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

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?

Today, my guest is Jessica Hich.

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 & Company, 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 Phil's 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.

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 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.

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 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.

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, Checkr, Dropbox, and Canva.

Topics included advanced identity management, compliance, encryption, and logging, essentially at 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 Work OS.

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 One schema, 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 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 schema 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.

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 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 have 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 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 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.

It's actually going to be launching right around the time of this episode going live.

This is, in part, a celebration of the new look and logo and brand.

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 because I think it'll just be people are like, what the hell?

How did this change?

Where did this come from?

Why this versus that?

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.

Broadly, how does that sound?

Sure. Yeah, of course.

Everybody that starts a company knows that they need a logo, right?

That that is 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 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 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 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 what I was 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 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 like we've 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 sophisticated it without losing like what was there in the first place that people got excited about.

**Matt Stauffer 2 .00 .16 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 you a logo, it's like, Oh, 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 higher studio, but take something to make it better.

**Bethany Stauffer 2 .00 .16 Well, one of the things is if suddenly you're starting to deal with 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, you're about to do a new one that kind of updates and 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 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 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 comes people climbing up behind you trying to copy your success.

And if that success is very easily copyable, like, 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.

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 the 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 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, they might have this really cool and successful like group of people that are like they're 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 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 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, 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, I was an ass and at the end of it, I'm like, no, this isn't right.

Because 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.

That is not an uncommon experience, though.

You know, like, there's a few things that I'm not opposed to that 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 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? 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 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.

Going back to the goals, the different goals people have when 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 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.

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.

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 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 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 the 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.

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.

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.

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.

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.

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 didn't quite work the way you thought.

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 it 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 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 a icon library.

Like I think that was like an interesting challenge.

Yeah, one of the impetuses 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 was making fun of my logo, saying it was a look like a clipart fireplace that anyone just could just plug and play.

And she's 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 start working together.

Yeah. And also too, I think that really talks to what I was saying earlier about, again, 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.

I just ate at restaurants and did take out 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 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.

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 I like the whole being able to recognize patterns thing, 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 that thing that's a little bit off.

And that thing that's off feels not safe to you.

Because and 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 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, and it doesn't matter, just give yourself permission to say whatever is happening in your mind, like the first

thing it does, like, don't over analyze 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 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 I like it would have don't worry about that, like, you don't have to know like typography language to like, think about it.

But if 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, 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 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.

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 weight, 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 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.

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 specific feeling to you.

But it can inform your decisions about design, because you can be like, Oh, I'm not at 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, 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 exploder your intuition, you know, so you make a decision intuitively, or, 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 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 folders that like a place to go, just like, oh, totally, look at your 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 top level 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, because it reminds me of wedding invitations, and wedding invitations feel inherently bridy versus groomy, you know, 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, 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 of, 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 different things that you're trying to do?

And then you get 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.

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 a 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 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 most of the sans serifs that you think of that you're like, I'm in love with this of the last 10 years, like geometric

stanzas. 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 in Figma or doing it somewhere else, is just like, type out a couple of lowercase letters, lowercase specifically are really good for analyzing this, 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 combined, 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 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 have been perceived optically,

you know, had you like, 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 r's and lowercase n's.

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, 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, I can see all these weird things I've never seen before.

It's very fun. But anyway, a lot of people when they 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.

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 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 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.

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 people, what you think people might get 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, 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 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 could just share all the iterations somewhere that we can do.

Oh, yeah, I love sharing iterations.

Okay, cool. Sweet. 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, it's just like, what's why do we have this frigging 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 fireplace with marshmallows.

Yeah, I love the marshmallows.

So 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. And then I guess maybe one last thread there is we explored handwritten kind of topography that you created 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, 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 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.

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, don't change anything about this, this is the only way to use it.

Well, part of that is because like 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 over complicate 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 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.

Like my goal always when designing a logo is to design a logo that's 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 going to 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 into it most of the way that you should be able to use it without being explicitly told do not do this.

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 be to be SaaS organizations like ramp, dorada and electric use merge to access their customers accounting data to reconcile bill payments file storage data to create searchable databases and their product or HRIS data to auto provision and deep provision access

for the 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 slash Lenny and receive a $50 Amazon gift card that's merge .dev slash Lenny.

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 an issue for people where they almost overemphasize 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.

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, 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?

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.

Like if we think about the experiences that we have using products, right?

Sometimes there's products where there's a ton of fun and delight built into how you use it.

And that can happen through brand, through like 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 ethos of your company?

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 place in that equation.

I think some of this unique 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?

I mean, most of the folks that I know that work in brand or kind of traditional graphic design, print design, they don't necessarily have a lot of insight into how building companies works.

They're not friends with a ton of startup founders and things like that.

