Jessica Hische’s Little Shop of Wonders

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Maybe we should go through each of the interviews.

Yeah, yeah, yeah.

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

Jessica Hisch. I mean, her work is so distinct, so prolific, and I love that she's always been very tech adjacent. She has, for a long period of time, used emerging technologies to evangelize her own work and has found this incredible intersection of using graphic design tools to advance the state of lettering, an old practice in a new material, and to do so across a whole range of clients and projects and form factors.

Going to her studio, I was blown away at all the different mediums that she does, that her work shows up in.

Yeah, and so I love that before AI allowed for designers to be prolific and to generate a lot of work, she herself was extremely prolific. She had a high volume of work that shipped in a totally different context in software. I felt like as a moment in time, again, her starting off working on a software company felt like an important point to capture, to sort of see where she was on her journey transitioning from somebody who has been tech adjacent, working as a traditional designer in a new modern realm and a new modern material, transitioning over to trying her hand at startup entrepreneurship, but with an approach that's very different, very indie, totally different from the traditional, the classic, you know, venture scale startup. Taking more of a slow food approach to building up a business. So I'm kind of eager to see what that will look like in 3 years' time.

So when you guys go down and see my shop downstairs, there's a big like sign painted mural that says everyone loves beautiful, useful things. And it's this meeting of utility and beauty that is my favorite thing. You know, like I do not like create— and this is just for me, I'm not saying that beauty should not exist without utility, but I do not like creating things that don't serve a purpose, right? Like, it's really difficult for me to get motivated to create beautiful things that are just beautiful. Like, they need to solve a problem, or they need to, like, be a thing that becomes a presence in someone's life. Yes. So every single thing that I work on ends up moving those two things together. I think that's why with my professional work, I started leaning towards the logo work Because so much of it is like solving utilitarian problems and really like addressing the like core issues rather than just slapping a style on top of something.

Have you been tickled by work that's appeared in really random corners of the world? Like, have you seen yourself out in the wild that sort of like reaffirmed this approach to brand?

I feel like with the brand stuff, it's tough because a lot of the brands that I've worked on have been more like things where they're mostly appearing online versus things that are appearing like in person. But occasionally I will like see a thing where I'm just like, like, oh my God, they're still using that logo. Yeah, but I do work on things a lot where I'll be in some random location and like see an ad that I worked on. Or like when I worked with— on Moonrise Kingdom, I was in like Berlin and was on a bike ride with Eric Spiekermann, and there was a poster of Moonrise Kingdom. We stopped and took a picture next to it.

So cool.

I was like, that's me. Yeah, you know.

Yeah.

And that's really cool.

Tell me about that project in particular. How did that even like sort of arrive in your purview?

Yeah.

You know, you get that email, you get that call. You're like, wow, this is, this is real life. Like, I get to work on this project. And then how did that kind of unfold?

I never like dream. Like, what is, what is your best project you could want? Like, who's your dream client? What's your, like, what's your 10-year plan or like whatever?

Right.

I started having to have plans now because I have kids. And so, like, you have to plan just because of practicality reasons. You're like, someone's got to go to college at some point. It's time to plan.

Right.

But prior to that, I only really am looking at what's immediately around me and what's immediately around that because I'm moved by what do I want to do now? What's the thing that I want to react to now? What interests me now? One of the reasons is because then you're always working on things that you're interested in, which is nice. The other reason is because I always dream so much smaller than what actually happens to me. If you told me to, what's your dream thing? I would name something very, very achievable, something that is like, of course, that would stumble across your plate in 2 weeks, no problem. I feel like things happen to me all the time that are things that are beyond my wildest dreams. I think that part of that is that just always putting out that I'm just happy to be here vibe because everyone wants to just be around people that are just happy to be here. That project came, like a lot of projects that I get, because they were working with someone else and it didn't work out. Ah, interesting.

So you're like the rebound designer.

I'm often a rebound, and I'm, you know, I'm a very satisfying rebound. And so I'm like the one that, like, soothes you after you've had a, you know, a rough go of it, relationship with someone.

And, you know, you're just happy to be there.

I'm just happy to be here. I just want everybody to be happy. I want you to walk away and be stoked. I want you to feel like you're a better person at the end of it.

Yeah, yeah, yeah, yeah.

And I think that that's like every working relationship I've ever had is that. And so with that one, I think they had been working with a really great person, but that person was more on the calligraphy side.

I see.

And as a calligrapher, um, I should probably like tell the audience the differences of the things. So like calligraphers work with writing implements and, uh, painting implements and things, right? And so they're very, very, very informed by the tool.

Right?

And so everything that they do is about a mastery of the tool and what the tool's capabilities are, and also practicing and being rigid about the styles that you work in.

These are physical tools.

Physical tools.

Yes.

And then lettering artists are people that are sometimes informed by calligraphy, sometimes not. But we work with letterforms as a vehicle for creating artwork. And so we are the people that make like a one-off piece that's not meant to scale. And then type designers are the scalers. So they are the ones that approach typographical design from an engineering standpoint of like, how do we make a thing that can be endlessly bent and used? And we don't know who's going to use it, and it has to withhold and withstand the use of people, right, in all these different contexts, right?

Right.

And so that's sort of like as you walk up the ladder. And then typography and typographers are just people that arrange type. So any graphic designer is a typographer. So that's sort of how it breaks down. So I think that the Wes Anderson crew had been working with someone who had a really, really solid calligraphy background. And Wes, as you can imagine, has an extremely specific vision about what he wants to happen, right? And I think that that person might not have been able to bend their abilities into his vision, right?

Did you have to clean slate it, or was there some fodder in there that helped kind of inform this universe that he was constructing in real time?

There— I mean, he was clean slating it, I think.

Okay.

I didn't see any of that person's work.

Okay.

He did have some very clear art direction.

Yes.

And a couple of those things were sort of thinking about the time frame that it was meant to be occurring in and like kind of being steeped in that time frame.

Yes.

And then also he was really inspired by these titles from a Claude Chabrol film and so sent me a few stills of that. In terms of stylistic reference. And so we were sort of blending together a more classic script with something that felt a little bit more hand-hewn. And just because of the way that I work, everything always feels handmade. Just because I'm not like a snap-to-grid person. I'm not like a replicate and automate. And so no matter what, everything has a little bit of a— I don't want to call it—

A movement to it.

It's not like wonkiness, but it's not— like you can just see that a person made it. It's not perfect, right? In a very purposeful way.

Yeah, yeah. And as personality, as a character.

Yeah, exactly. And so I got hooked up with the project because one of his producers had been rec— like someone on their art team had recommended me, um, to one of the producers. And so we did a little testy in the beginning, and then it was just me and Wes emailing each other. And that was like a super intense amazing process, and I'm really glad for when it happened in my career, not just for, like, you know, it being a cool project and exposure and whatever. Yeah, but it was actually— it came at me right at that moment that I feel like almost every creative experiences, right? When you've sort of lost your 'I love design because design is new and fresh and fun,' right? But before you've gotten over that, like, 'clients are abusive and abrasive' hump and right back to being like, 'I'm just happy to be here.' Yeah, yeah, I felt like it was, it was the same It was the same time that that website like Clients from Hell was really popular and everybody was sharing all their bad stories.

Did you have any submissions in that?

I did not. I mean, I had them in my mind, but I think what it really made me understand is that if you approach every project that you have as a grateful collaboration with someone that you trust, who you feel is an expert in whatever it is they're trying to communicate through you, right? It just makes the whole process really fun for everybody, right? And so I think, like, it kind of pulled me out of that, like, clients are trying to ruin your work, right?

Like, this adversarial—

yeah, like an adversarial stance. It, like, completely evaporated that.

Yeah.

