Nick Tippmann is the Founder of TipTop Ventures where he invests in vertical AI and applied AI companies at the earliest stages. In this conversation, we talked about vertical AI, systems of work, and why distribution may matter more than ever in a world where software is getting easier to build.

Nick explains why vertical AI is not simply the next version of SaaS. In his view, the unit of value is shifting from time saved to work delivered. That changes the buyer, the budget, the pricing model, and the size of the opportunity. Where traditional vertical software captured a slice of software spend, vertical AI can go after much larger labor and services budgets by doing the work itself.

We also discuss what makes vertical AI companies defensible. Nick shares why the best companies are not just thin wrappers on top of foundation models, but systems of work that combine workflow, context, proprietary data, and domain-specific judgment. He explains why OpenAI and Anthropic moving up the stack may actually prove that intelligence alone is not enough.

A big theme in the episode is go-to-market. Nick argues that many fundamentals have not changed: trust, domain expertise, tight ICPs, fast time to value, and distribution still matter. But in an AI-native world, pricing is being rewritten, revops and go-to-market engineering are becoming table stakes, and founders need to think earlier about brand, community, and how they stand out in crowded markets.

We also talk about Nick’s journey from operator to investor, what he learned as CMO of Greenlight Guru, what he saw early in GC AI, and what VCs and founders often misunderstand about each other. It is a conversation about the future of software, the realities of early-stage investing, and how to separate durable vertical AI businesses from the noise.

Investing in Startups is produced by Seaplane Ventures and hosted by Joe Magyer.