Design Better Podcast Summary

Episode: Jessica Hische and Chris Shiflett: Designing business tools that support how creatives actually work
Date: December 9, 2025
Hosts: Eli Woolery & Aaron Walter
Guests: Jessica Hische & Chris Shiflett
Theme: Building human-centered tools and community for independent creatives, grounded in design values and lived experience

Episode Overview

This episode centers on how legendary designer/illustrator Jessica Hische and web veteran Chris Shiflett have teamed up (with Nick Sloan and Sean Coates) to create StudioWorks—a business platform for creative professionals built from lived frustrations and a shared commitment to community over hyper-growth. Recalling the magic and lifeblood of New York’s Studio Mates and the Brooklyn Beta conference, the conversation dives into how the best creative tools go beyond features, rooting themselves in generosity, professionalism, and authentic connection.

Key Discussion Points & Insights

1. The Magic and Lessons of Studio Mates and Brooklyn Beta

• Studio Mates’ “Embarrassment of Talent” Era (03:06)

  • Jessica recaps the power of transitioning from solitary work to a physical community: “I was super lonely...I heard of Tina’s spot...I moved in...me and Chris and everybody really hit it off immediately.” (03:26)
  • The beginnings of organic support culture: “Beer Fridays” and spontaneous connection.

• Golden Age of the Web & Early Twitter (04:44)

  • Chris: “It was this period of experimentation...It was just a really magical period of time. It’s a great time to get to know people.”

• Brooklyn Beta’s Founding Spirit (06:40)

  • Chris describes mimicking the radical hospitality of New Zealand’s Webstock, treating everyone as a VIP through detailed, friend-written badge bios.
  • Jessica: “...it brought diverse skill sets and perspectives into a single place...really speaks to how awesome the event was and the community that you built around it.” (09:50)
  • Creative events as culture-builders, not product showcases.

2. The Birth of StudioWorks: A SaaS for Creatives, by Creatives

• From Frustration to Founding (11:18)

  • Jessica’s urge: “No one's making stuff for the pure joy of it...I want to build cool products for a more niche audience.”
  • Chris: “We had a lot of the same pain points...helping people like us...[make] tools that were just a lot simpler and more bespoke.” (13:27)
  • Emphasis on bootstrapping, not VC: “We would rather dive into building a good small business rather than trying to shoot for the moon with everything.”

• Building a Team with Skin in the Game (16:28)

  • Identifying co-founders who “need it to succeed,” not just build a cool project (27:44).

• Turning Experience into Impact

  • Jessica: “StudioWorks was the thing that took every single thing that I've done in my life and just distilled it into one thing.” (16:33)
  • Helps other creatives “get paid better, manage their time better...so they can have a more sustainable career.”

3. What StudioWorks Does Differently

• Invoicing and Client Relations (18:19)

  • Prioritizes the real ways clients pay (“every which way from Sunday”).
  • Refuses to take a cut: “We're not trying to make money from your money. So we don't take any transaction fee from anything...” (19:19)
  • Allows clients to mark invoices as paid in various ways, offers advanced reminders (“heads up before a reminder gets sent”), and makes interactions human and dignified.

• Light, Human-First CRM (23:12)

  • Aims to be “a very human CRM,” not a generic sales pipeline.
  • Features like birthday reminders, top-of-mind nudges, and seamless contact management.

4. Design, Entrepreneurship, and the Power of Community

• Designer Superpowers Beyond the Obvious (26:06)

  • Jessica: “One of the biggest things is actually building for an audience that you really care about.”
  • Chris: “Designers bring a lot of observation skills...identifying weak points in experiences...details that other companies would never bother addressing.” (27:59)

• Anti-Venture, Pro-Sustainability Mindset (29:05)

  • Jessica: “Start by trying to make a modest small business...downsize as best you can...try to get that going.”
  • Describes the pitfalls of VC-driven product pivots for designers.

5. Community and Giving as Core Values

• Generosity Machine Vision (33:14)

  • “Our vision is to really make StudioWorks into this generosity machine for the community...a safe landing spot for [new freelancers]...we do not believe in the whole, because I went through a hard thing, you have to go through a hard thing.” (33:14)

• Resources and Built-in Education (36:04)

  • Community chat for advice, in-house workshops, resource libraries for both creatives and their clients.
  • “Giving our studios...the resources for their clients...a continually updated place...all the things you ever need to clarify with your clients.” (36:04)

6. Choosing Partners, Company Culture, and Growth

• What Makes a Good Co-founder/Team (38:30)
  • Chris: “Opinions need to be independent from the people who hold them...If no one really remembers whose idea certain things were...that’s a healthy culture.”
  • Jessica recalls her “Internet Sends Me Cake” project as a test of positive energy and trust. “If you build the thing that has the energy that you want, the people come to it that have that energy as well.” (41:44)

7. Thoughtful Product Design: Simplicity and Dignity

• Beautiful, Branded, and Simple (44:04)

  • “We wanted to make it feel like a white labeled, fancy pants, custom developed thing for each of the studios...” (44:46)
  • StudioWorks highlights their users’ brands, not its own.
  • Collaboration between Chris (minimalist, streamlined) and Jessica (adds warmth, narrative) enhances user flow and delight.

