Someone might panic if you call it a conference. Someone else wonders if ChatGPT would tell her if she's dumb. And a certain French bulldog named Gary refuses to get off the mic. It’s another classic episode: part community update, part philosophical debate, part dog-induced chaos.

In this episode, Megan and Nicole talk about what’s coming next for AI Portland: from a definitely-not-a-conference event to an upcoming build challenge with UFO-adjacent priorities. They also dig into the weird emotional weight of AI feedback, why sycophantic robots aren’t helping anyone get better, and what it means to be the human in the loop _with actual_ critical thinking.

Along the way:

📆 Why we’re hosting a half-day event that’s definitely _not_ a conference

🧠 Why ChatGPT's compliments feel like something your mom would say

🪞 Whether AI can _actually_ tell you what you need to hear to get better

💥 And why the productivity gap might just explode in the age of AI

Plus: Heather Havrilesky makes them feel weird, the robots are sycophants, and Gary attempts a full podcast takeover and a not-so-secret yearning for federal data privacy regulation.

Related Links:

• Hello World! Demystifying AI/ML/NLP

• Zero-to-One Build Challenge

• Perplexity is making a browser

• OpenAI rolls back sycophantic update
• Chat - Heather Havrilesky
• AI is coming for the unmotivated - Sinead Bovell