Roadmap: Streamlined Onboarding and Proposals

Jessica Hische and Chris Shiflett first crossed paths at Studiomates, a Brooklyn based co-working space where some of New York’s most talented designers built businesses and influential organizations.

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Jessica, known for her lettering and illustration work with clients like Wes Anderson and The New York Times, and Chris, whose career spans from the early foundations of the web to co-founding Brooklyn Beta, both experienced firsthand what happens when passionate, independent creatives come together.

Today, they’re channeling those lessons into Studioworks, a business platform built specifically for independent studios and creative professionals. They’re tackling the unglamorous but essential parts of running a creative practice—invoicing, project management, client relationships—with the same care and community spirit that defined those Brooklyn days.

In this conversation, we talk about the magic of Studiomates and Brooklyn Beta, what they learned from running their own studios for years, and why they decided to bootstrap a tool for the creative community rather than chase venture capital. It’s a story about building something sustainable, beautiful, and genuinely useful for the people who make things.

Bios

Jessica Hische is one of the most beloved and influential designers of the past two decades. She’s best known for her lettering and illustration, but equally for her generosity in sharing what she knows. Jessica was part of the original Studiomates community in Brooklyn, has worked with clients like Wes Anderson, The New York Times, and Penguin Books, and now brings her creative leadership to Studioworks, where she and Chris are building better tools for independent creatives and small studios.

Chris Shiflett is a longtime friend of the design community whose career spans the deep foundations of the early web and the heart of the creative world. His early books on HTTP and web security became unexpectedly influential at a time when the internet was still taking shape, opening the door to some extraordinary projects — including one that generated nearly half of the internet’s traffic and another responsible for a fourth of the world’s email. After years helping big internet companies solve scalability problems, he realized he was more inspired by the people creating them — the designers, founders, and builders making things people love. That shift led him to the original Studiomates community, to co-founding Brooklyn Beta, and ultimately to the work he and Jessica are doing today with Studioworks.

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