Whoa, Vol. 2: Conversations on AI × Creativity

Sublime
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22 snips
Oct 24, 2025 • 1h 11min

AI Critics Should Do Some Moral Soul-Searching — Venkatesh Rao

Venkatesh Rao, a writer and consultant focused on technology and culture, explores how AI challenges traditional notions of authorship. He argues that AI should be seen as a medium for our shared cultural heritage rather than a threat to creativity. Rao discusses the illusion of effort in creative work, claiming that originality comes with risk. He also emphasizes the importance of playful experimentation with AI, likening it to Lego-building, and envisions a future where AI facilitates collaborative learning and creative contribution.
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17 snips
Oct 17, 2025 • 58min

I Don't Care if a Robot Wrote It. If It's Good, It's Good. — Joan Westenberg

Joan Westenberg, a writer and strategist known for her insights on creativity and responsible AI use, explores fascinating ideas about the intersection of technology and artistic expression. She shares her journey of deleting her 'second brain' to regain authenticity in her writing. Joan emphasizes using AI for tedious tasks, not for creative passions. She discusses the importance of human oversight, the fear of being replaced by AI, and how absurdism can inspire unique creativity. Ultimately, she advocates for focusing on quality work over the medium it’s created with.
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25 snips
Oct 10, 2025 • 1h 2min

How David Perell Uses AI to Unlock His Playful Side

Join David Perell, a writer and educator known for his insights on AI and creativity, as he explores the dynamic interplay between technology and artistry. He discusses the decline of beauty in modern design and how AI affects the quality of writing, asserting that exceptional nonfiction is more vital than ever. David shares his unique approach to using AI, blending humor and creativity while maintaining the essence of personal expression. He also highlights the burgeoning value of live performances in an increasingly automated world.
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Oct 3, 2025 • 50min

The AI Debate Is Not About Art, It's About Money — Jasmine Sun

In this discussion, writer Jasmine Sun shares her journey from Substack to full-time writing, driven by her fascination with AI. She reveals how she utilizes large language models like ChatGPT for research and creativity, promoting transparency around AI usage. Jasmine argues that economic concerns, not aesthetic fears, underpin the anxiety about AI in art. She highlights the potential of AI to enhance human creativity, urging artists to adapt and upskill in response to these technological shifts.
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Sep 25, 2025 • 1h 9min

Quit Optimizing for Algorithms. Make Something Weird — Robin Sloan

In this conversation, Robin Sloan, a writer and creative technologist, dives into his unique approach to AI and creativity. He reflects on his early experiences with GPT, noting how AI writing often lacks the depth of human choice. Robin highlights the challenges AI faces with comedy and surprise, while advocating for a return to analog formats like zines for richer connections. He emphasizes the importance of criticism and discovery over algorithmic noise, predicting a future where creators embrace offline mediums alongside digital tools.
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41 snips
Sep 19, 2025 • 39min

The "Talking Dog" Theory of AI — Seth Godin

In this discussion, Seth Godin, a bestselling author and marketing guru, dives into the evolving relationship between AI and creativity. He likens AI to weather—unavoidable and disruptive. Seth shares how AI has boosted his daily creativity from one to seven hours. His intriguing 'talking dog' theory highlights that while AI can generate content, it lacks true understanding. He urges creators to think about making their work harder with AI, rather than easier, and emphasizes the growing value of community in a tech-driven landscape.
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Sep 4, 2025 • 1h 12min

Why Substack's Head of Design Thinks LLMs are Overrated -- Mills Baker

In a thought-provoking conversation, Mills Baker, Head of Design at Substack, discusses how AI is reshaping the creative landscape. He critiques LLMs as producing mere pastiche instead of true creativity, sharing his bearish views on their reliability and ethical implications. Mills highlights the importance of maintaining human voice in writing and warns against the hype surrounding AI, predicting that genuine creative talent will always be in demand. With insights on tech’s future, he emphasizes focusing on what creators love, not what they dislike.

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