Updated re-release. A year ago we left one question unresolved. Where do foundational AI models end and where do the applications begin? Nick Tippmann returns in a fresh epilogue. A year on, the tension has only sharpened.

Specificity is the differentiator when inches matter. Nick Tippmann, founding partner of TipTop VC, explains how vertical AI is rewriting the software industry by going deeper instead of wider. From the transition beyond SaaS to the gray zone between foundational models and high-stakes applications, we get into how vertical AI can transform laggard industries and why Austin might lead the race.

The Agenda
00:00 Defining vertical AI
05:07 Where general AI fails
09:36 Vertical AI software, not just chatbots
16:44 Pricing logic after the seat model
24:04 Underwriting at pre-seed and seed
27:20 Capital intensity and seed-strapping
36:48 TAM analysis and the Frontiers Market example
41:46 OpenAI's Instacart hire and the gray zone
45:55 Austin as a vertical AI hub
58:21 Epilogue: Where the models end and applications begin

Guest Links and Bios
Nick Tippmann: https://www.linkedin.com/in/nicktippmann/
TipTop VC: https://www.tiptop.vc/

Nick Tippmann is the Founder and Managing Partner of TipTop Ventures, an early-stage venture fund focused on Vertical AI. Before becoming an investor, Nick spent nearly a decade as a founding team member and CMO at Greenlight Guru, where he helped scale the company from zero to category leader with more than 250 employees, tens of millions in ARR, and a nine-figure investment from JMI Equity.

An operator turned investor, Nick now partners with founders building industry-specific AI and software businesses, bringing hands-on experience in go-to-market strategy, scaling, community building, fundraising, and company development. He has also been an active angel investor since 2021, with more than 100 startup investments.