185. “Blessed” Teams, Pseudo Deal Leads, and Caps at Pre vs Post (Ash Rust)

Ash Rust of Sterling Road joins Nick to discuss "Blessed" Teams, Pseudo Deal Leads, and Caps at Pre vs Post. In this episode, we cover:

  • His beginnings in tech and how that led to starting the fund
  • What's the investment thesis at Sterling Road?
  • What's unique about your approach that other firms aren't doing?
  • Something that I think is frustrating for many founders is seeing these idealistic stories of founders that are raising $5M on a $20M cap with zero traction. And, it's also misleading in that I have a number of founders that think they need to be raising a lot more than they are... very early on before indications of product fit or even a focused commercial plan. Can you talk about the profile of these teams that are able to raise seemingly irrational seed rounds and then later let's jump into consequences.
  • The seed round has now divided into a series of phases... we have pre-seed, seed, mango seed, seed+, seed exensions, etc. We've spoken to Semil Shah about this and how it's no longer a stage it's a series of phases and gates. Can you talk about these phases and how founders should think about milestones and raise amounts prior to raising an A?
  • At New Stack we've encountered some strange and troubling circumstances regarding who the lead investor is on a deal and who is not. What are you seeing in terms of who takes the lead and how has that evolved over the past (Read more...)