The Art and Science of Diligence in Early-Stage VC

The Art and Science of Diligence in Early-Stage VC

Author: Paige Soya October 9, 2025 Duration: 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.


Behind every major innovation, there's usually a risky bet and a tense conversation that made it happen. High Stakes pulls back the curtain on those pivotal moments by focusing squarely on the world of early-stage venture capital. Instead of abstract theory, each conversation pairs a founder who has lived the grind with an investor who has backed the vision, creating a dynamic and often revealing dialogue. They tackle the specific trends and tough questions shaping the venture space right now, from evaluating a team's potential to navigating a market downturn. You'll hear the nuanced strategies, the candid mistakes, and the real-world compromises that define building and funding a company from the ground up. This podcast is built for anyone curious about the mechanics and human drama of startup investing, offering a genuine sense of how capital flows to ideas and what it truly takes to succeed. Tune in for unscripted perspectives that clarify how high-risk decisions are made and what both sides learn when the stakes are at their absolute highest.
Author: Language: en-us Episodes: 64

High Stakes
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