Season 2 of the ProducTea! Seasoned tech leader Ravi shares his insights on founding a business amidst AI disruption, the evolving capabilities of AI in empathy, and the challenges we faced of leadership post our careers at Microsoft. We also explore the concept of dual career ladders, some crazy pivots we both experienced as product leaders. Ravi also addresses dealing with insecurities after achieving significant career success and balancing opportunity cost with efficient time use. Timestamps: 02:00 Ravi’s introduction 07:25 Ravi’s Origins & Gossip about Microsoft 10:30 Founding a business in a domain that is getting shaken up by AI 20:03 AI products outperform humans on empathy. What “really” matters to people 27:30 What do people get wrong about Ravi? Leading small companies with a big company resume 32:00 When you lose the possibility to micromanage everything. Tripadvisor 36:50 Opportunity sizing for initiatives, Conviction vs Healthy skepticism 44:00 IC careers vs. Manager career Dual Career Ladders 52:55 What kind of insecurities do you deal with once you have “done it all already”: opportunity cost and how to use time efficient Leah on Linkedin / Twitter / Youtube