And even though, like, of course Wes was extremely particular about what he wanted, like, you know, I was, like, redrawing the lowercase R for the 8th time at 3 AM when I was Sydney at a conference, you know, like whatever. And that's like the extreme, but of course I fully trusted his artistic vision. And so I didn't come at it being like, you don't know what you're talking about, Wes Anderson. Like I came at it being like, okay, I guess I just haven't nailed it yet, you know? And I think that after that project, every time I worked with a client, if they had feedback for me that I didn't agree with, I would be like, completely open to being like, okay, I totally get that's what you think we should do. Let's figure out why you think that that's the right move, because I just really want to understand it because I just want you to be happy.

Yeah. Yeah.

And I think in the end, like, one of the reasons why I love client work is because I, like, love working with other people and love solving problems with other people. And I do think that I'm very flexible and open to what the end result ends up being, right? Versus there's other people that are more like artists and they have a vision, and if their vision is not executed exactly as they originally thought, then they're disappointed in the result. Whereas I think one of the things that makes me successful just in general is that I always think that there's 100 ways to solve a problem, and it's just about what is the solution that works best in this time and place on this particular thing in the time that we have with the budget that we have with the people involved. So I never think we're working towards the one true vision. I always think like, we're gonna get the thing that based on all of these things in front of us is the thing that makes the most sense with those things.

Where do you find yourself taking the most pride in? Is it like in this process, this collaboration that going into it is a little bit open-ended and you don't really know where you're gonna end up, or is it in the eventual output, the thing that exists out in the world that, you know, makes an impact on people's lives and where, like, the actual process is invisible to the end consumer?

There's parts about all of it that I love. Like, pride is not the word that I would use for it, you know? So, um, like, for me, the process of creating it is necessary, like, just for both making the work, for feeling good about the work, and being proud of the work. Because if the process gets diminished or manipulated or destroyed, then I can never be proud of the work because I always second-guess the work.

Interesting.

Because we haven't, like, gone through the steps of validating it along the way.

Yeah, yeah.

You know, it's sort of like in the product world, like, doing the MVP, testing it, and all that kind of stuff. Like, I need my version of that, which is We've brainstormed, we've consolidated and synthesized ideas, we've made sketches from the ideas, the sketches have been discussed, the sketches have been landed upon. All of those stages have to happen so they all become these flags planted of moving on, moving on, moving on, moving on. Then if something goes wrong over here, we're not remaking everything, we're just going back to where the last flag was planted.

Do you ever have the temptation to skip steps with certain collaborators where it's like we're just mind melded and we can go straight to production? We can go straight to—

I do think sometimes you just know, like, or somebody's asking to do something that you're like, oh, this is like nothing for me. This is like batting practice. Yeah, exactly. And like, you don't want to do that all the time, right? Because then you end up in this sort of rut where you're just repeating yourself all the time.

Okay.

Like, I think I'm not like a Rolling Stone where I can just go on stage and play the same songs for the next 50 years and that works for me. I don't think that's a thing. I don't think that's like a secure career path.

Although they did pretty well for themselves.

No, exactly. But that's what I'm saying is I'm not putting myself on the same level. Like my work is not painted black.

Yeah. Yeah.

Yeah.

So you thrive on the variety and the newness of like every success.

I thrive on it. But then also I understand that like there is this— an issue that can happen where you get known for like one specific thing, like you become like a bit of a one-hit wonder. If you end up in that world, you're very insecure as a creative, you know, because it's very easy for someone else to come in and replicate that thing that is the one-hit wonderdom thing. Whereas if you really expand yourself and evolve, yes, you're so much more secure as a creative.

Yes.

And so I really don't mind playing my greatest hits if people have no time and no money, right? They're like, you come at me and they're like, can you make this exactly like this thing that we know and love? And, and, and I'm like, yes, sure, absolutely. And then I put on an audiobook and I sit there and I have my lovely make time and I send it off and I go, you're happy, I'm happy, cash that check, that's great. But if I did that all the time, it would put me in a really precarious position and it would also be really boring. I need to stay involved in the creative process for a couple of reasons. One of them is because I find that zero-to-one stage to be like really fun but also very taxing.

Yes.

You know, it's like, it's really difficult. It takes a lot of mental energy. It's stressful. Like, you're not sure how it's going to turn out, like whatever.

Yeah.

And there are people that love that part. That's like their whole part, right? And then they want to pass it off to someone else to execute it, right? But for me, I would burn out so fast if I spent my whole life in the ideation phase and the big ideas and big pictures phase and spent none of it in the execution. So, for me, it's a real balance of making sure that I'm still spending time physically making and physically creating so that I don't have to solve everything in the beginning and so that I don't have to put all that pressure on myself to get it perfect before it gets handed off. What's kind of nice about the way that I work, and because I really love working collaboratively with people and evolving things as we move through the process and changing how things are based on how they seem to be happening, it means that it's easier for me to go from zero to one. Yes, because I go, all this has to do is take a blank page and put a thing on a page. It just has to be a thing that we can talk about, right? So like my first goal, like I say this like jokingly to my studio mate and to other people, is like my only goal for round one work is to look like I've worked, you know? Like, right, I have to look at something to show. I have something to show. I have something to react to. It doesn't necessarily have to be something I'm I'm proud of. It just has to be something that I can talk about.

Right. That'll generate a response.

And generate a response, exactly. Because then if it's not something that I'm even 100% sold on, I can go, I'm not 100% sold on this. Tell me what you think. And then we can have a discussion about it. And then I can go back with their thoughts and intentions and, you know, ideas and mix them all together. And then ultimately what we end up with is something that the people that I work with feel bought into because they were involved in the ideation process and I haven't cut them out from it. And I think that that's like one of the biggest unlocks creatively is just making everyone that you work with feel as bought into the thing that you're working on as you are. You know, like give them skin in the game, make them an advocate for the work because that's how the work lasts. You know, like they don't want the thing to go away. If they build something with you, they want that thing to exist as much as you do.

How do you make space for skin in the game? Because I think that that's one of those things that's easy to talk about in the abstract, but you have a method for that, right, with creative collaborators? And you sort of know that you can't just be the sole driving force behind a project.

With my commercial lettering work, a lot of the thing that happens is I'm working with an art director or creative director that then has to take the work that we're creating together and sell it to another team.

Yes.

Right? So they're in meetings without me.

I see.

Talking about the work that I'm creating with them.

Yes.

So I have to give them the tools of how to sell the work. And so part of the process of working with them is making them really understand everything that we're doing. Right. So that they can defend the work in my absence.

Right.

You know, and it's not just about me making like a really great deck that then they're just reading. You know, like I need them to like know and understand.

Right.

So that's one way of doing it. And then the other way is actually like sort of telling people when I'm not useful to them. You know, so if someone comes to me for logo work but they are an early stage company and have no design on their team or anything like that, and they think the logo is going to drive their entire, uh, culture, you know, or whatever. Yeah, yeah, yeah, yeah, yeah.

I'm like, guys, it's their mission statement, right? Yeah.

I was like, if you feel like blowing $50 grand on a thing that's going to evaporate as soon as you have a design team, like feel free, but I don't know if that's the best use of your money.

Right, right, right.

And so—

and I find that refreshing that you come forward and you say like, this is what I'm exceptional at.

Yeah.

And this over here, we can probably take this area of expertise and apply it in this particular fashion. You're really comfortable with sort of drawing that circle of competence and saying like, I'm gonna be outstanding here.

It's also one thing, it's protective of my work, right? So not just of my time and what I want to do, But if you think about it, so if I make an outstanding logo for a company, but they have no design team, and then that company ends up doing really great, yeah, and then they grow, and then they hire an out-of-house agency, or they hire their own in-house brand team or whatever, yes, the first thing that brand team wants to do is a brand refresh. Yes, because they don't want to inherit someone else's work, right? And so if I I don't think about that. My work immediately evaporates if the company is successful. Right. So it's like, what is that good for? I designed a logo for an unsuccessful company and then someone threw away my work as soon as they became successful.

Right. Yeah.