• Radical Simplicity & Rethinking Bookkeeping (49:00)

  • “We really scrutinize everything...so we can make this product richer...without falling into the trap of so many other companies that just continue adding features and features and features until the thing feels overwhelming.” (49:00)
  • Jessica’s “Roman Empire”: convincing creatives they don’t need complex, expensive accounting tools—“just export your CSVs!”

8. The Why of Independence

• Freedom to Align Work & Life (54:31)

  • Jessica: “I love the flexibility to be able to have my business map to my family rather than having my family map to my business.” (54:35)
  • Chris: Independence as “the feeling of freedom.” Draws parallels with biking, backpacking—everything you need is with you.

• Embracing Fear, Survival, and Ultimately Curiosity (57:32)

  • “The entrepreneurial spirit is not natural to most people...it starts out as a survival mechanism...but eventually you operate out of curiosity and passion.” (57:32)
  • Jessica’s “Batman and Bruce Wayne” metaphor: financial stability allows creative risk (59:36).

9. Sources of Inspiration & the Role of Creatives

• Inspiration in Community (61:54)

  • Chris: “I'm inspired by everyone that's pursuing something that they really want to, even though it's hard.”
  • Jessica: “Artists and creatives...remind those people why the world is worth saving. We need to create joy and beauty.”

• Personal Creative Pursuits

  • Jessica: “The thing that's lighting me up right now is doing stained glass...even if it goes nowhere.” (64:27)
  • Creating for joy, not monetization.

Notable Quotes (with Timestamps)

• On Building Positive Energy:
  “You attract the energy that you put out into the world. If you put out trust, if you put out generosity, if you put out the things that you want reflected back to you, that's what you get. If you build the thing that has the energy that you want, the people come to it that have that energy as well.”
  — Jessica Hische (00:02, also reprised at 41:44)

• On Community:
  “We do not believe in the whole, because I went through a hard thing, you have to go through a hard thing...All we want to do is make something that can help other people on their path.”
  — Jessica Hische (33:39)

• On Launching for Love, Not Growth:
  “We would rather dive into building a good small business rather than trying to shoot for the moon with everything that they make and build.”
  — Jessica Hische (11:18)

• On Design’s Hidden Value:
  “Designers bring a lot of observation skills...help identify weak points in a lot of experiences...I think designers are really good at noticing things because anything that's not quite right really stands out like a sore thumb.”
  — Chris Shiflett (27:59)

• On Simplicity:
  “We almost want to be provocative with how simple we make these tools...wait, is that all I need to do? Is that all the bookkeeping I need to do?...We're really trying to give designers their dignity.”
  — Chris Shiflett (49:00)

• On Indie Life:
  “I love the flexibility to work on things that I'm passionate about when I'm passionate about them.”
  — Jessica Hische (54:35)
  “...there's also like this emotional part of it that's the feeling of freedom. I don't know why, but that's always felt really important to me. And I'm happiest when I feel free.”
  — Chris Shiflett (55:55)

• On the Role of Creatives in Difficult Times:
  “Artists and creatives...their job is to remind those people why the world is worth saving. We need to create joy and beauty. That’s really one of the main functions of art, is just to show what humans are capable of and the beauty in the world...”
  — Jessica Hische (62:58)

Key Timestamps for Important Segments

• Intro and Studio Mates Origins: 00:02–05:30
• Brooklyn Beta and Community Lessons: 06:04–10:49
• Why Build StudioWorks & Team Formation: 11:18–16:33
• What StudioWorks Does and Vision: 18:19–25:12
• Designers in Entrepreneurship: 26:06–29:05
• Company Culture and Sane Growth: 38:30–41:44
• Design & Product Philosophy: 44:04–53:11
• Independence and Balancing Life: 54:31–59:36
• On Creativity, Resilience, and Inspiration: 61:54–65:16

Memorable Moments

• Internet Sends Me Cake: Jessica’s quirky social experiment shows how whimsical acts can foster genuine community trust (41:44).
• The Batman/Bruce Wayne Metaphor: Frame your day job as “Bruce Wayne” enabling your creative “Batman” to exist (59:36).
• Resource Library for Creatives—and Their Clients: StudioWorks aims not only to empower its users but arm them to educate their clients effortlessly (36:04).

Summary

This episode is a heartfelt masterclass in designing for, and with, your community; it’s a powerful argument for slow growth, sustainable business, and tools that honor both the messiness and humanity of creative life. Hische and Shiflett make a compelling case: meaningful design is about noticing the details no one else does, and the best business tools are those that let you spend more time being a creative human—and less time feeling overwhelmed or overlooked.

Learn more about StudioWorks at the special Design Better link: joinstudioworks.app/appdesignbetter
— Discount available for listeners if you sign up before the end of the year (66:10).

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