High Stakes

episode artwork

Paige Soya

14 August 2025

33m 51s

The Relationship between Check Size, Ownership Percentage and Stage in VC Investing

00:00

33:51

“The Ownership Equation: Why Check Size, Stage, and Strategy Matter in VC”

What does a $2M check actually mean for the founder, the investor, and the future of the company?

In this episode of High Stakes, Paige Soya sits down with Michael Bosch to unpack the mechanics behind venture capital that most founders and even some investors get wrong. From rigid ownership targets to flexible fund strategies, and from GenAI-fueled capital efficiency to cap table waterfall risks, this conversation gets into the tactical realities behind early-stage funding.

You’ll learn:

  • Why check size, ownership percentage, and stage must be aligned
  • How generative AI is reshaping team size, round size, and outcomes
  • What investors really mean when they say they need 10%
  • Why early investors can get wiped out even when a company wins

If you're a founder raising capital or an investor navigating the new VC landscape, this episode breaks down what really matters and what’s changing fast.