So I—

What does that say?

What does that say? It doesn't say anything positive about the work that I've made.

Yeah.

So what I would much rather do is let them use a placeholder logo that's vibey enough until they get to that point. And then when they do start hitting that, like, we need to really think about the overall brand for this company because there's enough bandwidth and leeway and it clearly is going somewhere.

Yes.

Then I want to be involved with that team to help them shape it.

Right.

Because even if you have like an out-of-house agency or an in-house brand team or whatever, what you don't typically have is a world-renowned expert in letter forms on that team. That's not a first hire for that group, you know? But I, you know, I don't want to go work for someone else and do that, like, do that specific thing for one particular company. But I love being like an out-of-house asset to people. And so I like invented this whole fractional leadership thing before it even was. No, I'm kidding. I do, I do love poking at fractional leadership because it's just consulting. And so, yeah, exactly. So I'm just like, 20-term of the age. Yeah, if anybody needs a fractional typography leader, I'm here for you, you know.

Well, you know, when we were talking about folks to line up for these interviews, your name bubbled very high on the list. Because when I think about the independent designer, like people who really embodied that in their work and their approach and how they've structured all of their commercial activity, like you're on that podium. Was that always the plan? Like, why is it like— what does independence mean to you?

It kind of was always the plan, but I feel like it originally came from a place of feeling like I needed to be nimble all the time. Like I was a bit of a prepper in a lot of ways.

Got it. So when shit hits the fan, you're like the first to react. You have a plan.

Yeah. I mean, I grew up in a small town in PA. I was like, you know, kind of upper middle class, but then not really once my parents got divorced and just kind of saw what it is to not take charge of your— not be able to take charge of yourself financially and like really guide everything and put any of your trust in like other institutions.

Right, right.

And so sort of seeing firsthand that things can just evaporate if you have all of your eggs in one basket was really frightening and really shaped how I feel. Like, and it just so happened that as I got into being a creative, the sort of idea of like freelancing and being a gig worker and all that kind of stuff was just becoming more normal. Yeah, you know, because there really weren't a ton of like— other than illustrators, which illustrators are always independent— but there weren't as many freelancers that were like building independent one-person studios. Like prior to the early aughts. Correct. You know, it was like everybody was going to like work for a major design studio and that was their goal.

Their portfolios reflected that. Yeah, sort of like that was the aspiration.

And anybody that was an individual, they were talking with the royal we and, and making a design studio that was them.

Right.

But because I was really interested in illustration, illustrators were always their own name. And it like, it started from this place of feeling insecure and that the only way to feel secure was to be in command of my own destiny.

Right?

Right. And so everything had to be like, I could do it myself. If everything blew up, what's my game plan? You know, I, like a lot of people that come from non-wealth, I won't say that I came from like lesser than, but, you know, I like didn't understand that debt could be okay and that could like enable things.

Right.

You know, it was always very scary to me. I was like a person who like, Bought cars in cash and, like, I paid off my student loans in 2 years and just worked like a crazy person and ate 3 pizzas, like, free pizza from the bar that gave you pizza if you got beer, you know, just because I was really afraid of debt. I realized that, like, a lot of the independence was— and, like, wanting to be completely independent was about fear of letting control or letting someone else, like, have any say on what my future was.

Right. You know, a certain degree of like self-reliance.

Yeah, self-reliance. Like just, just being like, I know that I can figure it out if I'm in command of it, but if someone else is in command of it and I just have to follow along with them, I don't know what's going to happen.

Yes.

You know, and that has been a hard thing to let go of because obviously you can't live your whole life like that. You can't do everything, especially if you want to do fun, interesting stuff.

Did you feel like it was essential to let that part go at some point?

It was. I actually think that what happened was like even—

what was that threshold in your career? How far along were you?

I was pretty far along. And so I— and then also there was this thing of kind of like always knowing that I wanted to be a parent.

Yeah.

And that my life was gonna have to flex around parenting.

Yeah.

Um, and that's like a whole thing because apparently that's like one of the biggest contributors to the wage gap is that women go into more flexible fields knowing that they're going to be parents.

Fractional leadership.

And men never make that decision for themselves because they suddenly stumble into like, "I guess we're having a baby now," you know, and then they are well along whatever path that they were choosing that did not think about the future of children.

Right.

When Russ and I got married, we had to sort of start integrating more, and I didn't feel like I had to like fully contribute everything in the same way all the time, that I could like put my trust in another person. And like my center of gravity started shifting away from like me constantly feeling like I have to be building the concrete pad underneath myself, right, to being like, oh, I have this stable foundation.

Yes.

And because I have the stable foundation, I can operate instead of out of fear, yeah, out of just guiding my career and life around my interests and what I want to do, right? Not because I'm afraid of what happens if I involve other people, but because I want the ability to sort of pursue things that I'm interested in, right? So yeah, it was just like the actual reality of it didn't change that much because I still mostly do things myself and I only collaborate with other people when we really vibe. Yeah, it made me feel like I I didn't have to operate out of a place of like fear, and I could operate out of a place of like excitement and curiosity.

Did your creative instincts evolve along with that?

Yeah, I mean, I'm, I'm like a sponge, so I absorb the environment that I'm around, which is why it's like really important for me to like be surrounded by people that are like curious and interested and excited and happy and, you know, like or at least pursuing happiness if they're not currently happy.

Right.

You know, like people that are out there trying to do things and make a difference because I am so sensitive to energies around me and I'm better at it now than I was when I was younger. But I was like a complete semi-permeable membrane and would just absorb everything around me. Yeah, but that was good because I would find myself in these environments with people doing really different things from me, and then I would just be really interested in what they were doing and wanting to kind of understand it. So I ended up walking down a lot of paths that I probably wouldn't have walked down had I not been surrounded by the people that I had been surrounded by. Probably my mom downstairs. Hey, Mom, is that you?

Good morning.

How are you? This is Donna.

Hi, Donna. Very nice meeting you. Thank you. Yeah.

I keep wondering about, like, your two worlds. You were so data-driven at Facebook. Like, is there, like, And tech is so data-driven. You talk about being this translator. Is there an assimilation somewhere? Is there some, I don't know. I just keep thinking, I'm usually looking at you two like, oh wow, move fast, break things, handwrite things.

No, but I feel like I'm very data-driven as well. I mean, all the work that I do is informed by data. The information that I'm given, you know, like it's like informed by the data around it. And then I'm also like a weirdo that thinks that like intuition is just data that we're accessing without needing to understand the path to it.

Right.

You know, because— and I would do this all the time when I was younger where I would try to walk back intuition. This was an exercise that I did with myself. So I would be like, why?

On purpose?

On purpose.

Interesting, because I feel like I'm like at a stage in my career where I'm like, No longer apologizing for my intuition. No, no, it's almost like kind of getting to the— in the opposite direction.

Yeah, yeah, yeah.

Why do I keep second-guessing myself?

But the— what I just find it to be a really fun exercise. So if you have a really strong feeling about something, like, like really strong, and you know that whatever it is is true, you have to defend it to people that have a different feeling about it, right?

Yeah.

So it's like you'll be in conversation with someone and they'll be like, well, I see things differently.

Yeah.

So you have to take your strong feeling and figure out how to verbalize where it came from and why it came from that thing. And so to me, it's like just training for defending your intuition, right? And when I was younger, I did it more often and on purpose to just kind of like, again, like kind of media train myself. I think that that training allowed me to really like think off my feet, like, when I was called into question.

Right.

And then I found it to be just kind of like a fun, challenging game.

Right.

Because every now and then you'll get, like, someone will ask you a question in a, in like a client meeting or whatever, and the answer to that question is so obvious, but you can't make that person feel like a dummy.

You can't say, yeah, you can't say it's so obvious. I'm the expert.

