“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 ChandraAnurag 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/achandra41OUTLINE:[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 sceneFollow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP

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