The Full Ratchet: Venture Capital Demystified

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 few years?
  • Pro Rata has always been a hot button issue, for a variety of reasons and we're seeing some new challenges emerge as our portcos are raising up-rounds. What are the key issues you're observing with pro rata and what's your opinion on how it should be handled?
  • A number of my founders are either raising more in their seed round or trying to pull-in and raise their A rounds before their ready b/c everyone is sounding the alarms about an impending recession... raise the money now, before it dries up. This seems curious and a bit misleading from my standpoint... What are your thoughts on founders raising more money or raising sooner because of a potential recession?
  • I've been getting a number of pitch decks from so-called "CFOs" at startups... yet, upon review of a LinkedIN profile, it's pretty clear that these folks are bankers. Are you seeing the same and what are your thoughts?
  • I think it was about eight months ago that YC changed its SAFE to a post-money cap, instead of a pre-money cap. They claimed to have the right intentions when they made the switch but we were immediately suspect for a few obvious reasons, some less so. Talk about about SAFEs as an investment instrument and your thoughts on the switch to post money caps.

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