Hische30:48

      ... juice for, like, picking other things, you know?

   7. LRLenny Rachitsky30:51

      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 and just go through them?

   8. JHJessica Hische30:58

      Totally. Look at 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 basic category of fonts, serif, sans-serif, script, like whatever, like the, 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 full of screenshots, and then you can kind of take those screenshots and start categorizing them, "Oh, 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 'cause it reminds me of wedding invitations, and wedding invitations feel inherently bridey versus groomy." You know? (laughs) Like... And then all of a sudden you're like, "Okay, well, now I know that if I'm going to do, use a script for something, this zone of script feels very wedding, so maybe I avoid that for this brand that's actually, like, a cutting-edge food packaging company or whatever."

   9. LRLenny Rachitsky32:04

      Mm-hmm.

   10. JHJessica Hische32:04

       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 sor-... 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 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 'cause 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 s- 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."

   11. LRLenny Rachitsky33:08

       Yeah. Uh, I'm thinking green. The color green has to be a part of the logo if you want to be a fintech company.

   12. JHJessica Hische33:13

       Yes. Yeah, exactly. And if you're trying to be weird, then you're like teal, you know? (laughs) So...

   13. LRLenny Rachitsky33:19

       On this topic of seeing like a designer, is there any, 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?

   14. JHJessica Hische33:30

       Yeah. Another thing to notice, um, 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. And so I can always tell when there's an engineer that has suddenly got, taken an interest in type design and is now a type designer, because everything is very, very regular, right? So ev-... 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 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-serif, for instance, that's like a category of sans-serifs, and they're meant to have a lot of really strong geometry, be very regular, you know, like m- most of the san-serifs that you think of that you're like, "I'm in love with this over the last 10 years," like geometric sanses. 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, is just, like, oh, type out a couple of lowercase letters. Um, lowercase specifically are, are really good for analyzing this 'cause 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 a two-story A is, like, the one that's like this and then a bowl, right? You might notice that the, 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've been perceived optically, you know, had you, like, uh, had you kept everything perfectly regular. And so it's weird because you end up, like, creating something that's perfect and then 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 Rs and lowercase Ns. 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. 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 w- and, and the answer of like why it happens is 'cause you're like correcting for, uh, 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 could never see before." (laughs) 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.

   15. LRLenny Rachitsky37:21

       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-

   16. JHJessica Hische37:27

       Like a single letter.

   17. LRLenny Rachitsky37:28

       ... zoomed in.

   18. JHJessica Hische37:28

       Like make-

   19. LRLenny Rachitsky37:28

       A single letter.

   20. JHJessica Hische37:29

       ... a single letter. Like the whole page. And then just draw some vertical lines-

   21. LRLenny Rachitsky37:33

       Mm-hmm.

   22. JHJessica Hische37:34

       ... um, 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 join 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.

7. 37:53 – 44:07

   Lenny’s new logo: where we landed

   1. JHJessica Hische37:53

   2. LRLenny Rachitsky37:53

      I want to come back to my logo, and just to close the 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 peop- what you think people might get from it. Whatever comes to mind.

   3. JHJessica Hische38:07

      Yeah, totally. I think like the final answer, uh, or the final logo, we, we took it down a lot of different paths trying to see where it was gonna land, but ultimately ended up keeping it like pretty close to home and really focusing on that asset of the, 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, uh, 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, I just feel like, um, 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 in a place where it's like much more, you know, in line and, and consistent across the board.

   4. LRLenny Rachitsky38:55

      Yeah. Maybe what I'll do is we'll share... I don't know if you're comfortable with that. We could just share all the iterations somewhere that we-

   5. JHJessica Hische39:00

      Oh, yeah.

   6. LRLenny Rachitsky39:01

      ... went through.

   7. JHJessica Hische39:01

      I love sharing iterations.

   8. LRLenny Rachitsky39:02

      Okay, cool.

   9. JHJessica Hische39:02

      It's a lot of fun. Yeah.

   10. LRLenny Rachitsky39:03

       Sweet. Like the biggest issue we had with the podcast logo specifically is originally, uh, I was thinking the mic made sense to differentiate it from the newsletter, and then at the end of it it's just like, "Let's... Why do we have this friggin' mic in there? It just feels strange." So that's where we kind of revisited the whole idea and killed the mic, and went back to a different version of the mar- of the fireplace but with marshmallows. (laughs)

   11. JHJessica Hische39:24

       Yeah.

