Episode #33: Do $1B Outcomes Matter?, Vibe Investing, The Agentic Web and The Original Sin

This week, Mia, Charles and Leon break down three timely topics shaping the future of venture and technology: VC Exit Math is Changing: David Clark (VenCap) expands on Packy McCormick’s analysis of billion-dollar exits, showing how top-tier venture returns are moving from $1B to $20B+ outcomes. We explore what this shift means for fund pacing, graduation rates, and why mid-sized funds are feeling the squeeze. “Vibe Investing” & Perishable Knowledge: Collin Wallace (Lobby Capital) dives into AI’s impact on investor behavior and startup creation. We talk about the limits of pattern recognition, the risk of thesis mimicry, and why real conviction still requires “showing your work.” Was Advertising the Web’s Original Sin?: Ben Thompson’s latest Stratechery essay revisits internet economics in the age of AI. We unpack the idea of an “agentic web,” what AI-native payments might look like, and how stablecoins could become critical for creator monetization. (0:12) Introduction and episode overview (1:28) Venture exit values, fund size, and returns (4:18) Advising founders and team assessment in venture investing (6:46) Vibe Investing, AI's role in venture decision-making, and perishable founder knowledge (12:11) Showing your work in investing and Ben Thompson's essay on advertising and AI (16:22) The future of digital content: Agentic web, AI native payments, and monetization challenges (19:52) Closing remarks