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June 2, 2025 78 mins

Markets can stay irrational longer than you can remain solvent.


If you’re a VC, you’ve likely lived through this.


Both public and private markets change in a flash, but human nature stays the same.


Amidst this, an anti-VC investor emerges.


Meet James O’Shaughnessy, Founder and CEO of O'Shaughnessy Ventures LLC.


Previously, James founded and chaired OSAM, an asset management firm, and served as Director of Systematic Equity at Bear Stearns Asset Management.


In this conversation with Primary GP, Jason Shuman, James dives deep into avoiding biases as an investor, why he has no LPs, and how it pays to be lazy as a VC.


ABOUT US:


Primary is the largest early-stage venture firm in the world, with over $1B in Assets Under Management, and notable investments under its belt include unicorns like Slice, Chief, Electric, and more.


With a dedicated team of Partners, Associates, and Advisors, Primary operates with one clear modus operandi: to allocate unreasonable resources toward building unfair advantages.


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00:00:00 Trailer

00:01:02 Introduction

00:06:33 How history repeats itself with every innovation

00:09:34 The role of premeditation in achieving success

00:18:25 Differing views on premeditation in investing

00:20:23 What sparked James's passion for the stock market

00:25:21 The story behind O’Shaughnessy Capital Management

00:32:32 Thinking Like a Quant in Venture Capital

00:38:13 The evolution of market structures in AI technology

00:46:25 Why private companies win

00:53:13 Using AI to enhance critical thinking

00:59:22 The secret to becoming a top Venture Capitalist

01:05:40 How to avoid 50% of failures in Venture Capital

01:10:27 How the Internet revolutionized philanthropy

01:14:46 Why parents should encourage kids to Google

01:17:19 The one change James would make as Mayor of New York

Mark as Played

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