   12. LRLenny Rachitsky39:24

       It sounds so-

   13. JHJessica Hische39:24

       I love the marshmallows, so... (laughs)

   14. LRLenny Rachitsky39:26

       Awesome. I love it. That was my wife's, uh... My wife loves the marshmallows also. And it's so versatile. We can use it in so many different ways.

   15. JHJessica Hische39:33

       Indeed.

   16. LRLenny Rachitsky39:34

       And then I guess maybe one last, uh, thread there is we explored handwritten kind of typography 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.

   17. JHJessica Hische39:51

       The handwritten one I really liked 'cause 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 wanna blow that out, if you want to include other handwriting throughout the rest of the brand, finding something that matches that perfectly without creating a custom typeface is a whole thing. And so I really liked being able to kind of combine the two where we have this like broader visual vocabulary that we can pull from, because you're gonna have headlines, you're gonna have subheads, you're gonna have all these other uses for typography moving forward. And if you just have one thing to pull from, um, 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?

   18. LRLenny Rachitsky40:32

       Mm-hmm.

   19. JHJessica Hische40:32

       Like if you have only one pair... one shirt and one pair of pants, 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.

   20. LRLenny Rachitsky40:44

       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, outline-y one, and it's not like, "This is it. Don't change anything about this. This is the only way to use it."

   21. JHJessica Hische40:57

       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, uh, 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, uh, you're not a massive company and you have creative 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, uh, there might be even just parts of the logo that make it difficult to work with. Like 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. Like that's my number one goal, because I know not everybody is gonna be at a stage where they have like a brand, 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 of 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."

   22. LRLenny Rachitsky42:59

       (instrumental music) 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, but for everything B2B SaaS. Organizations like Ramp, Dorada, 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 de-provision access for their customer's 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/lenny and receive a $50 Amazon gift card. That's merge.dev/lenny.

8. 44:07 – 50:04

   Brand’s role in company success

   1. LRLenny Rachitsky44:07

      This is a good circle back to something you touched on earlier that I wanted to 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 a, an issue for people, where they almost over-emphasize the power of brand?

   2. JHJessica Hische44:31

      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. 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 recommunicate 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, they're the ones digesting all of this, like, 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? Uh, 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 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 everybo- 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 place in that, in that equation.

   3. LRLenny Rachitsky46:42

      I think some of this, uh, unique, uh, perspective on the power of brand and the need for it in tech companies comes from, you're not like a tech person and you work with tech people, you work with 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?

   4. JHJessica Hische47:01

      I mean, most of the folks that I know that work in brand, um, 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, like, very fun position being, like, everyone's token creative person (laughs) in, like, the, in the Bay for a while. And, a- and this has been for a long time, right? So I, 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, uh, 'cause we were, like, 28, 29, like, coming over to work at Facebook, and everybody there was, like, 23, 24. 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 got, 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, uh, 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.

   5. LRLenny Rachitsky48:50

      Mm-hmm.

   6. JHJessica Hische48:50

      You know? Like, I understand that you have limited resources, and those resources aren't necessarily going to get devoted 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 opini- (laughs) 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 who is a real expert in whatever it is that they do just as you need them, you know, and they just get kind of, like, consultant, uh, equity kind of thing. Like, that, 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.

9. 50:04 – 57:14

   Jessica’s flexible pricing strategies and collaborative design process

   1. JHJessica Hische50:04

   2. LRLenny Rachitsky50:05

      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 so they're like, "Oh, okay. We could, we should actually do this."

   3. JHJessica Hische50:19

      So again, like, 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 the 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 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 of approaching everything. And so sometimes people will bring me on really early in the process where, um, 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 gonna try to do this as much as we can inside of our business, but then can we hire you at the end to, like, 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 what 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. And it sucks as a designer who started a company and thinks that you might be able to get a chance to, like, 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...

   4. LRLenny Rachitsky52:51

      Mm-hmm.

