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Super Data Science: ML & AI Podcast with Jon Krohn

Super Data Science: ML & AI Podcast with Jon Krohn

1027: Building an Always-On AI Agent for Busy Parents, with Dr. Dilani Kahawala

Sep 15, 2026 · 1h 3m

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About this episode

In Episode #1027, Dr. Dilani Kahawala (Co-Founder and CEO of Anna) joins Jon Krohn to explain what it takes to build an always-on AI assistant that busy parents will trust with their inboxes. Anna watches the email, school apps, WhatsApp messages and calendars flowing into a family's life and surfaces what matters, over text and voice, with barely any app to speak of. Dilani came to it by way of a Harvard physics PhD, McKinsey, and a decade of product leadership at Etsy, Meta and Atlassian, and says she has had to throw away most of what that decade taught her about how products get built. In this episode, she lays out the three hardest problems in building Anna, why the eval loop is the…