It was a pleasure to sit down this week with Josh Kopelman, one of the original architects of seed stage investing who continues to re-invent what it means to operate within venture.

Josh co-founded First Round Capital, which has invested at the earliest stages in companies like Square, Uber, and Roblox. Some of Josh’s more recent investments include Notion, Pomelo Care, Loyal, and Perpay. Since First Round’s inception in 2004, Josh has invested in 500+ startups and has frequently made the Forbes “Midas List” which ranks the top 100 tech investors.

Josh has been a founder three times (four if you include founding First Round). In 1992, while in college, he co-founded Infonautics Corporation – and took it public on NASDAQ in 1996. Josh co-founded Half.com in 1999 and led it to become one of the largest sellers of used books, movies and music in the world. Half.com was acquired by eBay in 2000, where Josh remained for three years. In late 2003, Josh helped to found TurnTide, an anti-spam company that created the world’s first anti-spam router. TurnTide was acquired by Symantec just six months later.

We covered:

His “Venture Arrogance Score”
The role of relevance in venture
Making money in disequilibrium
Overlooking margin superiority
Decision-making as a product

Timestamps:

(0:00) Intro

(0:25) Current landscape

(4:39) Venture Arrogance Score

(10:49) Comparing fund models

(14:24) The role of relevance in venture

(21:03) Small funds vs large funds

(26:36) Making money in disequilibrium

(33:57) Overlooking margin superiority

(43:17) First Round’s strategy

(49:02) Operating like a company

(56:49) Future of First Round

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