High Stakes

episode artwork

Paige Soya

09 October 2025

47m 6s

The Art and Science of Diligence in Early-Stage VC

00:00

47:06

How do investors evaluate founders when there’s little or no traction? What really drives decisions in early-stage venture capital?

In this episode of High Stakes, host Paige Soya sits down with early-stage investor Matt Gittleman to unpack the art and science of diligence. From scorecards and rubrics to founder storytelling and grit, Paige and Matt explore why rigid frameworks can fall short and how experienced investors read between the lines.

You’ll learn:

  • Why scorecards and rubrics can be gamed (and what to use instead)
  • Matt’s “levers and hurdles” approach to evaluating startups
  • How speed, style, and grit signal founder potential
  • Why the way a founder articulates their vision can matter more than the metrics
  • The limits of AI in a process that’s deeply qualitative and human-driven

Whether you’re a founder preparing to fundraise or an investor refining your own diligence process, this conversation offers a candid look into how early-stage deals really get done.