Lettering artist to software founder: Jessica Hische on founding Studioworks

"The most successful people are people who just made the thing they wish that they had."

Aug 21, 2025

Jessica Hische has built a legendary career that spans from lettering for Wes Anderson films to designing stamps for the USPS, establishing herself as both a New York Times bestselling author and one of the most recognizable names in design. Now she’s channeling that expertise into something different: Studioworks, a suite of business software designed specifically for independent creatives.

The idea came from her own frustration: existing tools for managing creative businesses weren’t built by people who actually run them. So Hische and her three co-founders decided to build their own, without investors or a traditional corporate structure. They’re bootstrapping, staying small, and building what they wish they’d had as working creatives.

What we cover:

How Jessica got her start in design and lettering
Why necessity is the mother of invention when it comes to web design
How Studioworks’s co-founders make decisions without a CEO
The case for bootstrapping over taking VC money
How Studioworks built revenue from day one
Jessica’s pragmatic take on using AI in creative work

Key takeaways for designer founders

Find your own funding. Bootstrapping has benefits. Venture funding isn’t always the right move for all companies and all founders. Consider if you might be able to move more nimbly if powered by your own resources.
Build the tool you wish existed. The idea for Studioworks came from Jessica’s own frustrations running a creative business, which helped made the product specific and the positioning clear.
Charge early. Studioworks skipped the free trial and asked users to connect Stripe accounts pre-launch, which helped filter for real intent and gave the team signal on what features actually mattered.
Build loyalty with your earliest adopters. Your first users are taking a risk by paying for your product. Consider rewarding them with a lifetime founding member discount, or other benefits that will turn them into evangelists for your brand.
Learn the tools before you negate them. Take the time to learn how to use new tools so that your decisions are coming from a place of knowledge, not fear. Treat AI like any other tool. Jessica uses AI where it helps (e.g. verbal ideation, prototyping) but draws a hard line when it compromises the craft.

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Below is an edited transcript of the full conversation:

What led you to become a lettering designer?

Growing up, I loved drawing. It’s the one thing that has always given me joy. As a kid, I would draw for seven or eight hours a day. Even though I grew up in a small town and didn’t know what an art career looked like, I knew that I was going to be an artist.

I was really lucky to go to an art school that didn’t force you into a major when you first got there. I took graphic design for the first time as a sophomore and realized that I’m a very 2D person. I love all 2D mediums. Even in my sculpture classes, I basically ended up making 2D carvings or drawings on any of flat surfaces. I even did this really ambitious project in ceramics where I made 200 tiles that all had hand-carved dates and facts on them, and my teacher was like, “This isn’t really like what we were going for in terms of you taking a class within the 3D discipline.” Even in my painting classes, I’d get told my work was so graphic.

I was also not your typical art kid. There are artists who are always artists, and they have a lot to say about a lot of things. I just wanted to draw all day, and it didn’t matter what I was drawing. My passion was not necessarily about the subject or the feeling—it was about the doing. I really liked the idea that I could be given a project or a problem to solve, and that I could make art in response to that. I love constraints. If you give me an open brief and tell me I can do anything, I just freeze.

I also had a drive to learn new skills on my own. You learn X so that you can make Y. That’s always how I’ve worked. Part of that is, I went to kind of a scrappy school. I didn’t grow up surrounded by a lot of art, and it was expensive to hire other people. I had to find my own way through a lot of things. I’ve always tried to learn as much as I can on my own, to do the work as best I can on my own.

All of that led me to lettering. I realized I was best suited to illustration as an art form, and that I liked projects that were in response to problem solving.

You’re one of the most well-known working lettering artists today. How did that come about?

The reason why I ended up being such a big deal within lettering is because there were very few people doing it at the time that I started. It had kind of fallen out of favor after the 80s and 90s because of the massive explosion of display type that you could use on computers. Then people realized there were way too many options to sift through on their own and that they needed to hire a professional. There were a few of us who discovered this medium in 2007-2008 who were incorporating a lot of lettering into our work as illustrators or designers, which helped it emerge as a discipline on its own within this new context.

Two of Jessica’s iconic film title designs

When did you start getting exposed to the digital design world?

When I graduated in 2006, it was a turning point for web design. It was one of the last years of Flash being the thing. It was also the early years of Blogger. I wanted my blog to look like my website, so I started using the WYSIWYG editor, which led me to CSS manipulation. Then I moved my portfolio website and completely rebuilt it in WordPress. I ended up building a whole bunch of WordPress websites one year, and they got messed up by viruses because they were all on one Rackspace and accidentally got cross-pollinated. And so then I had to rebuild them as static HTML sites, which got me into PHP and jQuery. I had a button on my website for a while where you could turn my whole thing into “teen girl mode” or “field notes mode,” which was a jQuery style switch thing where it swapped out the regular CSS file to one of four other insane CSS files.

