Super Data Science: ML & AI Podcast with Jon Krohn

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

Super Data Science: ML & AI Podcast with Jon Krohn

Show Notes

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

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

Oct 23, 2026

In Episode #1038, Jon Krohn unpacks the remarkable and remarkably contentious run of mathematical results AI has produced in recent weeks, led by OpenAI’s claim to have cracked part of a million-dollar Millennium Prize problem. He lays out what was actually proved, the three big caveats that temper it, the chaotic bulk release of 722 manuscripts that followed, and why 25 Fields medallists are alarmed. His throughline for anyone building with AI: when generation gets cheap, verification becomes the bottleneck.

Oct 20, 2026

In Episode #1037, Dr. Richard Socher (CEO and Co-Founder of Recursive) joins Jon Krohn to make the case for automating the scientific method itself. Richard’s startup came out of stealth this year with over half a billion dollars raised to build recursively self-improving superintelligence, and his new book, The Eureka Machine, is already a national bestseller. He also co-founded You.com and the venture firm AIX Ventures, was chief scientist at Salesforce, taught the first university course anywhere on neural networks for NLP, and helped build the ImageNet dataset. In this episode, he traces how AI keeps replacing hand-crafted expertise with scale, lays out the four pillars of his Eureka Machine, argues that hallucinations can be a feature for science, explains why recursive self-improvement within a year or two still rules out an overnight takeoff, and names the software and jobs he expects to endure.

Oct 16, 2026

In Episode #1036, Jon Krohn digs into the question parents and teachers keep asking: does AI stop children from learning? Drawing on a wave of new studies, he shows the answer turns entirely on how AI is used, as a shortcut that outsources the thinking, or as a tutor that explains and gives feedback. Along the way: a 30,000-student natural experiment in China, a striking tutoring result from Turkey, and three practical takeaways that apply just as much to adults using AI at work.

Oct 13, 2026

In Episode #1035, Carly Taylor (Founder of Rebel Data Science) returns to join Jon Krohn for a wide-ranging conversation about leading engineering teams when the ground keeps moving. Carly shipped nine Call of Duty titles in roughly five years at Activision, where she led game security, and has since been a director of engineering at Microsoft and Field CTO for gaming at Databricks. She is also one of the most entertaining people in data on LinkedIn, where more than 200,000 people follow posts she cheerfully calls unhinged. In this episode, she explains why obsessing over the future produces analysis paralysis, which fundamentals never change, how to tell AI slop from AI used well, what the Buddhist practice of inviting Mara to tea has to do with public speaking, and what the glass cliff means for women being promoted into leadership.

Oct 9, 2026

In ICYMI Episode #1034, Jon Krohn moves from what sits underneath AI systems to what it takes to live with them every day. Hear from Aishwarya Srinivasan, Luis Serrano, Katie Malone, Ish Shah and Dilani Kahawala, discussing why the bottleneck in shipping software has moved from execution to judgment, how a physicist recast attention in transformers as words bending space, why years of managing people may be the best preparation for managing AI agents, how one weekend side project burned through billions of tokens and which three problems are hardest to solve when a product has no user interface and never stops running.

See all episodes →