And I've just been in this very fun position, being like everyone's token creative person in the bay for a while.

And this I remember speaking at like a Silicon Valley event that was like women in Silicon Valley in 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.

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.

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 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 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.

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 $500 ,000 of money at all for a year to try to get things going, you certainly should not spend half of that money on branding.

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 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 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.

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.

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 build 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 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 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 on what their needs are.

Because my whole thing too, is I don't want to step on 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, because someone inside is going to be like, it's time to shine.

And then they're just like, I'm going to 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 tailed 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.

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 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, 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?

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 the thing that we talk about down the line.

But always think big picture before you think minutia.

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 to 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 really could be like, this C has always bothered me, you know, like and then you're then you that 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.

Yeah, when I was thinking about this, I was like, 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.

Imagine that's enough for some people just like I think this could be better.

And then like, yeah, that that's definitely enough for some people 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 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, and I think like when you blow 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 closing questions.

One is, you have a lot of other stuff going on that is not just topography 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.

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 Dream House, 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 manual analog processes into my work a lot.

And I find it really important to 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 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'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, 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, 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 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.

While professionally, what I do is considered very niche.

I feel like all the things that I do are quite diverse.

And 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 been able to not 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.

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 JHNF.

Yeah, so I put JHNF 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 JHNF 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 book sellers, you'll find me.

Last question. I'm just gonna 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?

A little bit. I am sort of in this really interesting position in terms of AI, where my partner works at Meta on Gen AI stuff.

So he's like a director on the Gen AI 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 timeframe in which it's more novelty, is going to have not the best impact on things like illustration, but eventually will 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 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 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 I find that the sort of sloggy, slow dregs of work is very fulfilling to me.

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.

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 cerebral taxing.

And then I need a break from that by doing the more low key production end of stuff.

And that's kind of my favorite part of the process is we know what we're doing, and now it's just about going in and when it comes to Zhejiang logos, for instance, the days that I spend knowing exactly what I'm going to do, and all it is is me just moving little bezier handrails around and getting it

feeling right and whatever, those are pure therapeutic zen for me.

And so I think I will always have that as a part of my work.

And we'll 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 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 chat GBT 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 can just ask Claude, like, list 50 emotions, 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.

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 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 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, 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 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 22.

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 is that does that work?

Yeah, the only thing is on 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, Where are your books for teenagers?

And they're like, you're not all your 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.

And they 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 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.

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

Rick Rubens. 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 audio book is very Zen.

And I feel like it's just a very good palate 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 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 so and it's illustrated really well.

It has cool illustrations.

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 ringhurst or something like that.

So big ups to that book.

And then Oh, what's another book?

I don't know. I feel like I'm just going to 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 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 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 and things like that.

And then this is a wildcard 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, have a run a store?

What is your secret?

Well, you get pretty ruthless about your schedule when you're a parent where when you're at the office, you are just heads in working.

And so I think 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 switched 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.

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 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 going 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?

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

There's like 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 loved recently that I bought for the store.

Awesome. Pick two more questions.

Do your favorite life motto that you often think about come back to share with folks find useful and work your life?

You know, it's funny being a lettering artist because I'm not much of a quotes gal, like all things considered considered like I should be because I could like make a million dollars by just making live, laugh, 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 I it was one of those quotes that 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 Mariam a caba or Mariam caba, 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.

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 that.

I love any quote that inspires you to not feel like a victim and gives you agency and reminds you they have agency ever.

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 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 work with this amazing architect to help make it as amazing as it is.

As a designer, here's the question.

How do you find the balance between trusting someone that is, you know, their own perspective in 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 if like, my job totally blew up or whatever, I would probably be one of those people that just specialize 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 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 tunis.

I imagine architects and designers are like, Oh, no, it's gonna be a designer I'm working with.

They're gonna have a lot of opinions.

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 every one question.

You know, like 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 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 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, like, 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 % perfect.

And the most you can expire in like, you know, get to is like 99 .8 or whatever.

And that last like point 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 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.

Where 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 you can I have a website that I occasionally update.

It is Jessica Hisch .is slash awesome.

And I have a you'll notice I have a bunch of weird URLs on my website.

So, 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 Jessica Hisch .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 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 review as that really helps other listeners find the podcast.

You can find all past episodes or learn more about the show at Lenny's podcast .com.

See you in the next episode.

[The Art of Branding: Insights from Design Legend Jessica Hische]-[How to see like a designer: The hidden power of typography and logo design | Jessica Hische (Lettering Artist, Author)]

📋 Summary

Decoding Design: How Typography and Branding Shape Perception

The Role of the Logo in Early-Stage Startups

The Anatomy of a Successful Refresh

Learning to See Like a Designer

The Discipline of Hope

Conclusion

🎯Key Sentences

📝Key Phrases

📖 Transcript