It sounds like you were really interested in the web as a medium. What drove that?

I have just always really loved playing around with the web as a medium because I’m kind of an instant gratification gal. I was lucky I started getting excited about bespoke little web stuff right when other people were really excited about doing bespoke little web stuff too.

I was driven by this idea that people are going discover and see my work through the context of my website, so I wanted my website to always be the truest reflection of who I am, what I’m interested in, and showcase my work in the best way possible. Plus, as an independent creative, it’s not like I have like an available web developer in my back pocket that I can pay $20,000 every year to redo my website. So I felt I had to learn that skill myself.

Did you ever think about going in-house with a company?

I’ve talked about this a bit on the internet, but I’m a recent ADHD diagnosee. Looking back, Ive realized that I’ve basically created my career to exist in symbiosis with the way that my brain works and focuses. To join a company, I think I’d have to have a very, very trusting boss who would basically give me free reign to pursue the all the things I want to do.

How did the idea for starting your own company emerge?

It had been a while since I had done a fun web project, and I was starting to feel excited about possibilities again. I wanted to make resources for designers again, in a way that would help shape their businesses.

I randomly reached out to my old studiomate Chris Shiflett because he loves doing little bespoke projects for niche audiences, and we had a really exciting two-hour conversation. We put a pin in it at the end, because we realized we would need a whole team to help make our ideas a reality. Then a week later, the two developers that he had just worked with on a project both quit their jobs the same day, reached out to him, and were like, “hey, do you want to build something together?” And so he called me up and said, “hey, you know that thing we were talking about that we said we couldn’t do right now because we need a real team? I think we might have a team.” It felt like such kismet.

It quickly went from a side project to “oh my god, I think we’re starting a company.” It all felt right though. You know how it goes when you start something and you feel excited about it, but then it’s like you hit this vein of gold, when you were looking for something totally different? Then once you hit that, you realize there’s this whole ocean of good stuff underneath it? All of a sudden, it’s like you’re drinking the most intense Kool-Aid you’ve ever had in your whole life about the new thing that you’re excited about.

How do you know when you’ve found that “vein of gold” idea?

I’ve had enough things like that happen in my life where you can just feel how things that were misaligned have suddenly come into alignment. That’s the moment—run with it!

With Studioworks, it’s felt like that the whole time. We’ve been working on building the first part of the product, which is an invoicing and payments platform, but there’s so much more. We want to build a complete business management product for small studios. We’re trying to solve all of the problems that come up as we grow.

What sets Studioworks apart from the competitors?

One of the things that’s really unique about what we’re doing is that we’re not trying to attract our customers’ clients as our own customers. We basically white label our whole website to look like our customer’s, so when their clients interface with paperwork via Studioworks, it just looks like they hired this crazy custom backend to manage everything.

That’s what gets me really excited—you’re paying not very much each month to look like you paid someone tens of thousands of dollars to make this custom backend for you.

As a company of co-founders, how do you make decisions without a CEO?

We’ve been really collaborative about the decision-making. We each have our columns where we have the most power. I have all the veto power on design, for example. If I ever say, no, this is more important, it doesn’t matter what anyone says, my decision wins out. Chris has more veto power in certain product decisions, and Sean Coates has veto power in systems decisions. We all weigh in on all the things, but ultimately, whoever is in charge of their vertical has the final decision on that issue.

How are you funding Studioworks?

It’s self-funded. Chris and I have been splitting the bills—under $15K each so far, mostly money for lawyers.

It’s definitely been a challenge because Chris, Sean, and I have families to support. Chris is basically a single-income household with three kids (his wife is a school teacher). I’ve had more flexibility because of passive income channels and having a high-earning partner, but because so much of my time has been dedicated to Studioworks this year I’m not doing as much client work, which still makes up the majority of my income.

How are you thinking about pricing and revenue?

It’s a revenue-in-the-door-from-the-jump situation. We had a pre-launch signup period in which Founding Members can sign up, connect their Stripe accounts, and be ready to go at launch but are not charged until that time. There were just under 1,000 Founding Members when we launched the private beta, and we’ve only had about 60 cancellations. These folks are paying $29/month for life—at public launch, the price jumps to $39/month for all new signups.

