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In this episode of Verticals, Luke and Nic sit down with Nick Tippmann, Founder and Managing Partner at TipTop VC, to break down what is 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 to 24 months. Nick shares the operator playbook he learned as the 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 versus 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 is working right now: How the best teams win with distribution and disciplined execution. Why outcomes based pricing needs to start with micro outcomes rather than giant promises. The real moats in an agent first world including trust, audit logs, permissions, deterministic workflows, and brand. If you are building, investing, or selling in vertical AI, this is a full strategy session. Timestamps: 00:01 Intro. Nick Tippmann joins Verticals and shares his TipTop VC and Greenlight Guru story 01:16 Nick’s background from founder to operator to investor and why venture and vertical AI 05:52 The SaaS is dead narrative and what triggered the selloff 09:35 Why SaaS is evolving and the battle between AI native companies and incumbents 13:01 Public market moves and what is truly exposed 16:05 System of record versus applications versus the AI layer 18:54 Where value accrues in vertical software and data gravity 21:30 Why point solutions are a dangerous place to be 22:12 Why vertical SaaS looks hit hardest in public markets 26:12 Will agents replace software interfaces 27:06 Why UI is not dead but becoming more flexible 29:26 Embedded interfaces and the emerging decision layer 32:59 Seats versus usage versus outcomes pricing 35:39 Why micro outcomes matter more than big promises 37:31 Buyer psychology and predictability versus variable pricing 40:49 Defensibility when multiple teams build the same product 45:14 Why distribution matters more than ever 47:29 Tactical go to market lessons that work right now 51:59 PLG versus sales led versus forward deployed models 58:22 Seed to Series A metrics and what good looks like today 01:01:43 Founder profiles in the AI era 01:03:12 Technical talent and what actually matters 01:04:43 Rapid fire AI tools and stacks 01:07:48 Wrap up and thanks