VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)

VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)

Author: Paige Soya June 11, 2026 Duration: 37:26

How long does it actually take to raise venture capital?

In this episode of High Stakes, Paige Soya and Nick Duafala sit down with Matt Bressler, Co-Founder and General Partner at Lookout Ventures, formerly TDF Ventures, to discuss venture capital deal timelines, fundraising momentum, and the diligence process that takes place behind every investment decision.

From initial founder meetings to signed term sheets, they explore what causes fundraising processes to move quickly, what causes deals to stall, and why many of the fastest investments begin months—or even years—before a company officially starts raising capital.

Topics covered include:

  • Venture capital deal timelines
  • How investors evaluate startup opportunities
  • What creates fundraising momentum
  • Preparing for investor due diligence
  • Common fundraising mistakes founders make
  • Building investor relationships before a raise
  • Why some venture deals move faster than others

Whether you're raising your first round, preparing for a future fundraise, or simply interested in how venture capital works behind the scenes, this episode offers practical insights into how investors build conviction and make investment decisions.

Subscribe for more conversations with founders, investors, and operators shaping the startup ecosystem.


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: 50

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