We’re still working out how we entice people to sign up with that higher price point. We don’t want to do a free trial and get a bunch of false information about who’s interested and who’s not. We have a few incentives we’re exploring—one is a referral program in which members can “give” a free month to new folks and once they convert to paying customers they get a free month in return. It’s similar to Dropbox’s model in which you would get free space for referring folks to the platform.

How are you thinking about company growth? What happens if Studioworks gets big?

Because we don’t have to grow like crazy as a company, we don’t have to build for every person on earth. We can just make the thing that matters the most to the people that would benefit the most from it, and not chase the money in every direction.

Building on that, our model for customer acquisition is going to be quite organic. We don’t have this plan to do a big splashy marketing thing because we don’t want there to ever be a sudden flood of customers—we want to be able to scale more slowly and organically. Our immediate goal is 3,000 customers. If we can get to 3,000, we are rocking and rolling. Then everybody makes a decent salary.

We’ll hire as needed to handle the influx of people, likely in customer service to field incoming questions and issues. What I what I don’t think I ever want to be is a hundred-person company. I’ve always had a real pull towards keeping overhead low and just being able to be nimble. When you’re responsible for keeping that many people afloat, it’s much harder to do that. I could definitely see a future in which we have 15-20 employees, though.

What does success look like 5 years from now?

Even if we don’t plan to grow beyond building for graphic designers, I would love for this to be something that all people in artistic disciplines use. It just makes your paperwork look awesome—super pro.

As a designer founder, how are you thinking about the role of AI in your work?

I don’t think it’s ever been a smart move to decide to not learn about something if you’re afraid of it, or think it is going to have a significant impact on your field.

Whether or not you’re into AI, you have to understand it very significantly in order to decide to opt out of it. You have to know what you’re opting out of and to be able to defend those reasons who want to pay you—or require you—to use it. Personally, I need to test the fences on this and understand everything that it can do. Where it makes sense in my process, and where it doesn’t make sense in my process.

I also had another thought about this recently. I was in the process of releasing the new version of my book, In Progress, which is a compendium of my work. As I was looking through the first version, I thought: what do I want the book of my work to look like in 20 years? Sure, having some 3D work and AI experiments makes sense, but if that’s all of the work, I feel like it would be really hard for me to feel my own hand in the work anymore.

I’m using that as a north light in how I use AI as a tool. I make sure that even if I’m using AI to help prototype or test textures, ultimately I feel like I have the most control over the final output of the work. It’s all about control, feeling like the final version of the work has been given a very fine-tuned polish by me. As long as I can do that, AI may find its way into different crevices of my creative process.

The revised edition of Jessica’s book *In Progress*

What are some of the ways you’re using AI today?

I often use AI for verbal ideation, when it comes to writing and coming up with concepts. Trying to spitball different words for “common terminologies within volleyball” for example. Really specific stuff like that.

I’ve also been vibe coding a bit on the Studioworks marketing page. Basically, “help me write a jQuery thing that when you touch this button, it does this thing over here.” It’s sort of like when you learn a new language and you can’t speak it, but you can understand it being spoken—I know the general semantics of the code enough to be able to read and understand it, but I couldn’t write it from scratch.

I also think AI will be helpful for prototyping in my work. I can give it a prompt, which can give me a prototype to share with a client to communicate the vibe I’m going after for a photoshoot, for example. But I don’t think AI is going to produce the final output, or the final work—it’s more about prototyping.

How do you think these emerging AI tools are going to change the design industry?

The story behind the work and the story behind the person making the work is going to matter even more than it ever has. Even more than the influencer era.

That’s fine by me because I love being a person out in the world. I do get worried about folks that want their work to be separate. Not everybody wants to have their face on the internet all the time, sharing what they’ve created. But I think AI is going to make that a requirement. The things that are going to have value are the things that will have a strong story behind them.

A thoughtful reminder from Jessica on how we should talk about AI (threads)

“The story behind the work and the story behind the person making the work is going to matter even more than it ever has.”

Do you have any advice for other designers looking to become founders?

You don’t need to go looking for problems to solve. Usually there’s a problem within your own life you’re dying to solve—and no one has solved it.

The people that have had the most success are the people who just make the thing they wish that they had. The thing is, you are not that unique. So if you make things that are just for you, they’re actually for quite a few people. There are probably 2,500 people on Earth that are carbon copies of me, and I just have to make things for those people. And if they like what I’ve made, then people that are 80% like me might like it, and people that are 70% like me might like it—and suddenly you have a large audience you’re making things for.

Just find problems in your own life to solve. Worst case scenario, you can feel good knowing you solved a problem you had.