Building a Personal AI for the Messiness of Life: Sida Li

Most AI products today are built for work—a space with clear problems and established systems. One founder noticed a gap: personal life is messier, harder to systematize, and mostly left behind by the AI boom. So she built Cue, a personal AI that lives inside iMessage and group chats, to go where the other tools haven't.

In this episode, Becca Carroll, IDEO's Chief Strategy Officer, talks with Sida Li, co-founder and CEO of Shared Context Lab, about staying anchored to a human need while the technology around her keeps changing shape, why she treats her business model with the same rigor she'd bring to a product, and what it feels like to build a company at this particular, disorienting moment in AI.

The conversation also gets into how Sida makes design decisions: the language Cue uses to describe itself, the tradeoffs behind building inside iMessage instead of a new app, and a real story about a business idea that didn’t pan out.

This is the second in a two-part series profiling founders from IDEO's Startups-in-Residence program. The first conversation is with Johannes Seemann, founder of Sooner, on designing GenAI for the emotional side of money.

Related Resources:

Join the Cue waitlist — https://sharedcontextlab.com

Sida Li on LinkedIn — https://www.linkedin.com/in/sida-li-35729698/

IDEO U's AI x Design Thinking Certificate — https://www.ideou.com/products/ai-design-thinking-certificate

IDEO U's Designing a Business course — https://www.ideou.com/products/designing-a-business

Listen to our episode with Johannes Seemann: Designing GenAI for the Emotional Side of Money — https://shows.acast.com/creative-confidence-podcast/episodes/designing-genai-for-the-emotional-side-of-money-johannes-see

In This Episode:

Timestamps are approximate due to edits and ad breaks

(00:00) Mina introduces the Startups in Residence series

(02:32) Becca Carroll returns as guest host

(03:11) From consulting's rulebook to IDEO's blank page

(03:43) Sida's zero-to-one path: IDEO, a venture studio, and a Series A with Arcade.ai

(07:14) AI has democratized building — and that's not entirely good news

(08:52) The long tail of personal life: "death by a thousand cuts"

(12:43) What Cue actually is: part assistant, part advocate

(14:37) Why she built for personal life instead of work

(16:01) The deliberate choice to live inside iMessage, not a new app

(17:57) Proactive, not reactive: the line between helpful and creepy

(20:38) The word Sida refuses to use, and the conversation with Tim Brown that confirmed it

(22:21) AI is less trusted than ICE right now — designing for that

(23:28) Total transparency: why users can see, edit, and delete everything Cue remembers

(25:40) Bringing Cue into a group chat changes everything

(27:44) The founder's journey isn't linear — it's a squiggle

(29:01) "Wandering in the dark": IDEO's desirability, viability, feasibility framework in practice

(32:17) Finding investors who can see through the pitch

(34:08) The business model is a prototype too

(35:01) A B2B idea everyone loved — until the budget didn't exist

(37:19) Why she's keeping pricing simple for now

(38:26) Building a company while the tools underneath her keep changing

(39:10) From not knowing how to code to building the front end

(42:02) The sci-fi problem: building something that knows everything about you

(42:47) The open question nobody's answered yet: what is this relationship, exactly?

(46:22) The bank-app test: designing trust into a world with no fixed screen

(47:06) What she got from building inside IDEO that she couldn't get alone

(48:57) Inside Sida's toolbox: the stack behind Cue

(50:10) The five-to-ten-year vision: software defined by the people who use it

(52:45) Lightning round: Mitch Albom, pull-ups, and doing the thing before you're ready

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