Creative Confidence Podcast

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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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.

Most personal financial tools are built to run the numbers and optimize towards a budget. While that works for some, most people experience money as a lived relationship that doesn’t neatly fit into a spreadsheet. Johannes Seemann spent years interviewing people about their personal finances and came away with a different premise: Money is inherently emotional before it is mathematical. Accounting for people’s psychology and context first creates, he argues, creates the foundations to make smarter, more confident financial decisions.
In this episode, Becca Carroll, IDEO's Chief Strategy Officer, talks with Johannes Seemann, founder of Sooner, about the problem space he knows so well, why he sees generative AI as a unique opportunity to design a solution for it, and what a genuinely human-centered approach to building an AI product looks like in practice.
The conversation also gets technical. Becca and Johannes dig into the engineering and design challenges of building an AI moderator, from models that try to resolve human ambiguity rather than embrace it, to the normative assumptions they carry that can lead to biased interpretations.
This is the first in a two-part series profiling founders from IDEO's Startups-in-Residence program. The second conversation is with Sida Li, co-founder and CEO of Shared Context Lab, on building Cue, a personal AI that lives inside your text messages and group chats.
Related Resources:
Take the Sooner Money Mindset quiz — https://mysooner.com
Sign up as a beta tester — https://hellosooner.com
Follow Sooner on Instagram — https://instagram.com/hellosooner
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
In This Episode:
(Timestamps are approximate due to edits and ad breaks)
(00:00) Mina introduces the IDEO startups-in-residence series
(01:34) Becca Carroll kicks things off as guest host
(04:03) From IDEO's first data hire to two years inside Wells Fargo
(05:51) The blind spot: why people assume financial advisors aren't for them
(07:36) The loneliness of money, and what happened when Johannes's own team opened up about it
(09:33) Where the name "Sooner" comes from
(12:08) Trust over expertise: why finding a financial advisor is like finding a therapist
(13:41) Rose's story: she paid off her house, then lost $25,000 trusting the wrong person at the gym
(15:55) The light bulb moment: why people confide in chatbots when they won't confide in a person
(17:12) Money as an identity issue: Homo economicus, Kahneman, and the trouble with "rational vs. irrational"
(19:13) Turning the equation on its head: budget as output, not input
(20:54) Getting laid off, a no-code AI course, and a rough first prototype in Python
(22:57) Testing the psychographic profile on real people
(24:43) What people won't tell an advisor, they'll tell AI
(25:48) The data engine behind the future Sooner AI partner
(28:52) Identity-driven spending: a real example of the pattern
(31:56) From goals to intentions: what the product actually does today
(34:28) The vet bill: why an intention can flex where a goal would break
(35:33) Finding the right amount of control vs. ease
(37:06) Designing for how it should feel, not what AI can do: why push-to-talk beat free-flowing conversation
(39:57) Human-centered design as Sooner's competitive advantage
(43:37) How to keep applying human-centered design after the research phase is over
(46:13) What it takes to build with AI as a two-person team
(47:32) The three architectures: AI brain, interface, and retrieval layer
(51:32) The technical challenges: normative contamination, false coherence, and context rot
(56:56) Testing an example: helping someone buy a car without spiraling
(59:17) What success looks like for Sooner
(1:02:03) Lightning round: Mossy Earth, dog training, and symmetry as a philosophy
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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.

