E30: AI, Anti-Patterns, and the Dangers of Elephant Hunting with Itamar Novick

Our guest this week is Itamar Novick, Founder of Recursive Ventures. Itamar is a solo capitalist with a focus on pre-seed startups built around data and AI. We talked about the opportunities and challenges that AI presents, anti-patterns to avoid in startups, winning deals, and why Itamar thinks that most VCs do NOT add value to startups. Itamar has been a founder, executive, and investor, so this was a really thoughtful, nuanced conversation. 

We also covered:

• Common startup mistakes that feel smart but kill companies

• Lessons from a failed $50M strategic deal with ADT at Life360

• What actually creates defensibility in generative AI startups

• Why valuations in AI aren't a full-blown bubble—yet

• Building a solo VC firm with AI as leverage (“Portfolio GPT”)

• The new era of lean, high-output startups—and what it means for VC

• Itamar’s go-to founder question: Why will you stay ahead five years from now?

• Why most “value-add” from VCs is overhyped

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