In this episode of The Vertical SaaS Podcast, host Gavin Savage sits down with Nick Tippmann, Managing Director at TipTop Ventures and founding CMO of Greenlight Guru, to unpack what it really takes to scale, stand out, and survive in the world of vertical SaaS and AI.

From scaling a medtech SaaS to tens of millions in ARR to backing the next generation of AI-native vertical products, Nick brings a rare blend of operator empathy and investor clarity. He shares the playbooks that still work, what founders get wrong about category creation, and why “AI wrappers” aren’t dead — they’re just the beginning.

We explore:

• How Greenlight Guru built a dominant founder brand in a compliance-heavy niche
• Why narrow ICPs win in early-stage SaaS and how to avoid the “go broad” trap
• How to use media and domain expertise to manufacture trust at scale
• What it really means to create a category (and when not to)
• The evolution from Vertical SaaS 1.0 to 3.0 (Workflow > Fintech > AI)
• How TipTop Ventures spots real defensibility beyond LLM hype
• Why culture is a second product and how “Alligator Blood” became a core value
• What makes a startup uninvestable in today’s market

Whether you’re a founder chasing product-market fit, an operator scaling go-to-market, or an investor backing AI-native vertical plays this one’s packed with honest frameworks, founder-level wisdom, and a forward-looking map of what’s next.

Key Takeaways

• Greenlight Guru scaled from 0 to $120M+ PE-backed outcome with domain-led GTM
• Founder brands and media strategy were key to early traction
• Category creation is a powerful tool, but only when the market needs it
• AI wrappers are valid wedges — if you have a strong Phase 2/3
• The best vertical SaaS companies build for workflow, not just data
• Speed + specificity > size in early-stage markets
• Culture should be built like a product from day one
• TipTop looks for wedge clarity, domain edge, and $50B+ TAMs

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