   5. JHJessica Hische52:51

      ... because someone inside is gonna be like, "It's time to shine," and then they're just gonna 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, 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, $60,000 or $70,000 at a minimum to do all this kind of stuff." 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 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 (laughs) into the brand, you know? That's a very different experience.

   6. LRLenny Rachitsky53:51

      Awesome. Thank you for sharing that. Before we get into s- other stuff that you do 'cause like you said at the top, there are many other things you do outside of this specific kind 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?

   7. JHJessica Hische54:11

      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, uh, 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. Like, "What is the thing about this that bothers me?" And don't, don't get specific. Don't be like, "The way the R is," or whatever. Like, maybe that's a thing that we talk about down the line. But always think big picture before you think minutiae 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. 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, it really could (laughs) be like, "This C has always bothered me." You know, like, and then you're, then, 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 but might not bother anybody else.

   8. LRLenny Rachitsky55:35

      Yeah. When I was thinking about this, I was like, the, it feels like it could... Like, my whole feeling was this could be better. That's kind of all it was for me initially, is 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-

   9. JHJessica Hische55:49

      Yeah, that, that's definitely-

   10. LRLenny Rachitsky55:51

       ... have been wrong.

   11. JHJessica Hische55:51

       ... enough for some people, 'cause 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.

   12. LRLenny Rachitsky56:07

       Mm-hmm.

   13. JHJessica Hische56:07

       And, 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, um, sort of vision and vibe that you get from everything. Like, I always, uh, tell people that, like, having terrible vision can be, like, your, your best asset when it comes to, like-

   14. LRLenny Rachitsky56:27

       Mm-hmm.

   15. JHJessica Hische56:27

       ... 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, what is the overall look of this thing? And just trying to get as broad and noodley as you can with it instead of it being about those really specific one-by-one stuff. You know?

   16. LRLenny Rachitsky56:54

       Mm-hmm.

   17. JHJessica Hische56:54

       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, uh, consistent, professional-looking place.

   18. LRLenny Rachitsky57:07

       Well, I, uh, I can't look at the old logo anymore now that I've gotten this thing coming together. So I'm really excited-

   19. JHJessica Hische57:13

       (laughs)

   20. LRLenny Rachitsky57:13

       ... for this to come out.

10. 57:14 – 1:01:48

    Balancing multiple creative projects

    1. LRLenny Rachitsky57:14

    2. JHJessica Hische57:15

       Love it.

    3. LRLenny Rachitsky57:15

       Just a couple closing questions. One is, uh, you have a lot of other stuff going on that is not just typography and logo refreshes. 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.

    4. JHJessica Hische57:32

       Sure. Yeah. Of course. So I'm based here in the Bay, as we've talked about, and I, I have a studio in Downtown Oakland, and my studio is kind of like Barbie's Creative Dreamhouse 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 w- 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 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, um, 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 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 is a story behind it. Um, 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, uh, 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 a thing that you've had since you were in fifth grade or whatever that is still magically in your possession in your house? 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 lasting 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 kid, the kids book stuff, that's also sort of about creating, like, lasting stuff. Like, I like creating physical things in 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, um... While professionally what I do is considered very niche, I feel like all the things that I do are quite diverse, um, and 'cause 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 been able to not...... uh, to generally avoid feeling burnt out as a creative is just being able to move on between different kinds of work and just feel excited about different things at different times.

    5. LRLenny Rachitsky1:01:05

       For folks that want to maybe check out the store, how do they find it? It's called Jessica & Friends? Is that right?

    6. JHJessica Hische1:01:10

       Yes, it's called Jessica Hisch & Friends. You can-

    7. LRLenny Rachitsky1:01:12

       Jessica Hisch & Friends.

    8. JHJessica Hische1:01:13

       You can just Google JH&F.

    9. LRLenny Rachitsky1:01:15

       Google Maps, yep.

    10. JHJessica Hische1:01:16

        Yeah. So I-

    11. LRLenny Rachitsky1:01:17

        That makes sense.

    12. JHJessica Hische1:01:17

        I put, uh, JH&F on as, as a part of the Google Maps name so I don't have to spell my name to strangers 'cause I have like a weird German spelling last name. Um, and I also have a second store called Drawling, which is like drawing with an L thrown in there. And that one is a, like an all-ages art supply store, that's sort of a kids art supply store. So that one is, uh, kind of grew out of JH&F as well. So those two stores exist. And then with my books, if you just look up my last name on any of your favorite, uh, book sellers,

11. 1:01:48 – 1:05:50

    Using AI in creative work

    1. JHJessica Hische1:01:48

       you'll find me.