No, exactly. Like, the clearest example I can give to you is that I was like working on a holiday campaign I was making art for the holiday campaign. I was in the meeting and presenting everything, and everything was going fine and whatever. Then someone came out of left field and was just like, "I just have one question. Why are we leaning so heavily into using red for this?" The answer is like, "It's for a holiday." It's Christmas, bozo. It's Christmas, bozo. Exactly. But you can't say it's Christmas, bozo.

Wildly unproductive.

Yeah, wildly unproductive. So then in that moment, you have to come up with like, what is the way I can say I can defend the use of red on a Christmas campaign that doesn't make this person feel like a bozo?

Right.

And so then I was like, well, you know, we're working with these really modern letterforms. Yes. Right. And so we could go a completely modern path and choose a really interesting new color palette. But I feel like because the actual visuals themselves are really modern, that we should inject some tradition into it just so that we can really bridge that gap between modernism and traditionalism.

Otherwise it's just like unrecognizable.

Otherwise it's unrecognizable. Exactly. But the first thing that you want to say is because it's Christmas bozo, right?

Yeah. And you said like red is an affordance.

Yeah, exactly. And so like that's one of those examples where you know what the answer is. Yeah. But always asking yourself why is that the answer, right, is always really helpful.

Was this something that you learned through your time in New York? Was it like, was there a period of time which you like realized, oh wait, a big part of this work, this craft, this trade is my ability to steelman my ideas and persuade the hostile party? Yeah, see things my way.

I think also just being a person on the internet had really steeled that for me. Like, I actually—

people are shitty on the internet.

Oh my Oh my God, did you know? All I want to do is communicate to you clearly what my intention was. You're perceiving it this way. I take that feedback. I think that's important feedback. I'm going to look at this and evaluate whether or not I should make any changes based on that feedback because you are one person, but one person is many people. There's many people in the world that could have that same perception. Just being really receptive to feedback is a very good way of bulletproofing yourself against criticism. There's the whole like don't feed the trolls thing.

Yeah.

But if you just come at every antagonizer with just grace and understanding and noted. Yeah. And that's valid and like whatever. And you're just—

Acknowledgment.

Acknowledgment. Yeah, exactly.

But like, I feel like the theme that I keep kind of hearing is like the clarity of expression and clarity of thoughts and also just actually like not thinking everyone on earth is a shithead. Right.

You know, right.

Yeah.

Like feeling like no matter what, whoever that you're dealing with is a good person at their core.

Right.

And whatever they are experiencing or going through or have experienced or dealing with is making them react in a way that is unfavorable in that moment. Or if people seem incapable of empathy or like are much more limited in their capacity for empathy.

Right.

I think, okay, some people are not semi-permeable membranes, right? Some people do not feel the energy in the world.

Yes.

Some people cannot walk into a room and understand what everyone in that room wants out of the experience with them.

Right.

And that doesn't— that just makes me feel grateful that I am one of those people that can do that. But it doesn't make me think less of that person.

Correct.

It just makes me know that I can't force them into my space. I have to meet them at their space because they can't see my space the way that I can see theirs. I always want to make sure that the things that I say can't be taken out of context very easily. If they can be taken out of context easily, everyone around us can look and go, "That was a weird read of that situation." Right.

Yeah. It's a very charitable interpretation, what she just said.

Exactly. Exactly. Everyone who's been a public person on the internet for any period of time has had some rando or whatever come at them and be like, "I have receipts," or whatever. You want to be in a position where you're like, "Please publish the receipts. Go ahead. I feel great about the receipts." If you're very considerate about what you say and what you do and always think about how that thing that you're saying or doing could affect other people, and not just in like a, like, I want to make sure the trolls can't come at me, but in like, I don't want to do accidental harm by doing a thing that might harm people. What you're doing is just creating this giant repertoire of trust that is all built around your reputation of actually caring.

Yeah.

And I just really, really care about people knowing that I'm not a bonehead. I really think about stuff and I, and I do really care and I'm not doing it to be performative.

Yeah. It's a form of integrity.

Yeah, exactly. Because I, because I respect people.

Yeah.

And I respect that everybody comes at things with different experiences and different needs and different places in their life and happiness levels and whatever. And I just want to come at them with respect. And I want them to understand that I, you know, that we can have this relationship and we are equals and that I think that they're great.

Yeah.

Yeah.

I want to talk about mental engines. One of the things that struck me about your video of like the studio tour, this beautiful space that we're in, is you walk through the very physical nature of the work that you do. And that sort of— my spidey senses said there's another mental engine hiding there. There's something more about the physical nature of this work. I'd love to hear more about how you think about the physical nature of your work and how it plays into not just design writ large, but maybe in how you just sort of carry yourself through the world and how you sort of approach everything.

We can go real deep on this.

Let's do it.

I will walk us back to probably one of the the core starts of it, and this is going to seem way bigger than it should be for what it is, but it does a little bit have to do with sort of like spirituality and perceptions around spirituality. I grew up Catholic, and I've got no hate in my heart for monotheistic religions and people that want to practice whatever it is that they want to practice. You know, some people need organized religion and some people don't. Yeah, I'm a failed Catholic, but yeah, yeah, no, as an adult I am a person who absolutely does not need organized religion because I have found my own religion, which is this feeling that there's this subatomic connection that we all have that is this shared energy and that some people can access it and some people can't, and some people can access it all the time and some people can access it sometimes. I feel like I was reading Rick Rubin's book and he talks about that shit all the time, and I was like, This is my new Bible.

Yeah, you know, but it's like, it's like he doesn't have quite the right language for it, but it's right there. He's like right on the surface of it.

Very close. He talks like a lot of the things that he talks about are things that I think about quite a bit. And it's like a lot of the work that I do, especially personal projects. One of the things I'm still, even though I'm doing stuff for me, I'm always visualizing who this is for, you know, whenever I work on anything.

Okay.

I develop such a clear and intense picture of that person sometimes, or people, that when I hit on something, it's really difficult to describe the feeling that I get in my body. It's like a vibration of just like, this is going to— this is it. I found the thing. And then I can't not walk towards that thing, whatever it is.

And it's another party's interpretation, their reaction.

It is, but it's an imagined— it's an imagined thing. I have like a weird way of like manufacturing that Right, like with new people, with, with new imagined people, you know, like, you know, like I— it's like I can create chemistry for a persona.

Yes.

And feel the energy of that connection.

Yes.

And then that energy pushes me towards pursuing that thing because I really understand how that imagined person is going to perceive it. So that's like a whole weird thing. Yeah, but To tie it back into sort of the spirituality thing, because I'm like kind of a "it might be lights out when this is all over" person, and not in a negative way, I'm really like, we have— this is it. This is our time on Earth.

Yes.

How do you have any lasting impact on Earth? It's about what you make and what you leave behind, whatever that is, whether it's relationships or physical things or whatever. It makes me want every interaction that I ever have with someone to be a story that they want to take with them to other places and parts of their lives. It makes me really excited to make physical things that might have a lasting physical impact on people.

Right.

I was definitely a person that, like, all of my stuffed animals had souls and they, like, couldn't go away and all this kind of stuff. Yeah, I imbue a ton of meaning in physical objects. And I feel like touch and just our senses lock us into memories and allow us to, like, access parts of ourselves. You know, I'm always interested in making things that become a physical item in real life. And so I've surrounded myself by lots of maker equipment. Like, I have a Vandercook letterpress, I have a riso with 12 drums, I have a foil stamping machine, a Glowforge, a micro TIG welder, just a whole bunch of random shit to make stuff because if I ever have an idea, the easiest way for me to get excited about making it is to either visualize the person that it's for or to turn it into a physical thing. If I have an idea of a word or phrase that I want to illustrate, I do not get excited about making a thing to post it on Instagram. That's not a thing I get excited about. I do get excited—

Because it's so impermanent, because it's sort of just in the ether.

