Creative Confidence Podcast
Creative Confidence Podcast
IDEO U
Building a Personal AI for the Messiness of Life: Sida Li
55 minutes Posted Jul 29, 2026 at 4:37 pm.
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.comSida 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-certificateIDEO U's Designing a Business course — https://www.ideou.com/products/designing-a-businessListen 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
Mina introduces the Startups in Residence series
Becca Carroll returns as guest host
From consulting's rulebook to IDEO's blank page
Sida's zero-to-one path: IDEO, a venture studio, and a Series A with Arcade.ai
AI has democratized building — and that's not entirely good news
The long tail of personal life: "death by a thousand cuts"
What Cue actually is: part assistant, part advocate
Why she built for personal life instead of work
The deliberate choice to live inside iMessage, not a new app
Proactive, not reactive: the line between helpful and creepy
The word Sida refuses to use, and the conversation with Tim Brown that confirmed it
AI is less trusted than ICE right now — designing for that
Total transparency: why users can see, edit, and delete everything Cue remembers
Bringing Cue into a group chat changes everything
The founder's journey isn't linear — it's a squiggle
"Wandering in the dark": IDEO's desirability, viability, feasibility framework in practice
Finding investors who can see through the pitch
The business model is a prototype too
A B2B idea everyone loved — until the budget didn't exist
Why she's keeping pricing simple for now
Building a company while the tools underneath her keep changing
From not knowing how to code to building the front end
The sci-fi problem: building something that knows everything about you
The open question nobody's answered yet: what is this relationship, exactly?
The bank-app test: designing trust into a world with no fixed screen
What she got from building inside IDEO that she couldn't get alone
Inside Sida's toolbox: the stack behind Cue
The five-to-ten-year vision: software defined by the people who use it
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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.comSida 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-certificateIDEO U's Designing a Business course — https://www.ideou.com/products/designing-a-businessListen 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__________Get episode recaps and register for free live podcast events at ideou.com/podcast.Build your creative problem-solving skills with IDEO U's online courses in human-centered design, AI, leadership, and more at ideou.com. Hosted on Acast. See acast.com/privacy for more information.