Most weeks, as a VC, I’m talking to founders who want to build huge, global, venture-scale companies. So this conversation with Jessica Hische was a breath of fresh air.
Jessica is one of the most recognised names in modern graphic design, illustration, and lettering — known for work that ranges from book covers and rebrands through to designing the titles for some well-known Wes Anderson films. She’s also now the co-founder of StudioWorks: a beautifully designed tool for proposals, invoicing, and the unglamorous admin that quietly decides whether a creative business runs smoothly or feels like chaos.
What makes StudioWorks interesting isn’t just the product. It’s the ambition behind it. Jessica isn’t trying to boil the ocean. She’s building a small, ethical, indie software company for a community she understands in her bones — because she is the customer. She knows the proposal scramble, the client wrangling, the awkward money conversations, and the way most business software makes creatives feel like an edge case.
We talk about the decision to skip traditional VC — not as a humblebrag, but as a design choice. One that shapes incentives, pricing, and what gets built. The goal isn’t “growth at all costs”, it’s something closer to the Basecamp philosophy: a calm, profitable, sustainable business with thousands of customers, not millions.
And Jessica gets refreshingly concrete about the maths. With the right audience and the right price, you don’t need massive scale for this to work. A thousand paying customers can already be meaningful — enough to support a small team, build something beautiful, and keep the company human.
If you’re a designer who’s ever thought “surely there’s a better way to run a studio”, or a founder curious what bootstrapping looks like when you choose it on purpose, this episode is for you.
