Can artificial intelligence actually be funny, or is humor still a human stronghold? We explore that question with Eric Doyle, co-founder of ComedyBytes, a Brooklyn-based multimedia comedy show where AI and humans face off in roast battles, dating games, and other interactive formats. Doyle combines the craft of stand-up with the tools of generative AI, building AI characters like “AI Kanye West” or “AI Sarah Silverman” that deliver pre-scripted jokes in real time.

In this episode of AI-Curious, we dig into:

• [0:52] The story behind ComedyBytes and its AI-powered format
• [3:46] How AI roast battles work, from concept to stage mechanics
• [7:53] Using tools like ChatGPT, Claude Sonnet, and Gemini AI to write jokes
• [12:55] The art of prompting for humor and boosting the “funny hit rate”
• [16:36] Why specificity matters in generative AI comedy
• [23:43] Inside the “Data-ing Game,” an AI twist on the classic dating game
• [25:58] Can AI really be funny—or just imitate the structure of humor?
• [32:30] The triple, listing technique, and other joke-writing structures AI can learn
• [39:10] Advice for non-comedians using AI to add humor
• [41:24] The future of AI in entertainment and its impact on creators

From the structure and anatomy of a joke to the ethics of deepfake comedy, this conversation blends technology, performance, and the evolving role of AI in creative work. Whether you’re an AI enthusiast, a comedy fan, or simply curious about where these worlds collide, this is a look at AI and humor you haven’t heard before.

Is Kant the new code? If AI can write, code, and even plan, which human skills suddenly become scarce—and valuable?

In this conversation with Robert Capps (former Editorial Director of Wired, contributor to The New York Times Magazine), we dive into his widely shared NYT Mag feature, “AI Might Take Your Job. Here Are 22 New Ones It Could Give You.” We unpack the three big buckets of new work he sees emerging—Trust, Integrators, and Taste—and explore why philosophy majors, auditors, and “AI translators” may be the surprise winners. We also get frank about hallucinations, over-extrapolation, inequality, lethal autonomous weapons, and why Rob still comes out more optimistic.

In this episode of AI-Curious, we:

• Break down Rob’s three buckets of future AI jobs: Trust (auditors, ethicists, legal guarantors), Integrators (the translators who know both your business and the models), and Taste (the Rick Rubin-esque role of vision, judgment, and curation).
• Talk about why Ethan Mollick refuses to let AI write his first drafts—and why that matters for your own thinking.
• Examine how “the tools will be commodities, not the people,” and what that means for founders, creators, journalists, and scrappy upstarts.
• Get into the very real risk of inequality and policy paralysis—and why UBI isn’t a satisfying answer.
• Preview Rob’s documentary on AI weapons and the fight to keep humans in the loop.

Takeaways

• Trust work explodes. Expect a cottage industry of auditors, ethicists, and “legal guarantors” to ensure AI output is accurate, defensible, and compliant.
• Integrators win inside companies. The most valuable people will be those who can translate between business reality and fast-moving model ecosystems.
• Taste is leverage. Vision, taste, and editorial judgment—knowing what good looks like—become the human moat.
• Beware first-draft capture. Letting AI write your first draft can quietly dominate your thinking (Mollick’s rule is worth adopting).
• Inequality is the real threat. Most experts Rob spoke with fear a rapid widening of inequality more than mass permanent joblessness.
• Tools, not people, become commodities. When everyone has Goldman-tier tools, expect disruption from the bottom, not reinforcement of the top.

Rob’s NYT Magazine piece: “AI Might Take Your Job. Here Are 22 New Ones It Could Give You.”

https://www.nytimes.com/2025/06/17/magazine/ai-new-jobs.html

Could AI actually improve public education? Not just automate it, but make it more personalized, more equitable — and even more human?

We explore this possibility with Dr. Michael Everest, founder of edYOU, an AI tutoring platform being piloted in a Denver-area school district. While many worry that AI could become a shortcut for students to avoid real learning, Everest argues the opposite — that AI can reinforce understanding, boost confidence, and offer 24/7 support tailored to each student’s needs.

In this episode of AI-Curious, we dig into the real-world mechanics of how this works — including partnerships with schools, how teachers interact with the platform, and what kind of results they’re seeing so far.

We also ask the tough questions: What about data privacy? What about bias and hallucinations? Is there a risk we’re outsourcing critical thinking? And what does the future of education look like if every student has a lifelong AI companion?

Topics include:

• The promise and pitfalls of AI in classrooms
• edYOU’s pilot program with Adams 14 School District
• How the AI tutoring platform personalizes learning
• The role of teachers in an AI-enhanced education system
• Oversight, privacy, and academic integrity
• The vision of a lifelong AI learning companion

Whether you’re a parent, educator, technologist, or just curious about where education is headed, this conversation offers a grounded, hopeful — and at times provocative — look at the future of learning.