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 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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