We talk a lot about curiosity as a mindset. Scott Shigeoka lives it as a practice. Right now he’s driving a 25-foot purple van across the country, finding and documenting the stories of ordinary people making their communities better. He's not just curious about what's possible. He's out there finding out.
In this episode, Mina Seetharaman talks with Scott Shigeoka, author of Seek and Head of Curiosity Cultivation at the Eames Institute, about what distinguishes a genuinely curious leader from a performative one, how power dynamics play into curiosity, how the Curious 100 project reveals the many forms curious leadership takes, and why curiosity, when practiced well, can restore your energy rather than drain it.
Scott was previously on the Creative Confidence Podcast to explore why curiosity is a business imperative. That episode is linked below.
This episode is part of an ongoing series on navigating uncertainty. We're exploring this topic from multiple angles with several guests this year. Also in this series: How to Not Know with Simone Stolzoff and The Decisiveness Crisis in Senior Leadership Teams with Sam Conniff.
Related Resources:
Seek: How Curiosity Can Transform Your Life and Change the World, by Scott Shigeoka — https://scottshigeoka.com
The Curious 100 — https://thecurious100.org
Curiosity Club (free newsletter) — https://scottshigeoka.com
Scott Shigeoka on LinkedIn — https://www.linkedin.com/in/scottshigeoka
Scott's Curiosity Toolkit (free guide for building curiosity at work) — https://curiosity-toolkit.netlify.app/
Scott's first Creative Confidence interview: Why Curiosity Is a Business Imperative — https://www.ideou.com/blogs/inspiration/why-curiosity-is-a-business-imperative
IDEO U's Foundations in Creative Leadership Certificate — https://www.ideou.com/products/creative-leadership-certificate
More episodes on navigating uncertainty:
How to Not Know: Simone Stolzoff — https://shows.acast.com/creative-confidence-podcast/episodes/how-to-not-know-simone-stolzoff
The Decisiveness Crisis in Senior Leadership Teams: Sam Conniff — https://shows.acast.com/creative-confidence-podcast/episodes/the-decisiveness-crisis-senior-leadership-teams-sam-conniff
In This Episode:
Timestamps are approximate due to ad breaks.
(00:00) Cold open — the grace curious leaders earn when they make mistakes
(02:47) The Curiosity Mobile — six months on the road, the belief gap, and why stories close it
(07:36) Stories from the road — a florist, a group of librarians, and rafting across political lines
(12:11) How getting curious refilled Scott's own hope and energy before the trip
(14:57) Busting the echo chamber — curiosity as "what else are we missing"
(15:58) The Curious 100 — what the project is and what separates real curiosity from the performative kind
(20:50) Curiosity looks like many things — storytellers, editors, and activists on the list
(23:10) Being an "admitter" — why owning your mistakes makes leaders more trusted, not less
(28:11) Power and directionality — why the most powerful person in the room needs to be the most curious
(33:28) Inclusion vs. belonging, and why curiosity is the difference
(34:44) The question of the day — a research-backed practice for any meeting
(39:34) Why the curious leadership framework matters — a menu of options, not a personality test
(43:42) The four curious leader archetypes: Explorer, Provocateur, Reflector, Imaginator
(48:11) Your dominant archetype — and why leaders can shift between all four depending on the moment
(48:42) Curiosity vs. conviction — why staying open doesn't mean abandoning your values
(51:28) Predatory curiosity — what it looks like, why it backfires, and deep canvassing as its antidote
(59:16) Lightning round: Queer Eye, Lady Gaga, learning to surf, and curiosity as an act of love
__________

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.

We're told more is always better—more options, more resources, more freedom. But David Epstein spent years looking at the science, and what he found challenges that assumption. Constraints don't just force creativity. According to the research, they often generate it.
In this episode, Mina Seetharaman talks with David Epstein, author of Inside the Box: How Constraints Make Us Better and the New York Times bestseller Range, about why total freedom tends to produce mediocre work, how the best leaders design limits on purpose, and what the history of companies like General Magic and Pixar reveals about the relationship between boundaries and breakthrough.
David was previously on the Creative Confidence Podcast to discuss Range: Why Generalists Triumph in a Specialized World. This conversation picks up where that one left off.

Related Resources:
Inside the Box: How Constraints Make Us Better, by David Epstein — https://www.davidepstein.com
Constraint exercises for teams — https://www.davidepstein.com
David Epstein on LinkedIn — https://www.linkedin.com/in/davidepstein
David’s newsletter, Range Widely — https://www.davidepstein.com
David’s first Creative Confidence interview: Generalist vs. Specialist: Choosing a Path for Career Success — https://www.ideou.com/blogs/inspiration/generalist-vs-specialist-choosing-a-path-for-career-success
IDEO U’s course Leading for Creativity: How to create the conditions where great work—and the people doing it—can thrive. — https://www.ideou.com/products/leading-for-creativity