Yeah. Is it even in the ether? I'll post something and whatever, 15% of the people that follow me will see it. It feels like a waste. And it's also just like you're creating art not to necessarily move people or have them have a moment with it because it's almost impossible to have a moment with art on your phone. There's not the— It can't stay with you just because of our behaviors. That we have. So you have to find ways of slowing people down so they can experience the things that you've made in a way that lasts more than half of a second, right? You know, and tactility and holding a thing or having a thing that moves from space to space with you, right? You know, that's, that's a whole other thing.

Yeah, yeah. And is it like a visual cue in your environment, or is it like an object that you treasure? Or that you pass on to somebody else.

Yeah, exactly. And like, I did a bunch of work for Neiman Marcus a couple years ago for their Christmas stuff. It was a great project. I was excited about it. I was excited to make a bunch of cool Christmas stuff. I love making stuff for holidays and all that. It's great.

Yeah.

And I knew that it would be executed really well because they care about craft. Yeah. But what I didn't anticipate, because I couldn't have known, because I had no idea what they were going to make out of my work— yeah— was suddenly there would be all of these pieces that I would get my hands on and I would be able to sort of think to myself, holy shit, this is going to be someone's grandmother's cookie jar. Yeah, like this is a thing that is going to get passed down in a family. It's not something that just gets far. It's going to travel really far. And even though, like, they're not going to know who I am.

Yeah.

You know, the fact that that is a thing.

Yeah.

Is incredible. Like, you know, like, and so I just—

Does that give you a high?

It's— it— I mean, it does because it's like all of us just want to have an impact, you know, like especially anybody that you're interviewing for this series. We're all trying to be helpful leaders and, you know, make the world better and all that kind of stuff.

Yeah.

But we also, you know, if we're not super religious, We know that this is our one chance.

That's, you know, spiritual.

Yeah. Like, this is our chance to impact people and to do what we can to make the world around us more beautiful, more interesting, you know, and everything. And the idea that things that I make can influence people, yeah, is great, is amazing. It's amazing, you know, like. And you just never know what that thing is going to be. I was with a bunch of students at SVA last week or 2 weeks ago.

Okay. Are you teaching there?

No, no, no. Randy asked me to come and talk to the grad students because he was like, "Oh, I think you'd be a good random entrepreneurial fire-up person." Yeah. But a couple of them were asking me what they should focus their thesis on and things like that because they're about to start. And obviously it's a really crazy time to be thinking about what to make. My advice was like, literally just make something that you are personally excited about because whatever it is, you just have no idea what kind of impact it's going to have on other people. Right. And I was like, if you think about it, like, think about an object that you loved when you were a child, like a thing that you were obsessed with for some reason. Yeah. It doesn't matter what it is. Just think about it and visualize it. It was a thing that you like never wanted to get rid of and brought with you everywhere. And it was really important to you for whatever reason, think about the person who designed that and you telling the story of loving that thing 30 years later. They never would have imagined that you would be telling that story about a thing that they made, right? You know, because every— there's artists behind absolutely every object that ever gets made, right?

You know, even like a little stuffed animal, right?

Yeah, exactly. And that's one thing that I've learned kind of over and over again is that it doesn't necessarily mean that the things that you make have to be world-changing, right? Because you— the things that you make that aren't world-changing still have an impact, right?

Yeah.

So like, of course, if you're a person that wants to like go out and disrupt and change everything, go forth and do it. Yeah. But if what motivates you is making weird miniatures and doing whatever it is that you want to do with your fun crafty time and time on Earth, That will still have an impact. It will have a different impact, but it will have an impact. It just has always kept me really focused on wanting to just pursue things that I'm personally really invested in because I know that even if the thing that I'm making is not the thing that's going to flip the table, the person that sees that thing might be the table flipper. It still trickles out.

This bias towards making physical objects. Square this with making a software startup.

So the— okay, well, it's all—

Are you allowed to talk about?

Yeah, no, of course. Yeah, I'm a tech bro now. Yeah. So I co-founded a software startup with my friend Chris. And so when you were talking to about these inflection moments in our life, I shared a studio in Dumbo when I was in my early 20s. With Chris Shifflett and Cameron Cozon, who ended up founding Brooklyn Beta, right? And so I only ended up in that studio because I was in another studio space, the Pencil Factory, up in Greenpoint with a bunch of illustrators, and it was awesome, like, you know, literally one of the best times of my life. But when I quit my day job to go full-time freelance, I had also just bought an apartment, and I was like, I don't need a studio because I could work from my apartment., but I'm, like, actually the most social person on the planet, and that did not work for me for more than a couple of months. And the studios in the Pencil Factory were full up, but Tina Roth-Eisenberg told me that there was a desk that I could part-time rent in her space, and so I ended up down there, and it was right at a moment when I was, like, really interested in— like, I had always been interested in, like, HTML and CSS and stuff just for, like, being able to manipulate my own portfolio website and things like that. But then being surrounded by a bunch of web people all the time, I like really dug in. Yeah, yeah, yeah. Because I could ask, I had like Wikipedia next to me.

You just absorbed.

Being like, how do I do this? How do I do this? You know, like right next to me. Yeah, exactly. And it's just really nice to feel well-resourced. And so I went from just being like the person who edited their blogger's CSS to being a person who could build things from nothing. That year, I think I released 11 different projects. But then I realized that I probably shouldn't do that because when you make new businesses, you kind of have to maintain them. And so then I was like, okay, I probably shouldn't do that for a while. Recently, I had been thinking a lot about how much I missed working on fun, cool internet stuff. I just kind of really missed that, like, frenetic era of making weird internet projects where it's just like hacking on a thing for a couple of days and pumping it out there. And it was like, I had a project called The Internet Sends Me Cake. Where people would literally send me cake in the mail and I would review their cake and then link to their portfolio website. There was like, I just did so much random stuff like that. It was just like the time of weird internet. Yeah. Yeah. And I was thinking about how I hadn't done that in a while. And the person that came to mind was Chris, who I hadn't talked to in years. Like, you know, like I'd seen him socially, but like, I'm not— he's not one of my out-of-the-blue-call people, you know? Yeah. But I was like, oh, I should call Chris. I bet he would want to work on weird internet stuff. And so I called him and I was like, hey, I feel like, I feel like you're also interested in making stuff for like niche markets. Like, what if we just made some cool, very usable things that, you know, 100 people would really like, you know, like, like, you know, not go crazy, just like solve some real problems for people, make a thing that you and I would want to use. Right. And then otherwise, just like, like, that's it, we'll just hack on it for a couple of weeks. But then we ended up having this total, like, mind-meld 3-hour conversation in which we're like, and then we could do this, and then we can do this, and then we can do this. And at the end of it, um, it was basically like the whole vision for Studio Works, which is like to make a business management platform for small creative studios. Because there's plenty of business platforms out there, but they're all meant to like capture every small business. Right. And because of that, they, they solve some problems, but not specific ones that you would need as like an independent creative or like a small studio. Yeah, they're very back of house instead of something that you feel like you could be confident sharing with a client. You know, like if you think about like you, no one ever like feels like using QuickBooks makes them look like a boss, you know, because also your gardener uses QuickBooks.

Correct.

You know?

Yeah.

And so we wanted to like We were talking about making the thing that's like, you know, since we don't have to make this for everyone and nobody wants to bake things for specific people because they think it's not attainable, that it's not a real business, right? But we're good. Like, why don't we do that? Yeah. And just make the thing and then solve the problem for these people and make them really happy.

Yeah.

And he was like, oh, this is so great. I love this. But, you know, we need like a whole team to do this. This is like— I learned CSS before, or I learned building before CSS existed, like proper engineers. He had been more on the leadership end and like operation stuff. We let it rest, but then 2 weeks later, the 2 engineers that he had worked with at a neuroscience startup that he had co-founded quit their jobs the same day and reached out to him to be like, hey. Independently.

Independently.