    2. LRLenny Rachitsky1:01:49

       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, in their life, to be more productive, do cool things. Is there some way that you've found a way to use AI in the work that you do that makes you do more interesting stuff?

    3. JHJessica Hische1:02:09

       A little bit. I, I am sort of in this really interesting position in terms of AI, where my partner works at Meta on GenAI stuff, so he's like a director on the GenAI team at Meta, and is very bought into AI as a whole thing. And I am a little like, "Ew" 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 timeframe in which it's more novelty, um, is going to have kind of a not the best impact on things like illustration, but eventually we'll all come out of it and it'll be fine. In terms of how I've been able to integrate it into my process, I did some work for, um, Salesforce last year, where the theme for, uh, Dreamforce was going to be very AI driven, and I felt like I needed to explore AI, uh, as a part of the generative process for creating that art. So I did have fun creating custom lettering, and then, um, 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.

    4. LRLenny Rachitsky1:03:21

       Mm.

    5. JHJessica Hische1:03:21

       We ultimately didn't end up using it. Um, but it was still really neat to see, and I, I could see the validity of that in the creative iterative process. I think the biggest thing for me is that I find that the sort of sloggy, slow drags 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 'cause 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 love thinking and I love coming up with conceptual stuff, I find it to be very, like, cerebrally taxing, 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, uh, 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, um, both through generating sketches with that project 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, and ChatGPT are very good for things like that. Like, I'm working on another kids 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 could just ask Claude, like, "List 50 emotions." (laughs) And then I can cherry pick the ones that come up that feel right. You know, so I do find it's really good for that early brainstorming stuff, and that's been, that's been really nice.

12. 1:05:50 – 1:08:24

    Upcoming projects and final thoughts

    1. JHJessica Hische1:05:50

    2. LRLenny Rachitsky1:05:50

       Is there anything else that you, uh, want to share or leave listeners with before we get to our very exciting lightning round?

    3. JHJessica Hische1:05:58

       Yes, well, I do have a new kids book coming out in October.

    4. LRLenny Rachitsky1:06:01

       Ooh. Do tell.

    5. JHJessica Hische1:06:01

       And so, um, aside from all the logo stuff, like, please, uh, do check out my kids books. I- It's called My First Book of Fancy Letters.

    6. LRLenny Rachitsky1:06:09

       (laughs)

    7. JHJessica Hische1:06:09

       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 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, uh, be drawn in. So each of the letters is dr- is drawn to represent the word that it sounds like. So-

    8. LRLenny Rachitsky1:06:42

       Mm.

    9. JHJessica Hische1:06:42

       Uh, letters can be athletic, bubbly, or creepy. And then it's like, "Well, what does a creepy C look like?" And then when kids are starting to understand letter sounds and recognizing letters, 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, uh, it's been really fun, like, showing it to other preschoolers and, like, TK and kindergarten kids because they're immediately like, "Well, R should be 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. Um, it's up for pre-order now and comes out October 22nd.

    10. LRLenny Rachitsky1:07:21

        That is so delightful. Uh, 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? Is that... Does that work, I mean, for once?

    11. JHJessica Hische1:07:31

        (laughs) Yeah. The only thing is, um, 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 is just like, "Where are your books for teenagers?" And they're like, "You're not all- You're nine. We're not gonna 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. Um, they... Kids don't want to buy anything you're selling, as a parent. So... (laughs) There's a little bit of that, where I feel like I get so many wonderful letters from, uh, 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... (laughs)

    12. LRLenny Rachitsky1:08:22

        Oh. That's bittersweet.

13. 1:08:24 – 1:15:59

    Lightning round

    1. LRLenny Rachitsky1:08:24

       Well, with that, Jessica, we've reached our very exciting lightning round. Are you ready?

    2. JHJessica Hische1:08:30

       I'm ready.

    3. LRLenny Rachitsky1:08:31

       Speaking of books, first question. What are two or three books that you've recommended most to other people?

