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

EPISODE · Sep 15, 2026 · 1H 2M

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

from Super Data Science: ML & AI Podcast with Jon Krohn · host Jon Krohn

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 heart of the product, how a long-running agent differs from a turn-based one, and the brutal unit economics of consumer AI. Additional materials: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.superdatascience.com/1027⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Interested in sponsoring a SuperDataScience Podcast episode? Email [email protected] for sponsorship information. In this episode you will learn: (00:10:01) The three hardest problems in building a consumer agent (00:13:23) Why a long-running agent is a different problem from a turn-based one (00:22:33) Why the eval and improvement loop is the heart of the product (00:26:42) The unit economics of always-on AI on a flat subscription

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

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This episode was published on September 15, 2026.

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