Is Vertical SaaS Breaking? Where AI Actually Creates Massive Value | Episode 18

In this episode of Verticals, Luke and Nic sit down with Nick Tippmann (Founder & Managing Partner, TipTop VC) to break down what’s really happening as AI agents and workflow tools trigger panic across the markets, and where the real value (and money) will accrue over the next 12–24 months.   Nick shares the operator playbook he learned as founding CMO of Greenlight Guru (a bootstrapped vertical SaaS success story) and how it now shapes his investing thesis in vertical AI. They debate AI-native upstarts vs legacy incumbents, why the system of record is still the “oxygen for AI”, and why the most dangerous place to be might be point solutions and broad horizontal tools.   They also go tactical on what’s working right now: How the best teams win with distribution + disciplined execution Why outcomes-based pricing needs to start with micro outcomes (not giant promises) The real moats in an agent-first world: trust, audit logs, permissions, deterministic workflows, and brand If you’re building, investing, or selling in vertical AI, this is a full-on strategy session.