As we put our course together, I want to have conversations with people who are thinking about things deeply, creatively, and responsibly. That's why it was an absolute pleasure to chat with my long-time internet friend, Jem Gold, technology as a creative medium, the soul of the early web, and the new era of AI-assisted making.

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Topics Covered:

◉The counterculture lineage of the web and why reclaiming it matters now
◉ Technology as artistic expression — Jem's concept of the "technology artist"
◉ The flow state in music and how it translates to building with technology
◉ Should designers code? Why the answer is changing fast
◉ Skill-driven development and teaching LLMs how to design (not just what to build)
◉ One-shotting beautiful, branded interfaces with minimal input
◉ Jem shows off some wonderful one-shotted demos
◉ Generative UI as superposition: interfaces that adapt to the person observing them
◉ Design systems, Web Components, and building durable foundations for a non-deterministic future
◉ AI as a creative process tool — not replacing the music, but clearing the way for it
◉ ADHD as a superpower in the agentic era

Links & Resources:
◉ Jem's newsletter: https://superposition.jem.computer
- Support Jem and her work for $8/month; and use code JEMANDBRAD for an annual discount
◉ Jenny Wen's interview on Lenny's Podcast: • The design process is dead. Here's what's ...
◉ The Grid (Jem's AI design startup, ca. 2015) https://thegrid.io/
◉ Everything Just Gets Built: https://superposition.jem.computer/ev...
◉ I Don't Miss Code https://superposition.jem.computer/i-...
◉ Real-Time UI https://bradfrost.com/blog/post/real-...
◉ "Ghostwriter" by RJD2 drum/synth cover • Ghostwriter by RJD2 -

• (00:00) - Chapter 1

Georgia Lupi shares what she’s excited to wake up for with us. She recounts getting COVID in 2020, developing worsening long COVID symptoms with reinfections, becoming house- and sometimes bed-bound, and stopping work in 2023 before beginning recovery in early 2024. Lupi and Brad discuss the anxiety and trauma that can persist during physical recovery, the scientific mind-body connection, and how nervous system regulation, brain retraining, and visualization became central to her healing. She describes publishing a New York Times visual op-ed using her symptom data, the messages it sparked, and how a conversation prompted her to commit to brain retraining, leading to slow but meaningful functional return and recent confidence saying she’s fully recovered, alongside an ongoing reintegration into work, creativity, and life.

Links:

• Giorgia Lupi
• "1,374 Days: My Life With Long Covid" — NYT Visual Op-Ed
• Dear Data
• Caravan Palace
• Parov Stelar
• Kormac
• DNRS (Dynamic Neural Retraining System)
• Gupta Program
• Post-Exertional Malaise (PEM)
• Limbic System / Vagus Nerve / Nervous System Regulation
• Psychedelic Therapy & Neural Rewiring
• Subway Map as Information Design
• Music Notation

Chapters:

• (00:00) - Morning Excitement Check
• (00:25) - Yoga Team Gratitude
• (01:18) - Long COVID Journey
• (02:46) - Trauma And Body Trust
• (05:38) - Brain Retraining Turning Point
• (06:18) - NYT Visual Op Ed
• (08:41) - Feeling Fully Recovered
• (15:02) - Reintegration After Recovery
• (17:11) - Returning To Creative Work
• (19:29) - Presence Priorities And Limits
• (23:21) - From Darkness To Acceptance
• (25:57) - Art Data And Experience
• (28:56) - Art Beyond Words
• (30:22) - Branding as Narrative
• (32:28) - Sketching to Think
• (33:25) - Designing Shared Languages
• (35:42) - Healing and Tracking
• (38:16) - Vulnerability and Sharing
• (39:27) - Dear Data Origins
• (43:36) - Learning Through Speaking
• (48:23) - Finding Your Style
• (52:31) - Obsessions as Projects
• (56:31) - Electro Swing Picks
• (57:40) - Where to Follow
• (58:03) - Closing Reflections

Ben Callahan joins Brad to discuss what’s currently motivating him, from enjoying homemade ham and bean soup in Ohio to a deeper focus on connecting people through curiosity-led facilitation. Ben reflects on a transitional season of life, the importance of personal and organizational values, and how communities work best when they’re allowed to form organically. He describes his annual values exercise, the role of sharing and teaching in web culture, and the need to reintroduce humanity after COVID. The conversation also explores music’s ability to create presence and unity, with recommendations including Chanticleer, Jacob Collier, and Radiohead.

Books

• Get Together — Building Community

Music / Artists

• Chanticleer
• Jacob Collier
• Bobby McFerrin
• Radiohead

Websites / Communities / Projects

• ben callahan.com — Ben's home base for everything
• The Question — Weekly open community design systems research project
• Redwoods — Ben's new paid community for design systems practitioners
• Sparkbox — Ben's consultancy
• Design Downtime — Podcast by Guy Siegall (Ben was a season 1 guest)

Chapters:

• (00:00) - Introduction
• (00:26) - What has Ben waking up excited?
• (09:37) - Community as Resistance
• (13:55) - Values and Learning Mode
• (35:08) - Hardship Resets Trajectory
• (37:52) - Sharing Culture Of The Web
• (42:46) - Music Presence And Connection
• (50:39) - Consciousness Curiosity And Openness
• (57:02) - Music Recommendations
• (01:01:00) - Where To Find Ben