In This Episode:
Timestamps are approximate due to ad breaks.
(00:00) David on what good leaders actually do with constraints
(00:25) Introducing David Epstein and the through line from Range to Inside the Box
(03:28) The explore-exploit trade-off: why breadth and focus aren't opposites
(05:00) What a constraint actually is and why your brain is designed to avoid thinking whenever possible
(06:45) Two things constraints reliably do: clarify priorities and force new exploration
(07:22) The blank canvas problem: why total creative freedom tends to produce average ideas
(08:09) The green eggs and ham effect: what the research says about constraints
(11:19) Dr. Seuss starts hemming himself in on purpose and changes children's literature in the process
(12:18) General Magic: the most important company nobody's ever heard of, and what happens when engineers are limited only by their imagination
(16:29) "I just couldn't figure out what not to do"—the common thread across dozens of former General Magic employees
(19:30) What leaders who design constraints on purpose actually look like—Pixar, Tony Fadell, and the literal box at Nest
(22:33) The legacy constraint exercise: a thought experiment that gets people to reprioritize without feeling punished
(25:11) When does a constraint go too far? The creativity-killing conditions and what the research on deadlines actually shows
(27:32) "Give me the freedom of a tight brief"—why definitional constraints work and prescriptive ones don't
(28:28) Brooks' Law, additive bias, and why we're wired to add instead of subtract
(29:46) The subtraction audit: how a genetics lab doubled its output by making commitments visible
(32:12) AI, prototyping, and the danger of skipping the thinking-slow phase
(36:23) Designing for edge cases: how the U.S. Army's body armor redesign for women improved gear for everyone
(41:10) The Hemingway Principle: the last-act-of-the-day habit that protects your most important work
(42:51) Audience Q: Can artificial constraints be as useful as real ones? (Yes, and here's why)
(45:04) Audience Q: How do you get buy-in on constraints when people push back?
(48:50) Lightning round: In Praise of Shadows, Daniel Kahneman, shuffle dancing, satisficing, and the decks that are never clear
__________

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.

Two thirds of leaders say they would rather be seen as decisive and get it wrong than appear uncertain and get it right. It may sound illogical, but it's actually the result of decades of organizational culture training leaders that decisiveness equals strength and that not knowing is a liability.
In this episode, Mina Seetharaman talks with Sam Conniff, founder of Uncertainty Experts and author of The Uncertainty Toolkit, about the data behind what he calls the decisiveness crisis, why senior leadership teams are the most likely layer in most organizations to get uncertainty wrong, and three learnable questions that help leaders make better decisions without pretending to have answers they don't have.
This is part of an ongoing series of conversations about uncertainty on the Creative Confidence Podcast. Subscribe to catch them all.
Related Resources:
The Uncertainty Toolkit: How to Feel Calmer, Happier, and More Confident in an Uncertain World, by Sam Conniff — https://www.uncertaintyexperts.com/the-uncertainty-toolkit
Sam Conniff on LinkedIn — https://www.linkedin.com/in/samconniff
Uncertainty Experts — https://www.uncertaintyexperts.com
How to Stop Fighting Uncertainty & Start Working With It (Simone Stolzoff episode) — https://www.ideou.com/blogs/inspiration/how-to-not-know-simone-stolzoff
Read the blog recap — https://www.ideou.com/blogs/inspiration/the-decisiveness-crisis-uncertainty-toolkit-sam-conniff
In This Episode:
(Timestamps are approximate due to ad breaks)
(00:00) Sam on changing your relationship to uncertainty
(01:09) Introducing Sam Conniff and the decisiveness crisis
(02:08) What drew Sam to studying uncertainty and the personal story behind the research
(05:14) The Q-test warm-up: a simple exercise that reveals how your brain handles uncertainty
(10:36) The false brief: why trying to eliminate uncertainty is the wrong goal
(11:24) The top five uncertainty safety behaviors at work and why they feel so familiar
(13:27) Why the best leaders don't try to eliminate uncertainty—they navigate it
(17:00) Fear, fog, and stasis: the three ways uncertainty shows up before it reaches the boardroom
(20:58) What makes Sam and Catherine's research different from the books on your shelf
(21:37) The data: 20,000+ participants, six years, three sources
(24:41) Career is the number one uncertainty every year since 2021
(26:15) The decisiveness question: a binary choice that reveals everything
(29:04) Why two thirds of leaders choose the negative outcome
(30:04) The hierarchy finding and where the numbers go off the scale
(36:41) The decisiveness crisis as an identity problem and why transformation programs keep failing
(39:00) The uncertainty-ready leader: knowing which mode to be in
(40:00) Altitude, horizon, and agency: three questions that transform the pressure
(43:36) Why setting a deadline is actually a decisive act
(44:04) Turning a decision into a hypothesis
(44:12) Obama and Ardern: what saying "I don't know" with authority actually looks like
(46:59) The unlikely experts: what gang leaders, refugees, and recovering addicts know that most leaders don't
(54:13) Lightning round: The Walking Dead, Catherine Templar Lewis, nail polish, and more
(58:20) Mina's takeaways
__________

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.