Helen Huang on Trove, Behavioral Identity, and Building an Authentic Life in the Age of AI

On today’s episode, we speak to Helen Huang, a product leader and two-time founder building Trove, a “behavioral identity layer” that helps people understand and represent themselves through what they do rather than what they say. Helen recounts immigrating from China to Canada, studying earth science at Waterloo, pivoting into product roles at Zynga, Microsoft, and GitHub, then bootstrapping edtech company CoLab to seven figures while graduating 2,500+ learners before taking a 2024–2025 gap year to learn AI and explore playful experiments (including a garbage-bag fashion show). She describes Trove’s interactive story “Tangles,” early traction and intense user responses, and her aim to invert typical AI use: AI prompts us, and we supply instinctive answers. All while fundraising and hiring a founding team!

00:00 Show Mission Shift
00:48 Meet Helen and Trove
02:38 Reconnecting and Background
06:05 Earth Science to Tech Pivot
08:14 800 Applications and Resume Limits
10:28 PM Lessons to Founder Leap
14:55 Building CoLab and Scaling Education
18:19 AI Hype and Learning Friction
24:59 Gap Year Doubts and Rediscovery
28:01 Garbage Bag Fashion Show
28:26 Immersive Fashion World
29:44 Fun Over Goals
31:48 Civic Tech Detour
34:11 Finding Trove Mission
35:46 What Trove Is
37:54 Actions Reveal Identity
39:58 Early Drops And Metrics
41:59 Real Life Impact Stories
44:47 What Comes Next
46:25 AI Prompts Us
49:36 Use Cases And Ethics
52:51 Closing Reflections

Building Change Capacity: Jillian Reilly on Permission, Automation, and Portfolio Careers

Earlier this year, I interviewed Jillian Reilly, author of The Ten Permissions: Redefining the Rules of Adulting for the 21st Century about why people change (or don’t). And how “permission” and agency shape behavior more than resources, training, or workshops.

In part two of my conversation with Jillian Reilly, we talk about why “change management” often becomes performative and why real transformation depends on building ongoing capacity for change. She describes her role as a catalyst who creates conditions for teams to have hard, honest conversations, run experiments, and rebuild trust, emphasizing that leaders must explicitly allow disagreement and learning rather than rely on one-time programs. We discuss how automation will replace repeatable “corporate cog” work and increase the value of human adaptability, critical thinking, and innovation.

Jillian frames the current era as an “unraveling” of old social and career scripts and a “renaissance” of choice that requires agency rooted in clear-eyed optimism. She offers practical career guidance: design flexibility early, think in portfolios (“I can” vs. “I am”), build temporary/project-based value like a DJ reading the room, and experiment without dopamine-chasing by matching focus to one’s current season.

00:00 Change Management Trap
01:17 Consultant as Catalyst
05:19 Permission Over Performance
09:26 Building Change Capacity
11:00 Automation Ends Cogs
12:48 Unraveling and Renaissance
21:10 Optimism Creates Agency
27:15 Reclaim Local Control
28:21 Designing Flexible Careers
31:47 Portfolio Skills Mindset
35:14 Build Temporary Projects
40:57 You Already Know This
45:11 Experimentation Versus Dopamine
51:41 Closing Takeaways

Earlier this year, I interviewed Jillian Reilly, author of "The Ten Permissions: Redefining the Rules of Adulting for the 21st Century," about why people change (or don’t). And how “permission” and agency shape behavior more than resources, training, or workshops.

She recounts leaving a prescribed path and law school plans to go to South Africa during the of apartheid, followed by two decades in international aid across Africa. During that time, she led an HIV/AIDS program in Zimbabwe, where she saw how cultural and safety constraints make “novel choices” dangerous. She describes disillusionment with the kind of change driven by funding incentives, moving into consulting, and later prioritizing motherhood despite career trade-offs. We explore the ideas of permission, conviction over certainty, experimentation, avoiding regret through intentional choice, and building “permission-rich” environments in villages and boardrooms alike.

00:00 Why Permission Matters
00:17 Meet Jillian Reilly
01:59 Ten Permissions Explained
04:53 Leaving the Midwest Script
08:11 Aid Work Lessons
10:03 Zimbabwe and Permission
13:32 Agency and Modern Careers
17:46 Moving to South Africa
22:33 Conviction Over Certainty
24:02 Feel Your Way Forward
27:05 Transition to Consulting
27:28 Aid Work Disillusionment
29:39 Spending Versus Impact
31:52 Leaving the Dream Job
36:09 Consulting as Truth Teller
36:55 Permission and Change
41:12 Motherhood and Tradeoffs
46:33 No Regrets Framework
50:57 Returning Through Experiments
53:22 Frontiers and Explorers Way
55:50 Closing Reflections and Tease