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A talk show style series focusing on entrepreneurs, investors, & ecosystems building tech companies differently, hosted by Rob Kenedi.
AI startups in 2025 are throwing out the roadmap. In this episode, investor Ryan Henry shares what he’s seeing at the frontier: agentic workflows, founder-led experimentation, and why traditional product roles are fading fast. We also revisit a debate about “vibe coding” - intuition-led building in a world of moving targets.
📍 Key Moments
00:00 - Introduction to Ryan Henry and his family office VC approach
02:40 - Ryan's fund structure: investing in other funds for deal flow
07:12 - Different return expectations compared to traditional VCs
18:30 - Debating "vibe coding": what it is and its implications
21:32 - The evolution of AI-assisted development capabilities
27:10 - Concerns about rapid prototyping vs. proper customer discovery
33:30 - Current YC trends: AI agents, robotics, and advanced manufacturing
41:55 - The state of AI agents today and what they can reliably do
47:38 - Building companies with anticipation of improving AI capabilities
