NO Diligence is Ever Enough | Anurag Chandra | Superclusters | S6E2

“There are a thousand ways to put lipstick on the pig and there are a thousand skeletons [in the closet]. I’ve only seen five or six because I’ve only seen three startup experiences. And so you need to deputize as many people as you possibly can to essentially triangulate.” — Anurag Chandra

Anurag Chandra has spent over two decades in Silicon Valley as an investor, operator, and allocator. He has helped lead four venture capital funds, managing over $2.0B in aggregate AUM. Anurag has also been a senior executive in three enterprise technology startups, two of which were sold successfully to public companies. He is currently the CIO of a single-family office with an attached venture studio and a Trustee for the $4.5B San Jose Federated City Employees Retirement Fund, serving as Vice Chair of the Board, and Chair of its Investment and Joint Personnel Committees.

You can find Anurag on his socials here:

LinkedIn: https://www.linkedin.com/in/anchandra/

X / Twitter: https://x.com/achandra41

OUTLINE:

[00:00] Intro

[02:10] Why is what Anurag is wearing a walking contradiction?

[06:08] The man without a home, but comfortable in everyone's home

[10:17] The Stanford Review

[12:55] The four @%#-holes of America

[20:13] How did Anurag schedule regular coffee with Mark Stevens?

[25:31] Mark Stevens' advice to Anurag about staying top of mind

[26:42] How often should you email someone to stay in touch?

[30:33] Why should you be an asymmetric information junkie?

[34:21] Where should you find asymmetric information in VC?

[36:02] The 'Oh Shit' board meeting

[40:09] How San Jose Pension Plan views GPs

[43:55] Defining the 'venture business'

[49:09] Process drives repeatability

[54:06] How San Jose Pension Plan built their investment process from scratch

[58:43] What is a risk budget?

[1:01:52] What did San Jose Pension Plan do about their risk budget?

[1:05:05] The people who changed Anurag

[1:11:10] Post-credit scene

Follow David Zhou for more Superclusters content:

For podcast show notes: https://cupofzhou.com/superclusters

Follow David Zhou's blog: https://cupofzhou.com

Follow Superclusters on X: https://x.com/SuperclustersLP