    4. JHJessica Hische1:08:36

       Rick Rubin's, uh, creativity book is so good. Definitely recommend that. I feel like it was a real, uh... 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 palate cleanser, in terms of being an artist and creating, 'cause it feels, uh, both high level but also very actionable. So, um, really recommend that. Uh, in terms of learning about and understanding typography, um, 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. (laughs) You know? And so... And it's illustrated really well. It has cool illustrations. So, if you wanna 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. Um, so big ups to that book. And then... Oh, what's another book? I don't know. I feel like I'm just gonna end up recommending all the books that I'm currently reading. This month, I read both Patti 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, uh, 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, trying to be an artist and make art, and having that be the thing that drove everything that she and Robert Mapplethorpe 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, uh, career-based milestones and things like that.

    5. LRLenny Rachitsky1:10:28

       Mm-hmm.

    6. JHJessica Hische1:10:28

       And then, uh, this is a wildcard one too. I, uh, just finished, um, uh, 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.

    7. LRLenny Rachitsky1:10:41

       I can't help but ask. How do you have time to read, raise children, work on so many projects, have a... run a store? What is your secret?

    8. JHJessica Hische1:10:49

       Um, 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, uh, 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, um, I will start my day one way, and then as soon as I start losing steam, I switch to a different 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.

    9. LRLenny Rachitsky1:11:33

       That's an awesome tip.

    10. JHJessica Hische1:11:35

        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 gonna be 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 in what that means is gonna allow you to, like, maintain enthusiasm for doing all those different things for much longer. And actually, like, the more, uh, homogenous your life and career and job is, the faster you're gonna burn out. So, just making sure that you have enough variety in all the things that you do.

    11. LRLenny Rachitsky1:12:27

        That was an awesome tip. I'm glad I went there. Okay. Back on track-

    12. JHJessica Hische1:12:30

        Yeah.

    13. LRLenny Rachitsky1:12:30

        ... to our lightning round. Is there a recent favorite movie or TV show you've really enjoyed?

    14. JHJessica Hische1:12:34

        Uh, Severance was, like, my favorite TV show I think I've ever watched.

    15. LRLenny Rachitsky1:12:37

        Mm.

    16. JHJessica Hische1:12:37

        Like, that is, like-

    17. LRLenny Rachitsky1:12:37

        There's a... Second season's coming out.

    18. JHJessica Hische1:12:39

        I know. Uh, that, that... So that came to mind because I knew the second season was coming out, so I'm just, like, really excited about it.

    19. LRLenny Rachitsky1:12:44

        Mm-hmm.

    20. JHJessica Hische1:12:44

        Um, but yeah. I think that's... that was probably tops for me.

    21. LRLenny Rachitsky1:12:48

        Is there a favorite product you've recently discovered that you really love?

    22. JHJessica Hische1:12:51

        Um, oh, yeah. Well, there's a few thing- 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, um, 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, uh, 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 loved recently that I bought for the store.

    23. LRLenny Rachitsky1:13:28

        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 and work here in life?

    24. JHJessica Hische1:13:38

        You know, it's funny being a lettering artist 'cause I'm not much of a quotes gal. Like, all things considered. Consider- like, I, I should be because I could, like, make a million dollars by just making Live Laugh Love pillows or whatever.

    25. LRLenny Rachitsky1:13:50

        (laughs)

    26. JHJessica Hische1:13:50

        (laughs) But, but I, 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, um, in recent memory, and I feel like this is my new... I, I, it was one of those (laughs) quotes that, like, I was like, "Maybe I should get a tattoo of that." You know, like, when, 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, um, "Hope is a discipline," and I just really loved that, and it's by, um, Mariame Kaba or Mariam Kaba. 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 have to actually have, like, a practice around being hopeful and positive. Like, I just really liked that as a concept 'cause 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.

    27. LRLenny Rachitsky1:15:14

        I really love that. I, I love any quote that inspires you to not feel like a victim and gives you agency and reminds you that you have agency over...

    28. JHJessica Hische1:15:23

        Exactly. And, and that's I think was the biggest thing for me is just... 'Cause I, I feel like, um, I feel very well resourced in being able to deal with hardship because I'm always able to sort of, like, re-contextualize 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.

Episode duration: 1:21:47