“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
Listen to the episode on Apple Podcasts and Spotify. You can also watch the episode on YouTube here.
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 assh*les 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
SELECT LINKS FROM THIS EPISODE:
- San Jose FCERS Pension Plan
- Peter Thiel
- Keith Rabois
- Bill Draper
- Mark Stevens
- Rebecca Goldman
- Philz Coffee
- Boston Red Sox
- New York Giants
- Bill Russell
- Boston Celtics
- Bobby Orr
- Boston Bruins
- Carl Yastrzemski
- ESPN
- New York Yankees
- New York Mets
- Matt Curtolo
- “How to Bet on the Underdog” with Matt Curtolo
- Sean Warrington
- “Why Individuals Can Be Better than Teams” with Sean Warrington
- Jamie Rhode
- Verdis Investment Management
- Screendoor
- “The Bull and Bear Case of Early Distributions” with Jamie Rhode
- The Stanford Review
- Stanford Law School
- California Institute of Technology (Caltech)
- Sequoia
- Sand Hill Sundeck
- Michael Moritz
- Doug Leone
- Intel
- NVIDIA
- Golden State Warriors
- YouTube
- Yahoo!
- Margo Doyle
- Regulation Full Disclosure (FD)
- OpenAI
- Museum of Modern Art (MoMA)
- Noah Lichtenstein
- Coupa Cafe
- Lightspeed Venture Partners
- Y Combinator
- Harvard University
- McKinsey & Company
- RAISE Global
- Akkadian Venture Capital
- Andy Weissman
- The Diary of a CEO
- “The Hidden Link Between Marriage & Money – Kevin O’Leary” on The Diary of a CEO
- Kevin O’Leary
- Shark Tank
- Steve Jobs
- Myers-Briggs Type Indicator
- Australian superannuation
- Prabhu Palani
- Jerry Yang
- Goldman Sachs
- Sullivan & Cromwell
- John Robert Held Sr.
- Chipcom
- 3Com
- Rob Held Jr.
- 23andMe
- Mayfield
SELECT QUOTES FROM THIS EPISODE:
“You seem like a good guy. I’d love to find ways to work with you, but I’m going to forget you in two or three weeks. And you got to make sure that you stay in the front of my mind when I’m in a board meeting and there’s a company that could use your money. The best for you to do that is to shoot me an email from time to time and let me know what you’re working on. But do not make them long. I don’t need dissertations.” — Mark Stevens’ advice to Anurag
“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
“You can do two weeks or two years of due diligence on a company, in particular if you’re a mid-stage or later-stage investor. And it’s after the first board meeting—I have a friend who affectionately refers to it as the ‘Oh Shit!’ board meeting where you show up, and now you’re on the inside and you learn all the bad stuff about the company that was hidden from you. Now is that to suggest you should just invest after two weeks because even after two years you’re still going to end up with skeletons you were unable to uncover? No. I still think process matters.” — Anurag Chandra
“Look for GPs who are magnets, as opposed to looking for a needle in a haystack.” — Noah Lichtenstein
“Process drives repeatability.” — Andy Weissman