Welcome to Patrick O’Shaughnessy's podcast series, Invest Like the Best.
This week Patrick takes a deep dive into the world of Venture Capital with Craig Shapiro, founder and CEO of the New York-based Collaborative Fund, which was an early investor in companies like Lyft, Kickstarter, and Reddit. We cover Craig’s investing roots, his process for sourcing and evaluating investment opportunities, and the very useful “villain test.”
2:19 (First Question) – Start by looking into Craig’s personal roots and how they led him to start the Collaborative Fund.
Post – Celebrating our Strong Roots
5:03 – Why the Collaborate Fund of better for me, better for the world drives them and is effective
8:26 – Looking into how Craig identifies investment opportunities 14:08 – How do the relationships with their limited partners get cultivated
17:16 – Going back to Craig’s entrepreneurial roots
21:37 – How does Craig evaluate a company/management before making a decision to move forward
27:33 – Is there an example of a company now that is both doing good in the world and is appealing to the masses
33:07 – Are there negative factors that would rule out an investment for Craig
36:15 – What advice does Craig have for entrepreneurs, and specifically for those exploring who are hoping to engage with the venture capital world
39:57 – A look at Craig’s biggest miss
41:16 – Patrick asks Craig to pick one of the categories of investments listed on their site (cities, money, consumer, kids, and health) and describe the importance of that category in their investments.
46:15 – Exploring Craig’s daily routines and systems that help him
48:13 – A Look at how Craig got into meditation 49:49 – Most memorable day as a venture capitalist for Craig
51:39 – The kindest thing anyone has ever done for Craig