Wow. To be like, do you want to build something together? Yeah. He called me immediately and was just like, The universe is aligned. I think the future is now. Yeah. And so he got together with them, and of course it wasn't like an immediate go because, you know, they had worked together on a bunch of stuff. They're all smart people. They all had a lot of ideas, right? And so they had basically like a weekend where they all pitched all the things that they had been thinking about, and Studio Works just kind of floated to the top of the pile.

And I love that this has sort of been a recurring theme for you. It's like, it's like focus on what's tractable. Yeah, here and now that you have like full agency over. Yeah, and do an exceptional job of that.

Yeah, right. Make, make a real impact. Yeah, to a few people instead of constantly trying to make a massive, like, a superficial impact to a lot of people. Yeah, you know, like, go super deep, help someone now. Yeah, solve a real problem. Yeah, and that's like every, all of my work is just about like, what do I do to like Be impactful now. What do I do to solve a problem now? But not in a way that's like ignorant of the greater problem. Of course, you know, it's like if you think about folks that want to like donate to organizations and stuff, they, they're like, oh, I want to solve the homeless problem, but I don't like donating to the organization because I want the money to go right into someone's hand. And it's like, well, the organization does things like set up healthcare and buy toilet paper and like a lot of the, like, non-sexy stuff that needs to happen, right? And if you're just giving to individuals, then the, like, greater take-care-of-ness of the problem never gets solved. Being aware that there's, like, greater problems to solve, but being like, how can I most effectively use my time to solve the problems that I can?

Yes. You know, and I like— I love that you joke that you are now a tech bro because you've been operating within the orbits. I've been a tech rep for a while, right? You sort of been in the gravitational well in the Bay Area.

I say I'm tech adjacent.

You're tech adjacent, but you're very adjacent, right? Your partner works at Meta on AI, right? Like, you are surrounded by friends and colleagues who are at the helm of incredible businesses in tech. When you think about creating a new software startup, what's the way in which you're going to break that pattern? What are ways in which you are going to absorb the common wisdom that, you know, it's sort of like tried and true in tech? And what are the aspects that you think are gonna be unique to Studio Works?

I think it's funny because it's a— like, I feel like the thing that's been really interesting about Studio Works is it started as a, I want to make this thing because I want to use this thing, which is like the— every project that I've ever made that I've been really passionate about that has worked has been like, I I want to make this thing because I want to use this thing.

Right.

You know, I sort of just started realizing that it combines absolutely every single thing that I have been interested in over the course of my entire creative career.

Interesting.

You know, it combines my desire to create utilitarian but beautiful things. You know, make sure that there is joy in the process of using very utilitarian, basic stuff. It combines believing that it's worth solving the problems of niche groups of people instead of just thinking that everything you make has to be good for everyone. Because if something's good for everyone, it's perfect for no one. And it also is a bit of a prepper thing, you know, talking about like business prepper stuff. Of just making a business that actually works. You know, like a lot of people perceive the things that I've done in my career as being me not being afraid of taking risks, right? You know, when really I am very risk-averse. I never do a thing unless I think that that thing is going to pay me back or translate into something, right? And some of it is just vibes. Like, I know just based on my lived experience, the vibes come back, you know, like it's on whatever timeline it's going to be. It might be tomorrow or it might be in 10 years, but I know that they circle back. Yes. And sometimes it's things like spending $15 grand on a letterpress and being like, okay, well, if I sell X amount of prints over X amount of time, this thing pays for itself. Okay, sounds good. Yeah. And I think the real thing that has worked for me with my business is not needing everything to be like a quick fix. You know, it's sort of that slow, steady growth model versus the like 50x model. And I've just approached almost everything that way, where it's like there's going to be things that I do that are like financially epic, you know, where it's just like I do that thing, it's absolutely worth it for the time. Wow, that was a great decision. And then there's going to be stuff that never really goes negative, but it never does all that much like financial positivity, but it has all these other ancillary benefits. Right. And I love exploring all of those spaces. Yeah. Like, I think if you are just making decisions based on the financial outcome, yeah, you leave out so much cool opportunity. And if you are in a space where you have a fortified enough ground to start from, right? I have my client work and I have other things going on. So even with, with, um, doing studio works, like, we are going to be like a sustainable business, but at first I'm probably not going to take my share and I'm going to let that go to our developers because this is their whole thing right now. Yeah. And this isn't— it doesn't need to be my whole thing right now. Yeah. And so it's about this, like, relationship and about, like, building a thing where I'm not only, like, solving the problems of our team, but also really just trying to solve the problems of the people using the product, right? You know, right? And not wanting to grow beyond that because I am such a believer in relationships. Yes. You know, like, relationships have just gotten me absolutely everywhere in my career. Like, all of my people are like, how do you get that work or whatever. It's always because someone recommended me. The only reason why Studio Works is rocking and rolling like it is is because people really trust that I will make something and I will not disappoint them. Yeah, because I have just spent 15 years proving it to them. Yeah, you know, and I would never ever want to betray that trust, right? Never. Yeah, and I think people know that, and that's why they're like invested in it and And it's also why this thing will be successful for these people. And it's like people have asked me if they, like, want to help. They're like, how do we advertise it? How do we do all this stuff? And I was like, don't. Like, we haven't launched the founding members yet. What I don't want are a bunch of people that don't understand that relationship involved in the project yet. When it's at a place where I'm ready for any random person off the street to walk in and use it, and to feel like they're having exactly the amazing experience that I promised, then by all means, we'll pound the pavement. We'll pound the pavement. But right now, what I want is word of mouth. I want slow and steady. I want the people that are bought in so I can have this as be like they're my advisory board. We're like having a relationship as we build this together. And then the people that they bring in, they will be the enthusiasts of like, this is great. You should trust this is going to be great. Really come follow us, you know? And that's what I want. Like, if it blew up tomorrow, I think it would be bad. Like, what I want for it to be is slow growth, sustainable. I want it to just be our team, maybe some customer service people. But if we have to grow well beyond that, I think that's actually like a failure of our vision. Like, we want it to be small.

Yeah. You want to be small, punch above your weight.

Exactly. Yeah. We all— and ultimately, like, my vision for it, which I think is shared with Chris and with and with Nick and Sean as well, is that we are not people that believe that any one person should be sitting atop a pile of emeralds, you know, ultimately in their life. Like, we want to, like, obviously make sure our kids can go to college and that we can, like, you know, help our aging parents and all that kind of stuff. But my ultimate goal is to turn Studio Works into, like, a vehicle for giving back to the community. If we do keep the team really small and don't grow beyond our needs, that becomes possible. Yeah, but if we decide to like make this into like a proper company and have, you know, 100 employees and whatever, that becomes less possible, right? So it's about like, what are the goals? Yeah. And the goals are make a thing where every— like, make a tool that's exactly what people need and not what they don't. Make the team whole for all this time and energy that they put into it, and then ultimately look for every way to make Studio Works a vehicle to give back to the creative community.

Amazing. You know, we talked about being nimble, we talked about being reputable, about having high integrity. When you look at like tech startups today and all the conventional wisdom that they're soaked in, what do you wish you could convey to people starting technology businesses in the year 2025? What do you wish you can just airdrop into the minds?

