Dennis Mortensen, 20-year NYC entrepreneur and founder of x.ai (the AI scheduling assistant), joins Rob May and Ryan Eppley to share war stories from building one of the first real AI agents—years before LLMs existed.

We dive into:

→ The insane complexity of AI scheduling (what does "soon" actually mean?)

→ Why perceived errors were harder to solve than real ones

→ ChatGPT's move into advertising—should we be worried? → Is the AI bubble real? (Dennis sold his AI stocks last week 👀)

→ Apple licensing Gemini for Siri: brilliant move or generational fumble?

→ What Dennis is building now at Launch Brightly

Topics discussed:

ChatGPT & ads: https://www.msn.com/en-us/news/techno...

Quantum computing & Bitcoin: https://www.investors.com/news/techno...

Apple & Gemini: https://www.cnbc.com/2026/01/12/apple...

Connect with Dennis: LinkedIn: / dennismortensen Launch Brightly: https://launchbrightly.com

From x.ai to ChatGPT Ads: Dennis Mortensen on AI Scheduling, Bubbles & Apple's Mistake | AI in NYC

AI in NYC Show

From x.ai to ChatGPT Ads: Dennis Mortensen on AI Scheduling, Bubbles & Apple's Mistake | AI in NYC