For daily thoughts on the venture landscape, follow me @samirkaji on Twitter.

Chris Douvos is the Founder of Ahoy Capital, a boutique Fund of Funds that focuses primarily on allocating into early-stage venture capital funds, while selectively co-investing directly into companies.

Chris started his career at Morgan Stanley while still at Yale earning his MBA. From there he worked at Princeton University’s endowment fund where he got his start in venture before moving onto The Investment Fund for Foundations (TIFF). At TIFF he decided that the right strategy was to make “heroic investments” and invest in very early stage, and often unproven managers.

This method paid off as Chris was one of the first institutional Limited Partners to back First Round Capital (and remains so).

Chris then went on to Venture Investment Associates  (VIA) prior to spinning out to start Ahoy Capital in 2018.

Ever engaging, Chris covers a whole host of emerging VC topics and he and I discuss the following:

6:20 Why Chris started a fund that invests in emerging managers and how he’s arbitraging people’s inattention to get to true outsized returns.

9:00 The process for raising a FoF, and what his LP’s are looking for.

10:59  Ahoy’s portfolio model on managers, and why he thinks concentration is the right avenue for them.

11:54 Why looking at past performance shouldn’t always be the leading indicator in evaluating firms, and why he looks at other specific factors.

13:35 His thoughts on GP/Thesis fit

16:51 How he was introduced to Josh Kopelman of First Round Capital 

22:13 Why you need to be able to articulate a sustainable competitive advantage; funds that are good examples of this

25:21 Why Chris looks to invest in Venture business builders, not option seekers

28:18 The “return the fund” mental model managers should use.

33:00 Why there’s currently a need for liquidity in the ecosystem and why SPACs and direct listings are helpful

37:25 Why he’s excited about the diversity, equity, and inclusion GP investments

39:25 Thoughts on Rolling Funds

42:18 Chris’ missed investment opportunities

43:11 How to pitch Chris (and Fund of Funds in general).

Mentioned in this episode:

* Ahoy Capital

* David Swenson’s Pioneering Portfolio Management

* Chris’ blog post: “All About the Benjamins”

* Micro VC - Smaller is better, but the math is hard.

I’d love to know what you took away from my conversations with Chris Douvos; Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest.

Podcast Production support provided by Agent Bee Agency

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