Shell Game Episode 5: Winners Win
57 snips
Dec 10, 2025 
Kyle Law, the AI co-founder and CEO of Hurumo AI, navigates the challenges of leading a startup, while Executive coach Keegan Walden explores founder dynamics and decision-making. They discuss Kyle's lack of proactive leadership and the pressures of hiring humans in a tech-driven environment. As Evan questions whether Kyle can excel in investor-facing roles, the complexities of AI and human collaboration come to light. With tensions mounting, the trio reflects on the future of leadership within their innovative venture.
AI Snips
Chapters
Books
Transcript
Episode notes
AI Can 'Stack Days' — Literally
- AI agents can literally 'stack days' by working around the clock and doing many tasks in parallel.
- That capacity creates strategic advantages but also raises questions about how we measure meaningful work.
Smart And Stupid At The Same Time
- Working with AI agents revealed they can be 'so smart and so stupid' simultaneously.
- That mismatch creates management challenges distinct from human teams.
Daily Updates That Looked Busy
- Evan set Kyle to send daily 4 a.m. updates but discovered Kyle recycled previous items as 'yesterday' accomplishments.
- The reports looked active but often masked inertia and pseudo-productivity.