I think what I could airdrop is that it's like absolutely possible to just make a real business. You know, like, I think people operate out of a place of both fear and sort of like not wanting to leave opportunities on the table where they're like, this could be this, so we have to do this. Best guess. You know, like, like, it's sort of like if you think there's a chance you could win the lottery, why not play the lottery? Right? Interesting. But the problem is very few people win the lottery. And if you operate in that space and only in that space, then the chances of you being one of the very few people that win the lottery are very, very small. Whereas if you don't think about winning the lottery, and what you do is you just try to solve a real problem in a unique way to a unique audience, you know, the chances of success are way higher. And I think, like, also, if you are building with integrity and people see that, the chances of people shifting winds to a different company just because they dropped their prices or just because they offered one extra feature or, like, whatever, are way less. Yeah, I'm not actually worried about someone coming up behind us and building the exact same thing as us. Us. If people trust us and they're into what we're doing and they believe in what we're doing, no matter what another company is doing, they're not going to run that way. And I think that's the biggest thing is it's like anybody that's owned a business knows hiring is very expensive. Retention costs less. Right? And so once you have your people, you just do everything you can to retain them. And the best way to do that is to just really serve them and not be constantly, like, looking out for, like, who is the next person that I should be bringing into it. And I think that's the thing that everybody makes a mistake with, is that they, like, grow beyond the people that are their core folks. And then eventually the winds shift and they don't have a really loyal base and everybody leaves, you know, because the first people felt that you ignored them and left them behind. And then the new people are not bought in. Yeah. And so, I don't know, it's just about really having a relationship with the people that you build for, right? When I'm working on lettering pieces or typography pieces or whatever, people are like, well, how did you like land on this or whatever? And I was like, the work told me what to do, right? You know, like we were working through it and that is what it told me it needed to be, right? And that's why, um, you know, when we were talking earlier about process and why I really like to keep the process both like segmented and whatever, but I also don't want to think I can solve every problem before we get started because you're gonna encounter new problems as you're working.

Yeah.

And you need to be able to evolve the vision of a thing based on the reality of the experience of the thing, right? That's another tie-in to studio works and why it's been really fun to be a product designer and like to think about product thinking is like, I've always sort of— like, even when I learned web design stuff, like, I learned web design in college in like Flash and Dreamweaver and then left it alone, of course. And then it was just about editing existing CSS. So then when it came to like building websites, I never designed in Photoshop or anything. I just designed in the browser. So I would build the structure and then start carving carving the structure like it was a sculpture, you know? And I feel like that way of working, sort of thinking about everything as a raw material that you have to kind of like hone and push towards a final, it's— it totally translates from art to product design. Yeah. You know, with product design, it's about really understanding the material and how people are going to relate to the material, right? Because you might have a vision about what you want that material to look like, right? But if the material doesn't behave that way, you can't make it look that way, right? You know, and so it's about like following the material and following the experience with the material to the end. Yeah, you know, to where it will be, right? And I think that like a lot of people that get into the visual arts, um, they, they sometimes do just have a really clear picture about what they want a thing to look like. And for me, it's never about what it looks like, it's just about what it became.

And I think that's maybe when I think about like the great sins of software as a field in its industrialization. I think a lot of designers got divorced from production. They sort of got to a place where like working on the blueprints, on the schema, on what it should look like, and stopping there, it sort of seems to be this recurring folly. Yeah, yeah. People who sort of stay close to the metal, stay close to production, are the ones who ultimately shape what's out there in the world.

Yeah. I think it's also been interesting to watch the sort of templatification of everything infect product design. Yeah. Where there is this idea that the best way to build is a way that is more template-based and more, I mean, I guess by default scalable because you can easily roll lots of things out based on a very small set of of visuals and constraints, but it never really gives the content that the design is around its full breadth of interest and shine and whatever. They're never really fully married. They exist in the same space, but they're not married. They're not one. It is sort of like a marriage. Sometimes you'll meet people and it's two people and it's two people that are their own islands and they happen to be married., and you're like, I guess it works. Yeah. And then you'll meet people where over time those two islands turn into one mega island, and then you just can't tell the difference between who's one and who's the other. You don't see the boundaries anymore, and you're like, that's kind of incredible that I can't see the boundaries. Clearly they're two independent people with independent minds and whatever it is that they do, but they're so intertwined that you feel like that relationship just must be the solid thing that has ever existed. And I feel like the whole treating content and experience separately of the visual design and not completely integrated is— you never get to that point. And that's why it's really easy to throw away the design and why people can just like, oh, we should rebrand or we should do this or we should do that because it was never integral into the experience.

Yeah, you know, it's like a space that's wholly furnished in IKEA furniture feels that disposable in that way. It's like easy to compose, easy to put people in. Yeah, but it doesn't sort of feel like a coherent object, like one thing.

What it also shows is a lack of trust in the thing you're designing, right? Because if you don't invest in the thing and kind of treat it as a thing that is disposable, you're showing that you don't believe it will last. Right. You know, interesting in that way. That's why I do think, like, you know, people talk, does craft matter, blah, blah, blah, blah, all that kind of stuff. I think that there is something that happens when you see a real investment in how things are built and how things are made, where you really believe that this thing is going to last. Yeah. Because of how people are making it. Yeah. If you've bought a house that was like in like a quick fab flip off the shelf thing and look behind the walls, Everything behind the walls is total garbage because that person doesn't care about that house lasting. But if a person takes the time, builds it right, starts from absolute nothing and cares about every wire, every pipe, every whatever, they're doing it because they believe that thing is going to be here in 100 years.

Yeah.

You know? Yeah. And it's really interesting to work with people that think that way. Yeah. I think about that in terms of like building software and stuff too. But also I'm kind of into like Let's just get it out there and, like, see what people think.

Yeah, I was gonna say, I can't wait to revisit this conversation. Yeah, 2, 3 years. No, but what you're really kind of immersed in.

No, I mean, what has been interesting though is that, like, I have been coming at it in terms of the engineering from, like, a shouldn't we just, you know, see, like, get this out, get it in hands, evolve it, whatever. And our engineers such flippin' purists. They are like craftspeople. I know. And so, no, but in a good way. Yeah. Because they're like, we're taking the time and building the infrastructure of this thing in a way that will make everything in the future easier and better. You know, we're not going to be unmaking our work. We're not going to be like completely rethinking things. It's going to be like, like, it'll— we're building on top of it, right, in a way that's not putting Band-Aids on top of it, you know, like we're actually like, you know, using it as a foundation rather than us like slapping things together and like doing a bunch of workarounds to make sure it still works, you know, is that the one approach presumes that you have to meet problems as they arise over time.

Another approach says we will manage profitably our own sustainability and growth. We don't need a million people to sign up. Yes. For us to be successful. Yeah, we would chart a different course. Yeah. And in both models, and this is the thing I've loved, like, talking to designers from different walks of life, is that the reaffirming thing to me, the thing that makes me optimistic, is that there's like no one true path. No. Yeah. Right. Because it also, you can sort of choose a game to play. Yeah.

How you win at that game. And it depends on what's in front of you. Yeah. You know, because if you're working on a brand new thing that there's no past experience of that thing existing, you're innovating, you're doing something new and fresh and awesome, and you need the world to see it. If you spend a year handcrafting a thing without ever putting it out there, you're missing your opportunity to like come in and be that person that does that thing. Yes, absolutely. Yeah. But if you are making a more succinct, better, more well-crafted version of a thing that does exist, right, that still for whatever reason with all the people that have ever worked on it has a bunch of insane pathways and experiences and flaws to the process of working with that thing, yeah, then you're like, okay, well, the thing that we are bringing to this is that all of those bugaboos that people have had to work around over time are just not there. And then all the things that that place didn't want to do because it didn't serve enough people, we are going to do. It's a totally different thing. And I think our engineers would feel really differently and would be building really differently if we didn't have like 900 people signed up to like be paying on day one. Yeah, you know, like if it was like still no feedback, we don't know how this is going to land.

Right.

It would be a very different thing. But because we know that like the second that we launch our invoicing platform, we have 900 paid customers. That's like a totally, totally different way of operating. Very different stance. Yeah. So you can come from a place of like trust of just like, this is worth it. What we have to do is meet the expectation of all these people that are here and waiting, right? You know, versus we need to be the first out the gate or we have to, you know, do the thing that's different and we have to like, see if it works.

Yeah. You know? Yeah. And I think for the, like, steelman the case, your end users will intuit all that work and craftsmanship in a way that maybe other target market segments may not. Yeah.

And also, too, like, we can show them, you know, like we've done AMAs and walkthroughs and like talked through how we think about color and like all kinds of stuff, right? In a way that not only allows us to sort of let them in on the process. And again, like, the more you bring people in on the process of creation, the more they become advocates for the thing that you're giving them.

Yeah, yeah. They're not just paying for the software.

No, they're paying for the whole thing. Yeah.

And they feel like—

patronizing the whole— we want them to feel like this is for them, you know, it's theirs. Yeah, you know, and that they have a say. And if they understand why it's better and all the thought and intention that went into everything and is going into everything, then if they're staring at their bank account at the end of the year going, I only sent like 10 invoices, should I keep paying for this thing? They might not think about canceling it because they're like, no, I think this thing is still good.

Yeah. Well, my hope is that in much the way we've seen like the rise of like boutique hotels, we'll see like boutique software shops. I hope so. Serving a really loyal fan base that are not just buying like the utilitarian aspect of it, a roof over my head, but a full-blown experience and the intimacy with the makers of said software.

I think a lot of like, that's really like Chris and I have talked about this, and one of his biggest goals is to be an example of what other people can do. You're a parent. I'm a parent. I'm sure many of your future viewers of these videos will be parents. Like what you learn is that you can't tell kids what to do, but you can model the behavior you want in them. And I think that there just really aren't enough examples of people that, like, are truly respecting the people that they're building for. Yeah. And have them in mind at every step and want to make a business that is not about enriching yourself necessarily. It's just about making a thing that will last.

Yeah, yeah, yeah. And treating them like their aspirational selves. Right. Condescending to them. Them. Exactly. I also think that's sort of like a balancing act with parenting too. You want to make sure that you're treating your children in their highest form. Yeah, rather, rather than kind of like regressing to reacting to children being children. Can we end on that note? Like, how has parenting reshaped everything for you in a way that you feel like has at least allowed you, afforded you the ability to maintain some continuity between pre-parent and post-parent Jessica?

It's obviously— parenting changes a lot about your life, and it changes a lot about your priorities. Yeah, I feel like it shifted things in a really good way for me because I feel like it just became a lot easier to say no to things that I didn't feel like were gonna be the right thing. If it didn't pay well enough, or my heart wasn't in it, or it just didn't seem cool enough, or the people didn't seem very nice, or whatever, it's just easy for me to say no because I'm just like, if it's between me spending extra time doing this or me going to a school play, I'm gonna pick a school play any day of the week. Yeah. Unless it's like insanely compelling and then the school play can get recorded, you know? So you just get like a much higher bar for like what's going to eat up your non-work time. Yeah. And so it really has to be like an incredible opportunity to take you away from family stuff. Right. Being close to the world of tech and entrepreneurialism and of course, like being an entrepreneur. But I'm like me, you know, like I definitely also get like imposter syndrome when I get invited as like a leader or whatever to things. And I'm like, they're like, oh, how many employees do you have? And I was like, 2, me and my mom. And I've got a couple of people that work in my shops that are actually just underemployed designers, you know, like whatever, which is a really different thing than when you talk about people that are like empire builders, you know, like I— Yeah. I got invited on like a ladies retreat thing, and the two other like creative women there were Anna Bond, who founded Rifle Paper Co., and Justina Blakeney, who is like the founder of the Junglo. And it was like the three of us, and I was like, I feel like this is a false comparison because you guys actually have like made massive shit. And they're like, no, no, it's different. Like, you know, and Justina, you know, she was like a fan of mine before her thing And I'm, like, obsessed with her and both of them, such big admirers of, like, everything that they've made and built. But what I've sort of realized is in building things around the life that I want to live, I've actually sort of, like, I've come to the other side of the hill that a lot of people are always trying to get to. You know, I was, like, hanging out with all these, like, really powerful people and they were talking about like, man, I can't— I'm actually in the process of selling my company. I can't wait because then I can do this thing and I can pursue this creative interest and I can do this and whatever. And all of it just made me realize like I'm already doing the thing that they dream to do. Right. You know, and that was like, at first I came at it and I was like terrified and, you know, like felt like an imposter and felt like I was Oh my God, have I just been leaving all this stuff on the table? I could have been doing this. Look at all these opportunities and I'm just not doing them. What's wrong with me? But the more I sort of started listening to other entrepreneurs and really powerful business people's dreams of the future that they want for themselves, the more I realized that everybody dreams about living a life that looks a lot like mine. And then it just made me so grateful. And I think that knowing that As a parent, I bring so much of that to parenting of just being like, all I want for you is to find the thing that makes you happy. I don't care what it is. It doesn't matter. If my kids see me working after hours, because I wasn't working after hours hardly at all, and then Studio Works happened, and now I'm kind of a workaholic. Whenever they comment about, man, mom, you work a lot. I'm just like, only because I love it. You know, I always say that. I'm like, only because this is really fun for me. Yes. You know, like, I'm only doing it because I'm really interested and this really makes me happy to do this right now. Right. And that's what I want them to get, you know. Yeah. Who they become in the world is really my biggest priority and the thing that I should be the most concerned about. But that actually living my life in a way that I pursue joy pursue creativity, like I'm doing all the things that I'm trying to do to make myself happy, yeah, all it does is show them that that's important, right? You know, and it shows them that it's worth it and that you don't have to not do that. You can be successful and also chase joy.

Yeah, you know, and you have a fluency in that, like that you— it requires a degree of self-knowledge, knowing how you thrive. And at the end of the day, it's like giving yourself exposure to the things that make you thrive and almost in an unapologetic way.

Yeah. And honestly, like, it's been really interesting because we've just kind of discovered that our whole household is like neurodivergent, which is like, of course. And so, which I think is just a very common creative space. I just feel so lucky for it because I feel like all the things that made me who I am is just because like my mind has to operate a certain way. It works at a certain pace. Rather than feel like I'm operating at a pace or in a way that is non-compliant to the way that the world works, I just made my own world. I hadn't really realized that because I didn't think of myself as being all that different, but when I actually walk through all the tactics and whatever that I've done and the ways I've navigated burnout and all that kind of stuff, it's all just like, coping and tools and like building a universe around my unique way of working and walking through the world. And so what's amazing about that is now that I see my kids, and at least one of them, probably two of them, have ADHD, I'm not coming at it as like, this is a disability we have to deal with. I'm like, oh my god, you guys have this crazy superpower. We just got to see how to harness it. You know, like, yeah, not everybody has this. Yes. And not everybody can access the things that you can access. Yes. You're going to be able to do things that other people cannot do. Yes. There's also going to be stuff that trips you up, but we can deal with that. Yeah. But how do we figure out how to take this superpower that you've been given and pump it into something that you love to do?

And I love that stance because what you just described is harnessing luck. That's exactly it. It's like that. It's like it's not being resourceful. Yeah, it's like there's a degree of like optimism. Yeah, and expecting the best out of every circumstance.

It's looking at everything that you encounter in life that there's an opportunity to find from it. Yes, you know, like I think there's— if you come at it from the religious end, it's like there's a plan. This is the plan. Like, oh, this bad thing happened, but it doesn't matter because it's part of the plan. But if you come at it from a How can this thing inform me and help me? Whatever it is, negative or positive, what do I take from it to turn it into something positive? Then it's like every bad thing that happens, like some bad stuff just fucking sucks, correct? Yeah, but there's literally always a good thing that comes from it.

Always.

There's never Yeah, I think even the worst thing that could ever happen, there's always something good. Yeah. And it's really hard to see that good when you're in the middle of it. But the good is there. And trying to focus on that is always like the thing to do. And if you can just keep pursuing that, you just will always find your way. You know, like you'll always find your way out of anything. You'll always find your way into something that's successful. Because you're looking for the good thing.

Yeah, I think that's a beautiful place to stop. Um, thank you for having us here. Yeah, this conversation in this beautiful space in the world you've built.

Well, thank you very much for having me.

Thank you.